Book Insider: Hybrid Publisher vs Self-Publishing (and applications to leadership)

Photo by Markus Spiske on Unsplash

My first book, Make Space to Lead, comes out on November 2nd. I chose to self-publish the book and am now sharing brief lessons about two options for self publishing that I know of. These lessons are also universally applicable to leadership:

When you’re doing a work project, when should you hire a full-service agency (go to a hybrid publisher) vs assemble your own team (completely self-publish)?

I started writing content for my book in February 2021. However, I’ve been consistently sharing my coaching & leadership journey via weekly blogs since October of 2019. Perhaps about 10–15% of that blog writing was repurposed into the book, yet the writing muscle and practice, including getting feedback in the form of views and comments from readers, has been an integral part of my process.

I started researching how I wanted to publish Make Space to Lead in January. I already know that traditional publishing, via an agent > book proposal > book deal wasn’t something I was willing to wait for. I wanted the messages in my book to come out in 2021 or at latest early 2022, and from my research I thought that going traditional publishing would take 2–3 years. This is a brief overview on the process of getting traditionally published from Tim Ferriss. My understanding is that first-time non-fiction authors will typically get a low 5 figure advance, and the royalties (15% of sales, I think) won’t get paid out until the publisher has made back the advance money.

If you’re curious about all the book publishing options, check out this informative chart from Jane Friedman.

Hybrid Publishing

When I started in January, I honestly didn’t know much about hiring a full-service agency (hybrid publisher) versus completely doing it all myself. I fell into the latter approach, more by accident then intent, though I believe that this DIY approach I lucked into suits me well. Using a hybrid publisher means that you spend some money, roughly $15–25K with a small publishing company that soup-to-nuts helps you from book idea to launch. They provide the expertise through the publishing journey and the resources to help you with:

• Writing. Assigning a book coach to help with you through early writing, including support & guidance, and reading everything you write. This can take 6–18 months.

• Editing. Once there is a rough first draft, a developmental editor reads through the structural makeup of the books. After you’ve written a second, third, fourth?, fifth? draft, the manuscript goes to a copyeditor, then a proofreader to help with edits. Reference from Jane Friedman if like me, you’re confused between all the editor types.

• Book design for the cover and interior formatting

• Physical act of publishing from printing to ebook conversation and distribution

A hybrid publisher helps you project manage through the entire process like using a general contractor for renovations to your house. Similar to self-publishing, the author retains full profits from the book. In leadership, this is also analogous to hiring a full-service agency for technical projects such as a branding, creating a microsite, or a Salesforce migration.

My Self-Publishing Resources

In contrast, in the DIY method, you assemble your own team piecemeal. This is what I did, and I believe that it was the right process for me because I am notoriously picky and have high quality standards over many steps of the process, including the cover design. If you’re curious, this is the team that I assembled. If you’re looking for specifics on any of individuals, feel free to contact me directly via all the social channels on my site.

• Book coaches: Patti M. Hall and Sarah Chauncey

• Bood design: Dino Marino

• Editing: Developmental (Sarah Chauncey). Copyediting and Proofreading will be through Wendy Muruli and Shamaila Anjuming via Tessera Editorial, an all-remote BIPOC editorial team.

• Support for ebook launch and the Amazon publishing process: Emee Estacio

To date, I’ve spent about $15,000 and I expect to spend another $5K. The financial investment is similar to the hybrid-publisher option and I will retain 100% of the book sales.

Through this process, I’m specifically not talking about the marketing and promotion aspects of the book, as it’s still very much in-progress. My understanding is that regardless of being traditionally published, or self-published, authors are always responsible for the bulk of the marketing.

Lessons for Leadership

On to the leadership lessons, after that publishing-related preamble! Three things for people to think about when considering hiring a full-service agency or expert (this is the hybrid-publishing model) versus building your own team (my DIY model).

1. Time and Money

There’s going to be constraints on every part of the process. The biggest two are time and money, so ask yourself:

• How much money are you willing to invest?

• How much time are you willing to invest?

• What are the real deadlines for this project?

For my book publishing, I was willing to spend the money, and much of my personal time to make it high quality. However, my biggest constraint is that I wanted to publish it in 2021, with the flexibility of a 3 month delay. That led me to the unequivocal decision of assembling my own team.

For a leadership project, ask yourself these same three questions. If you have more time than money, it may make most sense to go with assembling your own team of internal resources or contractors. The project deadlines make the decision more ambiguous. If there is a true hard deadline, hiring a full-service agency, with its own project manager, can help keep the project to a timeline better than relying on your own internal shifting priorities. This is the path that I’ve seen for most projects through my career. Finally, if you have a specific tight deadline and have lots of time, assembling your own team is one way to make it happen.

2. How hands-on will you be?

Consider listing out all the different aspects of the project that you know of. What aspects of the project truly matter to you? These aspects are where you want to put your personal attention on. This is where you can invest more time or money, and be hands-on, either in the creation or the review process. For me, in addition to the writing, as a designer, what I really cared about was the cover design and interior layout. One challenge for me if and when I choose to go the traditional publishing route is that I may have little to no creative control over book design.

For a leadership project, consider how and where you want to be involved. Where do you need to personally approve every detail and what can you delegate to someone else? You will need to have a detailed project manager that you trust, unless you’re willing to do it yourself. An agency will have this point person for you. If you’re assembling your own team, consider who will play this role to ensure the project’s success.

3. What is the project context?

Finally, consider how this project compares against everything else you’ve got. Why are you involved and why does it matter to you? For me, launching Make Space to Lead was my top priority in 2021. That singular focus helped me to prioritize and ladder up all other activities to support it. Yes, I had a number of other important initiatives in my business, and others became temporary urgent #1s for a period of days or weeks, but this book was the clear #1 priority. Given that context, I was willing to invest most of my time and money towards the book.

In leadership, I’ve had periods of time when agency projects such as a company rebrand became my #1 priority over a period of time. In those cases, especially when I was closely supporting the CEO or executives, that project stayed #1 on my list. In other cases, projects like mid-size product launch or building a marketing microsite, were important, but not the most crucial company priority. I needed to have a team complete the work, but it wasn’t a do-or-die situation. Understanding relative priority helps with understanding the work. For a high priority project, it may bring some peace of mind to have a full-service agency with high quality execute the work. Or, you may want a black ops internal assembled expert team to do so.

Bottom-Line

As part of being a new writer, I’m sharing my learning and process around self-publishing options. Yet as with everything I do, the growth journey ties back to leadership. When making project decisions about working with a full-service agency vs. assembling your own team, consider the following factors of 1. Time vs money, 2. How hands-on you’re willing to be, and 3. The project context.

The Three Intentional Spaces Needed by All Leaders

Photo by Aaron Burden on Unsplash

We all aspire to be good leaders, supportive of our teams & companies and also at home. The core of this aspiration is that leadership starts with ourselves. We must believe in these qualities and model them for others. One physical instantiation of leadership is the ability to create intentional spaces, or experiences for our coworkers, team and ourselves. The three intentional spaces that all leaders need are 1. External spaces of service, 2. Internal strategic / introspective space, and 3. the Liminal spaces in between.

1. External Spaces of Service

Many leaders I work with believe in a philosophy of servant leadership, where unlike a traditional command-and-control style, a leader’s job is to be in service to the people on their teams and to the organization as a whole. People come first, and that priority is additive to the company’s overall performance and success.

As part of this model, leaders create spaces of service for their teams. This can be an intimate space such as a 1–1 meeting with a report or a skip level, a staff meeting of your direct reports, or as expansive as a company all-hands. Most leaders will immediately focus on the agenda—the nuts and bolts of details to be covered including key messaging, long-term strategic plans, short-term updates, and interactive brainstorms or question & answer sessions. These to-do items are the typical—and crucial—tactics that first come to mind and are often captured in an agenda or a slidedeck.

What’s often overlooked is the feel of the space or the intention of the experience. This is a fuzzier, more woo-woo area that’s de-prioritized for the rational get-shit-done brain. Creating this intention involves asking questions such as:

• What emotion do I want the people in this space to feel?

• What is the arc of that emotion throughout the meeting? e.g. How do I share the positive, celebratory news versus the pragmatic downers that need to be announced?

• How should people feel at the end of the meeting?

• Afterwards, what do I want people to remember about the meeting?

• How should they describe the experience to their partner or roommate when they go home later that evening?

This intention serves as the foundational north star for the external space, be it a 1–1 or an offsite. These can be based upon a written set of company values. Yet the lived company culture is how these multiple external spaces are curated over time and by all the leaders in the company. It takes time, consistency, and intention.

2. Internal Strategic / Introspective Spaces

For a leader to hold space for others, they must also carve out the time for themselves. Each day or week will have mini-crises and immediate fire-drills to be solved—that’s the rhythm of a modern workplace—however leaders can create structures to come back to strategy and contemplation.

For introspection, some of us need a physical break, whether it’s a vacation or a retreat to go inwards and reflect on how the daily or weekly activities matter towards a long-term goal. Others can create a weekly time to reflect and reset for the next week. Many of us need all of these rhythms in a year. This is the personal introspective space. We loos inward at how we continue to get energy from activities and people at work, and how this matches with life values and career aspirations.

There’s also strategic space where where as leaders in a company, we carve out the time either alone or with key partners to take a 10,000 foot view of where the company should be going. It gets out heads out of the trees and looking at a long-term view of how our weekly priorities map to the overall company direction. This is where we can also get outside counsel from a board of advisors or trusted mentors, and make sure that the company is on the right track.

3. The Liminal Spaces in Between

Finally, through our work lives we have many transitions between external spaces of service and internal spaces. We have to switch gears when moving from a visioning offsite to the day-to-day operations of finalizing a budget or shipping products to retail stores. We switch gears between a rejuvenating vacation, and jumping back into the rapid-fire of email triaging. We may have a carefully planned out schedule for the week that must be thrown out to address an urgent crisis that may derail the company.

These ambiguous liminal spaces are challenging. We are out of routine or switching from one routine to another. Be gentle with yourself. Slow down and create more space for the inevitable messiness or discomfort that will arise. Some ideas to consider:

• If you’re coming back from a vacation, consider blocking the first day back to be a re-entry day that’s meeting-free. Use that day to review material, catch up on emails, and do a debrief with a trusted lieutenant.

• If your team has been pushing towards a huge event, give the entire team the rest of the day off. Or schedule in common days off for the coming weeks. When the entire team is off, there is less pressure to check-in and be productive.

• Build in some daily mental space between activities. This can be as short as a five-minute solo regroup to breathe or taking an hour-long walk after delivering a challenging performance review.

Pick an experiment for liminal spaces that you can try out. Notice how you are afterwards. See if it made a difference in your energy or performance.

Bottom-Line

As leaders, we must hold space for ourselves and our teams. Consider how we want to intentionally design these experiences. Remember the three intentional spaces that all leaders need — 1. External spaces of service, 2. Internal strategic / introspective space, and 3. the Liminal spaces in between.

Company Culture and the Great Resignation

Photo by Jackson Simmer on Unsplash

Through this pandemic, most of us have re-evaluated our relationship to work, whether it’s through remote work, struggling with unemployment or keeping a business afloat, or serving others as an essential worker. Now in the middle of 2021, millions of people are quitting their current job in this post-pandemic workplace. Leaders are trying to figure out how to fight the attrition and also to take advantage of the surge in job seekers. It’s no longer business as usual, and it’s now time to look at ways to shift company culture to fundamentally value the people who work there. Leaders, use the three Rs of Relationships, Recognition, and Revision to build strong company processes and systems for long-term employee fulfillment.

Relationships not Transactional Leadership

In the day to day of work, it’s easy to get caught up in transactional leadership. Corporations have quarterly goals to meet which get translated down to team goals and personal OKRs. We have launch dates, deadlines, and leadership presentations to march towards. The best leaders are able to balance both this transactional leadership of accomplishing goals as well as slow down for the relationships which are key to achieving these outcomes.

