Leading When the Number Is Uncertain
When the number slips, the problem is rarely too few explanations. It’s too many, each one reasonable, none of them tested. I spent three quarters learning that the hard way.
September 14 2026
Recorded at M3, September 2026.
When revenue falls short, most leadership teams don’t lack explanations. Sales has one, Marketing has another, Customer Success has a third, and each describes something real. Dashboards and AI can produce a fourth in seconds. The difficulty is telling which of them rests on evidence from the buyer and which is the company’s interpretation of the buyer.
In this talk I describe three quarters spent selling security technology to banks, where demonstrations, architecture reviews and free pilots all looked like progress and none of it was. The person we were talking to agreed the problem was real and owned none of its cost. When we finally found the person who did, we found them by accident.
The session closes on the question I’ve returned to ever since. How do we know?
Gus Byleveld
The Wondering Perspective
When revenue falls short, leadership teams rarely lack explanations; the challenge is knowing which are supported by customer evidence and which are simply assumptions. After spending three quarters selling security technology to banks, Gus learned that activity can look like progress without creating buyer commitment. That experience shaped a question that remains central to The Wondering: How do we know?
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