Eight people on a call Thursday morning.
A former CIO. A fractional CMO. A QA expert calling in from the UK. A chief data officer. A strategy consultant. A couple of guys still figuring out where they fit.
Combined experience in the room? Over 150 years.
And every single one had the same problem.
They couldn't describe what they do in one sentence.
The Trap Nobody Talks About
You've got 20 years of real results, VP and C-suite titles, companies you've actually built and fixed. But when someone asks what you're doing now, you give them four paragraphs and watch their eyes glaze over.
If you can't boil it down, nobody calls you.
One guy on the call nailed it. One sentence. Every CEO in his target market would lean in hearing it.
Another kept describing his three-stage methodology instead of the pain he solves. His prospects don't care how he does the work. They care that something's broken and nobody on their team can tell them why.
I stopped him mid-sentence. Lead with the pain. Not the resume.
"Lead with the pain. Not the resume."
We spent 45 minutes workshopping positioning statements in real time. One person talks, everyone else pressure-tests it. Would a CEO take a meeting based on that sentence? Would you hire this person based on how they just described themselves?
What AI Can't Do
A lot of you are using AI to write your positioning. And AI is a great tool. I run agents across my entire business.
But here's what AI can't do. It can't hear the thing you're not saying.
When someone describes what they do and I hear the hesitation, the overexplaining, the moment they drift into resume mode instead of problem mode — that's where the real coaching happens.
AI will polish your tenth iteration and tell you it's great. I'll tell you a CEO would scroll past it. Because I've been that CEO. I've hired fractional executives. I created the category. I know what makes someone lean in and what makes them hit ignore.
"AI can't hear the thing you're not saying."
Iron Sharpening Iron
The best part? It doesn't stop when the call ends.
Our Slack community is coming alive. People posting positioning drafts between calls. Reacting to each other's work. Giving honest feedback — not "looks great!" but actual pressure testing.
Someone posts a statement, and three people respond within hours telling them what lands and what doesn't. Iron sharpening iron. All week long.
I created the Fractional CMO category over 15 years ago. But what I'm watching happen in this community is something I didn't expect. These people are making each other better. I just lit the match.
Your Next Move
If you're an experienced professional sitting in a home office trying to figure this out alone, that's the problem. Not your skills. Not your experience. The echo chamber of one.
Corporate broke the promise. Build your own — with people who've been in the room.
See if The Crew is your room: theretern.com/crew
The work is serious. The life doesn't have to be.
Now if you'll excuse me, I have a tee time to keep.
Kirk Coburn is the founder of The ReTern and category creator of the fractional executive movement. He introduced the term "Fractional CMO" to the market in 2009 when he co-founded Chief Outsiders, which has since served 2,000+ clients. When he's not helping corporate refugees build fractional practices, he's usually on the golf course by 2 PM.