As we rise in our careers from doing hands-on work to managing teams and running companies, the performance of tasks and projects matters less than building relationships. People are drawn to both company cultures and leaders that create time for relationship rituals. Consider experimenting with some of these:

• Take the first 5–10 minutes of each 1–1 meeting to connect with the other person as a human. You could ask about their weekend, their children, or simply what’s going on in their lives right now. Should this be unfamiliar or new in this relationship, you can be the one to share first. Be vulnerable and offer up insights into what’s happening with you.

• In team meetings or company all-hands, build in relationship rituals such as shout-outs for team members, celebrations of success or mistakes, and highlights of individual stories.

• Figure out which relationships are most key at work and intentionally build in structures to nurture them. Regular 1–1s, whether it’s weekly, monthly, or quarterly is a good place to start.

Recognition: What We Want Evolves

Traditionally, companies have looked at compensation and promotion as the primary way to recognize employees. Yet as I’ve found when supporting clients to negotiate for money and more, the changes of the last two years has many of us rethinking what we value.

Yes, companies should always have a fair system for performance reviews and monetary recognition. Yet even with those recognition mechanisms in place, people are still leaving. Increasingly, companies are recognizing how difficult the past year has been to many employees and are offering recognition that people need space and flexibility. Some examples I’ve seen include:

• Some companies that offer unlimited PTO are enforcing the spirit of “unlimited” while also requiring that employees take 2-weeks of mandatory vacation

• Leaders are modeling this behavior by taking their own vacations or midweek breaks and trusting their team to handle delegated tasks

• Companies are offering choice for all types of work needs—people who never want to return to a physical office and people who can’t wait to leave their cramped work-spaces in a shared home

Company culture needs to evolve and expand the definition of recognition. That’s how they’ll meet the post-pandemic needs of more employees.

Revision: Always be Experimenting and Stay Open

Vision is the ability to think and plan for the future with creativity and innovation. Revision is being willing to adapt to unexpected changes with a fresh perspective. Leaders are dealing with unprecedented changes in ambiguous times. Some lean towards radical transparency, sharing every detail of the business with employees. Others are more measured and share on a need-to-know basis. To address the Great Resignation, there may not be one correct answer. Employees want transparency, yet leaders must continue to experiment with how much is healthy and how much is too much.

Bottom-Line

In the middle of this Great Resignation, leaders now have the perfect opportunity to make changes to best serve their people. Company processes and systems can be adapted to help retain and attract the best people using the three Rs of Relationships, Recognition, and Revisioning.

Five Unexpected Workplace Powers

Photo by Guille Álvarez on Unsplash

A common fallacy I see in people looking to grow their career is believing that leadership equals management, that you’re only a leader when you have direct reports. These emerging leaders fail to realize that they can lead from any position.

One tool to help shift this limiting belief is the five unexpected workplace powers¹ of which a title — positional power—is only one. Understanding each power helps us unlock and experiment with different aspects of our leadership.

Power One: Positional

Positional power is the leadership many of us think of first. A person’s title, be it Manager, Vice President, or CEO, gives us some external legitimacy. We think, If other people have given me this title, then it gives me some authority over others, or at least that’s what I thought when I got my first manager title.

Relying on positional power made me feel like I had to be in control, know all the answers, and be the superwoman who would solve all the problems for my team. In reality, I was just a bad manager. New managers often use their title and positional power as a crutch, and many of us have experienced those managers.

Instead, consider a servant leadership style of positional power, where by having that title, you are in full service to the people on your team.

Power Two: Knowledge

Knowledge power is based on having expertise in the hands-on skills of what you do, whether it’s in sales & marketing, engineering, design, operations, or something else entirely. You are closest to the work you do each day and have the full power over the work. This is one reason that engineers are so highly valued in Silicon Valley—without their code, there would be no digital products and services.

Power Three: Task

Task-based power is the opportunities you have to accomplish tasks & projects. Consider a task such as leading / planning / facilitating a design sprint or weekly team meeting. This task might take advantage of new skills that you’d like to practice, or it might be a dreaded task such as taking meeting minutes. In both cases, you have power over the meeting flow and agenda, as well as how the meeting is recorded afterwards. In a design sprint, you’re responsible for the process and working with a team of other people to orchestrate the flow of the sprint.

When looking to gain more task-based power, consider what tasks you enjoy doing and what additional skills you’d like to learn. Volunteering for tasks is also a fantastic way to demonstrate interest and ambition to your managers.

Power Four: Relationship

On a surface level, relationship power can be your network. Yet many people feel icky when they have to “network” or navigate “office politics.” Instead, think of it as building relationships with people you like. It’s helpful to break down relationships into three categories: those positionally above you, your peers in other teams, and people on your team.

Power is built on the trust and strength of these relationships. The majority of themes covered in my leadership coaching conversations is around building stronger relationships. If you’re not sure where to start, first ask yourself if your boss trusts you, and if you trust them. That’s the first and strongest relationship you should cultivate at work.

Power Five: Personal

Personal power is a mindset shift to realize that leadership starts with you. You have personal power when you best understand who you are as a leader, by knowing your strengths, areas of growth, and what you are most passionate about. Personal power is a development of your personal brand, or what you’re known for. YOU will be the expert on work areas that you enjoy the most. Others will come to you for guidance.

To better understand your personal power, start with defining your values.

Bottom-Line

Leadership doesn’t just come from positional power, or having that manager title. Instead, develop your leadership by considering all five workplace powers—positional, knowledge, task, relationship, and personal. The best thing is that all of them except positional power are 100% within your control. Which power would you like to develop more of today?

If you’d like to develop all these powers, I’m offering a group coaching program — Leading From Any Position.

¹This article comes from discussions with Jim Herman on this five power model. He draws inspiration from Ken Blanchard’s writing.

How Do You Want To Work: Sprint or Marathon?

Olympic steeplechase from London 2012. Image from flickr Michael Jones

Where are you with your work today? Would you describe your hours, energy, style as being in a sprint or a marathon? With a sprint, it’s an intense focus where you put in all your energy to burst over the finish line. The marathon is a longer, more sustainable effort where you pace yourself so you don’t burnout. Or perhaps, it’s neither. Instead, it might be something inbetween like a steeplechase — not an event with horses, but the 3000 meter run around a track with hurdles and water obstacles—which I only learned about from watching the recent Tokyo 2020 Olympics.

I have no judgements, being in a sprint or a marathon *can* be the perfect right place for work right now as long as you’re intentionally making the choice.

Starting a New Job

Many of my clients are starting new jobs. The first 30/60/90 days of a new job or even the first three to six months are going to be sprints. It’s a completely new situation to get used to. You don’t yet understand the company processes and culture, how to work with the people around you, or the new domain space that you’re jumping into. Routines are shaken up. And it’s even more difficult to adjust when you’re onboarding remotely without the in-person camaraderie or happenstance conversations in the kitchen.

A sprint is a short-lived burst of intense investment in your work time and energy. Several of my clients are in this phase of starting a new job where they know they must put in longer hours and more brain activity. They also know that this period will lessen and get more comfortable in three to six months.

They’ve intentionally chosen to hustle and grind for a short period because it’s worth the tradeoff to show up and establish their reputation at a new company. And they’ve established an end point for this sprint.

The First Two Years of a New Business

For other people, this sprint mentality may be for a longer period of time, perhaps even years. This First Round article shares the work hours of startup CEO Sam Corcos. With horror, I scanned his seven-day work week calendar and his weekly working hours—one rare low of 45 hours, more common are the highs of 100+ hours. Yet beneath my instant recoil of judgement, it’s clear that this is the right choice for him. Sam shares:

When you sign up for the role of CEO at a startup, you should know what you’re getting yourself into. Most of the time, it’s an all-consuming job, though some people are able to do it while maintaining more “life” in their work-life balance. The goal of this piece isn’t to glorify working to the point of burnout — but don’t expect it to be a normal desk job.

Sam writes as a thoughtful, self-aware leader looking to share his experiences and optimizations to help other leaders in the necessity of fast-paced, intense jobs. For him, it sounds like he has the capacity and tradeoffs to approach his work like an extended sprint. And by that point in time, perhaps an extended sprint automatically becomes a marathon.

If your work style feels like a sprint, make sure that you know when the finish line is. An extended sprint is not sustainable for most of us.

A Comfortable Ten Years at One Company

Some of my other clients came to me because they had spent seven to ten years at their existing company. They had risen through the ranks with the appropriate title, salary, and respect. Yet after the years — and the marathon of enjoyable work with the single company— they were bored. They were comfortable with the pace and the work / life balance it offered. They loved their boss and adored the teams they had built up. But something was missing. Their energy was slowing down and they simply felt like they needed a trigger of excitement. It was the right time to do something new.

They were in a marathon, but wanted to stop running and switch up the pace. Some people choose to interview and find another company. Others look for new responsibilities or positions within the same company. They intentionally decided that they wanted to get off the marathon path and choose something new.

If your work style is a marathon, know when it’s appropriate to pick up the pace and switch things up.

What’s Your Sustainable Pace?

The definitions of sprint or marathon or steeplechase aren’t what matters the most. More important is to set the intention to decide “What’s your sustainable pace?” And to also be aware of the tradeoffs you’re making to other aspects of your life.

Many people start a new job thinking that they’re in a short-term sprint to prove themselves. Sometimes they fall into the pattern of working extended sprint hours and before they know it, they’re unconsciously trapped in a state of busyness, overwhelm, and burnout. They look for a change and sometimes instead of looking for their own sustainable pace, will quit and jump to the next job.

Instead, truly ask yourself what work pace are you choosing today and why you’re doing the work you do.

Bottom-Line

What race metaphor best encapsulates your work today or this week? If you’re in a sprint, name it as one, and clearly identify when the sprint will end. If you’re in a marathon, know when you want to switch up the pace.. Make space to be intentional about how you work. And perhaps, it’s actually a bit of everything and you can call it a steeplechase.

Creating Your Personal Brand

Tutti celebrating something in Mendocino, CA

When you hear the word “brand” do you think of websites and marketing materials? Or maybe Mad Men-style ad agencies creating campaigns for the Nikes and Coca-Colas of the world? Is there a whiff of something manufactured and inauthentic? A fake experience that’s purely created for advertising to get people to buy something? 

The reality is that identifying your personal brand is a deeply energizing journey of introspection to focus on what matters most to you. Once you figure out your personal brand, you can choose to share it externally, or keep it as an internal touchstone for your leadership.

Many years ago, I worked as a brand strategist for a design agency, and through that process learned that most people are focused on the outcomes. Branding is typically done for a company and expressed with a concrete deliverable—a set of brand guidelines, a redesigned website, or a social media campaign. But actually, the core of branding is getting clear on who you are, the people you serve, and what you’re known for. 

Let me share three examples to better contextualize where a personal brand (versus the brand for a business) comes into play: 

1. Celebrity / Creator / Influencer. This one likely makes the most sense. We can all understand how a celebrity-as-a-business has a personal brand whether it’s Oprah, Gwyneth Paltrow/Goop, or Michelle Obama. Beyond these celebrities, there are countless other creators or influencers who run their brands as their business.

2. Startup Founder. After a startup has experienced some product/market fit and is looking to scale, the company may start investing in its own marketing department that develops the company brand. Yet frequently founders come to me asking how to develop their personal brand separate than the startup. While there’s an overlap between the startup and the founder, they are not the same thing. For many of us, businesses are less interesting than people. And it’s the story behind the businesses, the story of the founders that’s most interesting. People care about the founder’s story, whether it’s why she started the company, how the cofounders decided to work with each other, or how they came up with the company name.

3. Regular Person. So now we come to you, a regular person who might work for someone else and you’re probably wondering why you need a personal brand. Your brand is important because it’s how other people view you in the world. It could be as frivolous as the content you post on twitter or instagram. And it could be as important as how you pull together your resume or CV. Whether you like it or not, you have a personal brand. So let’s be intentional about how to craft it.

