Reflection is a Crucial Leadership Skill
Growth doesn’t happen on Autopilot
A belated welcome to 2026! I hope that you got some down time, and took an opportunity in the liminal space during the holidays to reflect on how things are working for you and areas to work on in this new year. I took advantage of the flight back from Japan to do my personal planning and goal setting for the first half of the year while my family slept.
I was inspired to share this from that experience and also because I realized that I’m coming up on my 10th anniversary in the CTO role. I realized that if I’m not deliberate about my decisions, it’s gotten very easy to “pattern match” a situation in my company to similar (but not exactly the same) situations I’ve dealt with in the past. When I do that, it usually (but not always) works out, but even when it does, the process of how and why I came to that decision is opaque to my team (and sometimes even to myself).
Reflection is how I keep myself grounded in my day-to-day, make better decisions, and communicate them more effectively to my team.
Reflection is a Crucial Leadership Skill
At the start of every year, leaders are encouraged to look back and look forward. Most of us nod along, then immediately get pulled back into execution. Meetings stack up, priorities collide, and the reflection part quietly disappears.
That’s a mistake.
Reflection isn’t something you do when you have spare time. It’s what keeps you effective once the job starts to feel familiar.
I’ve been a CTO for about a decade now. One of the things experience gives you is comfort. You’ve seen the patterns before. You know how most situations play out. You can shortcut decisions that used to require real thought. That’s valuable. It’s also dangerous.
Comfort is where growth quietly stalls.
Why reflection gets harder as you get more senior
Early in your career, learning is unavoidable. Everything is new. You make mistakes constantly, and the feedback is often immediate. Over time, that changes. As you move into senior roles, especially at the executive level, feedback drops off sharply.
The expectation is that you already know how to do the job. That is why the company hired you.
You don’t really have peers at your company who do the same work you do. Your manager doesn’t focus on developing you. They don’t have the time. And if things are mostly working, no one is pushing you to examine how you’re operating.
That’s exactly when reflection matters most.
Without it, success turns into habit. Habits turn into autopilot. And autopilot is where you stop asking why.
The more senior you are, the more your blind spots matter. If you don’t have a structured way to surface them, you don’t even know what you’re missing.
Reflection is what makes you less busy
When I talk about my reflection process, the most common response I hear is, “That sounds useful, but I’m too busy.”
I get it. Blocking half a day, or even a full day, feels indulgent when your calendar is already full.
But reflection isn’t what makes you busy. It’s what makes you effective.
Stephen Covey called this “sharpening the saw.” Spending time improving how you work reduces the total effort required to do the work. When you skip reflection, you don’t save time. You push the cost downstream, usually onto your team.
If you’re helping your team plan their year, but you’ve never planned your own, that imbalance shows up in your decisions.
Growth doesn’t happen by accident
Earlier in my career, I didn’t reflect much at all. I was moving fast, learning on the job, and things seemed to be working. So I kept going.
Eventually, things stopped working as effortlessly as they used to.
The approaches that got me to one level weren’t enough to get me past it. I had leveled out without realizing it, and I didn’t have the tools to understand why. That’s when I started reading more deliberately, working with a coach, and learning from peers and mentors who already treated reflection as part of the job.
That shift changed how I approach new challenges. I stopped seeing them as interruptions and started treating them as learning opportunities. When things don’t work now, I don’t just move on. I try to understand what happened and what to adjust next time. When things are working well, I take a bit of time to understand why they are working and how I can apply those lessons in other areas.
That habit is what has kept me from topping out again.
Structure matters more than the exact process
I’m not naturally a journaler. I tried. It didn’t stick. What worked for me was creating a structured reflection process that removed friction.
Today, mine has a few layers:
Twice a year, I step back for a personal strategy offsite. I assess the last six months and set priorities for the next six. That takes about a day.
From that, I set quarterly goals. Small, focused things I want to work on in the next quarter.
Each month, I do a short review to revisit those goals and see what’s tracking and what isn’t.
Every week, usually on Sunday night, I look back at the prior week and ahead to the next one. What worked? What didn’t? What do I want to do differently?
You don’t need all of this. You might only do a monthly or weekly reflection. The specifics matter far less than having some regular practice.
The point isn’t rigidity. It’s structured flexibility.
Like good software development, this isn’t a waterfall plan. It’s a set of goals that’s tested against reality week by week and adjusted as conditions change.
The practice matters more than the plan
Over time, I’ve learned that the practice itself is more important than any individual insight. Some weeks, nothing profound comes out of reflection. That’s fine. The value is in consistently creating space to think.
When I stop doing it, I notice quickly. Decisions get sloppier. My calendar fills with other people’s priorities. I become busy without being intentional.
When I return to the practice, it gets easier again.
And your team notices. They can tell when you’re reflective and when you’re not. When you’re willing to say, “This isn’t working, let’s change it,” you’re modeling the behavior you want from them. You’re showing that thinking matters more than mindlessly following a plan.
You can’t expect deliberateness from your team if you don’t practice it yourself.
Start small, but start deliberately
If you’ve never done this before, don’t copy my process. I didn’t start here either.
Block a few hours. Use a simple reflection exercise. Borrow someone else’s structure. Ask yourself:
What’s working well?
What isn’t?
What should I try doing differently?
That’s enough to begin.
If you already have a process, reflect on it. Is it still helping? Or are you just going through the motions? If it isn’t working anymore, change it.
The goal isn’t perfection. It’s deliberateness.
Busy on purpose beats busy by default.
Final thought
You can’t lead others to grow if you’ve stopped growing yourself.
Reflection isn’t optional. It’s what keeps you sharp, adaptive, and intentional—especially once the job starts to feel easy.
The best leaders aren’t the ones who have it all figured out. They’re the ones who keep asking better questions.
To hear an extended discussion of this topic, please listen to my most recent podcast episode: Success Makes You Dangerous: Why Comfortable Leaders Stop Growing.
ConFoo!
I’ll be speaking once again at ConFoo in Montreal at the end of February. I’m presenting two talks: “The Director to CTO path: following it, or mentoring it” and “Rising After the Fall: Engineering Your Career Comeback.” If you’ll be there, let me know!
Thanks again for reading! If you find it helpful, please share it with your friends.
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