For years, I was an estimation sceptic. I saw it as a relic from the waterfall days, Gantt charts, and process-heavy project managers. Agile had saved us from story points, T-shirt sizes, and man-hour breakdowns. Why play planning poker when the future’s unpredictable anyway?
Estimation comes with baggage. The three-hour T-shirt size debates. The manager who weaponises story points. The agile transformation that becomes velocity theatre. It’s tempting to swing the other way: “Estimation is broken, let’s just build.” I’ve been there. I believed it.
But businesses don’t run on faith. Budgets exist. Customers have deadlines. The rest of the company can’t wait for engineering to find enlightenment. Without any signal, trust erodes. So estimation stays not as magic but as alignment.
My perspective shifted after watching a promising project implode. We’d refused to estimate “it’ll be ready when it’s ready.” Six months in, stakeholders were in the dark, dependencies misaligned, trust gone. The mistakes are obvious: using estimates for control, treating uncertain numbers as commitments, replacing conversations with metrics. That’s when it turns toxic when estimates become weapons, not bridges.
But estimation can be quiet and useful. Done right, it’s not a contract it’s an early warning, a conversation starter. It gives the business something to work with, lets customers plan, and shows engineering is part of the team, not a black box. The goal isn’t perfect numbers. It’s reducing surprise.
Good estimation looks like this: A team I worked with broke down a complex integration into rough T-shirt sizes. We found three critical dependencies we’d missed. Started talking to security early. That’s the value de-risking, not fortune-telling. Estimates highlight what might explode, surface dependencies, reveal what needs more thought. By admitting uncertainty upfront, we can prototype, spike, slice work smaller before risks become blockers. Good estimation exposes uncertainty before it’s an emergency.
Yes, estimates get weaponised. I’ve seen managers turn story points into productivity metrics. But that’s bad leadership, not bad estimation. Don’t abandon the tool, use it right. The best teams treat estimation as dialogue, keeping the partnership healthy. They’re honest about uncertainty, clear on trade-offs, quick to adapt. That pragmatism survives reality.
Estimation isn’t about control or purity. It’s about partnership. Everything else is detail.
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