What Matters Most to You: Values & Passions

Values are a set of principles or standard of behavior for what matters to you. They can be core ways that you’ve lived your life or they can be aspirational, how you want to live your life. Identifying your values helps set the core foundation for your personal brand. 

My values are Adventure, Challenge/Change, Family, Freedom, and Dance in This Moment. The first 3 are core ways that I live my life and the last one, Dance in This Moment continues to be aspirational, to remind myself to slow down, play, be present, and trust the process. It’s a counterbalance to my go-go-go drive and need to make impact in the world.

In addition to values, another way to craft your personal brand is to identify your passions. You can ask yourself these questions:

• What makes life worth living?

• What activities get you in a state of flow?

• What brings you joy?

• What do you love to make?

For me, a peek into my passions includes surfing, reading, travel, being a foodie snob (the COVID-version involves my own baking) and cats. Most of these are a part of my personal brand, what other people know me for. 

If you’re a person who is an entrepreneur or startup founder and want to build your personal brand as part of elevating your company brand, you’ve got to find a sustainable method to regularly post content, whether it’s photos/videos to social media or writing blog posts. Most people find that sharing about your passions is the easiest way to post regularly. These passions humanize you, even if they seemingly have very little to do with the business.

Your Brand is Your People

A second path into your personal brand is the people you’re around. These are your friends, your colleagues, and your chosen family. It could also be leaders that you look up to, whether they’re celebrities, public figures, bosses at your work, or inspiring people from your lives. 

The questions to ask yourself are:

• What qualities matter to me about the people I spend time with?

• What type of people do I click with? These can be people just like you or you may be attracted to them because of their differences.

• What do I love about my friends?

• Who are my friends at work? Why did I choose to spend the time with them?

If we look a layer deeper, and more into traditional brand strategy, your brand is the people you serve. For a business, it’s their customers or clients, and the strategic question is how does the business uniquely provide value for their customers. 

For example, I support leaders in tech, both executives in the big corporations as well as startup CEOs and co-founders, to further develop their leadership. I use the design process to help them envision bigger goals & dreams for what they want to create most in work and life, and shift their mindset so they get out of their own way. I support them using many design tools, and we co-create experiments for them to try something different. 

Your company likely has a good sense of its customers and the company’s unique value proposition, something only they can do to serve the customer. Yet, everyone serves people. As an individual ask yourself the questions: “Who can I serve?” and “How do I serve them?” For example, you might be a manager who:

• is empathetic and supportive of your team

• has standards and expectations for the highest quality work for customers

• creates a safe space and hires an intentionally diverse team

How you serve the people around you is part of your brand. You can lead and serve people from any position. If you’re not a manager, you could serve people by:

• mentoring new grads or people earlier in their career based on your experiences

• blogging to share out tips & skills you’ve learned

• volunteering for different initiatives at work

Both the people you spend your time with, and the people you serve are part of your personal brand. 

Your Brand is What You’re Known for— At Work and Outside of Work

You can create your brand by identifying values & passions, and by intentionally choosing your people, however, some parts of your brand are out of your immediate control. How others view you—what you’re known for—is another part of your personal brand. 

At work, think about what you’re known for. It’s both the hard skills of what you do—writing high quality code, creating compelling presentations, or blowing away your sales targets at the last minute—and the soft skills of how you are when you do these things. You could be known for directness, staying calm, being compassionate, or any possible type of mix. 

Parts of your personal brand can be intentionally created by you, however, you need the feedback loop to understand how others in the world react to you. What they remember about you and their emotional impression of you is what you’ll be known for to them. What you create vs what you’re known for can and should have an overlap, but it’s never 100%. Start honing in to the feedback by loop by asking the people around you what you’re known for. You can do this with colleagues at work, and with friends and family outside of work. You’ll get the most valuable information by asking a varied set of people who know you for different lengths of time and within different contexts. 

Bottom-Line: Make Space to Craft Your Personal Brand

Your personal brand is how people view you in the world, so take the space to be intentional and think about what you’d like to be known for. Start with your values and passions. Think about who your people are. Do the research and ask others what you’re known for. These are all steps to start crafting your personal brand. 

Work With Your Best Friends

Tutti and Irene; FloMo roommates, Stanford; 1994

For many of the busy professionals I work with, it’s easy to fall into the trap of transactional leadership. We focus on the work that needs to be done—the performance reviews to be written this week, the decisions that need to be made in this meeting, or the deadlines that must be hit to meet our quarterly goals. The days are split into 30 or 60 minute meeting chunks, leaving little space for connection in between all the tasks that must be done.

One secret to mitigating this transactional leadership is to work with your best friends. You may not always have this luxury. And there’s also several possibilities to start exploring. You could work on side projects with your friends. If you’re starting a company, make sure that you like your co-founders and are friends with them. If you’re currently working, consider who among your coworkers you‘d like to be better friends with.

Lead for Connection

Many solopreneurs I connect with, especially those that used to work with large teams, talk about the loneliness of not having coworkers. That completely resonates for me. I mostly work alone supporting clients one-on-one as well as speaking, teaching, and writing. How I choose connection is by teaching workshops and retreats with people I love.

Irene Salter is one of my best friends. I’ve known her for almost 30 years. The picture above shows us as happy-go-lucky college roommates. We each had a first career, hers in neuroscience & education and mine in design & technology. We found our way to working together when we both became coaches in our latest career swerve.

For as long as I can remember, Irene and I have taken a weekend away together every six months. Last fall, in the midst of the pandemic, we were socially distanced in Mendocino, California as we camped and hiked side-by-side. In the midst of missing travel and adventure, we hatched a dream to run a women’s leadership retreat together. Now it’s come to fruition, and I finally get to work with one of my best friends. Irene and I are running a 4-day women’s leadership retreat in Mendocino over Labor Day to help women discover their own Heroine’s Journey.

It’s our first experiment in working together. Above all else, we’re already connecting and having fun in as we co-create the program.

Make space for connecting with other humans in your workday. It could simply be taking the time to pause and listen to what really matters to them. It could be sharing a joke or an anecdote about the past weekend before diving into work. Embrace connection over transactional leadership.

Seek out the differences

A newer friend, Jim Herman, and I are teaching our third series of leadership workshops together. We met during our coaching certification program, and instantly felt intrigued by each other. While we resonated over living in different cities around the world, he could not be more different than me. On top of the obvious demographics—he’s a retired white man—our styles are as different as night and day. I am more planned, no-nonsense, and serious. He is outrageous and light-hearted. Together, we make a wonderfully diverse co-teaching pair and have learned how we adapt and improvise together. I’m grateful that Jim makes me a funnier person.

When you work with friends, there’s pre-existing relationships and a camaraderie that exists. You might know the person socially or have worked together in another job. You know more of their story. This depth of personal relationship makes it easier to celebrate how different they are from you. Because of this shared trust, it’s easier to learn from the differences rather than become defensive or resistant.

Trust and Agreements

The benefit of working with friends is that you have pre-existing trust and relationships. However, it’s important to intentionally transition the friendship to a working partnership by setting clear agreements and expectations.

I support many co-founders and have heard consistent themes over what could go wrong. It gets even more complicated when you add more cofounders—4 is the max I’ve worked with. Tensions can arise from these situations:

• Two co-founders have quit their jobs to work full-time on the startup but the third is still working at her day job. There’s a perception of inequity of effort.

• The details of the cap table aren’t transparent to everyone. Each person believes that they deserve more, and there hasn’t been a clear discussion of what division is most fair.

• Roles and responsibilities which continually evolve in a fast growing startup become murky when not made explicit

The solution to all of these is to have closer communication and an ongoing discussion on how much each person can contribute and what the financial compensation should be. These agreements need frequent revisiting as startups evolve quickly.

It’s especially crucial to set agreements and boundaries when transitioning from one set of relationship norms as friends to a new set of norms as co-workers. You don’t want to ruin the friendship by working together.

Bottom Line

To build more meaning into our professional lives, work with your best friends. There’s many forms this can take—working on side-projects with friends, picking friends to be co-founders, or looking for new friends in an existing workplace. This mentality helps us move away from purely transactional leadership to building more connections at work.

My Heroine's Journey

Photo by Toben Dilworth

My journey to leadership as an Asian female has had a long and meandering path to this present time when I am 44.

I grew up with a tiger mom who I believe is an undiagnosed manic-depressive. She loved me deeply. She gave up her career to follow my father’s job with Thai Airways, taking on the role of home holder to move our family every 3–4 years to a different country. She gave up her own aspirations and fiercely passed them on to my sister and I in the form of sky-high expectations.

I was a good girl. Culturally Thai-Chinese and raised to respect my elders and the Buddhist community we practiced in. I am Thai. Yet I went to international schools where critical thinking and western concepts of self were drilled into me. Even though my first languages were a mixture of Thai and Teochew (a dialect of southern Chinese spoken in Thailand), I’m now most comfortable in English. I sound like a native Californian to those of you who have met me.

I lived in fear of my mother’s moods and compensated by being a good girl. Quiet, obedient, and withdrawn. I excelled in school.

As I grew up and moved halfway around the world to attend college at Stanford, I learned what it was like to be a female in a technical field. I found my way into design via a mixture of computer science, psychology and philosophy, learning that I enjoyed being a translator between humans and computers. I started embracing adventure and letting my inner rebel start to emerge. 

And through the next decades, as I worked in tech corporations, design firms, and startups, I put on my armor and climbed the corporate ladder. I learned how to succeed as a woman. I learned to take on traditional characteristics of male leadership — confidence, assertiveness, directness, decisiveness — and this built upon my inner drive of high expectations and achievement.

It seemed like everything was perfect. My career was soaring. I was married to my college sweetheart and we had two playful little girls. We had a house in San Francisco with room for my parents to come visit for extended periods and a strong network of friends.

But something was off. I wasn’t truly content. I kept searching for something and driving myself more, faster, harder to achieve it.

On this questing journey, my leadership shifted. When I left the design firm environment, I learned to shed some pieces of the armor and open up to vulnerability and some understanding and acceptance of my strengths. Yes, I was passionate and had strong opinions… and, that assertiveness, especially in a woman, could be off-putting for many people. I found teachers, mentors, and coaches to support me along the way. I experimented with different styles in different contexts to grow my empathetic and compassionate leadership. I practiced these new muscles on the teams I supported, with my cross-functional partners, and also in presenting upwards to leadership at my companies.

Yet it never felt completely like me. I kept striving to find my professional leadership, adjusting to the feedback that I received and looking for my right path.

Something was still off.

And then it hit like a massive tidal wave.

I went through a twelve month period of extreme stress and transition where three major events happened — my father-in-law who I had known since I was 18 passed, my husband and I decided to get divorced after trying couples counseling for six months, and my father passed.

That was about two years ago.

In the time since, I learned to create a new version of family. I left my corporate job to build a new career as a leadership coach. I’ve now almost completely shed the professional armor. I’m still learning and growing on the path of my feminine leadership, yet I know that this job feels like the most authentic one that I’ve held.

I am still on my heroine’s journey. It’s a meandering path that can double-back on itself. I’ve encountered many guides and fellow adventurers along the way. For once, I’m loving the process, and not single-mindedly focused on the destination. 

If you’d like to explore your own Heroine’s Journey and uncover your leadership, I’m leading a retreat in Mendocino, CA over Labor Day weekend 2021. You’ll be supported by an intimate group of female leaders and fellow adventurers. Reach out to start a conversation. 

Make Space for Intuition

Photo by Jen Theodore on Unsplash

I am a life-long skeptic. My typical pattern is to listen and value my intellect and reason above all else. For decades, I would dismiss anything that didn’t follow rational thinking as being too “woo-woo.” But I was in a conundrum. Because, as a designer, I also know the value of my gut. There’s sometimes decisions or designs that I can’t rationally explain why and yet I intuitively know will work. I’ve written about how to follow your curiosity and express intuition at work. Deep down, I’ve always known that there was a subconscious mind that helps with creativity. It’s the same reason why sometimes we get our best breakthrough ideas in the shower or when taking a walk out in nature. Now I realize that the best approach is to treat all these factors—intellect, reason, intuition, emotions, and feelings—as inputs and perspectives into decision-making.

