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Leadership Under Pressure: Michèle Flournoy on Decision-Making in Uncertain Times
When the stakes are sky-high and the path ahead is foggy, how do great leaders chart the way forward?
That was the central question I posed to my mentor, Michèle Flournoy, former Under Secretary of Defense for Policy and current Managing Partner of WestExec Advisors, in a recent conversation for this leadership series. Michèle has been at the decision table during some of the most consequential national security moments in recent history, including the Bin Laden raid, and her insights are powerful guides for any CEO navigating risk, ambiguity, and urgency.
Here are three essential leadership takeaways from our conversation:
1. Listen First, Decide with Foresight
The best leaders don’t pretend to know everything, especially when the stakes are high. “The first rule of thumb,” Michèle said, “is listen. Try to listen to the experts. Don’t assume that you know everything or more than others do, even though that may well be the case.”
She stressed the importance of creating an environment where dissent is not just allowed but actively encouraged. “You will almost certainly have to make big decisions without 100% clarity,” she noted. “These decisions aren’t like checkers. It’s more like chess. You have to think two, three, four moves down the road.”
Her example? The decision to launch the Bin Laden raid, arguably one of the most significant U.S. national security calls of the past two decades. “At the end of the day, the President had to decide based on circumstantial evidence. There was no direct proof that it was Bin Laden. And there wasn’t consensus. But waiting could have meant losing the opportunity altogether.”
2. Encourage Dissent and Avoid Gatekeepers
If your team is afraid to disagree with you, you’re flying blind.
“Never shoot the messenger,” Michèle emphasized. “If you do that in front of others, the signal is clear: dissent is dangerous. And then they won’t bring you the truth.”
She shared a powerful example from the White House Situation Room, where President Obama would deliberately seek out quieter or less vocal advisors, even those seated in the back of the room. “He’d say, Michèle, you look like you don’t agree.’ That level of solicitation made it safe to speak up.”
Michèle also warned about the dangers of gatekeepers. “One of the biggest risks in large organizations is that their inner circle becomes barriers to information instead of conduits. A good advisor ensures the best experts are heard, not just that they themselves are in the room.”
The antidote? Leaders must intentionally create a culture of access and insight. “Sometimes the best thing I could do as Under Secretary was to say, ‘You don’t want me, you want our China expert. She knows the issue best.’”
3. Know When to Decide and How to Manage Risk
So how do you know when you have enough information to decide?
Michèle offered a crucial reminder: “Not making a decision is making a decision. And it carries its own risks and opportunity costs.”
To strike the right balance, she recommends being clear about the goal, understanding the range of options, identifying knowns and unknowns, and evaluating second- and third-order consequences. “I like tools like tabletop exercises and red teaming. They help you pressure test your assumptions and buy down risk.”
She returned to the Bin Laden raid to illustrate: “One of Secretary Gates’s biggest fears was a helicopter going down. And when one did, he blanched. But we had planned for it. We had fallback options, other helicopters in Pakistan, rehearsed contingencies. It didn’t eliminate the risk, but it managed it.”
And when it came to influencing a senior leader like Gates to shift his position? “You’ve got to be willing to be the skunk at the garden party,” she said with a smile. “We walked him through the facts, the risks, the contingencies. And to his credit, he changed his mind.”
Final Thought: Courage to Lead Means Courage to Rethink
As Michèle put it, “Great leaders are willing to change their minds when presented with better evidence. That’s not weakness, it’s wisdom.”
Whether you’re running a company, leading a team, or preparing for your next high-stakes moment, these insights from Michèle Flournoy offer a battle-tested blueprint: listen deeply, welcome dissent, decide with clarity, and never stop learning.
P.S. As you are navigating tough choices in your business or leadership role, remember this: common sense is like oxygen: it gets scarcer the higher you go, but you can keep it flowing by doing exactly what Michèle suggests.
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