Why Coaching Belongs at the Heart of Customer Success

I spent twelve years leading Customer Success in a US multinational, most recently as VP of Customer Success and Site Leader for the Irish business. Before that, I qualified as a coach back in 2010 and spent six years in executive coaching and training. So I’ve seen this from both sides — the operator carrying the number, and the coach sitting across from the person carrying it.

Process gets you started, but coaching is what makes Customer Success actually work.

The trap we fall into

Customer Success loves a system. Health scores, playbooks, QBR templates, renewal checklists, adoption dashboards. And all of that has its place — I’ve built plenty of it myself.

But somewhere along the way it’s easy to start believing the system is the job. That if you just tighten the process, tune the dashboard and add another stage to the playbook, the results will follow. They won’t. Not on their own.

Because a Customer Success team isn’t a machine. It’s a group of people having hundreds of human conversations a week — some easy, plenty of them not. A renewal that’s wobbling. A customer who feels ignored. An exec who’s gone quiet. No playbook covers all of that, and no dashboard has the conversation for you.

What gets you through those moments is judgement. And judgement isn’t something you can install. It has to be developed. That’s where coaching comes in.

Coaching isn’t having the answers

This is the part people get wrong, and I got wrong myself early on. When you’ve been in the trenches, the instinct is to jump in with the answer. Someone brings you a struggling account and you tell them exactly what to do, because you’ve seen it fifty times before. It feels helpful. It feels efficient.

But every time you hand someone the answer, you take a small learning opportunity away from them. You solve today’s problem and leave tomorrow’s untouched.

Coaching is the harder, slower, better path. It’s asking the right question instead of giving the ready answer. It’s “what have you tried?” and “what do you think is really going on here?” and “what would you do if I wasn’t in the room?” It’s listening properly — not waiting for your turn to talk, but actually listening.

Do that consistently and something shifts. Your people stop bringing you problems to solve and start bringing you decisions they’ve already thought through. That’s the goal. That’s a team that scales, because it doesn’t need you in every conversation.

Where I really learned this

I could talk about coaching in the abstract, but the truth is I learned most of it under pressure. A few years ago the company I was in went through a serious cybersecurity crisis — a genuinely tough, very public period. Overnight, my Customer Success team went from managing adoption to holding thousands of anxious customers through something none of us had a script for.

You can’t playbook your way through a moment like that. There isn’t a health score for “the whole industry is watching.” What carried the team wasn’t a process — it was people who trusted each other, who could think on their feet, and who’d been given the confidence to make good calls without waiting for permission.

That confidence doesn’t appear on the day you need it. It’s built quietly, over months and years, in ordinary one-to-ones and honest conversations. It’s built by coaching. When the hard day comes, you find out whether you did that work or not. We did, and it held. That experience did more to convince me of the value of coaching than any course ever could.

Coaching your team is coaching your customers

There’s a lovely knock-on effect to all of this, and it’s the bit I’d want any CS leader to hear.

How you treat your team is how your team treats your customers.

If your people feel rushed, second-guessed and managed by dashboard, that energy travels straight down the line to the customer. If they feel supported, trusted and genuinely developed, that travels too. Customers can feel the difference in a five-minute call, even if they couldn’t name what it is.

So coaching isn’t a soft, nice-to-have thing you get to once the “real” work is done. It is the real work. Coach your people well and your customers feel it in every interaction — the calm, the curiosity, the sense that someone actually has them in hand. That’s retention. That’s advocacy. That’s the number, arrived at the honest way.

Where to start

If you’re a CS leader wondering how to bring more of this in, I’d keep it simple. Start with your one-to-ones. Talk less, ask more. Resist the urge to solve the problem in the first two minutes and see where the person goes when you give them room.

Get curious about the account nobody wants to talk about, rather than jumping to the fix. Make it safe for your team to say “I’m not sure” — that’s usually where the best coaching conversations begin. And be patient with it. Coaching is slow-release. You won’t see the payoff this week. You’ll see it in six months when someone handles a tricky situation beautifully and you realise you weren’t anywhere near it.

I’ve come to believe the best Customer Success leaders aren’t the ones with the tidiest playbooks. They’re the ones who build people. Everything else — the health scores, the renewals, the growth — tends to follow the people, not the other way around.

I like to blend real-life experience with a coaching approach to leadership and team development, because I’ve seen what happens when the two come together. It’s the most durable advantage a CS team can have.

If any of this resonates and you’d like to chat it through, I’m always happy to. No pitch, no pressure — just a conversation about your team and where coaching might help.