Listen to How You Feel

I was recently working with a client on finding a new job. Throughout the interview process, we’d shared a google sheet with clear criteria for what mattered to her—the company’s culture and philosophy, the type of work they focused on, the people she’d work with, her title and its equivalent responsibilities, and the financial compensation. We’d been evaluating each company she talked to against these criteria, and one company, we’ll call them company A, was her top choice. She eventually got two offers, one from A and one from company B. Both were solid offers and she would have been excited to work at either place. A was the clear front-runner based on the criteria and she was prepared to accept that offer. She went to dinner with the partners, and called me the next day to share:

“I didn’t feel good about them. Something was off. I’m not sure what.”

She had follow up meetings with more people at company A, and that uneasy feeling continued. In the end, she spent some time talking with the people at company B, felt reassured by her interactions with them, and ended up taking the offer with company B.

It’s important to listen to how you feel. My client and I discussed the rational underpinnings behind the feelings as well, but that was after the fact. The “something was off” feeling was the first indicator that she needed to dig deeper beyond the obvious decision and listen to how she was feeling.

You Can Change Your Mind

A former client taught me that you can change your mind. She was a deeply intuitive leader and worked for a large technology company. She was in-touch with what really mattered to her—she wanted to start her own business in a deeply-meaningful space to her. But she wasn’t ready to make a move yet. She was earning a lot of money in the corporate world. As we worked together, she explored more deeply into her possible futures. She could go to business school and get an MBA that would give her more connections and business skills. She could explore paths to find cofounders. She could simply quit her job and get started with her venture.

What helped her explore the right path for her intuitive leadership was to simply pick a direction and move forward with it for some weeks or months. She would talk to advisors and ask them about the value of an MBA. Then she would switch and would talk to investors about her idea.

What helped her follow her intuitive leadership was telling herself that she was moving on the path for one possible future (of many) and “You can always change your mind.”

The path of logic and reason argues for us to commit to a single focused direction and keep moving with it. Yes, when more data comes in, or when there’s a logical reason to do so, we can switch directions, but otherwise, it’s important for us to focus and not get distracted from the plan.

The path of intuition says that it’s OK to change your mind. There doesn’t have to be a reason other than “Today, I feel differently. This is what I want right now.”

Practice the Muscle of Intuition

As leaders in tech, whether in the corporate world or startups, we’re used to being highly rational and continuing to follow our milestones, roadmap, and todo lists to achieve success in the world. I’m sharing another way—the path of intuition—which needs a little more practice because it’s an underused muscle for many of us.

When you’re next faced with a decision, ask yourself three questions:

1. What does my head say about this decision?

2. What does my heart say?

3. What does my gut say?

For my client who was deciding between company A and B, the answers might have been:

1. My head says to go with company A. We’ve laid out all the criteria and A scores the highest in all the things that matter to me.

2. My heart says that I don’t want to work with these people. Somehow, I don’t feel valued there.

3. My gut clenches. Something is off.

The important thing is to ask the questions of your head/heart/gut, and listen to the answers. Truly hear what matters. Know that you don’t have to choose or decide based on your intuition. You simply want to practice the underused muscle with a sense of curiosity to see what you can learn.

Bottom Line

I’ve spent decades of my life being driven by logic and reason, and once I’ve made space for intuition, it’s felt like my decision-making skills have become amplified. Making space for intuition provides additional perspective and nuance to understand what really matters. You can listen to how you feel, practice the muscle of intuition, and ultimately know that you can change your mind.

I’m offering a women’s leadership retreat, The Heroine’s Journey in September 2021, that combines the practical skills of leadership—finding clarity, working through self-critical voices, building trusted relationships—with the intuitive space for feminine leadership, magic and adventure. If you’d like to make space for your intuition you can learn more and apply to attend.

Embrace Adventure From a Place of Safety

Photo by Erik Mclean on Unsplash

Adventure and freedom are two of my core values. Yet I’ve learned that I can most honor those values when I come from a place of feeling safe and secure. The paradox is that safety provides the space for adventure. Safety is the low guardrails on a windy mountain road that provides the security to let you drive faster and accelerate out of the tight curves in a car that hugs the road.

If this resonates and you’re feeling the adventure, take stock of what’s safe and supportive in your life that’s allowing the risk to happen. And if you’re not feeling the yearning for risk-taking, it’s OK. There’s nothing wrong with you. Perhaps it’s not for you. Or if you’re hoping for something to be different in your life perhaps what needs to first change is building more of the foundation of safety.

Feeling Safe Provides the Space for Adventure

As the days get warmer and I’ve received both my Moderna vaccine shots, I’m feeling a bubbling yearning in my stomach that’s remembering the feeling of adventure and longing to experience it again. The past year and a half has simultaneously felt like a “lost year” and also a time of inward cocooning. It’s felt like I’ve missed out on travel, eating out, going to concerts, seeing friends and family, and also the camaraderie of working face to face with people. However, the pandemic has forced me to make space to be present and to focus on what’s happening right now. I’ve slowed down and done less. This has opened up more meaningful time with my girls, both at home and hiking together out in nature.

Over the past weekend, my partner and I took a grueling hike to Desolation Wilderness near Lake Tahoe, California. It was one of the first times this past year that I’ve felt wild and free. We were able to get lost on the ambiguous trail, climb up seemingly impossible granite crevices, and fearfully wonder if we’d get caught by the approaching thunder & lightning storm. It was glorious.

This moment of adventure only worked because I was two weeks past my second vaccination. I was feeling COVID-invincible, and once that milestone of safety had been achieved, the yearning for travel exploded.

I see this juxtaposition of risk-taking and security in many leadership situations.

Leaders Show Possibilities and Let Others Choose Their Own Path

As a leader, one of my innate traits is that I’m challenging and fierce. People are drawn to me because I push them out of their comfort zone. However, that might not be the right path for them. My role is not to control their path. Instead, the role of a leader is to show different possibilities, to paint the picture of the future that they cannot see for themselves. It might be a future that’s most adventurous, most challenging, most innovative, most creative, most authentic—whatever it is that helps people see different perspectives. And ultimately, it’s up to the individual to choose their own path.

I’ve recently been supporting many people who are in the midst of career transitions and offer negotiations. When I work with women and people of color, I strongly encourage them to ask for more as this group has historically been severely underpaid. Recently I was working with a female leader. We were on the phone on Thursday night, and she wanted to immediately accept a job offer she’d just gotten. She wanted to wrap it up and have it over with on Friday so she could give notice at her current job and quickly plan for the future. It had been a long interview process and she was it. She was done with interviewing and done with all the chaos in her current job. We talked through what she really wanted. While I have a framework to get the best monetary results for salary negotiations and I shared that with her, it wasn’t the right path for her to take that day. That was exactly the right choice for her. Rather than pushing into an aggressive negotiation, she chose her own path that pushed her slightly out of her comfort zone— she waited until after the weekend to accept the job offer and then lightly asked for some things that mattered to her.

As leaders, we can show possibility. We open a corridor of doorways for people and they choose which door and the right time that they are ready to step through it. Often, realistically when managing a team that needs to meet organizational goals, we have to inspire and persuade the team that this is the path they want to take. Yet it’s always best to give people the autonomy to choose their own path.

Safety Provides a Support Net for Growth

As a leader, when we want to push our team members to grow and be better versions of themselves, consider how to put up a support net for them. When I worked at Facebook, I managed the design internship program. Individual contributor (IC) designers could apply or be nominated by their managers to manage an intern for three months. This was invaluable experience for ICs who wanted to transition to management. We provided a safety net of support so that the intern manager could experience actually managing another person in a safety net of support. The intern manager was given a structure to follow:

• Identity goals and a project for the intern that could be completed and show impact over the three months

• Schedule regular 1–1s with the intern

• Monitor their intern’s performance against the goals and present/defend/rate their intern compared to all the other interns in a mid-way performance calibration process

• At the last weeks of the three months, present their intern’s impact including a hire/no hire recommendation at the final performance calibration process

• Deliver the final hire/ no hire decision (for future full-time employment) to the intern

Throughout this process each intern manager had a commitment of support from their manager as well as from me as the leader of the intern program. I had many conversations with intern managers who had to deliver negative news to their interns. It was a real situation—they learned the valuable leadership skills of empathy, managing someone else, communication, and how to hire and fire people. Most important was the feelings of accomplishment as a leader no matter what the outcome was.

This process provided a support net for the intern managers. They learned what it was like to manage. Some of them decided to go on to a long career as a strong manager, others decided that it wasn’t for them and that they preferred to lead as an individual designer. Most importantly, this safety net of the intern program allowed them to take risks, make mistakes, and grow into a new adventure.

Bottom Line

Feeling safe provides the space for adventure. I see this in my personal life after fifteen month in the introspective cocoon of social distancing. I see it with my clients who can take greater risks—leading to greater growth—when coming from a place of safety and security.

Focus on What’s Right, Not What’s Wrong

Photo by S O C I A L . C U T on Unsplash

I have a tendency to look for what’s wrong, to play devil’s advocate, and to contingency plan all the possible ways things can go wrong. Sometimes this can be a good trait for a planner, and it’s fantastic in a crisis-management situation. However, as a leader, only looking for what’s wrong can be hugely deflating to your teams.

Through most of my career, when I heard someone else’s idea, my first instinct was to put on the skeptical hat and ask many detailed questions. I sought to understand, and perhaps also to shoot it down and find out why the idea didn’t work. That first blunt reaction to an idea could really turn people off and destroy their confidence, especially if it had been difficult for them to present the idea in the first place. We’ve all known people in meetings who always respond to our contributions with a rebuttal. It’s not pleasant to be around them. Gradually over the years, I learned to replace the interrogation with (hopefully) a more curious inquiry. I could accept the brilliance of the idea first and then build it up with questions and together co-create a new version of the idea. I was learning to adjust and build relationships with people rather focusing on what’s wrong. 

Be the Inspiring, Supportive Leader

Instead, be the leader who inspires. Trust that the people who work for you have the skills to do their job. You don’t need to second-guess or perform risk-mitigation on them. Be the support mechanism to help them troubleshoot issues that they choose to bring to you. Rather than point out what’s wrong, encourage them to dream bigger, think wider, and reach larger scale goals. 

Think about the ratio of positive to negative feedback that you provide to people. Most of us, often only provide feedback when we want someone to fix a problem. It’s never pleasant to be on the receiving end of an endless stream of constructive criticism. Instead aim for 3:1 ratio of positive to negative feedback. 

Why? Most of us, when listening to performance feedback at work are hardwired to ignore the compliments and positivity. We nod, yeah, yeah, yeah, barely acknowledging the praise, and anxiously wait for the actionable, critical feedback so we can improve. People aren’t receptive to positive feedback— it’s hard to hear nice things about ourselves and it makes us uncomfortable. Instead, we over-index on the negative feedback as we think it’s actionable and we can fix ourselves. As a leader, mitigate these biases by providing more positive feedback, increasing the chances that it will land. Aiming for the 3:1 ratio of positive to negative feedback. Oh, also make sure that both the positive and negative feedback are timely and specific. 

Create a Culture of Celebration

Many of my high achieving clients focus on the next goals in front of them, whether it’s getting through the fund-raising round, negotiating a job offer, taking the company public, or closing a key hire for the team. The instant one goal is achieved, they move on to the next round of goals. It might have been challenging to do something for the first time, such as their first round of fund-raising, however, once it’s completed, we minimize our accomplishments and look towards the horizon for what’s next. This approach helps high-achievers continually push to do more. The downside of this approach is that we are endlessly pushing forwards and often never feel satisfied. We keep moving the goalposts whenever we achieve a goal. 

