Keys to a Great Leader Interview

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If you’re trying to help leaders communicate effectively, it only makes sense to gain a better understanding of what makes them tick, as well as the experiences and mindset that they brings to their roles. 

Further, you want to be able to capture a leader’s voice – not only her style of speaking, but also her unique perspective on how she views the world.

Too often, communicators lack the information and insight they need to do that well. That’s likely because they really haven’t had the opportunity to get to know the leader in a truly meaningful way. 

The solution? Conduct a leader interview. I’ve often refer to this as “the Rolling Stone Interview” approach. Ideally, it’s a relaxed, far-ranging conversation with a leader that allows you to dig deeper into what he or she is all about. 

If you have a willing leader, there are some key benefits to this interview.  

For starters, it can strengthen your relationship. Through this conversation, you’re not only getting to know the leader better, but they are getting to know you—and hopefully gaining trust and confidence in your abilities to help them communicate effectively and more strategically. 

Beyond that, you get unmatched insight into their style and voice.  Some people are natural storytellers and understand how a good story can help amplify a point they are trying to make. Others take a more literal fact-driven approach to making their case. Getting a clear sense of this can help the leader communicate in ways that are more authentic.

I’d recommend conducting the interview somewhere the leader feels the most comfortable, and hopefully won’t be interrupted every five minutes. Some key ways to make the most of the conversation. 

  • Make your intentions clear: Let the leader know that the intent of this conversation is to get to know them better with the goal of gathering insights and background that will help them communicate better with a range of important audiences.

  • Do your homework: Like any good journalist, you should go into this interview well prepared. That means reading any background information and perhaps even talking to some people who know the leader well. During your research, look for anything that would be out of the ordinary that might be worth further exploration. For instance, if the leader of a nonprofit graduated with an electrical engineering degree that is some fertile ground to dig into.

  • Avoid any blindsides: It’s a good idea to send a list of prep questions ahead of time so that the leader has a good sense of the types of questions you’ll be asking, as well as some time to think about responses.

  • Don’t be afraid to veer off script: While prep questions are important, be open to following the conversation where the leader takes you. I’ve been in situations in which the person leading the interview is so focused on sticking to the prepared questions, that they miss a golden opportunity for a simple follow-up question or two that might yield valuable insights. At the very least ask the simple question, why? as a tactic to get the leader talking in more depth. Another good follow-up is to ask if they can think of any stories that illustrate a point they just made.

As far as questions go, pepper the interview with several that will help the leader get out of corporate-speak mode. Here are a few that are worth considering. 

  • What was your first job and what did you learn from it?

  • What were the turning points in your career?

  • Who has had the biggest impact/influence on your life – and why?

  • Have you had career mentors, and what were the most lasting lessons learned?

  • What was the biggest mistake you’ve made in your career, and what did you learn from it?

  • What do you love to do when you’re not working?

  • Who are your heroes?

Once you’ve completed the interview, make sure you get it transcribed. You should have a strong resource to draw from when the leader needs to deliver a speech, make a presentation, or craft a great CEO letter.

Want to explore further ways to improve leadership communications? Shoot me an e-mail and let’s talk.