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WorkMatters is a newsletter and product studio focused on the future of work. Our weekly newsletter offers ideas and insights for building stronger, more resilient organizations.

Week 38, 2019

Estimation, Part 2: Expectations, Prioritization, Alternatives

3 min readJun 1, 2025

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Photo by Clem Onojeghuo on Unsplash

Each week I share three ideas for how to make work better. And like last week, this one is all about estimation. Specifically, why and how it should be done.

Why am I writing about this? I presented three reasons not to estimate in last week’s issue. Time now to look at the other side of the coin. If estimation is so rife with problems, why do so many still bother estimating work at all? And what, if anything, can be done to make estimation more effective?

Let’s dig in.

1. Expectations

This is so obvious it bears repeating: customers want to know what they’re buying. They deserve to know. And this holds true for routine labor on the one hand and knowledge work on the other. Yes, it’s much, much, harder to estimate knowledge work. But that’s no reason to throw in the proverbial towel; the fact that customers deserve to know still remains. It simply means we need better ways to manage expectations and risks.

For more on this, check out w82019 and how Agile contracts can help customers and vendors balance risk amongst themselves.

2. Prioritization

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Andreas Holmer
Andreas Holmer

Written by Andreas Holmer

I'm a designer, writer, and entrepreneur. Formerly CEO at MAQE. Current CEO of TeamStack. Editor at WorkMatters.

WorkMatters
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WorkMatters is a newsletter and product studio focused on the future of work. Our weekly newsletter offers ideas and insights for building stronger, more resilient organizations.