M47: Best Way to Handle the Failure Interview Question

Why the Best Leaders Tell Failure Stories Like Oprah, Not Obama

Here we are again, my friends, back for another Deep Dive.

But today’s a little different. Today we’re tackling one of those classic interview questions everyone dreads: “What’s your biggest failure?” Except we’re not doing generic interview prep. We’re doing it the Dear Lewis way—with real stories, real stakes, and a framework that actually works.

Marcus (not his real name) is a VP-level leader at a major tech company. Crushing his current role. Stellar track record. Glowing references. He’s interviewing for a Chief Product Officer position, and everything’s going perfectly until he gets to the behavioral interview prep.

“I don’t have a good failure story,” he tells me, anxiety creeping into his voice.

I’ve heard this exact sentence from nearly every executive client I’ve coached. They’ve spent their entire careers being excellent, and now someone wants them to talk about when they sucked at something.

“Marcus,” I say, “you have plenty of failures. You just don’t recognize them because you’re looking for the wrong thing.”

Here’s what most people miss: The failure question isn’t really about the failure. It’s about whether you can transform a setback into a leadership showcase. It’s a test of your self-awareness, resilience, and ability to extract wisdom from difficulty.

Marcus’s real problem? He was searching for “acceptable” failures—the kind that sound good in interviews. The sanitized stuff. The failure equivalent of saying your biggest weakness is that you “work too hard.”

The Master Class: Oprah vs. Obama

Let me show you what mastery looks like versus what damage control looks like.

In 2008, Oprah Winfrey gave a commencement speech at Stanford. Here’s how she talked about one of her biggest professional failures:

Many of you know that, as President Hennessy said, I started this school in Africa. And I founded the school, where I’m trying to give South African girls a shot at a future like yours—Stanford. And I spent five years making sure that school would be as beautiful as the students. I wanted every girl to feel her worth reflected in her surroundings. So, I checked every blueprint, I picked every pillow. I was looking at the grout in between the bricks. I knew every thread count of the sheets. I chose every girl from the villages, from nine provinces. And yet, last fall, I was faced with a crisis I had never anticipated. I was told that one of the dorm matrons was suspected of sexual abuse.

That was, as you can imagine, devastating news. First, I cried—actually, I sobbed—for about half an hour. And then I said, let’s get to it; that’s all you get, a half an hour. You need to focus on the now, what you need to do now. So, I contacted a child trauma specialist. I put together a team of investigators. I made sure the girls had counseling and support. And Gayle and I got on a plane and flew to South Africa.

And the whole time I kept asking that question: What is this here to teach me? And, as difficult as that experience has been, I got a lot of lessons. I understand now the mistakes I made, because I had been paying attention to all of the wrong things. I’d built that school from the outside in, when what really mattered was the inside out.

So, it’s a lesson that applies to all of our lives as a whole. What matters most is what’s inside. What matters most is the sense of integrity, of quality and beauty. I got that lesson. And what I know is that the girls came away with something, too. They have emerged from this more resilient and knowing that their voices have power.

Now contrast that with how President Obama handled a failure around the same time. Tom Daschle, his nominee for Secretary of Health and Human Services, withdrew after tax issues. ABC News asked Obama about it:

CHARLES GIBSON: Mr. President, has this been an embarrassing day for the administration?

PRESIDENT OBAMA: Well, I think it has. I mean, I think that any time one of your nominees pulls out, that’s an issue. And, you know, as I’ve said publicly, you know, ultimately, I take responsibility for the situation that we’re in.

Later in the interview:

PRESIDENT OBAMA: We can’t afford glitches because, right now, what I should be spending time talking to you about is how we’re going to put three to four million people back to work. And so this is a self-induced injury that I’m angry about, and we’re going to make sure we get it fixed.

Notice the difference?