How do I choose a coach or mentor for a CTO or head of engineering?
Short answer
Choose someone whose experience fits the decisions you face and with whom you can speak candidly. Discuss a real challenge, how they would work with you, and what remains confidential. Agree whether you need reflection, practical mentoring or direct organisational support, and how you will judge whether the relationship is useful.
Start with the situation you want help with
A founding CTO learning to lead managers needs different support from an experienced head of engineering navigating a difficult relationship with the CEO. Name the decisions you are avoiding, the relationships under strain or the responsibility you are growing into.
You do not need to be failing to benefit. A trusted peer can help you test your thinking before an important hiring decision, organisational change or board conversation.
What to ask before working together
- Have you held responsibility in a situation like mine, and where is your experience different?
- How do you balance questions, challenge and practical advice?
- What would you do if you disagreed with my approach?
- What is confidential, especially if my employer pays?
- How will we review whether this is helping?
Notice whether the conversation helps you think more clearly. A long list of credentials is less useful if you cannot disagree comfortably or discuss uncertainty.
Be clear about the relationship
Coaching can create space for reflection; mentoring can draw on relevant experience. The terms overlap in practice, so agree what you want rather than relying on a label. Coaching does not automatically give the coach authority over your team.
I coach founding and established CTOs and heads of engineering, alongside founder-to-founder and CEO-to-CEO support. We begin with your situation and agree where I can be useful.
Related questions
Can my company pay for coaching?
Yes, if you and the company agree. Establish the purpose, what progress will be shared with the sponsor and what stays between you and the coach before starting.
Is coaching a substitute for an interim CTO?
No. Coaching supports the leader making decisions. Interim leadership involves an agreed operational remit and accountability. If both are needed, make the responsibilities explicit.