Instead, create a culture of celebration for your teams. Acknowledge the milestones and achievements, both the personal ones and the team-wide ones. You can establish rituals built into team meetings or 1–1 conversations.

 With my clients, we often start out each regular session answering the question: “What do you have to celebrate since we’ve last talked?” 

Hold the Vision and Possibility

Finally, the biggest focus on what’s right as a leader is to push for bigger vision and possibility for the company or the team as a whole. In Silicon Valley, many companies exist to provide new services or products to different groups of people. As the leader, tie back every project or initiative to a bigger mission and vision. It doesn’t have to achievable this month or quarter… it can be further out as a North Star vision for the company. Painting a picture of this new possibility serves as mission & meaning. It helps the team get through the hardships and struggles of each day. The team can get easily trapped in the minutia of project details, the posturing and opinions within each meeting, and the energy needed to convince every stakeholder that it’s the right thing to do. As a leader, be the shiny star that reminds everyone why we’re here and what we’re truly trying to achieve together. 

Bottom-Line

As a leader, focus on what’s right, not what’s wrong. Be the supportive, inspiring voice for your team. Create a culture of celebration. And most of all, help guide the team through the daily grind of hard work by providing a big vision and always reminding them of why they work here. 

Negotiation—Ask for Money and More

Photo by Artur Łuczka on Unsplash

This week I’ve had the pleasure of supporting three female leaders, two of them women of color, through the final hurdle of their interview process—the dreaded offer negotiation.

I spent many of my formative years in Asia where bartering—either at the market for cute bangles or with the police officer to let you off with a warning and a small ”tip”—was simply a fact of life. I took these skills into the corporate world, and embodying an authoritative, masculine style of leadership, have always negotiated my job offers. I’ve been lucky enough to work in technology; I fully recognize that I am privileged to have coveted skills in this labor market. It’s been rewarding to support women in their negotiations through most of my career in tech.

College-educated women in the US make 75c to the dollar for each college-educated man. It’s even lower for LatinX and African-American women. The biggest mistake women make is not asking.

I’ve written many tips around negotiation in The Art of Salary Negotiation, and this piece focuses on something different, on what matters more than money in a negotiation. 

When you’re at the final stages of talking to a company, you’re evaluating fit. You’re trying to figure out what it would be like to work there. Of course, you should negotiate on the basics of money—base salary, signing bonus, stock—and, there’s more that you can think about in your decision-making. The first step is figuring out what really matters to you in the next job, and most people’s desires fall into these three buckets of Freedom, Relationships, and Legacy. 

1. Freedom

Some of us have discovered a newfound freedom during the pandemic in the ability to work from home. We’ve learned that we can do our work without the need to go into an office location, and some people prefer working like this. It gives us physical freedom. There’s a newfound ability to choose how to spend the time won back from commuting hours. I’ve heard people share how much they enjoy more time with their pets, their children, or with different home-bound hobbies that can be tended throughout the day. 

For one of my clients, the freedom to work remotely from China for some period of time to be closer to her family was what mattered most in her negotiation. For another client, it was working for a company that offered equitable family planning for the LGBTQ community. She negotiated a commitment from a startup to replace their current less-then-inclusive benefits provider. This gave her the freedom for her and wife to plan for their future. 

When thinking about freedom, ask yourself what you really want. How can this job best support the lifestyle you want to live. Negotiating to support your freedom could look like asking for: 

• Flexibility of permanent remote work. You may need to get specific permission to work internationally.

• Flexibility of hours to build in time for childcare, elder-care, or self-care

• Flexibility to transfer to a different role or pick up different skills in the company

• Health benefits

• Vacation and leave of absences

• Learning & development budget. Many of my clients get their companies to pay for all or part of their coaching.

2. Relationships

The process of negotiation also gives you a better sense of what it would be like to work with the people in this company. The way that the company negotiates is an early indicator that this is the way that they will conduct all their business. Carefully consider all the key relationships in this prospective company so that you understand and get as much information as possible. If they’re already showing some danger signs in how they negotiate, this may not be a place that you want to work. This is the nicest that they will ever be to you during this job relationship. 

Some people leave a job because they can’t get along with their manager. For others, it’s the company culture or leadership. Think about the places where you’ve thrived and what relationships have supported you the most. As you go through the negotiation process, consider how the other person shows up. 

If you’re negotiating with an HR person or recruiter, how they show up with you as a candidate will be indicative of the level of professional support you’ll receive when working at the company. If you’re seeking to hire up a team, this recruiter will be your right hand person, so evaluate if you like their style & process.

If you’re negotiating with your manager, don’t focus on whether they say yes or no to your request, instead watch how they behave. Do they give you an explanation behind their answers? Do they consider the relationship to be the most important thing or does it seem like a purely transactional negotiation? 

Finally, as you’re going through this process, ask to speak to the company’s leaders. It could be the CEO, cofounders, or the head of the organization. You’ll get a better sense of company culture and what the leader values. And if you choose to accept the offer, that leader will be personally invested in your success. 

3. Legacy

Many people who work in Silicon Valley have a bigger sense of purpose. The possibilities of technology at scale enable us to reach millions if not billions of people. We think a lot about impact. 

What legacy would you like to leave after your next job? For some people, it’s: 

• Working at a mission-driven company where you personally believe in the mission

• Being part of an IPO

• Using this job to transition from individual contributor (IC) to manager. Your legacy may be the people you impact and not necessarily your hands-on product impact.

• Perhaps the legacy is outside of the job and what matters most is having the time to support your side-gig, whether it’s speaking, podcasting, writing a book, or running an etsy store

You can negotiate around:

• The specific product you’re working on (if you have a choice) and the scope of your role within the product

• Future headcount and scope of the team you’re coming into lead

• Timeline and support to move from IC to manager track.

• Company support, and resources for your personal brand-building that mutually beneficial to the company

Most of these negotiation asks aren’t going to written into an offer or 100% tangible. However, they set up the foundation of a conversation that will extend into your work with the company should you choose to accept the offer. 

Bottom-Line

Yes, salary negotiation for the monetary value of what you’re worth does matter. Everybody should gently negotiate against the initial offer, especially women. However, it’s equally important to think deeply about what matters most to you in this potential job. Use the themes of Freedom, Relationships, and Legacy to shape what you desire, and what to ask for in a negotiation conversation. 

How to Win at Interviewing

Photo by Jeremy Perkins on Unsplash

Do you remember the last time you interviewed for a job? Most people put this off as long as possible. It takes a lot of work to put together a resume, start looking around for opportunities, and then going through the actual process. Most people wait until it’s absolutely necessary. When the situation means that you MUST now start looking for and move into a new job. Perhaps you got passed over for that promotion or raise. Perhaps you’ve moving to a different location. Perhaps your boss has broken your trust one too many times. Perhaps you’ve just been given a negative performance review. Whatever the situation, it might be the last straw the triggers you into finally starting the long, arduous process.

But what if we’re approaching this all wrong. What if interviewing was simply a natural part of your career? Could interviewing be an exploration and data-gathering process to better understand what fulfills and energizes you at work? What if you didn’t have to be unhappy with your current job to start interviewing?

Don’t worry, even if you’re already deep in the interview process, these 4 strategies will still help.

1. Ask yourself what you really want

If you’re currently working, take a long hard look at your current job. Ask yourself what you love the most about your job, and what frustrates you about it. These are common theme areas that I’ve heard from people; they can be causes of love or frustration:

• Mission and vision of the company

• The company’s top leaders. This includes how visionary, inspirational, trustworthy, or deserving of respect they may be

• Your boss / direct manager

• Company culture & processes

• Recognition, both in the form of verbal acknowledgement / praise as well as compensation

• Tenure

• How much you’re continuing to learn and grow

• Ability to meet job expectations and achievements

• What else is there that’s unique to you?

Consider which parts of this are lacking in your current job and leading to feelings of discontent. How bad is it truly? Consider tracking your happiness or energy level day-over-day and week-over-week in your current job to see if there are long-term patterns are trends.

When you dream and yearn for a new job, what do you concretely need to see in it that will make you feel more energetic and excited to go to work? Listing out these must-haves helps you get closer to knowing what you’re looking for throughout the interview process.

2. Interview for Learning

While it’s helpful to ask yourself what you want and what conditions you’d like to be in place for a dream job, the reality is that you may not know. And it’s OK not to know. Many people jump into the interview process because they envision themselves starting a new job in 1–3 months.

Consider a reframe. Instead of interviewing to get a new job, interview for learning. Talk to as many people and companies as possible to understand what working there feels like. Use these conversations to evaluate how much you’d like to work there. After each conversation, do a retrospective and ask yourself what excites you about that person, product, role, company, or industry. Does the conversation open up new things that you’ve never thought about? Similarly, notice what red flags come up for you. Watch all the little concerns and judgements that are already coming up.

Use the interview process to better understand where you’d like to be.

3. Are they a good fit for you?

One common fear that I’ve heard around the interview process is a fear of judgement. You’re going to put yourself out there to be judged. You’re putting out your work identity through sharing your resume, work experience, case studies, and stories. And you’re going to hear a black or white answer—yes, we want you at this company or no, you’re not right for us. We have a huge fear of being judged and found wanting.

Think of interviewing as being more like dating. It’s a dance, a conversation between two parties to decide how to move forward together. Rather than solely focusing on their judgement—am I good fit for them?— instead evaluate if they’re a good fit for you.

4. Negotiation to Get What You’re Worth

As you proceed through the interview process, there comes a moment of truth when the company makes a decision on whether to give you an offer. If you’re not getting an offer, ask for feedback so that you can continue your learning process and build out your network for the future.

However, once you’ve gotten an offer from the company, know that the power balance has completely changed. The power is now in your court. The company will do everything they can to hurry up the process and get you to commit. Your job is to slow down the process, find out as much information as you can about the company, and ask for what you want through the negotiation process. The recruiter or hiring manager on the other side likely has more information, data points, and experience than you have. But you still have the power because they’ve said that they want you. Never forget this.

You can read more specific tips about the tactics in one of my previous articles, The Art of Salary Negotiation.

Bottom-Line

The best time to interview is when you already have a job and you’re still relatively happy with your job. However, most likely you’re reading this article because you’re past that point. It’s OK. Regardless of where you’re at, depressurize the interview process and have more fun with it by: 1. Asking yourself what you really want, 2. Interview for learning, 3. Ask if they’re a good fit for you, and 4. Negotiate to get what you’re worth.

Vulnerability & Transparency at Work: How Much is Too Much?

Photo by Annie Spratt on Unsplash

In tech companies and startups, we’ve heard about and practice modern leadership with radical candor, transparency, and vulnerability. We want to bring our whole selves to work and be an authentic leader. We want to do this while delivering on impact and performance to the company.

But does being transparent and vulnerable work all the time? How much is too much? What if the company isn’t set up with the right performance incentives to enable authenticity? What if the company has set up a system of cross-org competition that rewards aggressive behavior? What if the particular person, or group of people I have to interact with are truly a$$holes?

Aside from delivering impactful work with a sense of purpose, high performing employees in tech also derive fulfillment from harmonious interactions with the people around them. People want:

• Collaborative, trusting relationships with their managers, their team, and their cross-functional peers

• The ability to express their authentic opinions and have their voices heard

• Recognition and appreciation for their effort

Often vulnerability and transparency are the first tools used to grow these relationships at work, but they can be overused and put people in an exposed place.

Mistake #1: Thinking of work as your family

I’m highly competitive and have struggled with being a workaholic for much of my career. A common trap that people can fall into is closely associating your entire identity with the work you do. This is common for hard-working, driven tech workers and even more so as a cofounder of your own company.

