The first year is the hardest — and the most important
Most first-time CTOs are technically excellent. That's why they got the job. But the CTO role is fundamentally a leadership and organizational challenge, not a technical one — and nothing in an engineering career prepares you for it.
The decisions and impressions you make in your first 90 days set the tone for your entire tenure. Move too fast and you break things that were working. Move too slow and you lose credibility with the business. Getting the balance right is harder than it looks.
The #1 mistake first-time CTOs make is continuing to operate as a senior engineer rather than stepping into the executive role. It's comfortable. It feels productive. And it quietly undermines your credibility as a leader.
What we work on together
First-time CTO coaching is structured around the specific challenges of the transition — from the first week through the first year:
- Building a deliberate 90-day plan before you change anything
- Assessing the engineering organization you've inherited — people, process, and technical health
- Establishing credibility with your engineering team without reverting to being a senior IC
- Building a productive working relationship with your CEO from day one
- Identifying the two or three things that actually matter most — and ignoring the rest
- Making the mental and behavioral shift from builder to executive
- Communicating technical strategy to a non-technical board and leadership team
- Knowing when to move fast and when to slow down
Why the first-time transition is uniquely hard
Every leadership transition is challenging, but the move into a first CTO role has a particular set of traps. You're often the only person in the company who has held this role — meaning there's no internal playbook, no predecessor to learn from, and no peer to pressure-test ideas with.
Your CEO expects you to have answers. Your team is watching to see what kind of leader you'll be. Your board wants to know your technical roadmap. And you're doing all of this while also trying to understand an organization and codebase you may have just inherited.
A first-time CTO coach gives you the outside perspective and structured support to navigate all of it — not by telling you what to do, but by helping you think clearly and act deliberately in a role where the cost of reactive decisions is high.
Why work with Leigh?
Leigh Newsome has been a CTO. He has lived the first-year transition himself — the uncertainty, the isolation, the pressure to perform in a role that nobody teaches you. He knows what the hardest parts actually feel like, not just what they look like from the outside.
Over more than 10 years of CTO coaching, he has worked with dozens of first-time CTOs across industries including technology, AI, fintech, healthcare, and edtech — at companies ranging from early-stage startups through public companies.
As a Partner at Hoola Hoop and an Adjunct Professor at NYU's Master's degree program, he brings both practical coaching experience and academic rigor to the work.
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Leigh Newsome
Former CTO. Partner at Hoola Hoop. Adjunct Professor at NYU. Has coached dozens of first-time CTOs through the transition from engineer to executive.
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