Written by Derek Mulhern, PCC
As leaders, we’re used to being the ones with the answers. So when we start wondering whether we need support, we tend to talk ourselves out of it. We tell ourselves to wait until it gets worse, or until we’re sure we can’t handle it alone.
That moment rarely arrives on its own.
Most of the leaders who end up on a discovery call with me have been carrying the question for a long time. By then, it’s usually clear the problem was never that they were doing something wrong.
In this issue, I’m sharing what that moment tends to sound like and what to look for when you’re ready to find the right coach.
Happy reading!
I hear it all of the time: "Do I need an executive coach?" "How do I know it's time to get a coach?" "What should I look for when picking a leadership coach?"
When the leader finally gets on that first discovery call, it's usually for a handful of reasons.
A leader tells me things feel like a lot. They’re not sure they’re doing it right. They’ve been turning it over in their head for weeks, sometimes years, and they can’t tell what’s real and what’s just loud anymore.
Signs You Might Need an Executive Coach
Over the years, the reasons have sounded similar. Some people are at a breaking point.
Some are stepping into something new or bigger. Some are working through one specific challenge. In their own words, I’ve heard:
“I don’t know what I don’t know.”
“I think I can do it, but I need someone to talk to.”
“I’m holding myself back.”
“I need someone external, someone I don’t have to perform for.”
“I’m the only one who understands this.”
“I’m not looking for a framework. I’m looking for a sounding board.”
Most of them waited until it got bad enough or until they were sure they couldn’t handle it alone. Until they had the space, which never shows up on its own.
None of them were doing anything wrong. They were just too close to it all.
A good leadership coach sees how you’re thinking, helps you identify patterns you can’t see and helps you name things in a new way.
And sometimes they say out loud that this is hard, and that some of it was never yours to control.
Coaching isn’t only for the rough patches. Oftentimes, coaching is what takes a strong leader to the next level. I’d argue every executive should work with a coach at some point, if only to know themselves better.
How to Choose a Leadership Coach
Trust. The more you’re willing to share, the more you get. Industry experience matters less than whether you feel safe going deeper.
Gut. One person told me she woke up the morning after our call excited about what was next. Notice that feeling.
Enjoyment. Do you like spending time with this person? It won’t always be comfortable, but it should be a relationship you value.
Training. Ask how they were trained. Plenty of people call themselves coaches when they’re really advisors, and an ICF credential is one useful signal.
What to Expect From the First Conversation
Talk to two or three coaches. Expect at least one real hour. Be ready to share why you’re looking for support, what you want to achieve, and how you’d want a coach to help. Expect the conversation to meander. That’s often how coaching works.
You don’t need to be struggling to deserve support.