How to get your coaching approved by your manager or CEO

You’ve stepped up, or you want the next job, and you’d like a coach of your own. Asking your company to pay can feel awkward. It needn’t: companies pay for coaching for the people they’re betting on, and most of the leaders I coach have theirs paid for.

The trick is to make it easy to say yes. Here’s how, in five steps.

I’ll use my own answers as the examples (I am a coach, after all), but this works for any coach.

1. Talk to a coach, early

You don’t need it all worked out first. The earlier you talk to a coach, the easier the rest gets. Coaching works because of the relationship, so meet the coach before you ask. Talk to more than one if you like: most coaches offer a free first conversation. Use it for three things:

• to find out whether you want to work with this coach: do they coach you, or tell you what to do? (If you want someone to tell you what to do, ask ChatGPT.) Do you trust them, and do they trust you?

• to get help with the next steps: what you want, the business case and how to ask

• to get a rough idea of the price, so you can make the case

Your manager can join, or have a call of their own.

For example, me: a free 20-minute Clarity Call. Is coaching the right help, is now the right time, and would we work well together? Your manager is welcome too.

Book a Clarity Call

2. Work out what you want to change

Pick one or two things that matter in your job right now: your first months in a bigger role, say, leading people who used to be your peers, or a gap your last review pointed out.

For each one, write three short lines: what happens now, what would happen instead in three months, and the benefit. For example:

Now: my team brings every decision to me, and I catch up on my own work in the evenings.

In three months: they make most decisions themselves, and I spend my time on next year’s plan.

The benefit: decisions get made in days, not weeks, and the plan is ready on time.

That last line is what your manager is paying for.

3. Make the business case

Your manager has to explain this to whoever holds the budget, and they care about a few things: revenue, costs (so profit), risk, and hiring and keeping good people. “I’ll be a better leader” isn’t enough on its own. Take the benefit from step 2, and work out what it’s worth in one of these:

• Revenue: decisions made in days, not weeks, get the product to customers sooner.

• Costs: a project that’s stuck because two leaders don’t agree costs a week of everyone’s time on it, every week it stays stuck.

• Risk: a plan that’s late, or a team that’s stretched, is a risk to the quarter.

• People: if someone good leaves, the company pays to hire and train their replacement.

Put a rough number on it, and set it against a rough price for the coaching.

4. Find out how your company decides

Ask your manager: are they open to it, is there a budget, and how does the company decide? Coaching often comes out of a training or development budget. Sometimes your manager decides. Sometimes they’ll send you to HR, or to a coaching platform or panel the company already uses.

If the coaches there aren’t right for you, go back to your manager and ask for an exception. Your business case is how you ask.

5. Make the request

Talk it through in whatever way suits you both. Bring it up in your next one-to-one, book half an hour called “Coaching for me: a proposal”, or send a short message first so they can think about it. Whichever you choose, cover four things: what would change and what it’s worth, the coach, how it works, and the ask.

If you’d like to send a message, here’s one to copy and change:

Using a different coach? Swap in their name and link.

Once they say yes in principle, take the longer session with the coach, then the proposal, and decide together. For example, me: a free Strategy Session, a real coaching session on what you want to change. You leave with a plan, even if it doesn’t involve me, and if it does, you’ll get a short proposal with the price.

If they say no

You can pay for coaching yourself. Ask the coach about it. For example, me: I have different prices for individuals and for companies. Then make the same case to yourself: where your career goes if you carry on as you are, where it goes if it moves even 5% faster, and what it’s worth to have more of you left for home.

Questions that might come up

You may not need these. If your manager or HR asks, here are short answers.

How long does it take? Most coaching runs for a few months, with a session every week or two. For example, me: usually three months.

Will I know how it’s going? Coaching is confidential, so check how each coach handles this. For example, me: I never report on you. You keep your manager up to date yourself, and with your agreement I’ll join a three-way check-in to help the conversation.

Can HR be involved? Usually, on the same terms. For example, me: HR often arranges the coaching, and what’s shared, and with whom, is agreed at the start, with you in the room. I don’t report to HR; you do, if you choose to.

How will we know it’s worked? You decide, with your manager, at the start. For example, me: we write your goals down in a few lines, and you can run a 360 at the start and the end. I don’t measure whether it’s working; you do.

Why this coach? Accreditation, like the ICF’s, is a useful signal. Experience matters more: has the coach worked with people like you? For example, me: six years at Google, two at Amazon leading a 100-person organisation, CPO of a 40-person startup, and ICF-accredited.

Can my manager talk to the coach first? Usually. For example, me: your manager or someone from HR is welcome on a Clarity Call before they decide.

Want help with this?

I coach leaders as their jobs get bigger, whether their company pays or they do.

Coaching for you, as a leader →