Being a CTO isn’t what it looks like from the outside. There are no capes, no magic formulas, and certainly no shortcuts. After more than two decades leading engineering teams, shipping products, and navigating the chaos of startups and scale-ups, I’ve realized that the real challenges and the real lessons aren’t technical. They’re human, strategic, and sometimes painfully simple.
Here are the lessons that stuck with me, the ones I wish someone had told me when I started.
Clarity beats speed every time
Early in my career, I thought speed meant writing more code, faster. I would push engineers to “ship now,” measure velocity in lines of code or story points, and celebrate sprint completions.
I was wrong.
The real speed comes from clarity. Knowing exactly what problem you’re solving, who it matters to, and why it matters that’s what lets a team move fast. I’ve seen brilliant engineers grind for weeks only to realize they built the wrong thing. Fewer pivots, fewer surprises, and focus make a team truly fast.
Engineers want to care, they just need context
One of the most frustrating things I’ve witnessed is engineers shrugging at product decisions. “They just don’t care,” I thought. Until I realized: they do care. They want to make an impact. But when they don’t have context, the customer pain, the market reality, the business constraints,they can’t make informed decisions.
Once I started sharing the “why,” not just the “what,” engagement skyrocketed. A well-informed team is a motivated team.
Vision is a tactical tool, not a slogan
I’ve been guilty of writing vision statements that sounded great on slides but did nothing in practice. The turning point came when I started treating vision as a tactical tool.
Vision guides decisions in real time: Should we invest in this feature? Should we rewrite this component? When the team knows the north star, debates become productive, not paralyzing.
Great engineers are problem solvers first
I’ve worked with engineers who could write elegant code in their sleep, but struggle when the problem itself is unclear. The best engineers are not just builders, they’re problem solvers.
My role as a CTO became ensuring the problem was well-understood, then stepping back. The magic happens when talent meets clarity.
Bad culture whispers, it doesn’t shout
I’ve learned to pay attention to the quiet. The subtle signs: meetings where no one speaks up, decisions made by guesswork, unspoken assumptions. These moments reveal more about culture than any HR survey ever could.
Great culture doesn’t need fanfare. Bad culture hides in silence and it spreads faster than you think.
Done is when the user wins
Early on, “done” meant shipped. A feature went live, the ticket closed, everyone celebrated. But shipping doesn’t equal solving.
Now, “done” only counts when the user’s problem is solved. I’ve had to unteach teams from thinking in terms of output and retrain them to think in terms of impact. It’s subtle, but transformative.
Teams don’t magically become product-driven
I used to blame teams for not thinking like product people. Then I realized the missing piece was me. Leadership must act like product thinking matters. Decisions, recognition, discussions, they all reinforce the mindset. Teams reflect the leadership’s priorities.
Product debt kills momentum faster than tech debt
I’ve chased the holy grail of perfect code only to watch teams get bogged down in building the wrong features. Clean architecture doesn’t save a product if no one wants it. Understanding the problem is far more important than obsessing over elegance.
Focus is a leadership decision
I once ran a team drowning in priorities. Tools, frameworks, and fancy prioritization systems didn’t help. The missing ingredient was leadership. Saying “no” to the wrong things, protecting focus, and consistently communicating what matters that’s what accelerates teams.
Requirements are not the problem
If engineers are stuck waiting for “better requirements,” don’t introduce another process. Lead differently. Engage with your team, clarify expectations, remove ambiguity, and give feedback in real time. Requirements are never the bottleneck leadership is.
The hard-earned truth
After twenty years, I’ve realized technology is the easy part. Leadership is where the real work and the real leverage lies.
Clarity, context, vision, problem-solving, culture, focus these aren’t buzzwords. They are the forces that determine whether a team thrives or stalls.
I’ve seen brilliant teams fail, and ordinary teams excel, all because of the way leadership showed up. And that’s the lesson I carry with me every day: if you want speed, impact, and results, start with the leadership that creates the conditions for them.
Why AI won’t solve these problems
With all the excitement around AI today, it’s tempting to think that tools can fix everything. Need better requirements? There’s AI. Struggling with design decisions? AI can suggest options. Want faster development? AI can generate code.
Here’s the hard truth I’ve learned: none of these tools solve the real problems. AI can assist, accelerate, and automate but it cannot provide clarity, set vision, or foster a healthy culture. It doesn’t understand your users, your market, or your team’s dynamics. It can’t decide what’s important, or make trade-offs when priorities conflict. Those are human responsibilities, and they fall squarely on leadership.
I’ve seen teams put too much faith in AI as a silver bullet, only to discover that the fundamental challenges alignment, focus, problem definition, and decision-making still exist. AI is powerful, but it’s a force multiplier, not a replacement. Without strong leadership, even the most advanced AI cannot prevent teams from building the wrong thing beautifully, or from stagnating in a quiet, passive culture.
Ultimately, AI is a tool. Leadership is the strategy. And experience with decades of trial, error, and hard-won insight is what turns potential into real results.