"Tell me about a time you failed."
It's the interview question that makes even the most experienced Product Managers sweat. You don't want to look incompetent, but you also don't want to give a fake "humble brag" answer that interviewers see right through.
Most PMs fail when it comes to answering this question.
After today, you won’t be one of them.
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Why interviewers ask this question
It's not to catch you out. It's to answer three specific questions about you:
Do you have self-awareness?
Can you objectively look at your own performance and admit when you messed up?
Everyone fails—from the junior PM to the CPO. The interviewer already knows this because they've definitely failed themselves.
Do you exhibit high agency?
Do you own the outcome, good or bad? Or do you blame the engineers, the market, the customers, or your boss?
Great companies want PMs who own the failure and the solution—refusing to be a victim of their environment.
Do you have a growth mindset?
Great PMs have failed…a lot. And each time you fail, you learn. They're hoping you'll bring the knowledge and experience from overcoming those mistakes.
If you can't answer this failure question well, you're telling them the answer to all three is No.
The two types of failure stories
There are two types of stories you can use for failure questions.
Each requires a different approach. Use the wrong framing and you either sound like you're blaming others for your mistakes, or taking credit for solving a problem that wasn't yours.
Type 1: The Failure Story
This is about when you made a bad decision. If the story doesn't make you cringe a bit, dig deeper.
When to use it: When the question specifically asks about a mistake, bad decision, or failure.
Here are three principles to nail this:
1. Own the decision clearly
Avoid "we decided" language. If it was your call, say so: "I decided to..."
2. Show senior-level engagement
Don't limit your story to just the tactical steps.
Include how you communicated upward and gained buy-in for the course-correction. Be specific and mention titles like “my Director of Product” or “the Head of Engineering.”
3. Land on concrete learnings
End with a specific behavioural change, framework, or checklist you now apply. This shows you’ve got that growth mindset they’re looking for. You don’t just fix the problem, you help prevent a recurrence, too.
Type 2: The Problem Story
This is about a challenge you solved, where something went wrong externally and you sorted it out.
When to use it: When the question asks about something that went wrong, an obstacle, or a challenge—where the issue wasn’t your own mistake.
Three principles here:
1. Clarify your scope vs. what you identified
Was this assigned to you, or did you spot it and take ownership? Be clear.
2. Name your cross-functional partners
Include specifics like "I worked with my engineering lead on X" or "I partnered with data scientists on Y."
3. Show strategic thinking, not just tactics
Elevate from "I did X, Y, Z" to "I identified that the root cause…and made a decision based on these circumstances."
How to know which one to use
Here’s a quick cheat sheet you can reference to know which to tell:
"Tell me about a time you failed" |
|
Type 1 — Own a bad decision |
"Tell me about a time you made a mistake" |
|
Type 1 — Own a bad decision |
"Tell me about a time something went wrong" |
|
Either — depends on context |
"Tell me about a challenge you faced" |
|
Type 2 — Problem you solved |
"Tell me about an obstacle you overcame" |
|
Type 1 — Problem you solved |
If you're unsure which to use in the moment—just ask them to clarify. This shows you're prepared for either.
Once you can confidently answer questions about your failures, you stop fearing them. You show interviewers that you are self-aware, accountable, and strategic.
But answering their questions is only half the battle. You also need to know what to do when the tables are turned and you get to ask the questions. I covered this in another video, or you can check out this issue of my newsletter.
In the meantime, hit reply and let me know—what's the hardest interview question you've faced?