On Estimates and "Annoying" Questions
Jun 30, 2026 · 1 min · Product
It’s a common trope that estimates are annoying. Engineers don’t want to be on the hook for a “best guess” at how long a project will take, particularly when there is still uncertainty involved. Product Managers don’t want to be constantly nagging colleagues, much like the “Are we there yet?” kid in the backseat during a roadtrip. Put it all together and many product teams end up associating a weird amount of pressure with a simple “4-5 days.”
Why Estimates?
At a glance, estimates are a means to plan out projects Gantt-chart-style, or evaluate if an engineer is dogging it or not i.e. “You said this would take 2 weeks and we’re at week 4 now. WTF?” But that shouldn’t actually be the point.
Estimates should be a jumping off point into a conversation. They’re a way to kickoff into something more meaningful. They’re a useful wedge to help develop a shared understanding between two people with different skillsets, views of the world, and sets of information at their disposal.
Annoying Questions
As a PM, if our expectations don’t match, that’s important to know and unpack so that we can make better decisions and work faster as a team. The inverse of this is also even more important in many cases. Engineers should frequently ask PMs “Why are we doing this? Why this, and not this? Why is this part fuzzy and this part prescriptive? What do you mean by this?” It’s these questions that lead into the juicy conversations that help teams do their best work. Even if they might be a little “annoying.”
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