Get the Most Out of Experts with These Two Questions

At this stage of my career—after more than twenty-five years as an entrepreneur and CEO—one of the most fulfilling parts of my week is meeting with other entrepreneurs. Whether it’s through office hours at Capital Factory or meetings in my office at Khorus, I enjoy giving what guidance I can. My hope, as always, is to help leaders steer away from the mistakes I’ve made along the way.

Most of the time someone books a meeting it is to get an answer to a very specific business problem.

How should I price this product?

How can I ensure that this make-or-break deal goes through?

What market should we attack first with our new product?

I remember early in my career when I was looking for similar answers. Along the way I got to meet with some very successful business leaders. What I realized was that while they had great expertise in certain areas, that did not make them experts about every business challenge. No one, no matter how successful in business, is an expert in all areas.

The entrepreneurs I meet with typically think that because I’ve been a successful CEO, I should be able to give them the right answer to any question. But the humbling truth is that I have sometimes given my thoughts on an issue, watched the person write them down, and then, as I hear their car rumble out of the parking lot, worry that they will actually take the advice. Many times, the advice seekers I meet with could get an equally useful answer to their specific business question from a random person on the street.

I’ve been a CEO. That means I might know a thing or two about being a CEO. It definitely doesn’t mean I know all about pricing or sales or marketing or whatever the issue at hand is. As CEO, I had people in those functions who knew much more about them than I do. My job was to lead them as a coherent team, not to do their jobs for them.

As I thought about this dynamic, I realized what the people I meet with should be asking me. Instead of seeking my insight on the hyper-specific issue they face, there are two questions that would help them get the most value from their time with me—or with any other expert or mentor they meet with.


1. If you had my problem, who would you take it to?

 John Maxwell once said, “The best way a mentor can prepare another leader is to expose him or her to other great people.” This first question reflects the truth in that statement.

While I might not know exactly how you should price your new service package, I definitely have the name and number of a pricing guru, someone who I consider world-class in that area. And I don’t know anyone who would turn you away when you come to them with, “So-and-so told me you were the world expert on pricing—can I get your take on this?”

If you have a specific problem you’re trying to solve, by all means, take it to your mentor or someone you trust. But don’t assume that their success in one domain gives them special insight into other domains. Instead, ask them who they would take your problem to if they were in your shoes.


2. What is your area of expertise, and what do I need to know about it?

Every successful person I’ve known has been really good at one particular thing. They might be good at other things too, but on that one issue, they have information that 99 percent of the population doesn’t.

When you meet with an expert or mentor, your second mission (after getting a referral to the person who can solve your most pressing problem) is to understand that person’s highly specialized expertise and glean what you can from it.

For me, it’s the specifics of the CEO role. I’ve practiced that role for decades, written a book on it, and have no hesitation consulting people on how to approach the job. I might have an opinion on how you could land your white-whale prospect, but I’m not a reliable source on that. It would be like asking a high-earning bartender how to grow hops—they seem related, but you want to know what the top-tier hop farmer knows about hop farming and what the top-tier bartender knows about bartending, not vice versa.


Use these two questions next time you meet with an expert or mentor. When used well, they can unlock gems of knowledge you never would’ve gotten otherwise—and prevent you from getting “expert” advice that is anything but.

Share on facebook
Share on twitter
Share on linkedin

Comments are closed.