How to Find a CIO Coach: What Works, What Doesn't, and What to Watch Out For
By Andy Sheats | Executive Coach to CIOs and CTOs | ctocoach.com.au
You've spent decades building technical credibility. Now you're in a role that demands something different — and nobody gave you a manual. Here's what I've learned about finding someone who can actually help.
A few years back, a CTO named Dave Schuman wrote a piece on Medium about finding a coach. He'd just stepped up to lead a well-funded, fast-growing startup and had a simple, clarifying thought: I don't want to be a good CTO. I want to be an excellent one. And the most direct path was finding someone who could help him understand what the role actually demanded.
I read it and thought: this is exactly the conversation I have with CIOs.
The details differ — the CIO role has its own texture, its own political dynamics, its own version of the "what am I actually supposed to be doing here?" question. But the underlying impulse is identical. A first-time CIO, a new CIO stepping into a bigger organisation, a VP of Engineering making the move upward: they all hit the same moment eventually. The credibility that got them here isn't automatically what makes them excellent here.
That gap is real. Here's what I've observed about how CIOs go about closing it — what works, what doesn't, and what to watch out for. If you're already curious about what CIO coaching looks like in practice, that's a good place to start.
Why CIOs Go Looking
Most don't seek out a coach because they're failing. They go looking because they're honest. They can see the distance between where they are and where they want to be.
The triggers vary. A first-time CIO appointment and the sudden exposure that comes with it — board presentations, enterprise politics, a CEO who sees IT as a cost centre. A digital transformation mandate larger than anything they've delivered before. An AI strategy brief that landed before anyone fully understood what it meant. A fractured relationship with a peer executive that's quietly derailing something important.
What these situations share is a need for thinking space — and a specific kind of thinking partner. Not HR. Not a well-meaning peer who gives you their experience instead of helping you build yours. Someone who genuinely understands the CIO context: the pressure, the translation demands, the particular loneliness of being the person who has to speak two languages simultaneously — technology and business — and be trusted in both.
The Search
Most CIOs search the same way Dave did: ask the network, follow a referral. That's not a bad starting point. But the search tends to be less rigorous than the role deserves.
You'd run a proper evaluation for a platform decision or a key hire. Do the same here. Talk to at least three coaches. Ask each for two references — and actually call them. What was the engagement like? What changed? What would you do differently?
The initial conversation is also data. Does this person already understand your world, or are you spending the first thirty minutes explaining what a CIO does? Are they asking good questions or giving you answers? Do you feel genuinely understood, or pleasantly processed?
When you're working with someone who's walked in your shoes, you get more than a neutral sounding board. You get a perspective that was hard-earned.
Mentor vs Coach — and Why It Matters
One of the most useful things Dave's search surfaced was the distinction between a mentor and a coach. It's worth understanding clearly before you start, because confusing them leads to mismatched expectations on both sides.
A CIO mentor has held the role themselves. They bring lived experience — the board dynamics, the stakeholder politics, the translation demands. They help you think by sharing their perspective. They have genuine empathy for what you're navigating because they've navigated it.
A CIO coach may or may not have held the role. They help you develop your own thinking — asking questions, surfacing assumptions, holding the mirror up. They set goals, observe your performance, give feedback on what they see.
Neither is better. They serve different purposes, and the right blend depends on where you are. A first-time CIO who needs to rapidly understand the dimensions of the role benefits enormously from mentorship — from someone who's navigated board reporting, built a digital transformation program, managed an enterprise AI strategy. An established CIO with a specific leadership blind spot benefits more from coaching — the kind that holds the mirror steady until something shifts.
The best CIO coaching relationships hold both. Dave found this in his coach: someone willing to bring experience into the room without letting it crowd out the coaching. That combination is worth looking for explicitly — and worth asking about directly in your initial conversations. You can read more about how I approach this blend in my coaching and mentoring approach.
What to Ask When You're Evaluating Coaches
Most people don't ask nearly enough. Here are the questions worth putting to every candidate:
- What's your background? Have you held a CIO or senior technology leadership role yourself? What does your lived experience of the technology executive world look like?
- How do you balance coaching and mentoring? Are you willing to bring your own experience into sessions, or do you work in one mode only?
- Will you do a Leadership MRI? A structured 360-degree leadership review — I use the Leadership Circle Profile with my clients — is one of the highest-value investments in any coaching engagement. It shows you how your leadership is actually experienced, not how you imagine it is. If your coach doesn't use a diagnostic, ask why.
