Who’s Calling You Out?

On a long walk Friday, a friend and I talked about working together more closely. When he asked what I’d want from it, I surprised myself with the answer.

“I don’t just want someone on my side. I want someone who’ll call me out.”

I’ve had plenty of people on my side over 25 years in business. That’s not a complaint. It’s a blind spot.

Think about who surrounds the average business owner. Family who love you and want you home for dinner. Employees who like their jobs. Clients who like working with you, and like the discount even more. Peers who cheer every announcement. They’re all good people, and almost none of them are in a position to tell you an inconvenient truth.

So you drift. It isn’t dramatic. It’s quiet.

Comfort says, “You’ve got this.”
Honesty says, “Are you sure?”

Growth rarely stalls because of critics. It stalls because everyone around you agrees.

Here’s what honesty looked like for me this week. I was teaching a session of Kauffman FastTrac for Launch Fayette when a founder admitted she’d built good products but never built the structure behind them. I could have nodded and moved on. Instead I told the room the truth: after nearly 25 years, I still feel that way.

My team has been running on three spreadsheets that don’t agree with each other, and we just found recurring invoices that slipped through the cracks during a system switch. With a small core team, every leak like that is capacity we don’t have. I’d been living with it because nobody was making me look at it. Saying it out loud to a room of new founders did.

That’s the first way to get called out: call yourself out, in front of people who will remember.

The second way is to put yourself in rooms built for it. At Thought Lab Thursdays at The Nexus, we spent this week on how AI is disrupting nearly every business at the table. The most useful thing said was a simple distinction. Losing a client is a fact. “Everything is falling apart” is a story. A good room won’t let you confuse the two, and it will tell you so with care.

The third way is the one I’m working on now: ask for it directly. My friend on that walk proposed something with almost no structure. A short call every couple of weeks, and a text or voice memo when something comes up. No formal coaching, just a standing invitation to be honest. The format isn’t what makes it work. The permission is.

If you don’t have that person, find one. Not a critic, who needs you to be wrong, and not a cheerleader, who needs you to be happy. Find someone who cares enough about where you’re headed to tell you when you’re drifting. Then tell them, out loud, that you want the hard version.

I went into that walk thinking the hard part would be finding the right person.

It wasn’t. The hard part was saying the sentence out loud.

Anyone can be on your side. The people who call you out are the ones who actually are.