The Mysterious Art of Estimating

And what you can do to get better at it

Christopher Laine
IT Dead Inside
Published in
9 min readNov 7, 2023

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“Have you seen their estimates for this work?” one of my peers asks me. It’s a rhetorical question. I’ve seen the estimates and he knows it. He’s mentioning it, because the estimates returned by the team in question are…inflated.

I try to be diplomatic. “These feel like they’ve been padded intentionally, out of fear of the unknown,” I explain, but I know this won’t really help. My explaining WHY the team wants so much time to do so little doesn’t make their estimate any smaller, and I know it.

I take a different tack. “Do you want me to work with them?”

That gets a good response. “Yeah, if you would,” my peer says. I get it. No one wants to get some bloated estimate of work and just be shackled to it like an albatross around their neck.

With that said, I meant what I said about fear of the unknown and the team overinflating their estimates because of this. I’ve seen teams give estimates over a long and bumpy career, and I think I’ve learned a fair whack about what motivates teams to estimate as they do.

Let’s go over them, and maybe some of what I say can help you and your team in future estimating sessions.

First up: What’s Estimating?

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