Leadership: Studying Leaders in the Wild

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The only way to learn leadership is to lead. It looks so easy from the outside, but there’s a whole lot of moving parts, and the only way that you can master the craft is to get in there and try it.

Okay, how do you figure out what to try? How do you learn who good role models are for you? There are two ways. You can read books about leadership by people who have studied it. Or, you can do a little bit of your own research and study leaders in the wild. Leadership is situational.

To learn about leadership by studying leaders in the wild, you must study specific circumstances. Context is king. There’s a long, long list of leaders who succeeded in one place but failed in another. There’s an equally long list of people who failed at a bunch of stuff before they found the right spot.

Find Leaders to Study

The good news is that you don’t have to do a lot of the heavy lifting when it comes to finding leaders to study. There are battalions of journalists out there who do the work for you. They write for newspapers and magazines and websites. And every day, they churn out, literally, hundreds of stories about real leaders in real situations.

Just reading articles about real leaders in real situations will help you learn about leadership. But you’ll learn more faster if you ask some smart questions. Here are three of them.

What Was the Challenge?

Good business stories are about leaders who had specific challenges that they either met or didn’t. Analyze the challenge to learn lessons that you can use yourself. What issue did the leader face? How did it come to their attention? When they came upon the situation for the first time, what did they know? What did they presume?

Who Were the People Involved?

Analyze the people involved in the situation on all sides. What relationships with people inside the company turned out to be important? What about relationships with people outside the company?

You may have to dig a little to find some of the details, but it’s worth the effort. Relationships are critical. So is character. As many writers have said, “Adversity doesn’t build character, it reveals it.” How would you act? Who would you call on for help?

As you study, imagine a similar situation. Identify truth tellers you can ask for insight. Develop independent sources of information. Who are good problem solvers that you could enlist to help you?

What Did the Leader Know?

Analyze what the leader knew in the beginning. What did he or she know about the company or the industry or the political world that helped or hindered the leader?

Analyze what the leader did and what the result was. Think about what they could have done differently. Remember, they didn’t know how things would end up. They made the best decision they could with the information they had.

Sometimes you get lucky and a poor decision has a good result. Sometimes you come to a well-considered decision and have things turn out wrong. If you want to learn how to make good decisions, study the process as well as the outcome. Remember that luck and the competition both get a vote.

Look for knowledge gaps. Analyze the decision making. Figure out why the leader chose a particular course of action. What would you have done?

Dig Deeper

When you stumble on a particularly interesting story or one that seems to have a lot of lessons for you, dig deeper. Search the web for stories about the same leader, the supporting cast, similar situations, the company. The different stories will give you different perspectives and some different facts.

Bottom Line

You’ll become a better leader faster if you analyze how other leaders performed in real life situations. Make the process of discovering lessons from real leaders in real situations a habit.


All the major business publications publish stories about leaders in the wild. The business sections of local papers also publish stories. Here are some of the newspapers that I think do a particularly good job. The Sunday edition usually has the best stories.

Finding stories about real leaders in real situations is part of my normal routine. Every week, I publish five of the best I’ve found in”Leaders and Strategies in Real Life.

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