- What does a typical engagement look like? Cadence, format, commitment on both sides.
- Can I speak with two references? Former clients in comparable roles. Then actually call them.
- What do you think I need? How a coach responds after one conversation tells you whether they're paying attention or selling a programme.
The Leadership MRI: Don't Skip It
Dave makes a specific point about the 360 and it deserves emphasis. A structured leadership diagnostic is one of the most valuable things a coaching engagement can include — not because it tells you things you didn't suspect, but because it names them precisely.
The Leadership Circle Profile, which I'm accredited to use, maps your leadership strengths and — crucially — the beliefs and behaviours that are holding you back. Clients consistently describe it as a game-changer. For a new CIO especially, this is invaluable. The transition from technical leader to enterprise executive often involves blind spots invisible from the inside: particularly around stakeholder management, communication style, and how you're perceived in rooms where you're not the technical authority. The diagnostic makes the invisible visible.
Ask whether your coach uses a structured diagnostic as part of their process. If not, ask what they use instead.
Pitfalls to Avoid
Hiring a generalist when you need someone who speaks the language. A skilled executive coach without technology leadership experience can do good work — but you'll spend a portion of every session providing context they should already have. For CIO-specific challenges — AI strategy, digital transformation, positioning IT as a value driver, board reporting — domain understanding matters. Not as a substitute for coaching skill, but as the floor that makes the coaching more efficient.
Shopping for validation. Experienced technology leaders are particularly susceptible to this. You've spent years being right about technical things. It can be subtly seductive to find a coach who confirms your read on situations. Watch for this impulse in yourself — and watch for coaches who seem unwilling to push back. A coach who consistently agrees with you isn't coaching you.
Going in without a clear goal. "I want to be a better leader" is not a coaching goal — it's a sentiment. The more precisely you can articulate what you need to change, the more useful the engagement becomes. You don't need a perfect brief, but you need something real.
Bringing only the polished version of your problems. The value of coaching is proportional to what you actually bring to it. The situations you're most tempted to sanitise — the relationship that's not working, the decision you're uncertain about — are exactly the ones worth bringing. That's what the space is for.
Treating it as something being done to you. If coaching is a suggestion from your CEO or board, that's fine — many excellent engagements start that way. But the mindset has to become yours. You have to want the examination. You have to be willing to look at how you operate, including the parts you'd rather not.
What the Engagement Actually Delivers
Dave's honest answer to "did she teach you how to be an excellent CTO?" is worth sitting with. Not exactly, he says. What she taught him was how to teach himself to be excellent. That's a subtler and more accurate description of what good coaching does.
It won't hand you a playbook. It will help you build your own capacity to navigate what the role demands — the stakeholder management, the board reporting, the translation between technical reality and executive communication. It will surface what you're not seeing about yourself. It will give you a thinking partner who is genuinely in your corner but not afraid to challenge you.
For CIOs dealing with the specific pressures of 2026 — AI strategy mandates, digital transformation expectations, boards oscillating between excitement and anxiety about technology — that combination of challenge and support is not a luxury. It's how you stay ahead of what the role is becoming.
A Final Thought
The CIOs who go looking for a coach are rarely the ones who are visibly struggling. They're usually the ones who are clear-eyed enough to see the gap between good and excellent — and honest enough to do something about it.
If you're a first-time CIO, a new CIO settling into a bigger brief, or a VP of Engineering eyeing the transition: this is worth exploring. The investment is real. So is the return.
Take the search seriously. Talk to your network, then speak with at least three coaches. Ask good questions. Call the references. Trust the first conversation as data — does this person already understand your world, or are you explaining it to them?
Find someone who can wear both hats. And then bring your real problems.
Find someone who can wear both hats. And then bring your real problems.
If you're a CIO wondering whether coaching is the right next step, I'm happy to have that conversation. No pitch — just a discussion.
About Andy Sheats
Andy Sheats coaches CIOs, CTOs, and senior technology leaders. He has led digital businesses for 30 years as CEO, founder, CTO, investor, and director.
As CTO at Open Universities Australia he modernised engineering culture and doubled team throughput. As CEO and co-founder of health.com.au he raised $85m, grew to $120m in revenue, and was named Growth CEO of the Year by AVCAL. At REA Group he led global strategy through mergers and acquisitions, growing shareholder value by 10x.
Andy holds an MBA from Melbourne Business School, a Graduate Diploma from AICD, and is an accredited Leadership Circle Profile practitioner. He limits his practice to six clients at any one time.
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