Every day working as a leader brings new challenges that make me question whether I'm doing it right. But I've learned a few things along the way—usually the hard way—that might be helpful to share.
Coaching Scales
Coaching creates more leaders, while dictating only creates followers.
Early in my time at thoughtbot, I was given the chance to work with the Mayo Clinic. They were a powerful, detail-oriented, impactful organization. But they lacked the tech muscles—things like design thinking, agility, lean principles—that we now take for granted.
As a leader, my instinct was to prove my value by demonstrating expertise. I brought in processes like the Google Ventures Design Sprint and introduced ways to validate ideas quickly. But it didn’t take long to realize I had no place being a domain expert in that room. The Mayo team had decades of medical expertise; I had deep knowledge of tech. What I didn’t have was the authority to be both.
At the same time, I noticed my design partner wasn’t contributing. When I asked why, they admitted it was because they felt overshadowed—I was trying to play both the medical and tech expert, leaving them unsure of their role.
That was my turning point. I had to stop leading by example and start leading by coaching.
I shifted my approach: instead of positioning myself as the voice of tech, I asked my design partner to co-facilitate the sprint. Each evening we’d run a short retrospective using a simple framework:
- What’s the goal?
- What did you try that worked?
- What didn’t work?
- What will you try differently tomorrow?
By giving them the space to lead and coaching them through the process, I wasn’t just solving the problem in front of us—I was building their capability to run design sprints long after this project ended.
Clarity Drives Execution
Empowerment without clarity isn’t leadership—it’s abdication.
Setting strategy is more than understanding the product and the needs. It's setting up the team to be able to execute on the strategy by empowering through clarity. I learned this lesson while leading a project at Dropbox to rework the admin control panel. My boss had asked me to explore the area and come up with a strategy for long-term impact.
I believed I was setting this up for success. I broke the work into parts—exploration, opportunity sizing, vision development—and passed it to a senior architect I trusted to lead the charge. But here’s where I failed: I didn’t wrap the work in clarity.
I never gave the business context. I didn’t spell out why this mattered, how it connected to strategy, or what trade-offs might shape the outcome. Without that clarity, the architect did what any strong partner would: thorough exploration, solid research, and a robust vision. But the vision leaned toward expansion, not evolution, and missed critical questions about how the product might change or even deprecate.
The result? The project eventually got derailed and had to be reset.
The lesson was sharp and clear: it’s not enough to delegate work—you have to create clarity in your asks. Why are we doing this? How will it connect to the business? What are the boundaries? Without that framing, even great work can veer off course.
Now, whenever I set direction, I make sure the why is explicit. Clear context doesn’t constrain creativity—it channels it toward impact.
Define Innovation
Define what innovation means for your company, then build a culture around that definition.
Innovation is one of those words that gets thrown around a lot, but rarely defined. For a long time, I thought it meant creating flashy, groundbreaking solutions. Over time, I’ve learned that innovation isn’t just about solutions—it’s about how you define the problems worth solving, and the culture you build around addressing them.
Too often, when leaders ask for “innovation,” what they really want is something else: incremental improvements, a competitive edge, or even a whole new category. Without a shared definition, teams default to chasing shiny solutions instead of understanding the purpose behind the call for innovation.
The most successful innovation I’ve seen has come when we start by clarifying what we mean. Is this about finding new problems? About defending our position in the market? About reshaping our category? Once that’s clear, you can create the conditions—a culture of exploration, constant scanning of trends and competitors, and space for people to push boundaries.
Hire for Evolution and Purpose
Teams that last are built by hiring for evolving roles, embracing culture add, and anchoring everything in mission.
If you want to build a team that lasts, you can’t just hire for today’s gaps—you hire for the role as it will evolve. Strong teams aren’t built around temporary needs; they’re built around people who can grow with the work and with each other.
One major factor of building the right team is seniority; it plays a huge role in how you think about focus, impact, and potential for attrition.
Junior hires tend to desire to be generalists and built a breadth of skills. They grow into the work, take on optimizations, and support smaller projects. Their impact scales over time as they gain confidence and breadth. Their focus areas should be obvious, and there should be space for skill development.
