I struggle to answer ‘When was the last time you did not meet a deadline?’

David Villarama
2 min readMay 17, 2021

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An alternate title: How I always meet meet my deadlines.

When was the last time you did not meet a deadline?

This is one of the toughest behavioral interview questions. The interviewee is looking how you failed, how you dealt with failure, what you learned and how you explain the situation. Hint: Never ever blame anybody else for what went wrong.

But I always meet my deadlines

Am I a super expert in estimating tasks that I never make any mistakes. No. I make estimating mistakes all the time.

Am I a super fast developer that I always make my deadline. No. I’m just as fast as the next programmer.

Do I just work 40 hours a day to make a deadline. No. I believe in working in a sustainable pace.

Do I just avoid deadlines. No. Deadlines are a part of software engineering. If you have been doing in Agile/Sprints/Stories, there are plenty of deadlines.

How then?

Whenever, I get the feeling that I’m going to miss a deadline, I let my team know immediately.

Do not look at it as your problem. You estimated wrong therefore you have to provide a solution. Look at it as our problem and as a team we are going to find a solution.

Did we try to do something that really required more information? We should do a spike first or create a ‘proof of concept’ before we continue.

Maybe we found there is more work involved. These are only 2 reasonable solutions to this. We either remove features from the project or move the deadline. The third solution is work your ass off till is done (This usually ends badly with burned out developers).

Meet your deadlines

From now on, always meet your deadlines! However, know that you will have a hard time answering this behavioral question, ‘When was the last time you did not meet a deadline?’

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David Villarama
David Villarama

Written by David Villarama

Software Doodler with 25+ years of Noodling Experience

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