Yet your work is not family. Working for a company is a financial transaction where you are paid to deliver high quality work that contributes to the company’s business or economic goals. Yes, it’s important to form strong relationships and friendships at work—they’re the people you spend the majority of your days with—and it’s also important to remember that your employment is conditional upon performance. Unlike with a family, there isn’t the sense of unconditional love and support.

Remembering this distinction helps to draw boundaries. There can be a sense of 100% vulnerability and transparency with family, if you’re lucky. Consider what boundaries you want to draw with your coworkers. How transparent and truly vulnerable do you want to be? You can practice range with these emotional skills.

Learning from this foundational reminder that work is not your family, there are four strategies to use to help determine exactly how far to go with vulnerability and transparency.

Strategy #1: Experiment with levels of vulnerability 

At Facebook one of our values when working with others is to “Assume good intent.” When building a new relationship, whether it’s with a boss, a team member, or a peer, assuming good intent is a great place to start. Remember that it also takes time to build a long-term trusting relationship. When you’re working with a new boss, it’s important that you can both trust each other. You can start running an experiment where you share something to spark a connection. It could be sharing:

• an inner fear you have around imposter syndrome

• a weakness or growth area that you’re activity working on

• some information about your personal life

What’s important is to choose how vulnerable you want to be. For example, let’s take imposter syndrome and how you might bring it up with your manager when starting at a new job:

• 5% vulnerable: I’m feeling a little nervous about starting at this company and not knowing how things work.

• 30% vulnerable: I’ve suffered from imposter syndrome when starting at new companies. I’ve sometimes compensated by needing to take control and show that I know my stuff, which can make me come across as an arrogant know-it-all. I’d love your support in watching for these blind spots.

• 90% vulnerable: I have a lot of confidence issues especially in these new situations. I suffer from severe anxiety and have been on antidepressants in the past. I’m also spending a lot of time with my toddlers at home, and caring for my mother-in-law and may not have the time or energy to fully hit the ground running.

These are examples of exploring the range of how vulnerable you could be in a conversation. In this experimentation phase of building a new relationship, start with 5 or 10% vulnerability and depending on the response & level of support from the other person, you can increase your % as the relationship builds.

Strategy #2: Experiment with curiosity, empathy & perspective

When you’re working on building influence with another person, perhaps a cross-functional peer or partner, the first place to start is with listening. Invoke curiosity and empathy to better understand this person, and see their perspective. This might include:

• Understanding their discipline or group (e.g. product/engineering/sales)

• Knowing their business goals and performance incentives

• Uncovering what they care about

• Learning what lights them up and gets them excited

• Asking about what keeps them up at night

• Offering any genuine support to help solve their problems

As you approach them with this level of empathy, treat it as an experiment to offer up curiosity and empathy. With their answers, notice what matters to them, and how much time and good intention they have towards you. I recently ran a workshop with design leaders at a major technology company. I made the mistake of teaching strategies for how to connect with their business leaders in a 1–1 meeting situation, when the reality is that the business leaders were too busy to make time to meet 1–1. If the person you want to influence is too busy, then it’s time to shift strategies from wanting that seat at the table to instead embodying a service mindset for how to get communications over to them in the most time-efficient manner given that they are time-pressured and stressed.

As you approach these partners with curiosity and empathy, you’ll also learn which of your partners have good intent. You can increase your transparency and vulnerability with those people.

Strategy #3: Watch out for oversharing

Relationships and trust are built on vulnerability. One of my clients works for a large technology company and has been open with his boss that he is looking to move to another team within the company. Yet there’s a double-edged sword with the level of transparency. His manager pulled him off the lead role on a big project, since he might not be around long enough on the current team to complete the project. In this particular case, he had to let his manager know about the internal exploration to get permission to move. However, he’s gathered data to see that his manager is watching out for the project success more so than his success, and now he’s learned that he doesn’t need to be as open about exploring external opportunities outside the company.

Considering holding back sensitive, personal information unless you absolutely need to share it.

Strategy #4: You can walk away 

I was recently teaching a series of workshops on working with difficult people. We worked through a series of exercises and strategies. And at the end, one individual shared a story of interactions with his boss, the company CEO. He’d tried everything — being vulnerable to build trust, trying a more direct communication style, being more assertive/aggressive, and working around the clock for many months to hit his boss’s high expectations. None of these worked. All these experiments simply gave him data that his boss wasn’t operating from the best intentions. No matter what he tried, he wasn’t getting back the same level of effort, trust, or change from his boss.

In the end, he ended up leaving the company. After months of trying to shift himself, he realized that he was at the end of his rope and at the end of the experiments. There was nothing else to do but leave. Ultimately, your work is not your family so there is the option, especially in the tech field, of interviewing and finding a different place to work. In some cases, all the transparency and vulnerability in the world isn’t going to make a difference, and you can walk away.

Bottom-Line

While I’m a huge advocate of practicing transparency and vulnerability, there are scenarios at work where holding boundaries is crucial. Don’t make the mistake of thinking that work is the same as family. Instead, 1. experiment with levels of vulnerability, 2. experiment with curiosity and empathy, 3. watch out for oversharing and, 4. know that you can always walk away.

How to Choose Between 1-1 and Group Coaching

Photo by Markus Spiske on Unsplash

So you think you want a change. There’s something you want to be different in your life. Perhaps your CEO friend got her own executive coach. Perhaps you’ve been wondering if there’s something you can do to work on some of your growth feedback. Perhaps you’d like to be a better leader and figure out the secrets that everyone else seems to know.

Most of my clients have never worked with a coach before. They’re typically in the technology and/or creative fields given my design background. People seek out coaching because they want something to be different in their lives. The first time I hired a coach was to address feedback that I’d received on my assertive communication style (backstory and more on selecting a 1–1 coach). And in the last ten years I’ve never been without a coach. I’m currently working 1–1 with a book coach and a somatic relationship coach, focusing on the two areas of my life that I’m most looking to be different.

When I worked at Facebook, I had my first experience of group coaching. Nine women had been nominated to be part of a women’s technical leadership program and we were supported by three coaches. We created visions for our career and discussed many things including our inner critics, imposter syndrome, and experiences of gaslighting. Hearing these common experiences made me feel that I wasn’t freakishly alone.

In the past two years, I’ve been in a seven-month long group program to help build my business and a coach certification group to practice coaching skills. I’ve run countless groups around topics ranging from negotiation to mental fitness to overall leadership. And I’ve also coached teams of two to three co-founders together.

1–1 coaching is somewhat straightforward to understand. Similar to a therapist or mentor relationship, there is one client to one coach. I work with my clients for a minimum of a six month period. For the high achievers I work with, it takes this longer period of time to run experiments around their behavior change. If it were easy and straightforward, they’d already have figured it out on their own.

Group coaching, on the other hand, has a large variety of sizes and formats. These are some of the common ones I’ve seen:

Synchronous small groups (2–8-ish)
These groups meet in a live zoom session (or in person) over a set period of time. It could be ongoing coaching (as with my co-founder coaching), for a short period (6–12 weeks) or a longer period (3–12 months) of time to work through a series of skills. There is an easy camaraderie to these groups from the continued relationship over time that develops between a small number of people.

Synchronous or Asynchronous midsize groups (9–40-ish)
When the group size gets larger, coaches often mix live sessions with self-paced video or audio learning. Not everybody gets the chance to speak or be coached, yet everyone learns from the teacher and the student who’s on the hot seat.

Asynchronous large groups (50+)
As the group size gets even larger, it starts to resemble more of a webinar or lecture setting with self-paced learning. The coaching continues asynchronously via online social networks such as Facebook Groups or other startups such as Mighty Networks.

If you’re curious about what type of coaching might be right for you, consider the following five aspects:

1. Coaching Focus

So you think you want a change. What do you want to be different in your work or life over the coming months and years? The 1–1 clients I work with typically look for support around:

• Developing their own unique leadership presence. This can stem from critical feedback they’ve received, or the impetus of a promotion / new job that triggers a desire to level-up.

• Career transitions. Clients may be actively interviewing or seeking support to explore a career switch, for example from marketing into product or from a large corporation into going independent.

• Feelings of stuckness and wanting a change. Coming in with this focus requires an investigative dance to explore where this stuckness comes from and to define visions for what’s next.

Clients typically seek out a group program to learn or develop more specific skills within a time-bound period. These skills could include any possible topic including negotiation, building a business, improving sales techniques, building a personal brand, create a business social media presence, developing confidence, or learning how to lead through influencing.

If there’s a specific skill that you’re interested in learning or developing, a group program may be a good match. If it’s more ambiguous and continually changing, then a 1–1 coach can co-create the focus with you over a period of time giving you much more individual attention and depth.

2. Communication Style

Coaching works best when you’ve able to be deeply vulnerable and willing to look at things from multiple perspectives. Everyone finds it easier to share in a 1–1 setting. Consider how open you’d be to sharing in a larger group setting.

For others, it may be exhausting to always have to come up with a 1–1 coaching topic and to have the focus be laser-pointed on you and your growth. It may be refreshing to listen and learn from how other people in the group are approaching their own growth.

3. Learning Style

In 1–1 coaching, most of the learning comes from your own insight, supported by the observations and challenges of the coach. In group coaching, the coach will likely have a loose learning curriculum. The learning comes from absorbing the curriculum, finding your own practice within it, and also learning from everyone else’s experience of the material.

Some of us learn best through live engagement with a 1–1 or group coach. Others prefer to go at our own pace with videos / audio / exercises to complete on our own and check in with the coach. Group coaching is likely to have a more structured curriculum with independent learning.

4. Accountability

Both forms of coaching help to create accountability for change. A 1–1 coach can design whatever unique accountability will work for you. With an group, you know that there are peers absorbing the materials and exercises at the same pace, and this group accountability encourages the actions and homework.

5. Investment

The time investment will vary depending on the nature of the 1–1 and group coaching. However, the financial investment is much greater for 1–1 coaching. 1–1 coaching is typically between a 3x to 10x greater financial cost than group coaching.

Bottom-Line

So you think you want a change… that’s wonderful. You can lead your own change with support from many sources including books, online classes, group coaching and 1–1 coaching. For the coaching options, consider all the facets of how you set yourself up for the best growth including your coaching focus, communication style, learning style, need for accountability, and willingness to invest.

Transform Fear Into Excitement

Photo by Sammie Chaffin on Unsplash

What causes you fear?

For many people in a professional setting, there’s a fear of public speaking and expressing your opinion. It can be on a large stage, perhaps TEDx in front of tens of thousands of people, fully mic-ed and camera-ready. It can be in a leadership meeting where you feel like you don’t quite belong, yet you have something to say. You see that something isn’t right in the work being presented, or the consensus of sameness in the room and you want to speak up and voice your opinion. It can be in a 1–1 conversation where you have to tell someone how you really feel about their performance, or communication style, and its impact on you, but you really hate these confrontations. 

When I feel this fear of public speaking, there are hundreds of butterflies in my stomach, flapping their wings against each other in the confined space and pushing and fighting to be released. It’s a feeling of palpitation and agitation. My heart beats faster and I feel a tightness in my chest. The temples of my forehead pulse and I can feel the shadow of a headache starting to form. I’m often flushed, with a pinkish-red tinge rising upwards on my cheeks. My jaw is tense and rigid. The words are choking in my throat. They’re on the tip of my tongue but still unable to come out. 

I’m afraid that when I draw attention to myself, everyone will look at me in anticipation and my mind will go blank with nothing to say. When I open my mouth, I think I’m going to sound like an idiot. What comes out will be dumb or obvious. Everyone already knows my point… it’s so simple they’ve already moved far beyond it in the conversation. My presentation is simply stating the obvious and wasting everyone’s time. I fear that I’m an outsider, that I don’t belong here amongst these brilliant people. 

Dr. Lisa Feldman Barrett, neuroscientist, psychologist and author has done extensive research about emotions. Her TED talk, You Aren’t at the Mercy of Your Emotions: Your Brain Creates Them, explains that: 

“…emotions are guesses. They are guesses that your brain constructs in the moment where billions of brain cells are working together, and you have more control over those guesses than you might imagine that you do.”

