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When Will It Be Ready?
Estimations Aren’t the Enemy — Unless You Use Them Wrong
The hardest question I’ve ever been asked — whether as a software developer or now as someone leading teams and focusing on product management — has always been:
When will it be ready?
I’ve faced all kinds of wild, unknown problems over the years, the kind that pushes you to think outside the box and leave you feeling like a rockstar when you solve them. But nothing — nothing — prepares you for the pressure of giving a good answer to that question.

Just last week, a client asked me, “We’ve struggled with accurate estimations. Have you guys figured out a good method for it?” My first thought was, Ah, here we go again. I wanted to say, “Ask me anything else!” But instead, I took a deep breath and said, “No one can predict the future, but we can find methods that work for your team and your organization. The key is to always acknowledge the uncertainty that comes with estimations.”
A couple of years ago, I gave a talk about this very topic. I compared software development estimations to predicting the path of a tropical cyclone. I even spoke to a meteorologist to validate my conclusions.
I’m from the Caribbean, so cyclones are part of life. Every year, we brace ourselves…