Boss approving a coaching invoice at desk

How to get your boss to pay for coaching

5 September 2021             
You might think you have no chance, getting your boss to pay for coaching. ummmm - think again. maggie did it....
Sinking into huge, sky-blue deckchairs overlooking Silent Pool, they swapped news. G&Ts arrived in beautiful blue & gold copas. Both women paused to admire their drinks before clinking glasses and taking a sip. Lockdown seemed to have agreed with Maggie – she was calm and in control, and had made time to have her hair done. Anne felt a little self-conscious and hoped Maggie couldn’t tell she’d cut her fringe herself.  

“Maggie, you look great!”

“Thank you! I feel great,” smiled Maggie.

“Good for you,” replied Anne. “I wish I felt great.”

“Oh! Is something wrong?”

“No, not really. It’s just work.”

“What’s happened?”

“Nothing’s happened. In fact, that's the problem. There’s the opportunity for partnership track. I should go for it, I know I should. I probably won’t get it, but it would be good experience.”

“Why wouldn’t you get it?”

“Because I’m not good at winning clients and generating fees.”

“Don’t you want to be a partner?” asked Maggie.

“Hadn’t really thought about it lately. All I know is I’m not happy at work, and I’m not sure why. Sorry – I’m all over the place, aren’t I?”

Maggie laughed. “Just a bit. It sounds like you need some clarity. To work out what direction you’re heading in. And if it’s even the direction you want! Look, have you thought about coaching?”

“Yes, but I can’t really afford it, and I don’t know if it would work.”

“Coaching’s great! And it benefits work so the firm will likely pay. Honestly, I speak from experience.”

That explained the positive change in Maggie!
Career coaching improves overall performance

“How did you get your firm to fund your coaching?” asked Anne.

“You know I changed teams?,” said Maggie. “Once I’d found my feet, Emily suggested coaching for me.”

“Your new boss?”

“Yes. She’s great. She thought I was punching below my weight so suggested I worked with a career coach. She thought it would make me more confident, and it did. I’ve increased my billings and I’ve taken over risk management for the team – it’s more responsibility and I’m loving it.”

“And work paid?”


“So was the coaching just about boosting your confidence at work, then?

“Actually, no.”
Deal with issues in your life to enhance the way you work

Anne looked confused – why would an employer pay for whole-life coaching?

“No, we didn’t just talk about work,” explained Maggie. “Work paid because Emily thought I’d work better if I were more confident. But once I started talking to the career coach, all sorts of things came to the surface. And once they were out, the coach asked me lots of questions. She helped me unpick them. Do you know, I might actually have got over Irvine now?”

Anne reached over and touched Maggie’s arm. “I know it was a tough time for you.” 

“I know. And I do miss him, but I cope. And if the coach hadn’t made me realise that losing him was making me bottle things up, I wouldn’t have increased my confidence with clients.”

“So, because you’ve dealt with your break-up, you’re better at work relationships now…?”

“Yes. Which sounds weird, but it's turned out to be true.”

“Actually, that makes sense.” Anne was starting to see what Maggie was driving at. “So, the coach helps you address your whole life, as well as work…”

“…but because the benefits show themselves at work, Emily was happy to fund it.” 
Coaching is confidential

“How did you feel about talking to your coach about Irvine?” asked Anne.

“It was OK, actually. I couldn’t have told Emily, but the coach…she was absolutely on my side, if you see what I mean, and that made it easier to talk. And everything’s confidential.”

“That’s good to know. So if everything’s confidential, I could talk to the coach about partnership track, and that I'm not sure I want to push for it, and no one would have to know?”

“Exactly. You can talk about anything, and it won’t leave the room.” 
A good boss supports your development & your career

“Look at you…” began Anne, “…you’re a new woman! Isn’t Emily afraid you’ll go after her job?”

“She’s OK with it. We talked about it, actually. She said that she could see I had a lot to give to the firm. That she wanted to get the best out of me, and for me to be happy at work too. Now I feel more confident in myself, I can see that unhappy workers are…well…just a bit of a drain on the business.”

“What if you leave and take all your talent and confidence elsewhere?”

“Doesn’t seem to be a problem for Emily. It’s a good advert for talent pipelining, which means our business can attract good applicants in the future. In fact, I’ve seen a vacancy somewhere else and I’m thinking of going for it. Emily’s being really supportive – she thinks I’d be good at it, and she’d love to have a contact over there. She’s building her network, which is good news for everyone involved.” 

“Do you think my boss would support me like that?”

“It’s Robert, isn’t it? I’m sure he would.”

“He’s never suggested it. I don’t think he’s like Emily.”
Coaching will help you meet your business targets

“Why don’t you make a business case for some coaching?” suggested Maggie.

