9 Questions to Ask Leaders

Imagine you are getting onto a plane and are headed to Colorado for a business trip. As you sit down, you realize that you are beside none other than Richard Branson. A million things go through your mind and all of a sudden you think, “what the heck should I ask this guy?!”

As an aspiring entrepreneur, I have met with many leaders and successful business owners. When I first began taking these people out to lunch or simply sitting down and speaking with them, I was unprepared and unsure of how to make the conversation a fruitful one for both the leader and I. Over time, I began to realize that I was wasting his or her time as well as mine, and I did not leave a good impression on the people I was meeting.
After a few months of this, I was given some great advice from someone I look up to that had been where I was. He told me that leaders are prepared, they have a plan, and their complete focus is executing on that plan. He also told me that networking and gaining knowledge needs to fit under the same parameters—that when I get the opportunity to talk to someone of influence, I need to make the most of it. I then took this advice and crafted some questions that I knew I would want to hear from every person that I talked to, and at this point I have dedicated them to memory.

I call these the necessary nine, and you are more than welcome to use them when talking to a fellow business owner that you look up to.

1.What do you believe are the characteristics and actions that you used to get to where you are today?

2.Looking back on your journey and knowing what you know now, what is one piece of advice you would have given yourself along the way?

3.Which is most important to your organization—mission, core values or vision?

4.How do you ensure your organization and its activities are aligned with your “core values”?

6.What is one characteristic that you believe every leader should possess?

7.What is the biggest challenge facing leaders today?
What is the one behavior or trait that you have seen derail more leaders’ careers than any other?

8.What are a few resources you would recommend to someone looking to gain insight into becoming a better leader?

9.What are you doing to ensure you continue to grow and develop as a leader?

Write the answers down as you hear them (or at least record the audio), so that you will be able to look back on these interviews and glean the knowledge that these leaders have spoken into your life.
These questions are in no way comprehensive, and I would even encourage you to bring your own twist to every person you talk to. You will know, based on the industry they are in, what wisdom they can impart based on the knowledge they have gained from that field. When you get on that plane, be confident about talking to Richard and let him see that you mean business!
There is a wealth of information out there waiting to be tapped, but most leaders will stay silent until you ask them the right questions. Go out there armed with some great questions, have the courage to approach those you admire, and see what you can dig up! If you have any other questions that you often like to ask other leaders, please email me or leave a comment letting me know your thoughts!

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