Senior and staff-level hires are different. You’re not hiring them primarily to grow; you’re hiring them to own. Their role is to take on a large, complex scope that the company knows will stay true over time. As Reid Hoffman described it, senior hires often operate on a “tour of duty”—they’re brought in to tackle a mission-critical challenge for a period of years, and to leave behind stronger foundations than they found.
Another major factor is understanding the cultural needs of those you might hire. I don’t believe in “culture fit.” What lasts isn’t sameness—it’s evolution. When building a team, I ask internally "What about our culture do we want to preserve?" and "What do we want to embrace as people bring themselves into it?". And when building the team, I ask "How do you contribute to evolving a team's culture?"
That’s culture add. A team that lasts is one where the culture adapts, grows, and evolves with the people who join it.
Lastly, I try to hire for purpose. The most important ingredient for longevity is purpose. If you want longevity, people need to care deeply about the mission. Impact and culture alone won’t sustain a team — purpose will. When people believe in the mission, they push each other, they evolve the culture, and they build resilience through challenges.
Transparency builds resilience
In storms, people don’t need a flawless leader—they need an honest one.
Leadership isn’t always smooth sailing. There are pivots, reorganizations, and the natural turbulence of building products. In those moments, I’ve learned that the job isn’t to have all the answers—it’s to create clarity where you can, and to be honest about what you don’t know.
When our company went through a major reorganization, I felt as uncertain as anyone about what the future would hold. Instead of pretending otherwise, I focused on what I could provide: helping the team understand what was changing, what wasn’t, and how we’d keep our commitment to great design intact.
In difficult moments, transparency is complex. It isn’t just about sharing everything you know; it’s about communicating in a way that provides clarity, maintains psychological safety, and respects the people affected. Timing matters. When people’s jobs or roles are on the line, transparency must come with care and urgency—you owe it to your team to treat them fairly and never leave them in limbo.
The takeaway for me has been this: in times of uncertainty, transparency is generally your ally. That means preempting questions, listening for murmurs of concern, and directly addressing the fear that sits beneath so many of them: is my job at risk? You can’t always remove the uncertainty, but you can remove the silence.
It wasn’t perfect, but by leaning on clarity, honesty, and timing, the team adapted. We came out stronger and more resilient—not because I had all the answers, but because we faced the uncertainty together.
Ambition Has Seasons
Your leadership journey maps to your ambition. Understanding its timing is what makes it sustainable.
Leadership is often described as a journey, not a destination—and that’s true. But what I’ve learned is that the shape of that journey is defined by ambition.
At different moments, ambition can expand or contract. Sometimes you want to push hard, take risks, and grow into the next stage. Other times, life outside of work is complex, stability matters more, or you need space to sustain yourself. In those moments, chasing constant ambition can lead to burnout, distraction, or lost impact.
As a leader, I’ve had to recognize this in myself—and in my team. Not every season of someone’s career has to be about acceleration. Part of building sustainable leadership is identifying ambition correctly, embracing it at the right time, and respecting when it needs to pause.
Lessons Learned
Across all of these experiences, a few principles stand out:
- Coaching scales – Coaching creates more leaders, while dictating only creates followers.
- Clarity drives execution – Delegation without context isn’t empowerment; it’s drift.
- Define innovation – Innovation isn’t novelty, it’s cultural. Start by defining what it means in your company.
- Hire for evolution and purpose – Teams last when you hire for roles that grow, value culture add, and anchor in mission.
- Transparency builds resilience – In uncertainty, timing and honesty matter more than polish.
- Ambition has seasons – Not every moment requires acceleration. Sustainable leadership respects when ambition expands and when it contracts.
Resources
A few books and frameworks that shaped these lessons:
- Good Strategy, Bad Strategy — Richard Rumelt | Clear thinking on setting direction.
- Radical Candor — Kim Scott | Frameworks for feedback and care.
- The Coaching Habit — Michael Bungay Stanier | Asking better questions, not giving better answers.
- Turn the Ship Around! — L. David Marquet | Building leaders at every level.
- High Output Management — Andy Grove | Timeless lessons on scaling teams and systems.