“You mean that if I showed him that coaching would enable us to meet our team targets for the year, he’d be more likely to fund it?”

“Yes.” Maggie nodded enthusiastically.

“That might resonate with him,” said Anne, thoughtfully. “He’s really target-driven. We’re supposed to be increasing our client base, but the team isn’t really pulling together. With some coaching, and more self-belief, I could certainly do my part better.”

“And you could pass on what you learn to others too,” added Maggie.

“…which would help us all work better, win more clients, and achieve our billing targets! And if I put that to Robert, he’ll look in the CPD budget and might agree to pay. I see what you mean.”

“I think the firm would more than get their money back. If the coaching costs, say, £2,000, what percentage would your billings need to go up by to cover it? 4%? That’s do-able, yes? If you're more confident.”
Coaching is different from training

“Hang on. He won’t just put me on an another assertiveness course, will he?” asked Anne.

“We did that one together, didn’t we?” said Maggie. “I remember it was quite good, but it only takes you so far. I realised that once I’d had coaching. Knowing how to tell someone what you want is useful, but it’s not enough unless you have strong self-belief. And if the course had worked, you’d already have higher billings and be a shoo-in for partnership track. So if Robert starts going on about assertiveness courses, tell him that!”

“Good idea. Actually, he has said that he’d like me to be more confident – it's come up in my last three appraisals.”

“Perfect! That’s your way in!”
Coaching has a ripple effect

“If you’re more confident, you’ll pull the whole team up with you,” continued Maggie.

“Is that how your new team is?”

“Yes, now I come to think of it. There’s a really positive vibe. We’re all energetic, can-do people. We can ask each other anything, and because we’re all in good places emotionally, no one ever feels criticised. I really feel like we’re achieving things together – I love it.”

“Have you all been for coaching?” asked Anne.

“Let’s see. I have. I think Emily has. The others haven’t. But Emily inspires us all – she always seems to know the right question to ask. She’s a role model.”

“I bet you inspire them too,” suggested Anne.

“Thank you! You know, I think I might!”

Anne’s eyebrows went up into her fringe.

“Wow, Maggie, you can even take a compliment now!”

“Yes. I can, can’t I?” They both laughed.
Coaching addresses specific areas of self-doubt

“I’m really happy for you,” said Anne. “When people say nice things to me, I think they don't mean it and that they feel sorry for me.”

“That’s not true,” said Maggie, kindly. “But you should tell Robert you feel like that. I’m sure he wouldn’t want you to doubt yourself so much. Quite apart from whether he has a kind heart, he knows that if you feel bad about yourself, you won’t be at your best with clients and colleagues.”
Next steps

Anne thought for a moment, then declared, “I’m going to do this.”

“I’m going to ask Robert to fund coaching for me.” She got out a notebook and started writing things down. “Just go through it again – what do I tell him?”

Maggie counted off the points on her fingers:

1. Start by referring to what your boss identified in your last appraisals. He said it himself - lack of confidence is holding you back.

2. Acknowledge that training was a good start but it only got you so far. Whereas you learnt techniques, you don’t yet have the self-belief to pull them off. One-to-one coaching will enable you to change your mindset.

3. Be specific about what you want the coaching on. If I was you, I’d say that you’re aware you have a lot of negative self-talk, and this stops you speaking confidently to potential clients about how you can help them. It’s this which is stopping you winning more fees.

4. Make the business case, and tie the coaching into specific business benefits. You could say, for example, if the coaching were to enable you to improve your billings by just 4%, which is quite modest, don’t you think?, we’d recoup the cost of investment. Anything above that, and you’ll be positively contributing to the firm’s bottom line.

5. Oh, and tell a good story. Stories can be very persuasive. Mention me and what the coaching did for me. I can be more specific.

Did you get all that?”

“Yes,” said Anne, putting the lid back on her pen. “Thank you, Maggie.”

Maggie raised her glass. “To coaching!”

“To coaching,” Anne agreed.

If you’re ready to get your boss to pay for career coaching and need a bit more help to make your business case, book your FREE twenty-minute consultation with me, Jo Maughan, now by clicking the button below. 
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About Jo Maughan
Jo Maughan is the founder of YourThinkingPartner. Her first career was as a FTSE 100 Tax Director. After suffering a fall and a significant brain injury, she overcame her fears to follow her calling as a coach and artist. She is now living the life she was meant to live, inspiring successful mid-life professionals at or near the top of their careers to rethink their careers & lives for more balance, fulfillment, purpose & joy. She and her clients use her 7 step system 'Rethink Your Life'. Jo is also a sought after speaker and is currently writing her first book.
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