Tips on Answering “What’s Your Biggest Failure?” – Barack Obama and Oprah Winfrey’s Approach

After reading the news, I wondered: what’s the best way for Obama to address the failure?  Or perhaps to word this in a context more relevant to our readers, how would Obama answer the popular job interview question, “What’s your biggest failure?”

Coincidentally, I read Oprah Winfrey’s 2008 commencement speech to Stanford graduates earlier today, and she gives us some inspiration on how to tackle this challenging question:

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.

When it comes to address one’s failures, Oprah’s response is as perfect as it gets.  I mentioned the springboard technique in a previous post, and Oprah uses it very well here.  The focus here is not what happened in South Africa.  Instead, the main takeaway message is that she is a strong, capable leader.  She makes mistakes like we do, and when faced with mistakes, you can fully expect her to:

1. Be honest and acknowledge the situation.
2. Demonstrate empathy to those who have been hurt.
3. Take action and fix the problem, giving others confidence that this is unlikely to happen again.