CEO OS
Learning ·April 12, 2026 ·reflection

Reflections

Where I Stand

  • Brooks says 10% of people prep for conversations. Am I in the 10%? Before a customer call, do I prep 3-5 topics and questions — or do I show up and pitch?
  • The distribution gap might be a conversation gap. Discovery calls that don't go deep enough because I'm presenting, not listening. Follow-up questions are free. Am I asking them?
  • Brooks's ZQ (Zero Questioner) concept: on my last 5 customer calls, what percentage of the time was I talking vs. asking? If it's above 50%, I'm the ZQ.
  • Boomerasking — asking a question just to pivot back to my own point. This is the founder's default move on sales calls. "What's your biggest challenge? Great, let me tell you how FeatureOS solves that." That's not curiosity. That's a pitch with a question mark.
  • Levity as status: one laugh on a pitch call tilts the vote. I care about craft and taste — but am I using humor to build rapport? Or am I too serious, too polished, too "professional"?
  • Every relationship is a repeated sequence of conversations. My relationships with churned customers were a sequence of conversations I lost. What did those conversations look like? Did I ever follow up after the first "everything's fine"?

What I Need to Change

  • Before every customer call, spend 30 seconds prepping 3 topics and 3 follow-up questions. Write them down. Do this for the next 20 calls without exception.
  • Track talk-to-listen ratio on calls. Target 30% talking, 70% listening. Record calls and audit.
  • Replace the pitch instinct with the follow-up instinct. When a prospect says something interesting, go deeper instead of pivoting to a feature.
  • Use churned customers as conversation practice. Call 5 churned customers this month with zero pitch — just questions. Find out what the conversations should have been.
  • Stop treating customer calls as demos. Treat them as conversations. The product should sell itself; the call should be about understanding.

The Hard Question

On your last customer call, how many follow-up questions did you ask — and how many times did you pivot their answer into a pitch?

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