Sunday, October 04, 2026
Owner-dependent businesses sell for roughly half the multiple of businesses that run without them. Dan Sullivan's Who Not How question is the simplest fix most owners never try.
Most business owners who try coaching once and don't go back had the wrong idea of what coaching is supposed to be. They expected motivation. What actually moves a business is accountability and a system.
There's a version of business coaching that's mostly encouragement — a friendly conversation that leaves you feeling good and changes nothing about how the business runs on Monday. It's not useless, but it's not what moves revenue, margin, or the owner's sanity either. A coach who only makes you feel better about where you are isn't doing the job.
Real coaching operates on two levels at once. The mindset work matters — most owners are their own biggest constraint, whether that's a reluctance to delegate, a fear of raising prices, or avoiding a hard conversation with a partner or a key employee. But mindset alone doesn't build a business. It has to pair with a mechanism: a documented system for strategy, marketing, sales, and customer success that turns intention into something repeatable, plus the accountability to actually execute it between sessions.
Three questions worth asking after every coaching session:
If the honest answer trends toward the second option on all three, the coaching isn't broken — but it also isn't working yet.
The owners who get the most out of coaching treat it the way they'd treat a board member, not a therapist: they show up with real numbers, they expect to be pushed back on, and they measure the relationship by what changed in the business, not by how the conversation felt. The coach's job is to hold that bar, not lower it to keep the relationship comfortable.
A coach's real job is accountability plus a proven system — not encouragement. That's what the Simple-Growth System™ is built around, across 200+ businesses coached one-on-one in 30+ industries. Get in touch with Kevin D'Ambros-Smith to see what that looks like for your business.
...and you become the owner who leaves every session with a dated commitment and someone to check it with you.