It is the job interview question that we all dread the most: what was your biggest failure? And according to Jeff Stibel’s recent Harvard Business Review article entitled, “For President, I Want the Guy Who’s Failed,” it is the most important question to ask both candidates who hope to lead our country for the next four years. Indeed, one true test of leadership skills is the ability to acknowledge and learn from one’s own mistakes. But that quality alone is not enough to go on. What questions do we need to ask our potential leaders?

Asking About Leadership Skills

1. “What’s Your Biggest Failure?”

Stibel insists upon asking such questions of potential job candidates at his company, because he believes that “you learn more from failures than you do from success, but only if you are willing to admit and own up to those failures.” The nature of contemporary politics often seems to be self-promotion and finger pointing, rather than owning up to one’s mistakes. But imagine the management development lessons we could gain from leaders being open about their failures!

2. “What’s the Biggest Risk You’ve Taken, and Would You Do it Again?”

Moving forward in a business or in a government involves weighing option and taking risks. Even if a risk ultimately results in failure, that situation can teach important lessons. As a result, Stibel insists that “calculated risk-taking is important” and is one of the leadership skills that we should expect from our president, as well as our business leaders.

3. “When Have You Taken an Unpopular Position Against Special Interest Groups?”

One crucial management development skill is standing up for what is right even if it is unpopular. This is not only an important attribute for a manager in a company, it is important for the person who manages our country. Stibel says, “I want a candidate who can demonstrate that he has taken a position that serves the broader public in the face of adversity.” In our world of constant commentary through polling and social media, it can be all too easy to be distracted by popularity contests.

4. “What’s the Most Unconventional Thing You’ve Done?”

One especially important leadership skills is being willing to break the mold and think creatively when it is necessary. No matter what position you are in, this characteristic is predictive of future success.

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