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How we estimate when nobody really knows
Estimating software is mostly lying with units. A few small habits (separating knowns from unknowns, tracking our own calibration, naming the buffer) make us less wrong.
Denshin Team · Delivery · 21 March 2026 · 2 min read
Estimation is mostly lying with units. The product owner asks how long, the engineer says two weeks, and what they really mean is: I have no idea, but I have to say something, and "two weeks" gives both of us permission to stop the conversation.
We've done it badly enough times to have opinions on how to do it less badly.
Estimate the unknowns, not the work
The first move is to separate "things we've built before" from "things we've never seen". Auth flow with email + password, dashboard with five tables, contact form: these are knowns. Custom payment integration with a regional bank, multi-currency invoicing, anything involving a third-party SDK for the first time: these are unknowns.
The known stuff has narrow estimates. The unknown stuff has wide ones, and we say so. "Three to five days" with a footnote that says "subject to whether the bank's sandbox actually works on weekends" is a much more honest answer than "four days".
Track our own confidence
We grade each estimate when we make it: high / medium / low confidence. After the work ships, we go back and see how the actuals lined up. Over time, the calibration improves. Our high-confidence estimates are within 20%. Our low-confidence ones are sometimes off by 3x. Knowing which is which up front is more useful than pretending they're all the same.
Don't pretend there's no buffer
Every estimate has a buffer. Naming it openly ("two weeks of work, three weeks on the calendar, here's why") earns more trust than hiding it. Clients have been burned by other vendors who promised four weeks and shipped in twelve. Our boring honesty is a real differentiator.
Re-estimate when reality changes
An estimate isn't a contract. If we find out on day three that the third-party integration doesn't behave the way the docs say, the estimate has to update. We go back to the client the same day. Nobody enjoys that conversation, but everybody prefers it to the conversation a week before launch when we can't ship.
Tags: Estimation, Process, Project Management
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