The Perfectly Imperfect Candidate

I had all the right answers until they asked the wrong question

My earliest memory of taking behavioral interviews seriously is the day I absolutely, unapologetically lied in one.

It was 2002, San Jose, California. The dotcom bubble had burst. Startups were folding like lawn chairs. Layoffs were the new morning standup.

I was a consultant working for a consulting company, which is exactly as unstable as it sounds. My contract at Cisco had just ended, and I was applying to every job I could find. Frontend roles, backend roles, vaguely defined “tech strategy” jobs—anything that sounded even loosely adjacent to the things I might be able to fake.

I had two years of experience and no business applying for a manager role. So obviously, I applied for a manager role.

It was a phone interview with three voices behind a speakerphone.

The first voice was female,

“If you have to tell someone to do some work, how would you ask them?”

I paused like I was thinking. Then said,

“I’d walk up to them and tell them to do it.”

I remember hearing static, some whispers, and the start of a giggle that cut off fast. Then an older, deeper male voice spoke:

“And why do you think that works?”

I said,

“Because I’m the boss.”

This time, they didn’t mute fast enough. I heard the full giggle.

I realized what I’d said, how it must’ve landed—I was 24, sitting in a leadership interview, hoping confidence would cover what I didn’t know yet.

That was the day I learned two things:

One, leadership interviews are not the place for improv.

Two, people don’t trust what you say—they trust who’s saying it.

For a while, that was enough to get me through.

I got better at interviews. Told better stories. Stopped pretending I was “the boss” and started acting like someone who’d seen a few things, made a few mistakes, maybe even learned from them.

Somehow, I was making it through—even the tough ones. Even the senior ones. But then I hit a wall.

Because at senior+ levels, interviews aren’t about polish anymore.

They stop being about what you did. They start testing whether you know why it worked, and whether you can see the holes in your own story before someone else points them out.

I tried to hold the line.

I memorized STAR stories!

S: Situation
T: Task
A: Action
R: Result

Also known as: Sanitized Talk Around Realness.

I showed up with bullet points. Case studies. High-resolution delivery stats.

And for a while, it worked.

---

Confidence Without Memory Is Useless

We were mid-interview. I was telling a story I knew cold.

It was one of those projects that looks clean in hindsight, but felt like chaos at the time—a roadmap turnaround in 90 days—cross-org confusion, PM drift, engineering misalignment.

I’d told it at panels. I’d dropped it in town halls. It had great timing.

I delivered it like a closing argument.

The interviewer nodded along. Then he asked:

“How did you get buy-in from the other orgs?”

Easy question.

I was sure it was in there. It should’ve been in there. But I hadn’t thought about that part in a while. I searched the mental script, hoping the line would appear. It didn’t.

I fumbled a vague answer.

He leaned in.

“What was the pushback?”

Longer pause.

I wasn’t sure.

He was testing for memory. I had rehearsed for admiration.

And I wasn’t in the moment. I was clinging to the structure, hoping it could carry me.

I heard myself drifting. The words sounded hollow. I could see his face, polite but bored, and suddenly I wasn’t in the story anymore—I was watching it collapse.

So I stopped. Mid-sentence. And said:

“I blew it at first.”

Now that I knew how to say. That wasn’t memorized. That I can’t forget.

“I tried too hard to impress the PM. Skipped discovery. Assumed alignment. The first sprint review was brutal. You could feel the room pull away from me. That’s when I realized I hadn’t earned the right to lead yet.”

He didn’t ask another question right away.

The air shifted. He wasn’t interrogating anymore. We were having a conversation.

That is when the interview really started.

---

Why STAR Stories Fail

They’re built for performance, not memory.

They make you sound competent. Smooth. Packaged.
They also make you sound like you’re trying to sell me something.

Not too perfect. Not too messy. Just enough to pass for real.

People say things like:

“I care too much.”
“I’m always learning.”
“I just really value trust.”

How convenient.

Here’s the thing about people in leadership interviews:

The more you try to look trustworthy, the more we scan for the lies. And once we start scanning, we always find something.

---

What Actually Builds Trust

Not polish.
Not posture.
Not a case study disguised as a confessional.

What works is when you stop selling and start showing.

When you say the thing that cost you.
The moment where the story went sideways.
The part where you were the reason it didn’t work—until you made it work.

That’s when people lean in.

Because scars don’t need case studies. They carry their own authority.

---

What I Wish Someone Had Told Me

If you’re preparing for a leadership interview, try this:

Don’t rehearse the clean version.

Say the messy one out loud.

Ask yourself:

• What part of this was my fault?

• When did I know I’d screwed up?

• What did I do next, when the room stopped believing me?

That’s the real test.

Show me what you’ve survived—not what you’ve staged.

And maybe—just maybe—you’ll stop telling stories that sound good... and start telling ones that feel true.

Thanks for reading.

If you want to see an example of how to deliver your failure story with raw honesty, check the following post I wrote about it:

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