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21 Apr. 2015 | Comments (0)

I often get the chance to work with emerging leaders in corporate leadership development programs. The programs that I co-design make liberal use of the concept known as “leaders as teachers” wherein a lot of the content is taught by the company’s own senior leadership team.  From an experience and “realism” perspective, it’s hard to beat the hands-on knowledge and expertise that senior leaders bring to the classroom.

One of the highlights of the “leaders as teachers” format is a session with the CEO. Interacting with the CEO gives participants a chance to get his or her perspective, ask a lot of questions, etc.  It also gives the CEO a chance to spend time with the next generation of leaders.

Generally, the CEO will speak for about 20-30 minutes, then take (or ask) questions for 40-60 minutes. It’s usually a win-win for everyone, as the CEO gets a chance to drive the vision and mission deeper into the company and in the process, learn what’s on the minds of emerging leaders. Likewise, the participants get to spend time with the top boss, share what they’ve been learning in the program, and ask really provocative questions. I’ve probably seen 25 or more of these interactions, and what strikes me is the consistency of the questions the CEO gets. In fact, three questions always seem to come up. Because I think there’s a good chance you could be asked these questions, I offer them here to help you prepare in advance.

Three Questions:

1) What keeps you up at night? I’m not sure where this question started, but it is a standard for Q&A sessions with senior leaders.  In the exchanges I’ve observed, it generally comes up pretty early in the session. Not surprisingly, most CEOs have heard this one before and are ready for it. Some say “nothing”, but most are honest and cite a few things that are worrying them. Typically, its things they don’t know or can’t do much about. What’s the competition doing? Where’s the economy going? What could cause cost of sales to go up next year?Where will we innovate?

So, what keeps you up at night? What are you worried about, planning for, asking yourself about?  Is it the competition, your products, services, employees, the economy, funding, etc? In a strict sense, hopefully nothing is – after all, a good night’s rest is critically important to your energy level. But you get the idea – what’s on your mind? It’s best to anticipate this question and have an answer ready, rather than stumble through a weak “I don’t really know” response. 

Trust me, you’re going to get this question – be ready for it.

2) What has been your defining moment as a leader?  What a great question!  It’s a lot rarer than the “keep you up at night” question, but I do hear it asked now and again, usually from a very bright participant who is really into leadership stories. CEOs that nail this question generally tell an unflattering story about themselves – a time when they learned a hard lesson. 

Usually, it’s early in their work life, and has some profound effect on the trajectory of their career (often times, it involves a mentor who helped guide them to the right answer). 

What is it for you?  What’s that crucible that really tells the story for you? Could be a mistake… could be a crisis… could be big bet or a risk that worked out. Think about this one – it will say a lot about what you’ve learned from your leadership journey. And if you want to set an example of lifelong learning, make it something that reinforces the importance of learning from your experiences.

3) What do you want your legacy to be?  Another great question, usually asked of CEOs who are nearing or in their “last job.” I think CEOs really like this question, because it allows them to put a fine point on what their tenure has been all about. The CEOs I’ve heard usually say the right thing – something about people, excellence, growth, or stability.  It’s an interesting question, because the answer reveals a lot about the CEO’s philosophy of leadership. 

So, how would you answer this question? How do you want to be remembered as a leader? Does it have something to do with building products, tools, or processes? Does it have to do with creating new markets or partnerships? How about building capability, and leaving behind a host of great leaders for the next 20 years? Think carefully about your answer to this question – if you can envision what you want your legacy to be, you’ll have a greater chance of actually making it come true.

Hopefully, this helps you prepare for your next all-hands meeting or encounter with a large audience. Give some thought to these three questions before your next Q&A session with employees.  Whether you’re about to go in front of an audience or just want to reflect on your leadership experiences, these can be great questions to prepare for in advance. Good luck!


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  • About the Author:Steve Arneson, Ph.D.

    Steve Arneson, Ph.D.

    Steve Arneson founded Arneson Leadership Consulting in 2007 to provide executive coaching, talent management, and leadership development solutions to corporations and non-profit organizations. Steve …

    Full Bio | More from Steve Arneson, Ph.D.


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