Could You Run Your First OKR Check-In Today?


Could You Run Your
First OKR Check-In Today?

PUBLISHED

Nov 6, 2026

READ ON

​HERBIG.CO​

​Dear Reader,​

One question I asked in an OKR workshop this week was: “Can you check in on these in two weeks?”
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Imagine an online clothing store where customers often order two sizes of the same shirt and return one. The team wants to help shoppers choose a size they’ll keep. They decide to try a size guide on their best-selling shirt.
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A reasonable Key Result would be to reduce the share of orders returned because the shirt didn’t fit. The team can pull last month’s number. The catch comes at the first check-in: some customers who used the new guide have barely received their shirts. A low return rate today tells you very little.
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I’d keep the return measure. I’d also ask what the team could learn while it waits.
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For this shirt, they could look at the share of orders that include two sizes. That’s visible as soon as someone checks out. If shoppers are more confident about fit, you’d expect fewer of them to order a backup size.

That expectation gives the team something useful to discuss. Suppose plenty of shoppers open the guide, but they still order two sizes as often as before. I’d hold off on adding the guide to the rest of the catalog. I’d want to watch someone use it. Can they tell which size to pick from the measurements we’ve given them?
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And if fewer people order two sizes? That’s encouraging. It still leaves open the possibility that they’re ordering one shirt in the wrong size. Once those orders have had a full return window, the team can check whether fewer shirts came back because of fit.

Try rehearsing your first check-in while your Key Result is still a draft.​
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Pick one decision you expect to make in two weeks. What will you know by then that could change your mind?

Thank you for Practicing Product,

​Tim​

Ways we can work together

1️⃣ Order my book: Real Progress: How to Connect the Dots of Product Strategy, OKRs, and Discovery, which readers call "a practical guide you can return to again and again."

2️⃣ Learn about my in-house training and coaching options for product teams, with a focus on creating strategic clarity, setting pragmatic goals, and implementing real-life discovery practices to reduce risk

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Who is Tim Herbig?

As a Product Management Coach, I guide Product Teams to measure the real progress of their evidence-informed decisions.

I focus on better practices to connect the dots of Product Strategy, Product OKRs, and Product Discovery.

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1 tip & 3 resources per week to improve your Strategy, OKRs, and Discovery practices in less than 5 minutes. Explore my new book on realprogressbook.com

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