CTO Coaching

What is CTO coaching?

CTO coaching is a one-on-one engagement between an engineering leader and an experienced coach who understands the specific pressures of the role. It's not mentorship, not consulting, and not therapy — it's a structured process for developing yourself as a leader and solving the organizational challenges that define the CTO role.

The hardest part of being a CTO isn't technical. Most CTOs are technically excellent. What holds them back is the leadership side of the job — managing a growing organization, communicating with the board, building a culture that retains great engineers, and making strategic decisions under uncertainty. That's what CTO coaching addresses.

What do we work on?

Every engagement is different, but the work almost always touches one or more of these areas:

• Scaling from a hands-on engineer to a true executive leader
• Building and managing high-performing engineering teams
• Developing a coherent technology and AI strategy
• Reducing technical debt without halting product development
• Creating engineering processes that build trust with the business
• Executive presence, board communication, and managing up
• Navigating mergers, acquisitions, and organizational restructures
• First-time CTO onboarding and 90-day planning

Why work with a coach who has been a CTO?

Most executive coaches bring frameworks. Leigh Newsome brings frameworks and firsthand experience — he has been an engineer, and he has been a CTO. He has lived the full arc from writing code to running large engineering organizations.

That means when you're talking through a difficult architectural decision, a team conflict, or an AI strategy conversation with your board, you're not explaining context to someone who has never been in that seat. You're thinking it through with someone who has.

Leigh has worked with engineering leaders across a wide range of industries — from Fortune 500 companies and growth-stage startups to venture capital and private equity-backed firms. His deepest experience in engineering leadership spans technology (software and hardware), AI, fintech, healthcare, edtech, and consumer products. He is also a Partner at Hoola Hoop, a full-service executive coaching firm, and an Adjunct Professor at NYU, teaching in the Master's degree program.

Who is CTO coaching for?

CTO coaching is most valuable for:

• First-time CTOs — navigating the transition from senior engineer or VP to full executive
• CTOs at scale — reinventing their operating model as the organization grows from 5 to 50+ engineers
• VPs of Engineering — maximizing impact in the current role or building toward the CTO seat
• Technical founders — evolving from builder to engineering executive without losing what made them great
• Engineering leaders in M&A — navigating the technical and people decisions that determine whether integrations succeed

What does a coaching engagement look like?

Engagements typically involve regular one-on-one sessions — weekly or bi-weekly — focused entirely on your current challenges and priorities. Sessions are confidential, candid, and structured around getting real things done.

The first step is always a no-pressure discovery call to understand where you are, where you want to be, and whether coaching is the right lever. No commitment required.

Book a Discovery Call →