How to lead others to excel is a question that preoccupies Craig Robinson. He has been an investment banker and entrepreneur, and re-invented himself as a college basketball coach at the age of 38. With close personal proximity to Barack Obama, Robinson also assesses—from close up—what's at the core of the president's leadership style.

From modest circumstances growing up in Chicago, Robinson vaulted to stardom as a basketball player at Princeton University. His business career was humming along—MBA from the University of Chicago Graduate School of Business; vice president at Morgan Stanley Dean Witter; and co-founder of a start-up investment firm, Loop Capital Markets—when he had a change of heart.

In 2000, he became an assistant basketball coach at Northwestern University. Six years later, he progressed to head coach at Brown University. He has been in his current post, at Oregon State University, since 2008. Robinson has earned accolades for lifting two teams out of the doldrums, and records he achieved at Brown in two years (30-28) and Oregon State in three (42-55).

Last year Robinson recounted how he made it in his memoir, A Game of Character: A Family Journey from Chicago's Southside to the Ivy League and Beyond. He recently spoke with contributor Joseph Rosenbloom about coping with setbacks, getting to No. 1, and Barack Obama.

You quit a career as an investment banker to accept a job as an assistant basketball coach at Northwestern University at one tenth of the salary. Why?
I was coaching part-time in youth leagues and high schools. My business success, albeit good—in fact, maybe even grand by some measures—wasn't bringing me the kind of pleasure and joy that I felt when I was coaching.

Both Brown and Oregon State are turnaround stories? How did you do it?
What we try and do is accomplish everything we want to do in a very hard, organized manner, like what you have to do in business. As the leader I try to delegate to all of my assistants responsibilities that will enable them to become head coaches themselves.

You've said that your Princeton coach, the legendary Pete Carril, was a genius at player development. But you also describe him as a curmudgeon who rarely gave compliments. What about that leadership model?
It worked for that era, that time. Kids are so different now. They are so used to not getting negative feedback. I think I'm more positive than negative. Coach Carril was big on negative character attribution.

You've referred to his style as character assassination? 
Right. He would kill you on your character. What I try to do, rather than kill you on your character, I try to build you up so you will develop a better character.

One of your techniques is what you call weekly open evaluations? How does that work?
At the end of practice the players sit down on the bench, and I go down the line. I do two to three minutes on each player. The only people who hear it are our staff. I don't want it to be a public flogging or a public admiration society. It is just for us.

What purpose does it serve?
It puts you in the best position to be successful, because you know what is expected of you. You know where you stand in the hierarchy. So you know what you have to do to get to the number one spot.

When I was in the business world, I tailored the tool. For people who aren't athletes sometimes that approach can be a little bit embarrassing. But I always kept in my mind letting people know, as honestly as I could, where they stood and what they needed to do in order to progress.

Your nickname is The Edge. What does it signify?
I'm always very quick to the point and very matter of fact. It comes off as kind of edgy.

Even when Barack Obama was a young law student and dating your sister, Michelle, you say that you pegged him as an inspired leader. What was it about him?
My sister asked me to play basketball with him and report back to her. When I got him out on the court in a pickup basketball game, I saw his character traits. He was honest, hard working and team oriented. He had high integrity.

What do you make of his leadership style off the court?
I absolutely love his demeanor, his calmness under pressure. He never seems to get rattled. On our team we call it body language. You want your body language to exude that you're going to win this game—or solve this problem.

Is that teachable or innate?
What you're teaching people is to act—sometimes. You're going to be stressed out—sometimes. I know I am in some games, and I was sometimes when I was a bond trader. You can't let that show. I think that's a character trait that you can learn.

With two other guys you started Loop Capital Markets, a minority-owned investment company in Chicago. What leadership advice do you have for African-Americans or members of other minority groups who are starting a business?
We're still in a time when being African-American can be viewed as a hindrance, especially in the business world. I've always found that you have to work a little bit harder to prove yourself when you're African-American. There's nothing wrong with that. You just have to be prepared for it.

And that goes for entrepreneurship?
Absolutely, especially for entrepreneurship, because your business is meeting people and customers. Your customers aren't going to be all African-Americans or people of color. Many of your customers aren't going to give you the benefit of the doubt.

Your team at Oregon State had a losing record of 10 wins and 19 losses this past season, worse than in your first two seasons as a coach there. How do you deal with that setback?
I'm pretty honest in evaluating myself. As long as I can point to where the issues are and they are correctible, I don't get too down on the team or myself. When you're rebuilding a program, it's not something that's going to happen in one or two years.

When I reevaluate at the end of the year, I ask if we're headed in the right direction. If I'm comfortable with that and we keep doing the fundamental things correctly, we'll get there.