Monday, October 12, 2026
The seven concerns SME owners raise most often in coaching, why each one happens, and what actually helps.
"It felt really useful" is the most common thing owners say about coaching, and it's the least useful measure of whether it actually worked. Feeling supported is not the same as getting a return.
Coaching sits in an odd spot for most owners — somewhere between a professional service and a form of moral support, and that ambiguity is exactly why so many engagements go unmeasured. Nobody would accept "it felt useful" as the return on a marketing spend or a new hire. Coaching should be held to the same standard, because a good engagement produces changes you can actually point to, not just a better mood after the session.
A coaching engagement worth continuing shows up in at least one of three places: a measurable business number moved in the right direction — margin, revenue per customer, time-to-close; a specific structural change got made and stuck — a system built, a hire made, a decision finally taken after months of avoidance; or the owner's actual behaviour changed in a way that's still visible months later, not just during the session itself. If none of the three show up after a meaningful stretch of engagement, the coaching isn't working, however good it feels.
Run this every quarter, not just at the end of a contract. List what was committed to in each session over the period. Check off what actually happened, honestly — not what got discussed again next time because it hadn't been done. Then ask what changed in the business as a direct result. A good coach will run this review with you unprompted, because they should want the evidence as much as you do.
The ones that stall are almost always the same pattern: sessions that stay conversational, no dated commitments, no follow-up on whether last month's action actually happened, and a relationship that's comfortable rather than genuinely useful. That's not coaching — it's a standing chat with a business flavour, and it's an expensive one to keep paying for without ever checking the return.
Want to see exactly what a coaching engagement should be producing by this point? Every client inside the Simple-Growth System™ gets a documented quarterly review tying sessions to measurable results — get in touch with Kevin D'Ambros-Smith to see what that should look like for your business.
…and you become the owner who can point to exactly what your coaching has changed.