The Real Reason You Struggle with Estimating Work
“Can you give me a quick estimate on how long this will take?”
Cue internal panic.
A shrug.
A number pulled from the void.
Spoiler alert: You’re not bad at estimating.
You’re just being asked to predict the future… with incomplete information… under pressure… and sometimes with a meeting invite titled “quick chat.”
Estimation Isn’t Broken Because You’re Incompetent
It’s broken because:
- Software is complex
- Requirements are vague
- Unknowns are everywhere
- You’re being asked for numbers before understanding the problem
If you feel like you suck at estimating, you don’t. You’re just trying to do math in the middle of a magic trick.
The System Is Designed to Fail
Let’s be real:
Estimates often happen:
- Before requirements are locked
- Without input from the people doing the actual work
- With pressure to “keep it under X hours/days/sprints”
In a culture where missing an estimate is treated like personal failure
It’s no wonder the estimates are wrong.
They were cursed from the start.
So How Do You Get Better?
You don’t need to be psychic.
You just need better patterns and better conversations:
Break down the work. Smaller is saner.
“Login system” is not an estimate; it’s a collection of issues.
Call out assumptions. Loudly.
“If we’re reusing the existing auth flow” is a very different estimate than “new integration with third-party OAuth.”
Estimate in ranges, not absolutes.
“2 to 3 days if nothing explodes” > “2 days.”
Pad for unknowns without shame.
Padding doesn’t mean you’re bad. It means you’ve been burned before.
Push back when asked too early.
“I can’t give a reliable estimate until I dig in” is a valid, professional response.
Your Job Isn’t to Be Perfect, It’s to Be Honest
Estimations go sideways when the culture demands precision without process.
You’re not a wizard. You’re a developer.
You can improve, but only if the system reflects reality.
Estimating is hard because the system is rigged, not because you suck
Break it down, ask questions, and pad with confidence
Be honest about what you don’t know, early and often
It’s better to miss a padded estimate than a lowball one and get burned
Hey, since you made it this far, you might actually care about becoming a better leader.
Good news: I wrote an ebook that’ll help you skip years of trial and error.
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