These emotions come from our brain making sense of all the experiences we’ve had in the world and creating patterns to make meaning from them. We can practice to influence and exert control over how we reframe these emotions. 

Think about the emotion of excitement. It might be the anticipation of a child the night before Christmas, or the feeling when you’re on a rollercoaster going up, up, up, and getting ready for that whoosh when the car rushes down over the first peak. My physical feelings of excitement are of butterflies in my stomach, my heart beating faster, and a jittery palpitation all around my body. The physical sensations of excitement are almost identical to that of fear. 

Instead of surrendering to the fear and the anxiety, we can remind ourselves that we have control over the emotion. We can call it fear, or we can reframe it to be excitement. 

The first time I was backstage in the green room, ready to give a keynote talk to tens of thousands of people, I felt ready to throw up. Outwardly I was prepared—hair and makeup, mic-on, and had my content practiced down to the second—but inside, I was terrified. An experienced speaker waiting in the room looked at me and gave me this advice that I’ve never forgotten: 

“Listen, right now imagine that you’re a dog. You see the dog park in front of you. On the other side of the gate is this wonderful space filled with other dogs. They’re all excited to see you. They want to play with you. And you know it’s the most fun you’ll ever have in the world. When that gate opens, you’re going to bounce out like a dog feeling the excitement, anticipation, and electric energy.” 

With that one simple message, she shifted my perspective. Rather than fear, the palpitations turned into a fierce lightning bolt of energy that charged me up and propelled me out of the greenroom on to the stage and into the spotlight.

I nailed the keynote talk.  

As Dr. Barrett’s research shows, our brains have influence over our emotions. With some practice, we can try reframing emotions to switch our perspectives from fear to excitement. 

So the next time you’re feeling some fear, whether it’s of giving a big talk, expressing your opinion in a leadership meeting, or giving someone difficult feedback in a 1–1 conversation, take charge of and reframe the fear. Let the physical feelings move into an energy change that builds up excitement. This switch elevates your energy. It makes you glow. It turns you magnetic. And with this small practice, you can try an experiment to play with how you move between fear and excitement. 

My Heartache as a Model Minority: an Asian Female in San Francisco

Photo by Bart LaRue on Unsplash

I am a Thai woman, of Chinese heritage and a first-generation immigrant. I’ve spent 22 years working in tech before leaving corporate to start my own business coaching and advising leaders in tech. Last year, after the murders of George Floyd and Breonna Taylor amongst many others, I started introspecting about my own role in racism, and remembering the casual racism of my youth. I wrote about my Asian privilege where in the world of Silicon Valley and tech, I’d personally experienced far more sexism than racism. This is when I first encountered the term “model minority,” often used to refer to Asian Americans, defined in Wikipedia as “a minority demographic…whose members are perceived to achieve a higher degree of socioeconomic success than the population average.” This success is often measured with education, income, and professional representation. Stanford degree, check. Tech salary, check. Representation of Asians in tech, at least in the rank and file, check. Yup, that’s me, the model minority in San Francisco.

Last year, I did my own work, reading through books on race, taking my children to the Black Lives Matter protests, and continuing my leadership coaching with women, people of color, and immigrants. And I kept working and building my own business. I focused on living through all the uncontrollability of the pandemic. I put my head down in the sand. I was the model minority. 

I ignored the media when the former president talked about the “Chinese virus” and the “kung flu.” In my liberal San Francisco bubble, I told myself: “Nobody takes those clowns seriously anyway,” ignoring the fact that half the country had voted a different choice than my own. I vaguely noted the spike of hate-fueled attacks on Asian Americans in cities throughout the U.S. and breathed a sigh of relief assuming that they would stop when President Biden took office earlier this year. But they didn’t stop.

The dam broke last week and I could no longer bury my head in the sand. I’d been avoiding the news of attacks on elderly Asian Americans in Oakland and San Francisco. Last Tuesday, a white man struggling with “sex addiction” killed eight people in three Atlanta-area massage businesses. Six of them were Asian women. I could no longer ignore the negative swirls of racism and sexism around me by diving into my work. This was too much. I didn’t want to face the hypersexualization of Asian women. It felt too close, too intimate. 

Sexism AND Racism

I thought I was the one with Asian privilege. I’d subconsciously spent much of my life trying to fit in. For most of my Stanford Computer Science classes and years working in tech, I’ve been the rare female in rooms of men. For much of my early career, I emulated the command-and-control style of leadership that I’d seen work so well for white men. I put on my armor and acted the part of what I thought a leader should be. It took me many years of introspection, vulnerability, and building up confidence to relax into my own feminine leadership style, full of big emotions, compassion, and tough love. 

Sexism was a familiar fight, racism less so. When I was in college, I’d briefly flirted with the Asian American communities but backed out when I was called a banana— yellow on the outside, white on the inside. The term was not meant as a compliment, but I proudly took it on as one. 

In tech, Asians had never been the minority. At Facebook, when we hired for underrepresented groups, we focused on women, African Americans, Latinx, Indigenous people, and people with a military background. Asians and whites were in the majority. I never felt like I experienced racism in my happy little tech bubble.

Racism in San Francisco

Today, as I raise my head out of sand, I am afraid and saddened. As a first-generation immigrant, I chose to settle in the United States after coming to college here, aiming for a different life, though largely subconsciously. I married a white American man. My children are biracial. 

As I raised my head out of sand, I scrolled through the news that I’d been ignoring. I stopped at a familiar photo. She looked like me, a person of Thai-Chinese heritage. She was holding up a framed formal photo of her father. Behind her was the statue of golden Buddha as well as a Thai monk in saffron robes. It was the traditional photo taken at a Thai Buddhist funeral. I knew because I had those same photos of myself from my father’s funeral almost two years ago. I felt a rush of grief, and I dove into the emotions to fully embrace all the details. I read the story of Vichar Ratanapakdee, an 84-year-old immigrant from Thailand, who’d been in San Francisco helping take care of his grandkids. He looked like my dad. They would have been the same age. I watched the surveillance videos of a young man crashing into Khun Vichar, knocking him down with the full impact of a raging bull. I started reading about the attacks on elderly Asians in Oakland.

I haven’t been out walking much in present day San Francisco so I’ve been inoculated from the present-day outbreak of racism against Asian Americans. I’ve lived in San Francisco for 18 years and reading these stories pulled up memories I’d been ignoring… 

…I’d grown used to walking through cities as a solo female. I knew the drill—confident bold stride, look straight ahead, and make no eye contact. My office for many years was near downtown at the corner of Mission and 6th Street on the edge of the grimy Tenderloin; only a couple of blocks away from the tourist center of Union Square. Yet it wasn’t there that I was yelled at for the color of my skin. I don’t remember where I was, I think somewhere in the Mission District near my apartment. My brain rationalizes that it wasn’t a bad incident. A man yelled a series of profanities at me calling me a “Chinese b*tch”and saying; “Go back home to China.” It was the familiar feeling of shame. I hollowly walked home and cried. I didn’t want to be different. I wanted to fit in. I wanted to be like everyone else…

… I was at a playground in Glen Canyon Park near my house. I had two biracial children. My youngest was very fair skinned — she looked like a white baby. I was on maternity leave and was pushing a stroller through the park. A white woman with her baby came up to make conversation. She spoke to me slowly, as if unsure how good my English would be. After some pleasantries, she asked me, “Do you like being a nanny? Does the family treat you well?” I froze in shock. I was overwhelmed with waves of anger at this woman’s presumptuousness. “I’m the goddamned mother. This is my baby,” I snarled, and marched away. Later that the evening. I retold the story to my husband, exaggerating my mock-outrage and making him laugh to cover up the hurt. I was good at burying the feelings. It was easier to be angry and funny. I didn’t have to deal with the mess of hormones or questioning of my identity as a mother with different skin color than my baby …

Remembering these incidents, my heart aches. I could not escape the racism in this liberal San Francisco Bay Area. 

Sexism and Racism as an Asian Female

As I read the stories of the Atlanta shooter, my heart keeps aching. I am enraged and saddened to hear familiar victim blaming. My daughters and I listen to the radio incredulously as we hear the white male gunman described as having a “bad day.” The media reports him suffering from “sexual addiction” and officials claim that the attacks were “not racially motivated.” I am sick and full of heartache with our society continuing to hypersexualize and blame Asian women while letting the perpetrators off the hook. 

Older memories come flooding back to me…

…In my mid-twenties, my white boyfriend and I had travelled around the world for seven months. I was using my Thai passport while he carried an American passport. In every country, we needed to apply for visas to our next destination. We were stuck for a long time in Turkey. We wanted to travel overland from Turkey via Syria and Jordan into Egypt. But for some reason, there were interminable delays. We made two or three trips from the beautiful places we visited in Turkey — Istanbul, Cappadocia, Konya — back to the modern capital of Ankara where all the embassies were located. After a couple of weeks of standing in line, submitting our passports, waiting several days, and returning to more waiting, we were finally admitted in to see a Syrian official. He told us that he was able to grant a visa for my boyfriend’s American passport, but that regretfully, he was unable to grant me a visa. Dumbfounded, I demanded why.

“Because you are an unmarried female with a Thai passport.”

I still didn’t understand and wouldn’t leave his office until I got an answer. The poor official looked away, blushed and stammered, “There are many Thai sex workers in our country. Clearly this is not you, however, this is the final decision that I got back from Damascus. I am sorry.”

The red flush of shame and anger on my face instantly grew to match his. We left the embassy and moved forward with our other plans. But I had been marked. That anger and shame was inside me, even though it had lain dormant for many years. 

…Another memory. On that same trip, the only time we experienced frequent harassment as an interracial couple was in Vietnam. My Thai-Chinese face could pass for Vietnamese. Many women would come up to me, knowing that I was different in my grubby backpacker clothes, hiking boots, and giant backpack. They would stroke my face and theirs and declare “Same same but different.” It was almost 30 years after the Vietnam War had ended. American soldiers had dallied with local women, and many of the soldiers had returned to the U.S. leaving behind mixed-race kids and generations of seething resentment. As my white boyfriend and I walked around, nobody directly addressed him. Instead I got spit on, hissed at, and many Vietnamese men got up in my face yelling at me in a language that wasn’t mine. I had no part in this war, and no formal relationship with either the U.S. or Vietnam. Yet I was being judged and hypersexualized …

Headwinds/Tailwinds

There’s a topic in psychology called the headwinds/tailwinds asymmetry. Most of us feel that we face more headwinds—the obstacles of life that keep pushing us back—than anyone else. In contrast, we tend to ignore or undervalue our tailwinds, the beneficial forces and resources that have helped us through our lives. This asymmetry leaves us resentful, ungrateful and unhappy. 

As a model minority, I’ve strived to fit in and coasted on the tailwinds of being Asian in Silicon Valley. And I’ve willfully ignored the headwinds of racism, hoping that I can put my head in the sand and pretend that they don’t exist, that they don’t apply to me. If I close my eyes and don’t think of them, then I can happily fit in. 

I can’t ignore the dualities of racism and sexism any more. I have no easy answer for what to do or how to process this. Unlike most of my articles, I don’t have a clear call to action with convenient links to worthy organizations. My heart aches and I’m living each day within this current pain and fear. I read common experiences of other women such as this one by the author R.O. Kwan and take hope from statements by Vice President Kamala Harris. I share conversations with my Asian sisters—we can be confused and broken-hearted together. I comfort my biracial girls and we talk about what’s happening. 

We Asian women are here, and we belong. I feel it deep inside. I have spoken out loudly through my life about feminism. I will now continue to do so about racism. 

Leading From Any Position

Photo by Jehyun Sung on Unsplash

I’ve worked with many people through the years both as a design leader in tech and now as a leadership coach. Many people continue to associate leadership with management, believing that you’re only a “real leader” when you have direct reports. This is a common limiting belief that we put on ourselves when we’re individual contributors. And on the other side of the coin, there’s been many years of my life when I’ve been a terrible manager of people. I had zero skills or training on how to lead and that negatively impacted the lives of people reporting to me.

