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The courage to say, “I don’t know”

4 min read


Interviews and panels at conferences tend to go one of two ways: The speakers are engaging, prepared, skillful and interactive, or they are dull, don’t mesh well with each other and have little new to say. In both cases, and even on all but the best of the best panels, the speakers are all tremendously confident their opinions and projections are correct, and they substantively agree with one another.

Keep this in mind when I say that, having gone to dozens of panels over three years at the Milken Institute Global Conference, I’m having trouble recalling any panelist ever saying, “I don’t know” in response to a question about a relevant, if tricky, aspect of the business. And I’m certain I’ve never heard anyone say it multiple times like J. Crew CEO Mickey Drexler did Wednesday during his interview session.

First, some background. Let’s not pretend Drexler lacks self-confidence or doesn’t take stands. His continued use of “this is just my opinion” was more of a weapon than a disclaimer — closer to a “this isn’t hard data but I’m right anyways” approach. Drexler is an unconventional but tremendously successful figure in the industry. CEO of three major brands in the past few decades; he’s created brands (Old Navy, for instance), revived others, and he does so with the sort of hands-on control that is usually not recommended for senior leadership.

But he was also in Wednesday’s session unusually interested in what the crowd had to say, what it was doing, in asking follow-up questions about the audience, their jobs, their lives — questions that are rarely asked of other panelists, much less audience members. He good-naturedly chastised Alex Rodriguez, who showed up late and cut across to front and center. Drexler polled the audience a number of times, and repeatedly went to one of his staff for answers he couldn’t remember or for insights into his personality and leadership.

When asked about his biggest mistakes, he talked for several minutes, largely around the topic of bad hires, with the lesson learned that you have to move on, but hopefully smarter. But he also separated avoidable mistakes (a hire not thought through) from less avoidable mistakes (not quitting a job he hated early on because he needed to pay the bills).

So far, this is the profile of a gregarious CEO who knows he is in a customer-centric industry and is comfortable talking about himself and with others. But, and this is what caught me off-guard, he twice said “I don’t know” in response to questions about the future — one about the broader future of the industry in a Web and mobile era, and the other about specific J. Crew expansion plans. These weren’t a version of “no comment”; instead, each answer lasted a few minutes, but with the understanding that, well, Drexler wasn’t really sure, but darned if he doesn’t have an opinion, a hope and/or a plan either way. He was thinking about the question, neither avoiding it nor thinking he had solved it.

And that’s fine — saying “I don’t know” doesn’t have to be so scary, legally or otherwise. More of us should acknowledge that we cannot reliably predict the future. Other times, “I don’t know” is a welcome acknowledgement of the complexity and contextual problems in life. A 30-second answer isn’t always possible, and saying so doesn’t automatically mean you’re going to suffer from paralysis by analysis.

What can you take away from this small example by the CEO of J.Crew? Well, I can’t tell you how he is all the time, or how he is at the office. But on Wednesday, there was an hour where he was the center of attention but consistently sought to hear from and listen to others, all while not confusing status for genius, or accomplishments for vision. Are you doing that with your employees? Your clients and customers? Yourself? Do you even know? Find out, and act accordingly.