The One Question That Filters Out Your Worst Deals

Sit in on enough coaching sessions and a pattern emerges fast: the owners who get the least out of coaching walk in with a polished update. Revenue's up, the new hire is working out, the roadmap's on track. It sounds like a good session. It's usually a wasted one.

The owners who get the most out of coaching walk in with something broken — a decision they're avoiding, a number that doesn't add up, a person on the team who isn't performing and they don't know why. That's not a worse session. It's the entire point of having a coach. Inside the Simple-Growth System™, Kevin tells every new client the same thing in week one: the value of this relationship is proportional to how honest you're willing to be about what isn't working.

Presenting good news to your coach feels productive, and it isn't entirely without value — momentum matters and should be acknowledged. But when a good-news update becomes the default format for every session, it's usually protecting the owner from something, not informing the coach of something. It's easier to talk about the win than the decision you've been putting off for six weeks.

A coach who only ever hears the highlight reel can only ever coach the highlight reel. The blind spots, the avoided conversations, and the slow-moving problems — the things actually capping growth — never make it into the room, which means they never get solved in it either.

This isn't about manufacturing crises or being negative for the sake of it. It's about walking in with the specific, current thing you're stuck on: "I don't know whether to let this employee go," "I can't tell if this new product line is worth the cash it's tying up," "I know I should be delegating this but I keep taking it back." These are uncomfortable to say out loud, which is exactly why they're the highest-value thing you can bring.

The best-prepared clients come to a session with one real problem, framed honestly, rather than five updates framed carefully. That single problem, worked through properly, is worth more than an hour of status reporting — because a coach's job isn't to be informed, it's to change what happens next.

None of the accountability structures Kevin has written about before — dated commitments, checked-in weekly, tracked against a scorecard — work if the input going into them is curated. Accountability built on a polished version of reality just holds you accountable to looking good, not to actually growing.

The shift starts with the owner, but a good coach should be actively pulling for it too — asking what's not being said, noticing when an update feels rehearsed, and making it clear from the first session that the goal isn't a good report card. It's a business that's actually further ahead in six months than it is today.

If bringing a real problem feels like a big shift from how sessions have gone so far, start small: one honest thing per session, even alongside the updates. Over a few months, that habit compounds into a working relationship where the hardest issues surface early, instead of six months after they should have.

If your coaching sessions have started to feel like status meetings, that's worth naming directly with your coach rather than quietly enduring. The Simple-Growth System™ is built on the assumption that the real value shows up in the uncomfortable conversations, not the comfortable ones — and that's true whether you've been coaching with Kevin for six weeks or six years.

…and you become the owner who brings the real problem to every session.