10 hard questions to ask before you invest in executive coaching
Most executive coaching fails not because of the coach — but because the buyer never set it up to work. Ten brutal, practical questions that separate programmes that transform leaders from ones that just burn cash.
Most executive coaching fails. Not because the coach is bad. Because the buyer never set it up to work.
10 hard questions to ask before you invest in executive coaching
Key takeaways
- Never start a coaching programme unless the leader is genuinely motivated and the direct boss is actively involved — without both conditions in place, you are wasting money and damaging trust.
- The only valid measure of coaching success is whether the people around the leader notice real, lasting behavioural change — comfort in sessions is not success.
- At C-suite level, experience, cultural fit, and genuine trust matter far more than formal certifications — stop choosing coaches by their credentials.
(1) Is your leader actually motivated?
Not "I think so." Not "they'll come around." Do they genuinely want to change?
If you have any doubt — stop. Do not sign the contract. An unwilling coachee is the single fastest way to destroy a coaching budget and damage trust at the same time.
Three months in, you will have your answer. Is she protecting the session time? Is he preparing between sessions? Are people around them noticing anything different? Behaviour does not lie.
(2) Where is the direct boss?
The boss who says "I'll leave it to the coach" is abdicating. Leadership responsibility cannot be outsourced.
Start with a three-way session. Have the boss give their honest briefing. Repeat it at the midpoint. Repeat it at the end. If the boss is too busy for three conversations over 12 months, this programme will fail. Guarantee it.
(3) Do you know what type of coaching you actually need?
Onboarding someone in their first 100 days is a completely different job than preparing a high-potential for a bigger role — or coaching a long-tenured executive on legacy and impact. Get specific before you get started. Vague objectives produce vague results.
(4) Would this leader pass your keeper test?
Before you sign anything, answer this honestly: if this person told you tomorrow they had another offer, would you fight to keep them?
If your gut says "actually, I'd be somewhat relieved" — close the file. Coaching is for people worth the investment. It is not a substitute for the difficult conversation you have been avoiding.
(5) Should your leader choose their own coach?
Often — no. Left to their own devices, leaders choose the coach they like, not the coach they need. And the best sales pitch does not belong to the best coach.
In our first session with every potential coachee, we ask: "I will tell you what you need to hear, not what you want to hear. Can you handle that?" There is only one acceptable answer. It gives us the mandate to make real progress — and sometimes real discomfort.
Decide case by case whether to offer a choice. But know the risks either way.
(6) How long will it actually take?
Six months minimum. Twelve to eighteen months is optimal. Anyone promising meaningful behavioural change faster than that is selling you something.
Creating new habits takes time. Automating them takes longer. Some of our most impactful coaching relationships have run for a decade or more — because the best leaders never stop developing.
(7) How will you measure success?
Not by whether the coach and coachee feel good about each session. That is not success. That is comfort.
The only measure that matters: do the people around this leader notice a real, positive, lasting change in behaviour? If the answer is no — the programme did not work, regardless of what anyone says.
(8) What makes a coach credible at this level?
At C-suite level, formal certifications matter far less than most HR directors assume. What matters: relevant experience, the right frame of reference, and a genuine bond of trust.
Your most senior leaders do not want a classroom facilitator. They want someone who has been where they are — and is willing to tell them the truth.
(9) Does the coach know your world?
A coach who understands your industry, your culture, and your key players will move faster and go deeper. Invest in building a long-term relationship with a firm or a small pool of coaches. Familiarity is not a risk. It is an accelerant.
(10) Can a business school replace individual coaching?
Sometimes. But the more senior the leader, the less they want to sit in a classroom with 30 other executives. What they value is personal, one-on-one, targeted learning — when they need it, on their terms.
Business school is a supplement. Individual coaching is the main course.
We have been in global executive and business coaching for 30 years. We live it every day. Ask better questions before you start — and you will get far better results.
Most executive coaching fails not because of the coach — but because no one asked the hard questions before signing the contract.
Over to you.