Digital Marketing Blog | Tips for Scaling Revenue Success

The Hardest Part of Coaching Is Keeping My Mouth Shut

Written by Sarah Shepard | Jul 7, 2026 4:02:01 PM

I was watching a teammate work through a client problem over Slack the other day. They were close. You could feel it in the way the messages came in, a little slower, a little more tentative, the answer basically forming in real time. And there I was with my fingers hovering, the whole solution already sitting in my head, ready to drop it in and move us both along.

I almost did it. I usually do.

I tell myself that's kindness. That I'm being supportive, saving everybody some time, sparing them the discomfort of being stuck while I sit there knowing the way out. It sounds generous when I put it like that. But if I'm being straight with you, the times I've jumped in weren't really about them. Watching someone circle an answer without landing on it makes me twitchy, and handing it over makes that feeling stop. For me, not them. The relief was mine. I'd just been dressing it up as a favor.

That took me a long time to notice.

 

Caring can make you a worse coach

Nobody really tells you this part when you actually care about the people you lead: the caring gets in your way. Not always, but in the exact moment someone needs to work something out for themselves, your ability to feel their frustration turns into a liability. You're not just noticing that they're stuck. You're stuck in it with them, and you want out about as badly as they do.

The leaders who don't care much can wait all day. They're not feeling any of it, so the silence costs them nothing. It's the invested ones, the people who lie awake wondering whether someone on their team is growing or quietly burning out, who tend to cave first.

I've done this with brand new team members who you'd expect to need the help, and with people who've been here for years. In performance conversations and over Slack with someone just trying to read a client situation right. The setting keeps changing. The impulse to hand over the answer and call it support keeps showing up the same.

 

"What do you think?" is not the magic trick we pretend it is

Somewhere along the way, I picked up the manager move everyone reaches for when they're trying to coach instead of just answer. You ask "what do you think?" and you feel very evolved doing it.

The trouble is what comes next. They answer. If they're close, wonderful, you're off to the races. If they're not, you're right back where you started, except now there's been another lap around the track, and the pull to just fix it is stronger than it was a minute ago. The question opens a door. It doesn't tell you what to do once somebody actually walks through it, and a lot of us never figured out that second part. We've gotten good at asking, and we're still a little lost in the quiet that comes after.

And that quiet is where the whole thing actually happens. The silence after the question is the work, and I spent years treating it like dead air I was personally responsible for filling.

 

The discomfort is sort of the whole point

What I've come around to, slowly, is that the struggle isn't a problem I'm supposed to solve. It's the thing that builds the capability in the first place. When I jump in, I'm not shortening anybody's learning curve; I'm deleting it. Then I'm quietly surprised when the same person comes back needing the same kind of rescue, as if I hadn't personally taught them that getting unstuck means waiting around for me to do it.

There's a phrase for the alternative: holding space. It means staying present while someone works without lunging toward the resolution. It means tolerating how uncomfortable it is to just watch. And it asks you to believe the person in front of you is more capable than your urge to rescue them is insisting they are.

Because that's what's really going on when I hand over the answer. I'm making a small, private bet that they probably won't get there on their own, while congratulating myself on being kind. That stings to say out loud. It's true anyway.

I want to be clear I'm not talking about letting people flail in a way that actually hurts them or the work. There's a real difference between someone in productive struggle and someone drowning, and reading that difference is its own skill worth getting good at. But when I feel the itch to jump in, nobody's drowning. They're swimming in a way that makes me nervous to watch, which isn't the same thing.

So the coaching move was never the answer I was so eager to hand over. It's trusting someone with the question a little longer than feels comfortable, and then actually staying in it instead of holding out for thirty seconds and caving anyway.

I'm still working on the staying-in-it part. Most days I'm still the person with her fingers hovering over the keyboard, talking herself out of typing.

Sarah Shepard is the COO of StringCan Interactive. She writes the String By String newsletter on LinkedIn most weeks. If this one resonated, it's worth subscribing.