Last year I spoke with a CFO who’d spent $18,000 on executive coaching over nine months. When I asked what changed as a result, she paused for a long time before saying, “I think I’m more self-aware?” That pause told me everything. She couldn’t point to a single concrete outcome – no promotion, no behaviour change her team noticed, no problem solved. She’d had pleasant conversations with a credentialed professional for nine months and come out the other side roughly where she started.
Contrast that with a CTO I know who hired a coach specifically to stop derailing his own board presentations. Within four months, his CEO told him unprompted that his communication had transformed. He got the additional headcount he’d been requesting for two years. Same price range, completely different result.
The difference wasn’t the coaches. It was the specificity of the problem.
The $20 Billion Question
Executive coaching has grown into a $20 billion global industry. That figure has roughly doubled since 2019, driven partly by remote work making leadership harder and partly by organisations throwing development budgets at the problem of senior leader retention. About half of what’s being delivered under the banner of “executive coaching” is genuinely transformative work. The other half is expensive active listening from someone with a certification and a nice website.
Your job is to figure out which half you’d be getting before you’ve committed $15,000.
When Coaching Works
Coaching delivers measurable results when three conditions are met simultaneously. Miss one and the engagement typically stalls.
Condition 1: You can name the specific behaviour holding you back. “I lose composure when board members challenge my numbers” is coachable. “I want to be a better leader” is not. The first gives a coach something concrete to work with – they can observe the behaviour, identify triggers, and help you build alternative responses. The second is too diffuse for coaching to get traction. You’ll end up in reflective conversations that feel productive but don’t change anything observable.
Condition 2: The problem is behavioural, not structural. If you’re burning out because your organisation expects one person to do three jobs, a coach can help you cope more effectively, but they can’t fix the root cause. That requires a conversation with your board or boss about resourcing. Coaching works when you’re the variable that needs adjusting – not when the system around you is broken.
Condition 3: You’re willing to be uncomfortable. Good coaching involves hearing things you don’t want to hear. If you’re hiring a coach to validate your existing approach, you’ll get a very expensive mirror. The coaches who produce results are the ones who’ll say, “That story you keep telling yourself about why your team doesn’t perform? It’s protecting you from seeing your role in the problem.”
Examples of coachable problems
- You consistently avoid difficult conversations and your team’s performance suffers as a result
- You micromanage because you can’t trust others to deliver to your standard
- You react defensively to feedback in ways that shut down honest communication
- You struggle to influence peers laterally and default to escalation
- You’ve been passed over for promotion twice and the feedback is about executive presence, not technical capability
Each of these is specific, observable, and within the individual’s control to change. That’s the coaching sweet spot.
When Coaching Doesn’t Work
Coaching is the wrong tool more often than the industry would like to admit.
When the problem is knowledge, not behaviour. You don’t know how to build an AI strategy. You don’t understand financial modelling well enough for your new CFO role. You can’t read a P&L with confidence. These are education gaps, not coaching gaps. You need a course, a programme, or a book – not someone asking you reflective questions about a topic you haven’t studied.
When you’re in the wrong role. Coaching can help you perform slightly better in a role that doesn’t suit you. But “slightly better in the wrong job” is still the wrong job. If you fundamentally don’t enjoy the work, don’t believe in the company’s direction, or are mismatched to the culture – no amount of coaching changes those facts. You need a career conversation, not a performance one.
When the real issue is mental health. Executive coaching is not therapy. Coaches aren’t trained to handle clinical anxiety, depression, burnout at clinical levels, or trauma responses showing up in the workplace. If you’re sleeping three hours a night, dreading Monday mornings to the point of physical symptoms, or using alcohol to manage work stress – you need a therapist, possibly a psychiatrist. A coach who takes your money in that situation is doing you a disservice.
When you can’t articulate what you want from it. If your only reason for considering coaching is that your HR department suggested it or your peers have coaches, you’ll likely waste the investment. Coaching requires active participation and clear goals. Passive engagement produces passive results.
Executive Coaching vs Executive Education
This is the fork in the road that trips up most senior leaders considering development investment.
Coaching is personalised but narrow. It works on your specific behaviours with a 1:1 practitioner over 6-12 months. You won’t get frameworks, peer learning, or credentials. You’ll get focused attention on your particular patterns and habits.
Executive education – programmes from institutions like Wharton, Berkeley, MIT, or London Business School – gives you frameworks, knowledge, credentials, and a peer network. A typical programme runs $10,000-30,000 and lasts 4-12 weeks. You come away with mental models for strategy, finance, leadership, and operations, plus a cohort of 40-60 senior leaders you can call for the rest of your career.
They solve different problems. Some people need both. But many leaders would be better served by a $15,000 programme than $15,000 worth of coaching sessions, because the programme also gives them a credential their board recognises and a network they’ll draw on for a decade. Coaching gives you personal growth. Education gives you personal growth plus external proof of development and a peer group.
If you’re not sure which you need, ask yourself: is my gap about what I know, or how I behave? Knowledge gaps point to education. Behavioural gaps point to coaching. If you’re honest, most senior leaders have both – but one is usually more urgent.