One distinction I make between the two is that management is getting things done through others, namely your direct reports, however, leadership in its simplest form is influence. It's both influencing yourself and the people around you to achieve maximum impact.

With this definition of leadership, you truly can lead from any position and I’m sharing four stories to illustrate this truth.

Story 1: Moving from Individual Contributor to Manager

There is a prevailing belief that after you spend some years as an individual contributor (IC), then the next obvious step up the career ladder is to move into management. I’ve spoken with hundreds of people who have this desire, and it resonates with me, because this is how I felt after working for about five years and not knowing where to go next. Management seems like the next logical career progression.

At the same time, I know many design managers who after having tried managing people for years, switched back to being an individual contributor—they wanted to be more hands-on and in closer touch with the craft of design, while still maintaining their influence on the organization. There’s no judgement about what is the right or the wrong path. You may not know because you’ve only had one experience, that of being an IC. It’s perfectly fine to try management next to see if you’ll like being a manager.

The most common question I get when I speak at conferences and to a broader audience in tech is:

“I’m an individual contributor. How to I move into management?”

I ask the same two questions as a response to this inquiry:

• What are your current strengths?

• Why do you want to be a manager?

Make sure that you have an answer to these two questions and practice the answer because your managers will ask this of you. There is no right or wrong answer, simply look at answering them honestly and with self-reflection & curiosity.

The advice I give runs along these same lines:

“Don’t wait for someone to give you the manager title. Instead start leading right now. Claim your autonomy and step in to do the work of a manager. Raise your hand and volunteer for the extra tasks, sometimes they will be glamorous and more often they may be trivial grunt-work. Step up and take on the administrative responsibilities of a team lead.

Look around and see who you can help and mentor. Start having 1–1s with them. Teach what you know—share your knowledge and learnings in a lunch-and-learn presentation. See if you can try on management by working with an intern for a summer.”

Try on being a manager by doing the parts of the role that you can. Do things that map to your strengths and do things that stretch you in unfamiliar ways. Treat it like a experiment. But above all, jump in and start playing the role, and soon enough you will have the official title.

Story 2: Scaling up as a Startup Founder / CEO

I work with many startup founders, especially in early seed or pre-seed stages. At the beginning, they have to be a jack- or jill- of-all-trades, taking on many different roles and doing the work themselves. At some point in time when the startup is ready to scale and add more people, the founder realizes that they can’t do all the work. The founder needs to delegate and be the leader who creates more leaders.

Carla Harris is an accomplished financial leader, author, and singer. I first heard the story behind Carla’s Pearls, her lessons of wisdom, from Margaret Stewart Gould one of the first design VPs at Facebook. Carla shares that as you first start out in your career your currency is based on the work you do, whether it’s creating spreadsheets, project plans, design prototypes, or code. This is your performance currency. As you rise in your career, this currency starts to evolve and performance matter less. As a leader who influences others, what becomes important is relationship currency, or the strength of the bonds and trust that you build with other people, whether it’s peers, people above you in the hierarchy, or people on your team.

Startup founders need to learn this lesson when their company transitions to scale. That it’s no longer a small enough company that they can do everything by themselves or with their trusted co-founders. Everything performance currency related, whether it’s operational, sales & marketing, or product development needs to be delegated to other people. Instead, founders need to move towards relationship currency, to ensure that they’ve set up the right processes and culture for their teams to be autonomous and succeed, to build the right network of advisors, and to cultivate external partnerships.

Story 3: Quiet Leadership

I work with many leaders who don’t fit the traditional mold of a confident, extroverted leader who’s comfortable in the spotlight. Many women, people of color, and/or immigrants seek to work with me to learn the secret of leadership. They want to be more confident, louder, and make sure that their voice is heard. That feels like the path towards influencing others. Many people feel that there is only one flavor of leadership or one way that’s most commonly accepted. In some way, we all seek to emulate this traditional archetype of white, male command-and-control leadership (this is an archetype, not reality). So if you’re a quiet leader, it can feel that you’re not right, you don’t belong, and your leadership is different.

The genius of leadership is that it can and should be uniquely yours. It’s terribly difficult to put on the armor of someone else’s leadership. I should know, I’ve been doing it for years.

The path towards defining your own leadership starts with your strengths and values. And the first experiment is to live in to where you feel safe.

Many quiet leaders feel more comfortable in 1–1 meetings. There’s only one other person to relate to. It’s easier to get airtime and make sure your voice is heard. It’s easier to build a trusting relationship. It’s easier to read body language and emotions (even when on a Zoom meeting) when there’s only one other person. As a quiet leader, live into what works for you. How do you show up in a 1–1 meeting? Remember what gives you energy and confidence from this safe setting and bump it up a little to play in other settings. Play with turning up your loud leadership by 10% when you’re in a small group setting.

Another trend I’ve seen with quiet leaders is feeling more comfortable with writing and taking more time to respond rather than being put on-the-spot in-person (or on a video call) to come up with a brilliant verbal solution. Live into where you feel safe and where you can, say, “Thanks for the suggestion. I’ll give it some thoughts and share a response on email.” Instead of presenting live via video in an all-hands, instead write out a blog post or an essay outlining your vision and strategy.

Lean into your leadership strengths and build upon the areas where you feel safe. From that core of strength, you can then experiment with turning it up a little bit, perhaps just by 10%. You can lead from any position. It’s easiest to lead from your core of strength and safety.

Story 4: Leadership Starts With Me

One of my clients had been an overachiever her entire life. She did well in school, in her first jobs, and quickly got promoted to the coveted position of managing teams. She worked at name-brand companies and kept climbing the career ladder. She was always running fast, comparing herself to others, and was driven by the external success metrics of achieving another raise, more people on her team, more projects, and the next promotion. There’s nothing wrong at all with external validation. It’s useful feedback to let us know how we’re doing and how other people see us, which is what we all care about as humans. Yet there can be a danger in always indexing to external measures of success.

When COVID-19 hit last year, the entire world went on pause. Everything was different. We all had to deal with disrupted plans, sheltering-in-place, the emotional toil of sick loved ones, working from home, and taking on the second shift of being our children’s teachers, all while undergoing the stress of our first global pandemic together. Amidst this giant pause, something shifted for my client. Because the entire world went on pause, she didn’t have to play this hyper-achiever game any more. For the first time in her life, she had freedom from the constant climbing up the ladder and comparison of how she was doing against others. Everyone was on pause, so she could take the time to go inward and think about what she really wanted.

Leadership starts with me. Inside-out leadership had her stop to think about how to be the best version of herself. She dove deep into understanding her strengths, what gives her energy, what type of work she really wanted to do, and how she wanted to show up as a leader. Yes, the external achievements still mattered, but it was more about learning what would give her internal validation. The pandemic pause, the lost year of 2020, finally gave her the freedom to look within and realize that leadership starts with her.

Bottom-Line

It doesn’t matter what title you have, anyone can be a leader who influences others and lead from any position. I’ve shared four stories of leadership, whether you’re an IC, a startup founder looking to scale, a quiet leader, or someone who has the courage to start looking at embracing leadership from the inside-out. We can all lead and know that leadership starts with me.

When You're Waiting to Hear Back About a Job

Photo by Charles Deluvio on Unsplash

Waiting. Waiting. Waiting.

We might be waiting to hear back after a fantastic interview for a dream job, a pitch for funding, or that sales meeting that could save the business. We’ve all been there and many of my clients are actively waiting to hear back about something right now. 

This isn’t a great place to be, especially not for active, high-performers who are used to springing into action. It feels like everything has been done—all the prep work before the meeting, showing up and presenting yourself well, and the requisite follow-ups afterwards. This can be a place of severe judgement that spirals down into second-guessing and anxiety: 

• Why did I give such a dumb answer to that question?

• I should have practiced the presentation more.

• I didn’t really speak up and say what I meant to. I froze in the moment.

• I couldn’t stop speaking so fast. I should have listened more.

• Did I give my opinion too strongly?

In addition to the endless self-rumination, it feels like you are in a place of judgement. You’ve done all you can and now you’re waiting to hear the other person or company tell you if they want you or not. If they say yes, then magical rainbows(!) you’re headed on the path of your dreams. If they say no, then you’re a rejected failure. We can get stuck in this black or white thinking, passively suspended waiting for someone else’s judgement.

This is a normal and human place to be. It’s normal for us to feel powerless and out of control. It’s OK to be anxious and antsy, AND, it’s also important to realize that we do still have power, and it’s never a complete black or white scenario. 

I’m mainly sharing examples for what to do while waiting to hear back about an interview, however, the three point framework is also applicable for other situations when you’re waiting to hear back. 

1. Just Keep Swimming 

Dory, the little blue fish from Finding Nemo, tells her dejected friend Marlin to “Just keep swimming” in their quest to find Nemo. It can feel like supremely irritating advice, especially when voiced by a perky Disney animated fish, yet it’s helpful to remember that there are many other opportunities out there. Especially when in an interview process, it’s important to get out there and keep on interviewing. While waiting, make sure that you have a robust pipeline of companies to talk to. This one company you’re currently waiting on does not have to be the make-or-break solo option if there are other possibilities in the mix. Even if you have nothing else out on the horizon, reach out to friends or former colleagues for advice, an intro, or an informational interview. This starts to shift you from passiveness into taking control of your process. It also loosens the pressure, perhaps ever-so-slightly, that rides upon this one big decision you’re waiting on. 

If you’re currently working, you can use the time to focus back on your existing job. Are there projects that you temporarily shelved to prioritize the interview? Are there people you’d like to pay attention to or skills you’d like to keep building while you’re in this interview process? 

2. Discernment of the Process

Remember that this interview process is a two-way street. Right now you’re simply waiting to hear back from them. Instead, take the time to evaluate if you truly want to work there. Some questions to ask yourself include:

• Which people did I enjoy the most?

• What projects or impact were most interesting?

• What danger signs exist?

• What am I afraid of with working there?

Also, look back at how you performed from a sense of learning & growth. This isn’t about self-judgment and beating yourself up for not doing better. Instead, it’s recognizing that this one interview is part of a larger process of finding a new job, and there’s always ways to get better. Questions to ask yourself include: 

• What parts of my performance am I proud of?

• How might I have answered that question better?

• What other stories or case studies could I share?

3. Futurecasting

Finally, to loosen the pressure of waiting for this important black or white decision, start to explore all the shades of gray that truly exist by pushing your perspective out for a period of time. Imagine that it’s six months from now and write out multiple futures for yourself: 

Future A: You’ve been working at this job for 6 months. Capture what it feels like to go to work and interact with your boss, partners, and team on a day-to-day basis. Think about the projects you might be working on and what the rhythm of your day looks like. Imagine what it feels like to work there. What’s going to give you energy each day, and what’s going to feel overwhelming and frustrating. 

Future B: Perhaps you stay at your current job. What’s that going to feel like 6 months from now?

Future C: You’re continuing to interview and learn about many different companies. What’s this look like from a day-to-day rhythm? 

I don’t know how many or which of these futures make sense for your particular situation, however simply writing them out can help break out of the black and white thinking and open up to new possibilities. It’s a mechanism to move from passive waiting to start capturing what aspects of the future are in your control. 

Bottom-Line

The interminable waiting to hear back about an important decision, whether it’s an interview, or business outcome, is an anxiety-inducing place to be in. Move from this place of passivity and waiting for the external judgment. Instead remember to use the tools of 1. just keep swimming, 2. discernment of the process, and 3. futurecasting to imagine many possible outcomes. 

Leading Design Festival 2021 - Day 3 Live Sketch Notes

Notes from one session for Day 3 - Timothy Yeo

---

Design Leadership For Introverts (Iso-Edition)

by Timothy Yeo — Head of Design, Finder