And Then What? Reveal Your Leadership Blindspots With This Question From A Top Gun


Hal Gregersen

January 8, 2018

Innovate or fall behind. Even in a world that’s getting more uncertain by the minute, where threats can come from anyone and anywhere, the competitive imperative for nearly all businesses is still that simple.

For former Navy Top Gun instructor and current director of business development at Progeny Systems David Markert, the toughest and most pivotal question is “and then what?” Since his childhood through his military career and now in his leadership role in the private sector, Markert relies on this one question to help him and others around him see the future, reveal blindspots and focus on the system.

In an interview for the MIT Leadership Series, I spoke with Markert about “and then what” and more. A lightly edited transcript of our conversation follows.



Gregersen: You’ve worked in a lot of systems throughout your leadership career in a lot of different contexts. From your work, your world, your story, what are a few things that matter most when it comes to leadership and managing in uncertainty?

Markert: Somebody once described an executive to me as someone who must manage things they’re not an expert in. It’s probably a very good definition. You can have a background in a lot of different things, but you can’t be an expert in all things. All you can do is figure out what ground truth is. The military has a planning process that many think is rigid and perhaps not suited for modern day. It’s called “Courses of Action” and you’re supposed to present to the Commanding General three courses of action – distinct, different courses of action – as if they’re plausible and feasible, and how you would staff them. In weighing the best course of action, the General asks a lot of questions. Same goes for business leaders. What are other ways to do this? What are other ways to solve this problem? Are we doing something we’ve always done because that’s the way we do it or are we doing something different and unique? Or are we doing something because it’s the right answer?

Gregersen: That’s a great take on leadership and questioning. We’ve been studying the leadership styles of MIT-trained leaders and found that a common thread is deep expertise and broad working knowledge. These leaders gain their legitimacy because of their “T-shaped” knowledge, combining (often technological or scientific) expertise relating to the problems at hand with significant knowledge of the other domains across which that expertise must contribute. Questions are key to getting at those areas you might not necessarily be expert in. As you progressed in the military in the hierarchical sense, did you find yourself asking more questions or just different kinds of questions?

Markert: Even to this day, I find myself asking more people more questions. Let’s take a group of people. The person who talks the loudest and perhaps first, wins. The guy sitting in the corner has really good observations, but unless you say, “Hey, Bob! What do you think?” you might not know it. You must make sure you’re open enough to absorb the answer, to truly understand and listen to what they’re saying. This is how you get a diverse option set, and from there, make decisions.

In the Navy, there was an older leader who used to call it, “management by walking around,” which is right on. He’d be walking around the aircraft carrier, see the Admiral and say, “Aren’t you supposed to be on the bridge making big decisions?” Instead he’s down on the hanger talking to the sailors. He’s coming up to you as you’re manning up your jet going, “What are you doing? Will you see problems with what you’re doing here?” Very approachable, very empathetic individual who got his understanding of what was going on just by walking around talking to people. So, when I say that I ask more questions of more people, it’s essentially “management by walking around.” Filling in the pieces you don’t know.

Gregersen: You mentioned this notion that as you get closer and closer to the top – say, of an aircraft carrier or of a business organization – you’re leading people who know things you don’t. It’s a classic leadership conundrum. How do you systematically probe what you don’t know you don’t know?

Markert: There are some theories and thoughts that say you surround yourself with at least one or two devil’s advocates. The person or people who will always challenge you, who will always say black when you say white. Personally, it’s been hard to find that person; it’s also hard to accept those challenges all the time, every day. But it is easier to find people who think differently than you. If you understand who you are, and you’re honest with yourself, and honest about your strengths and weaknesses, you can find and count on people who think differently. You can rely on them to say, “Did you think about this?” “Did you consider that?” They’ll offer solutions you haven’t thought of because they’re independent thinkers. And that’s enormously valuable – for you as a person and as a leader, and for the organization. When you find that person or people, hang on to them.

Gregersen: You hit on an important point about building diverse teams and expertise. That requires a high tolerance of team members’ idiosyncrasies. Once you’ve found these people or “devil’s advocates” as you put them, what kinds of things can you do as a leader to keep them engaged and motivated toward solving the big problems?

Markert: People latch onto things because they want to be part of something bigger than themselves, something that leaves a legacy that perhaps you couldn’t otherwise do on your own. Make sure your folks, and particularly your counter-cultural thinkers, understand their value and worth because being the person who swims upstream all the time when the salmon are coming downstream takes its toll. You need to say to that person, “You are valuable. You are important – to me. I value your thoughts even though you might be the lone person crying in the wilderness.” That’s enormously important.

Gregersen: Clearly you have several different, articulated strategies to answer this pivotal question: “How can I get to my blindspot so somebody doesn’t get to it first?” A lot of that comes from your military training, work, background, career – but was there anything earlier in life that also primed and prepped you to approach leadership the way you do?

Markert: I’m number three of six kids and, of my siblings, the only one who went into the military. My parents are still scratching their heads. My father was an engineer, a very good thinker, a very demanding person. He had an egalitarian approach to parenting, like one size fits all. With six kids, he had to. My father would probe and ask questions until he found the weakness. He wasn’t looking for the personal weakness; he was looking for the fault in the system – like an engineer would. So he asks and questions and asks until the moment you say, “I don’t know.” As a youngster, it became a personal challenge. “Let’s make the questioning go on as long as possible. How long can I say, ‘I’ve got the answers. I’ve thought this through.’ How many questions can he ask me before I have to admit, ‘I don’t know.’” As I look back now, he forced me to ask and answer those, “And then what? And then what? And then what?” questions.

Today, I think about it as the third or fourth or fifth level knock-on effect. The follow-on effect of a single decision that ripples through the entire system. Even if you’re asking it of yourself, “And then what? And then what? And then what? And then what?” If you can get to the third or fourth “And then what?” you’re probably doing okay.


This article was written by Hal Gregersen from Forbes and was legally licensed through the NewsCred publisher network. Please direct all licensing questions to

Great ! Thanks for your subscription !

You will soon receive the first Content Loop Newsletter