We’ve written extensively about executive education ROI and how to build the business case for executive education if you want to explore that path further.
How to Find a Good Coach
Credentials matter less than the industry wants you to believe. The ICF (International Coaching Federation) certification tells you someone completed a training programme of at least 60 hours and passed an exam. It doesn’t tell you they’re good at coaching executives. I’ve met ICF-certified coaches who’d never held a senior role themselves and struggled to understand the pressures their clients faced.
What actually predicts a good coaching relationship:
- Have they operated at senior levels themselves? A coach who’s been a VP, a MD, or a founder understands the context you’re operating in. They know what a board meeting feels like. They know the loneliness of senior leadership. This lived experience matters more than any certification.
- Do they understand your industry? They don’t need to be a specialist, but a coach working with technology leaders should understand agile development, product management, and the dynamics of engineering teams. Otherwise you’ll spend half your sessions providing context.
- Can they point to specific outcomes from past clients? Not “my clients report feeling more confident” – that’s meaningless. Specific outcomes: “My client went from being rated ‘needs development’ on executive communication to receiving a board commendation within eight months.” Numbers. Stories. Evidence.
- Will they offer a trial session? Any coach confident in their ability will do a chemistry session for free or at reduced cost. If they demand a 6-month commitment upfront without a trial, that’s a red flag.
- Do they challenge you in the first meeting? If the introductory conversation is entirely pleasant and affirming, imagine twelve months of that. Good coaches show you within the first session that they’ll push you.
The Cost Question
Most executive coaches charge $300-800 per session, with sessions running 60-90 minutes every two to three weeks. A typical engagement lasts 6-12 months, meaning 12-24 sessions total. That puts the total investment at $5,000-$20,000 for a full programme.
Many organisations cover coaching as part of leadership development budgets. Before paying out of pocket, check with your HR or L&D team. Companies often have approved coaching panels or will fund coaching as part of a development plan – particularly if you’ve received specific feedback in a performance review that coaching could address.
If you’re paying yourself, treat it like any other investment: what’s the expected return? If better executive presence leads to a promotion worth $40,000 more per year, the $15,000 coaching investment pays back in five months. If you can’t articulate a plausible return, question whether you’ve identified the problem clearly enough.
A Blunt Take on Who Benefits Most
The executives who get the most from coaching are already pretty good at their jobs and want to eliminate specific blind spots. They’re performing well enough that nobody’s questioning their competence, but they’ve identified – or been told about – one or two behaviours that cap their upward trajectory. The gap between “very good” and “exceptional” is often a small number of behavioural adjustments, and that’s exactly what coaching is designed to address.
If you’re struggling fundamentally in your role – missing targets, getting consistent negative feedback from your team, losing the confidence of your board – you probably need mentorship from someone who’s done the job successfully, not a certified coach asking you reflective questions. Or you need to honestly assess whether you’re in the right role at all.
The Mentor Alternative
A good mentor costs nothing financially and often provides more relevant advice than a coach. Someone who’s been a successful CTO, CDO, or CEO and is willing to meet monthly can give you pattern-matched advice from direct experience. “I faced exactly this situation in 2019, here’s what I did and what I’d do differently” is worth more than any amount of reflective questioning.
The catch: mentor relationships are harder to find and maintain. They depend on chemistry, mutual respect, and the mentor’s availability. You can’t buy mentorship the way you can buy coaching. But if you can find the right person – through your network, through alumni associations, through industry groups – it’s worth pursuing before or alongside coaching.
Some leaders maintain both: a coach for behavioural work and a mentor for strategic guidance. That combination, when you can assemble it, is extremely effective.
Making Your Decision
Before you spend anything, write down your answers to these four questions:
- What specific behaviour do I want to change? (If you can’t name it in one sentence, coaching isn’t the right tool yet.)
- Is this a behaviour problem or a knowledge problem? (Knowledge problems need education, not coaching.)
- Am I willing to hear uncomfortable truths and act on them? (If not, save your money.)
- What would success look like in 12 months? (If you can’t describe it concretely, your goals aren’t specific enough.)
If you’ve got clear answers to all four, coaching is likely a good investment. Find someone who’s operated at your level, do a trial session, and commit to a fixed-term engagement with defined goals. Review progress at the halfway point and be willing to end it early if it’s not working.
If your answers are vague, consider starting with an executive programme instead. Our guides to the best CTO programmes and best CEO programmes cover what’s available at the senior level. You might also find our executive presence guide useful for identifying specific behaviours worth working on.
For more context on the coaching profession, the International Coaching Federation publishes research on coaching effectiveness. And HBR’s piece on leaders as coaches offers a useful perspective on how coaching skills apply beyond the formal coaching relationship.
Ben is a full-time data leadership professional and a part-time blogger.
When he’s not writing articles for Data Driven Daily, Ben is a Head of Data Strategy at a large financial institution.
He has over 14 years’ experience in Banking and Financial Services, during which he has led large data engineering and business intelligence teams, managed cloud migration programs, and spearheaded regulatory change initiatives.