How to choose a CTO coach

Pick a coach who has held a seat like yours, who agrees in writing how progress will be judged, and whose price and terms you have seen before you commit. Decide what kind of help you want first, shortlist two or three, then use a first call to test the fit. Only 4 of the 17 providers in our directory publish a price, so asking about cost is part of the process.

The process in five steps

From "I think I need a coach" to a decision

1
Name the need
A decision, a transition, or a skill gap.
2
Pick a kind of coach
Solo, community, program, hybrid, boutique or marketplace.
3
Shortlist two or three
Use the directory.
4
Hold a first call
Ask the questions below.
5
Get terms in writing
Price, length, how to stop.

Step 1 and 2: what do you need, and which kind of coach

Coaching, mentoring, advisory work and fractional (part-time) CTO work are different jobs. Know which one you are buying. The match below uses each kind's own description in our directory.

Our directory groups providers by kind and says who each kind suits best, so the match is made there rather than repeated here.

The checklist

Eight things to settle with any coach. Tick each one when you have a clear answer. Your ticks stay in this browser only, and you can print the list to take to a call.

Checklist: tick each one as a coach answers it

Coach or provider you are checking

They have held a senior technology seatAsk: Which roles have you held, and when? What is a hard decision you faced in them?
They know your stageAsk: Who have you coached at a company the size and stage of mine? What did they work on?
The conversation stays privateAsk: What do you share with my company, my CEO or anyone else, and what stays between us?
Progress is defined up frontAsk: How will we agree goals, and how will we know after a few sessions whether it is working?
You know what happens between sessionsAsk: Can I reach you between sessions for a board moment or a crisis, and what does that cost?
You know if there is a peer layerAsk: Is there a group, circle or alumni network, and is it included or extra?
Coaching, consulting and fractional work are kept apartAsk: Will you ever advise, or do the work, rather than coach? Where is the line, and does the price change?
Price and terms are in writingAsk: What is the full price, how long is the minimum commitment, and how do I stop?

0 of 8 answered

Questions to ask on a first call

Several providers in the directory offer a free first call or intro session, so this costs little. Ask the same questions of each shortlisted coach so the answers compare.

What kind of CTO or engineering leader do you usually work with, and who do you not work with?
Walk me through the first three sessions.
What have your clients changed after working with you? Can I speak to a past client?
What is your approach: do you ask questions, share what you did, or both?
How often do we meet, for how long, and how do we handle cancellations?
What would make you tell me to stop, or that I do not need coaching?

What you hear on the call, and what to do next

A clear answer on how progress will be judged
Tick it on the checklist and move on to price and terms
The answer is vague, such as "we will see"
Ask for a written goal and a review after a few sessions
The price or cancellation rules are only said out loud
Ask for them in writing before you agree to anything
You are pushed to sign on the first call
Take a day. A good fit will still be there tomorrow

Warning signs

None of these proves a coach is a poor fit alone. Two or three together are a reason to pause.

They cannot say how progress will be judged, or the answer is "we will see".
They have never held the kind of role you hold and do not say so.
The price, term or cancellation rules are only given verbally.
They push you to sign on the first call.
They promise outcomes for you with no way to check them.
The call keeps drifting into selling a separate product or service.
They will not explain what stays confidential.

Not ready for a coach yet?

Check where you stand with the free CTO assessment, or compare self-study with 1:1 coaching. If you are weighing paid programs, see the CTO programs table and CTO Coach vs CTO Academy.