You can’t clone the founder.You can clone the question.

Every founder-led business hits the same wall. The founder wins the work. Everyone else quotes it.

It shows up in the numbers before anyone names it. Conversion is strong when the founder takes the call and soft when they don’t. Leadership calls it a sales capability problem and starts interviewing senior salespeople.

That’s usually the wrong diagnosis. The team isn’t short of talent. The business is short of anything written down that’s worth learning.

The founder’s answers aren’t the asset

Watch a founder sell and you’ll see two things. The first is the pitch: the lines, the stories, the confidence. That’s the bit everyone copies. The second is quieter. Before they recommend anything, they ask a question nobody else thinks to ask, and the answer changes what they sell.

Take a photo studio, an illustrative one. A customer walks in with a shoebox of family photos and asks what scanning costs. A staff member counts the prints and reaches for the price list. The founder asks, “What are they for?” It turns out she needs one big portrait of her dad for his birthday on Saturday. The rest can wait. Same customer, completely different job. One question did that.

Ask that founder how they sell and they’ll say “just have a proper conversation”. It feels obvious to them, so they don’t think of it as knowledge. They think of it as being good at the job.

So the business writes down the wrong things. Credentials decks. Service lists. A sales script made from the founder’s best lines, delivered by someone who doesn’t know why the lines worked. The charm gets copied. The judgement stays inside one head, and it never leaves the building.

Here’s my position: the script is the least valuable thing a founder knows. Most sales playbooks fail because they document the answers, not the questions.

Diagnose before you hire

Bigger firms have the same problem with a fancier name on the door. There’s always one senior specialist dragged into every pitch to explain why one job takes a week and another takes a month. Each appearance moves a deal. None of them makes the next deal easier, because nobody captured what the specialist noticed.

Hiring a senior salesperson doesn’t fix that. It adds a second person with their own judgement and their own lines, and now there are two heads to empty instead of one. Hire if you need capacity. Don’t hire to solve a problem that lives in the founder’s head.

The fix is cheaper and less glamorous. Get the judgement out.

Interview a decision, not a career

Researchers who study expertise worked this out decades ago. Laura Militello and Robert Hutton’s applied cognitive task analysis, developed with US Navy funding to help training designers, doesn’t ask experts to describe their process in general. It walks them through real situations and probes for the cues they noticed, the strategies they used and the mistakes a beginner would make.

That’s the move. Don’t ask your founder how they sell. Ask them about one decision.

Pull a recent job where the recommendation changed mid-conversation. Put the original enquiry and the proposal on the table. Leave the credentials deck closed. Then ask five questions. What did the customer ask for, in their own words? What made you pause? What did you rule out, and why? What did you show them? What would have made you recommend something else, or walk away?

Then find a second job where the same opening question led somewhere different. This is the step everyone skips, and it’s the one that matters. Without it, a keen colleague concludes that everyone with a shoebox needs a birthday portrait. Judgement lives in the exception.

A line needs a story to stand on

Oceania Film Company had a version of this. The craft was strong, but so is every capable production company’s. Selling cameras, crews and polished work left buyers comparing Oceania with every other good video supplier. The real difference was human: the team was unusually good at putting real people at ease on camera and finding the human story inside corporate language.

Hum helped them name it. The core value proposition became “We make business feel human”, and the business repositioned from video supplier towards corporate content partner.

The lesson for a sales team is that a line like that is a handle, not a pitch. The person using it still needs one concrete example to stand on. A nervous interviewee, the choice the crew made, the moment you can see it in the finished film. Without the example, the salesperson goes back to describing the cameras, now with a nice line at the end.

What to do on Monday

1. Book one hour with the founder. Not to talk about sales. To talk about one job where the recommendation changed mid-conversation.

2. Bring the enquiry, the proposal and the person who delivered the work. Ask the five questions and write the answers down word for word.

3. Find the second job, the one where the same opening question went somewhere else.

4. Turn both into a single card: the first question to ask, the two paths it opens, and the point where you call the specialist.

5. Test the card on an awkward case before it goes near a customer. Same customer, tiny damaged photo, birthday tomorrow. Can your colleague explain the limit and offer a real next step without promising the impossible?

The founder doesn’t need to be in every room. They need to be in one interview, about one decision, with someone taking notes at the exact moment they change their mind.

Sources & notes

• Laura Militello and Robert Hutton, “Applied cognitive task analysis (ACTA): a practitioner’s toolkit for understanding cognitive task demands”, Ergonomics, 1998. The research is about eliciting expert judgement. It isn’t evidence about sales results.

• Oceania Film Company case study, Hum

• The photo studio is illustrative, not a client.

Continue with The best thing about your business never leaves the building. If you want a next step, see Hum’s fractional CMO page.