What is CTO coaching?

You've built systems that scale to millions of users. You've architected solutions that power entire businesses. But when it comes to your own leadership development, you might be wondering: do I need a coach? If you ask Bill Gates¹, everyone needs a coach. So you probably need one too.

Having worked with three different coaches over the past six years and now coaching CTOs myself, I've learned that this distinction matters more than most tech leaders realize. It's not just semantics—it's about getting the right kind of support at the right time in your leadership journey.

The Heart of Coaching: Discovery, Not Direction

Coaching isn't about someone telling you what to do. If you wanted that, you'd hire a consultant or get an advisory board. Real coaching is about self-discovery and mindset work—helping you uncover patterns, beliefs, and behaviors that either propel you forward or hold you back.

Think of it this way: a coach doesn't give you the answers because, frankly, you already have most of them. What you need is someone skilled at asking the right questions, creating space for reflection, and challenging you to examine your learned traits and how they show up in your leadership.

In my work with CTOs, I use what I call the Tools and Traits framework. We dig into both the practical tools you need as a leader and, more importantly, the traits you've developed over your career—some serving you well, others perhaps not so much. The magic happens when you start recognizing these patterns and consciously choosing how to respond rather than just reacting from old programming.

A coach also works across what I call the three Es: Energy (how you show up and manage your own sustainability), Excellence (your standards and how you drive quality), and Executive Mindset (thinking strategically rather than tactically). These aren't just nice concepts—they're the foundation of effective CTO leadership.

The goal? Helping you find your Great CTO Within. Not some idealized version of what you think a CTO should be, but the most authentic and effective version of yourself in that role.

Mentoring: Wisdom from the Trenches

Mentoring operates from a different premise entirely. A mentor has walked a similar path and can share specific guidance, advice, and insights based on their experience. They've been there, done that, and can help you avoid certain pitfalls or navigate particular challenges.

If you're dealing with a specific technical architecture decision, planning an IPO, or trying to scale your engineering organization from 50 to 200 people, a mentor who's successfully done those things can provide invaluable direction. They're sharing wisdom earned through experience, often saving you time and costly mistakes.

The relationship is typically more hierarchical—the mentor has knowledge and experience that the mentee needs. There's usually an implicit understanding that the mentor knows something the mentee doesn't, and the value comes from transferring that knowledge.

This is incredibly valuable, especially early in your CTO journey or when facing entirely new challenges. I've benefited enormously from mentors who helped me understand everything from board dynamics to acquisition processes to building engineering culture at scale.

The Blurred Lines (And Why That's Actually Good)

Here's where it gets interesting: most effective CTO coaches also do some mentoring, and good mentors often use coaching techniques. The lines blur because leadership development isn't purely about self-discovery or purely about receiving advice—it's usually a blend of both.

When I'm working with a CTO, I might spend part of our session coaching them through a limiting belief about delegation, and another part sharing specific strategies I've seen work for similar organizational challenges. The key is knowing when to put on which hat and being transparent about the shift.

Some sessions are pure coaching—deep dives into mindset, exploring patterns, challenging assumptions. Others include mentoring elements where I share specific frameworks, tools, or approaches that have worked for other CTOs I've coached or challenges I've navigated myself.

The best CTO development relationships recognize this fluidity. You're not looking for someone who rigidly stays in one mode, but rather someone who can skillfully move between coaching and mentoring based on what you need in the moment.

What Most CTOs Actually Need

Through my own coaching journey and working with dozens of CTOs, I've noticed something: most of us are over-mentored and under-coached. We're comfortable seeking advice and guidance—that feels familiar and efficient. What's harder is sitting with the discomfort of examining our own patterns, assumptions, and blind spots.

Yet that coaching work is often where the real breakthroughs happen. You can collect advice and frameworks all day, but until you understand why you consistently struggle with certain types of conversations, why you avoid specific kinds of decisions, or why your energy gets depleted in particular situations, you'll keep hitting the same walls.

The CTOs who experience the most significant growth tend to engage in both but lean heavily into the coaching side. They use mentoring for specific knowledge gaps and coaching for the deeper work of becoming the leader their organization needs.

Finding the Right CTO Coach for You

So how do you find someone who can provide the right balance for your needs? Start by getting clear on what you're actually looking for. Are you primarily seeking specific knowledge and advice, or are you ready to do the deeper work of examining and shifting your leadership patterns?

Look for someone who has both the coaching skills to facilitate your self-discovery and enough CTO experience to provide relevant mentoring when needed. You want someone who understands the unique pressures of the role—the technical complexity, the business demands, the organizational dynamics, the board relationships.

Pay attention to how they talk about their approach. Do they lead with what they'll teach you, or do they focus on what you'll discover about yourself? Both have value, but the emphasis tells you something about their primary orientation.

Ask about their own development journey. Have they done their own deep work around leadership? Do they have coaches themselves? The best coaches are often those who continue to be coached—they understand the process from both sides.

Consider the chemistry. Coaching requires vulnerability and trust. You need to feel safe being challenged and exploring uncomfortable territory. If the dynamic doesn't feel right in your initial conversations, it probably won't improve once you start working together.

The Both/And Approach

Here's what I've learned: you probably don't need to choose between coaching and mentoring. You need both, often from the same person, delivered skillfully based on what serves you best in each moment.

The question isn't whether you need a coach or a mentor—it's whether you're ready to engage in the kind of relationship that can provide both. Are you prepared to be challenged on your assumptions while also receiving practical guidance? Can you handle having your patterns questioned while also getting specific tools and frameworks?

Most importantly, are you ready to find your Great CTO Within rather than just trying to become a better version of what you think a CTO should be?

Your Next Step

If you're curious about what this kind of development relationship might look like for you, the best way to find out is through conversation. Every CTO's situation is unique, and the right approach depends on where you are in your journey, what challenges you're facing, and what kind of growth you're ready for.

That's why I offer discovery calls—not to sell you on coaching, but to explore together whether this kind of work makes sense for you right now. Sometimes the answer is yes, sometimes it's not yet, and sometimes you need something different entirely. The only way to know is to have an honest conversation about where you are and where you want to go.

Your leadership journey is unique, but you don't have to navigate it alone. Whether you need coaching, mentoring, or that powerful blend of both, the right support can help you unlock the leader you're capable of becoming.

Ready to explore what's possible? Let's talk.