The Board You Don't Have: How Solo Founders Build Strategic Challenge Without a Board

Thursday, September 10, 2026

Most SME owners make their biggest calls alone, with no one qualified to challenge them. Here's how to build a "kitchen cabinet" that gives you real strategic pushback — without a formal board.

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There are now more than 232,000 professional coaches working in the United States alone, part of an industry that has more than doubled in size since 2016 to around 16 billion US dollars a year, according to industry research firm Marketdata Enterprises. Executive and business coaching commands the highest fees in that market.

With that many options and that much money moving through the industry, the question is not whether coaching works. It is how an owner tells a coach who will genuinely change their business from one who will simply make them feel good about it for an hour a month.

The Cheerleader Problem

The enemy here is a coach selected on warmth and charisma alone, who agrees with every plan the owner already had. This feels supportive and changes nothing, because the owner never hears the thing they actually needed to hear. Most expensive coaching relationships fail quietly this way, not through bad advice, but through no uncomfortable advice at all.

Source: Marketdata Enterprises, US Professional Coaching Industry research

The One Question

In any conversation with a prospective coach, before signing anything, ask this: tell me about a time you told a client something they did not want to hear, and what happened next. The answer reveals more than any credential, certification or client list, because it shows whether this person will protect the relationship over the result, or the result over the relationship.

  • 1. A Specific Story — a real client, a real uncomfortable truth, not a vague I always tell clients what they need to hear.
  • 2. A Business Outcome, Not Just a Relationship Outcome — what changed in the business, not just how the client felt afterward.
  • 3. Evidence They Stayed in the Room — did they keep working with that client through the discomfort, or did the relationship quietly end there.
  • 4. No Trace of Self-Congratulation — the best answers sound like a hard conversation, not a highlight reel.

"One of the highlight presentations during OMP. Really enjoyed your wisdom and insight, thanks Kevin!"

— Liz Wotherspoon, Director, The Icehouse

Why Owners Rarely Ask This Question

Hiring a coach already feels like admitting something is not working, and most owners want reassurance in that moment, not more discomfort, so they gravitate toward whoever feels the most encouraging in the first conversation. The real obstacle is that the sales conversation and the coaching relationship reward opposite things, warmth closes the sale, candour delivers the result. Owners who ask this one question before signing are filtering for the second thing on purpose.

Quick Wins This Week

  • Before your next coaching conversation, write down this exact question and ask it word for word.
  • Ask for a specific example, and push once if the answer stays general.
  • Notice how it feels to hear the answer. If it makes you slightly uncomfortable, that is usually a good sign.

Key Takeaways

  • The US coaching industry has more than doubled since 2016 to over 232,000 coaches and roughly 16 billion US dollars a year.
  • A coach selected for warmth alone often becomes an expensive version of the agreement you already had.
  • Ask any prospective coach to describe a time they told a client something they did not want to hear.
  • A specific, business-outcome-focused answer is the clearest signal of a coach worth hiring.

If you are about to hire a coach and have not asked this question yet, ask it before you sign anything.

...and you become the owner who chose a coach for the hard truths, not the comfortable ones.

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