Lessons from John Cutler, former Product Manager at Zendesk

Srini Sekaran
2 min readAug 25, 2021

Bite-sized lessons from a product leader.

John Cutler has helped build products at Amplitude and Zendesk.

At On Deck, he talked about how product teams can tackle uncertainty.

Here’s what I learned:

Uncertainty is where the opportunity is.

Artificially creating hints of certainty (p-values, random frameworks) in a world of uncertainty may just mask the real problem at hand.

Focus more on experimentation, creating alignment, and reducing analysis paralysis in these moments.

How do you make it safe to talk about uncertainty?

  1. Use prompts

Prompts can help set the context for making decisions in these moments. It can frame topics.

Example: “If our assumption about _____ is wrong, that will put us at risk.”

2. Make it easy for the team to generate questions

Move away from a monologue on strategy followed by asking “any questions?” at the end of a meeting.

Instead, sit down and brainstorm with the team.

Generate as many questions on the who, what, and why of the situation.

3. Use PICO

For _________ (P: a given population segment), how does _________ (I: action) compared to _________(C: alternative) affect _______(O: outcomes)?

Example: For age 18–24 users (P), how does introducing ephemeral (I) instead of static content (C) affect engagement?

Make strategy, learning, uncertainty brainstorming a continuous thing.

Track all the assumptions you’re testing, the experiments you’re running, and the learnings on a board — similar to a Kanban board.

The art of validating strategy should look a lot like building products.

Use the level of uncertainty of initiatives to build a portfolio of bets.

Like this? Follow me on Twitter @srinisekaran for threads on product and more.

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Srini Sekaran

Product Manager at Amazon. Previously at NASA and startups. Optimist.