After serving as CEO of one of the Rockefeller family foundations, I spent several years acting as a stand-in CEO for a few different organizations. My role was two-part. I was responsible for keeping the organization running smoothly while also leading the search for its next permanent CEO. That included interviewing candidates and bringing the person I believed was best suited to the role to the board for final approval.
Over the course of those years, I interviewed dozens of people for senior positions, and I started every interview the same way.
I would look at the clock on the wall in my office, look back at the candidate, and ask one question:
“Could you please take the next 20 to 30 minutes and, in as much detail as possible, tell me everything you know about our company, our top three competitors, our industry, and where you see it in five years?”
If they couldn’t answer that question, the interview was over.
It still surprises people when I tell them how often that happened. Upwards of 80 percent of the candidates interviewing to lead a major company couldn’t go more than a few minutes before running out of things to say. The question wasn’t designed to trick anyone. It was designed to weed out the people who didn’t really want a career there. They just wanted a job. Anyone can show up ready to talk about their résumé, their leadership style, or their compensation expectations.
But someone who has studied your business, your competitors, and your customers is showing something far more valuable: genuine interest.
I learned that lesson early in my career. When I was right out of college and applying for a position at the foundation, I decided to take the process as seriously as a final exam. Instead of sending a résumé, I submitted a 28-page proposal with more than a hundred ideas for how I could help the organization succeed. This was 1989, long before the internet or artificial intelligence, so it took a great deal of research and effort to gather that information.
When I arrived to interview with Mr. Rockefeller, he told me that my proposal contained more good ideas than anyone in the organization had given him. Then he asked me only two questions:
“When do you want to start?” and “How much do you want to make?”
That experience taught me the value of thorough preparation.
A high-level candidate should be able to speak with confidence about your products and services, understand your vision and mission, and recognize how you create value for your customers. They should know your competitive positioning, the challenges facing your industry, and where new opportunities may be emerging. That level of preparation signals that they have done their homework and care deeply about the role they are pursuing.
I often told boards that this question was my filter for commitment. It instantly separated people who wanted a paycheck from those who wanted to make an impact. The ones who couldn’t answer weren’t bad people. They just hadn’t cared enough to prepare.
So here’s my advice:
The next time you are interviewing for a senior role, ask that same question. Let them take it as far as they can. Within half an hour, you will know everything you need to know.
I recently built a new landing page highlighting my updated sessions, created with association leaders in mind, but filled with insights that apply to any organization or business.
These programs focus on the future of leadership, building strong cultures, and executing strategy with clarity and discipline. I was honored to share this material at the ASAE Conference, where I was also inducted into the Speakers Hall of Fame.
Please fill out the form below to discuss your needs and discover how our solutions can drive your success.
We’re excited to partner with you.
