Questions to Ask a Leadership Coach
Questions for the introductory call with a leadership coach you are considering hiring, whether you are paying yourself or your employer is. They cover how the engagement works, what the coach is trained to do, confidentiality when a company is footing the bill, and how you would both know it was working.
The questions
Open any question for the note
What does a first engagement look like: how many sessions, how long each, over what period?
Why ask it
You are checking whether they sell a defined piece of work or an open-ended retainer. Something like six to eight sessions across three or four months is a normal shape. A vague answer about an ongoing partnership usually means the billing has no natural end point.
What does it cost, and what is included between sessions?
Why ask it
Ask specifically about calls and emails between sessions, assessment fees, and travel. The hourly rate is often the smaller half of the total, and coaches differ enormously in what they count as extra.
What is your policy on cancelling or moving a session?
Why ask it
A short-notice charge is normal and reasonable, but you want the number before it appears on an invoice. The answer also tells you how tightly booked they are, which matters if your calendar moves constantly.
What training do you have, and does anyone review your work with clients?
Why ask it
Coaching is largely unregulated, so a certificate is weak evidence on its own. Supervision, meaning a more experienced practitioner who goes through their cases with them, is worth more, because that is where a coach's blind spots get caught.
Who do you usually work with: what level, and what kind of organization?
Why ask it
Someone whose clients are all founders will misread a mid-level manager inside a matrix, and the reverse is equally true. Listen for whether they have worked with your particular constraint: no formal authority, an inherited team, a technical field, a family business.
Can you describe a client whose situation looked like mine?
Why ask it
This tests whether they can discuss a real case without giving anyone away, which is itself a skill. A story with no texture suggests very few clients, while a story with names and identifying details tells you exactly what will happen to yours.
If my employer is paying, what do they get told?
Why ask it
When a company funds coaching, someone there expects something in return. Establish now whether that is a written development plan, a verbal summary, attendance only, or nothing at all, because it determines what you can safely say in the room.
What stays between us, and what would you be obliged to pass on?
Why ask it
You want the exceptions named rather than a blanket assurance. Considered answers mention risk of harm, illegality, and whatever their contract with your employer requires. A coach who says everything is confidential with no qualification has not thought it through.
What actually happens in the first session?
Why ask it
A real first session covers history, what has already been tried, and what you want to be different, and it leaves room for you to decide against them. If the description sounds like a pitch with a close at the end, that is a preview of the relationship.
How do you find out how I come across to the people I work with?
Why ask it
Honest answers involve interviews with colleagues or a structured feedback exercise, both of which need other people's time and your consent. A coach working only from your account will spend months coaching your version of your manager rather than the real one.
How much of this is you asking questions, and how much is you telling me what you would do?
Why ask it
There is no right ratio, only a fit with what you came for. A pure questioner is frustrating if you wanted someone who has run a department; an advice dispenser is useless if the point is building your own judgment. Ask them to show you on a live problem.
What would you expect me to do between sessions, and how much time does that take?
Why ask it
Coaching that changes anything produces homework: a conversation you have been dodging, notes after each one to one, a behavior you track for a fortnight. If the sessions themselves are presented as the work, expect the effect to fade within a month of stopping.
What do you do when the real problem is my manager or how the place is organized, rather than me?
Why ask it
This is the question that separates an independent coach from a company asset. Some will help you weigh leaving; others route everything back to your own reactions. Their answer tells you whose interest they serve when yours and your employer's diverge.
How do you handle it when I keep agreeing to something and then not doing it?
Why ask it
Most clients do this, so the answer is not hypothetical. Strong answers involve stopping to ask whether the goal was ever really yours. Weaker ones offer more accountability structure on top of a goal you were never invested in.
What is outside your scope, and when would you tell someone to see a therapist instead?
Why ask it
Depression, grief, trauma, addiction, and formal workplace grievances all arrive dressed as leadership problems. A coach who cannot describe what they refer out is either undertrained or unwilling to give up the fee.
How do you decide whether coaching is right for someone, and when have you turned work down?
Why ask it
Anyone who has never declined a client will take your money regardless of fit. Look for a specific instance: someone who needed clinical help, an employer who wanted a coach to sell a decision already made, a person sent against their will.
How will we know whether this is working, and when do we check?
Why ask it
Push for a review date and a couple of measures written down at the start. Note whether the measures are things other people would notice, such as a stalled project moving or fewer resignations, rather than only your own sense of confidence.
Have you had clients where it did not work? What happened?
Why ask it
Every experienced coach has these, and the explanation is diagnostic. Putting it entirely on the client is a bad sign, and so is claiming an unbroken record across a long career.
Can I speak to one or two people you have coached?
Why ask it
Willingness matters more than whatever the reference ends up saying. An established practice can usually find someone who will talk to you. Hesitation, or written testimonials offered in place of a conversation, is worth sitting with.
How long do people usually work with you, and what tells you it is time to stop?
Why ask it
You are checking that they have an ending in mind. Good signals include clients arriving with fewer problems, or solving them before the session. Be wary of a practice where people stay on for years because nobody ever raised the question.
What would you want to know about me before agreeing to take this on?
Why ask it
Turning it around shows what they treat as relevant. Some ask only about your role and goals; others want the history, the relationships, and what has already been tried and failed. What they ask for describes their method better than any statement of philosophy.
Choosing and using a coach
Practical guidance for the conversation itself
Before the introductory call
- 1Write down the situation in three sentences, in concrete terms: the team, the decision, the relationship, the promotion you did not get. Coaches respond very differently to a real problem than to a request to work on your leadership.
- 2Decide what you would accept as evidence of progress six months out, and keep it to things another person could observe.
- 3Talk to at least two coaches. The main thing you learn from a single call is whether you like the person, which is not the same as whether they are any good.
- 4Ask both of them the same three questions so you have something to compare, rather than two pleasant but unrelated conversations.
- 5Check who holds the contract. If your employer signs it, read what it says about reporting before your first session, not after.
Signals worth noticing in the call
- Whether they ask you more questions than they answer. A coach who spends thirty minutes describing their model is showing you how the sessions will go.
- Whether they push back on anything you say. Total agreement in a first conversation is a sales technique, not rapport.
- Whether they can say what they are not good at. Everyone specializes; only some admit it.
- How they talk about previous clients. Warmth with no identifying detail is the standard to want.
- Whether they promise outcomes. Nobody can guarantee a promotion or that your team will stay, and offering to is enough on its own to end the conversation.
When your employer is paying
Find out why it was offered
Coaching gets funded for two very different reasons: as an investment in someone being groomed, or as a documented step before a performance decision. Ask your manager directly which this is. The answer changes how you should use the sessions and how candid it is wise to be.
Agree the reporting in advance
The usual arrangement is that the coach confirms attendance and progress against agreed goals, and shares nothing about the content. Get that stated in front of all three of you at the start rather than discovering the boundary halfway through.
Keep your own record
Note what you committed to and what changed. If the engagement later becomes part of a performance discussion, your own account of the work is worth having, and it also stops the sessions blurring into each other.
Once you have started
- Bring the thing you are embarrassed about rather than the tidy version. Coaches can only work with what is in the room, and the polished problem is usually not the real one.
- Book sessions close enough together that momentum holds, but leave enough gap to actually attempt something between them. Fortnightly suits most people better than weekly.
- Do one small experiment between each session rather than planning a large change. Real evidence about how people react beats another round of analysis.
- Say when a session was not useful. A coach who cannot take that feedback is not going to help you give it to anyone else.
- Set a stopping point and honor it. If you want to continue, decide again rather than drifting on because the invoice arrives every month.