The role of the Chief Technology Officer has never been more demanding or more consequential. CTOs today are expected to set technical vision, build and scale engineering teams, navigate AI adoption, manage board and investor relationships, and drive product strategy, often all at once. For many technology leaders, the challenge isn’t technical competence. It’s the leadership side of the job that catches them off guard.
That’s where CTO coaching comes in.
What is CTO Coaching?
CTO coaching is a structured working relationship between a technology executive and an experienced coach, designed to help the CTO grow as a leader, make better decisions, and perform more effectively in their role.
It’s very different from consulting. A consultant gives you answers. A CTO coach pushes you to develop the skills, self-awareness, and judgment to find better answers yourself.
At Hoola Hoop, our approach to CTO coaching draws on real-world operating experience. Our coaches have sat in the seat as CTOs, engineers, and product leaders at companies. That means the advice is concrete and practical, not theoretical.
Who Needs CTO Coaching?
CTO coaching is valuable at multiple career stages, but it tends to be highly impactful in a number of situations.
The first is the transition from engineer or VP of Engineering to CTO. This is one of the hardest professional shifts in tech. The skills that made you a great engineer such as technical problem-solving, individual execution are not the same skills that make a great CTO. Coaching helps accelerate that transition and avoid common pitfalls.
The second is rapid company growth. When a startup scales from 20 to 200 people, the CTO’s job changes dramatically. What worked at one stage breaks at the next. Coaching provides a sounding board for navigating those inflection points in real time.
The third is when the CTO is experiencing friction with the CEO, the product team, the board, or their own engineering organization. These dynamics are rarely purely technical. CTO coaching helps leaders understand what’s really going on and how to address it.
Areas CTO Coaching Addresses
Effective CTO coaching covers both the technical leadership dimension and the human side of the role. In practice, the most common areas we work on include:
- Technical strategy and vision. Helping CTOs articulate a clear technical roadmap that aligns with business goals, make sound architecture decisions, and communicate technical trade-offs to non-technical stakeholders.
- Building and scaling engineering teams. Hiring, developing, and retaining strong technical talent is one of the CTO’s most important responsibilities. Coaching addresses how to build a high-performance culture, develop technical managers, and structure the engineering organization for scale.
- AI adoption and innovation. Today’s CTOs are under significant pressure to integrate AI into their products and processes. Coaching helps technology leaders think through AI strategy what to build, what to buy, and how to lead their teams through the change.
- Executive presence and influence. CTOs frequently need to advocate for technical investments to a CEO, board, or investors who may not have a technical background. Coaching builds the communication skills and executive presence to do this effectively.
- Cross-functional leadership. The relationship between product and engineering is one of the most important, and most frequently strained, dynamics in a growth-stage company. CTO coaching helps leaders build stronger working relationships across the C-suite.
- Managing up and board relationships. As companies scale, CTOs increasingly interact with boards and investors. Coaching prepares technology leaders for these conversations and helps them navigate the challanges involved.
What Makes A Good CTO Coach?
Not all coaches are created equal.
First and most importantly, look for a coach with real operating experience in technology leadership. A coach who has never scaled an engineering team, managed technical debt under growth pressure, or navigated a difficult CTO-CEO dynamic will struggle to give you relevant, credible guidance. At Hoola Hoop, our CTO coaches have decades of hands-on experience in exactly these situations.
Second, look for someone who asks good questions rather than just dispensing advice. The best coaching unlocks your own thinking. A coach who just tells you what to do creates dependency, you want someone who builds your capacity to think through hard problems independently.
Third, look for a coach who will be honest with you. CTOs often don’t get candid feedback from their teams or peers. A good CTO coach will tell you what you need to hear, not just what you want to hear.
What to Expect from CTO Coaching
CTO coaching typically involves regular one-on-one sessions usually weekly or bi-weekly, focused on whatever is most pressing for the leader at that moment. Sessions are confidential, which creates the space for the kind of honest conversation that’s hard to have with a direct report, peer, or investor.
Early sessions often focus on understanding the CTO’s specific situation, challenges, and goals. At Hoola Hoop, we frequently begin with an interview-based 360 review speaking directly with the CTO’s peers, direct reports, and CEO to get an honest, multi-perspective picture of where they’re excelling and where the real development opportunities lie. This gives the coaching a grounded starting point rather than relying solely on self-assessment.
From there, coaching sessions evolve to address real-time issues as they arise such as team performance challenges, a board presentation, a team restructure, a conflict with the CPO. We also facilitate CTO leadership roundtables, bringing together technology leaders from across our client base/portfolio to share experiences, challenge each other’s thinking, and learn from peers who are navigating similar inflection points. Many CTOs find these peer sessions as valuable as the one-on-one coaching itself.
The best way to think about it: a great CTO coach is the trusted advisor you can call when you’re facing a hard decision and need someone in your corner who has seen it before.
Hoola Hoop provides executive coaching for CTOs, CPOs, and technology leaders at growth-stage companies. To learn more or start a conversation, get in touch.
This article was written by Leigh Newsome, Partner at Hoola Hoop and CTO coach with 25 years of experience scaling product and engineering teams. Leigh has worked with a wide range of startups and global enterprises, including Avid, Digidesign, WPP, and Kantar/Millward Brown. He successfully led TargetSpot, backed by Union Square Ventures, Bain Capital Ventures, and CBS, through its acquisition to Radionomy Group (Vivendi). When he’s not coaching CTOs, you’ll find him teaching digital audio to graduate students at NYU, building audio and signal processing applications, or flying fixed-wing aircraft — but never all three at once.
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