Let’s talk leadership

First, let’s get this out of the way: I’m not telling anyone how to lead. If there’s one thing that I’ve learned after so many years with Red Teams, it’s that no two environments or situations are the same. Leadership isn’t easy, and what works in one situation may backfire spectacularly in another. This effect is dramatically amplified during a crisis. I’m writing this as we’re in the early stages of grappling with the COVID-19 pandemic here in the US. People all over the world are absolutely in crisis mode, and we are starting to see everyone’s true colors, for better or worse.

Crisis definition from Merriam-Webster:

3a: an unstable or crucial time or state of affairs in which a decisive change is impending

especially: one with the distinct possibility of a highly undesirable outcome

During a crisis —any crisis— emotions are running high and information is scarce. People have a natural fear of the unknown, especially when decisions are potentially very consequential. In the absence of reliable information, people tend to grasp at anything in order to “fill in the blanks” and inform their decision-making…often with disastrous results. The below tweet is just silly, but clearly makes my point.


It’s no secret that people in leadership positions have a different perspective than those they lead, and even from those they follow. This is natural and indeed purposeful in a hierarchical organization, but it’s important to recognize this fact. Critical to this aspect is the leader’s comfort with ambiguity. This comfort is actually a requirement for people to develop as they grow in their careers. When a person is first starting out, they are still learning, require more hands-on management, and often direct specific tasking (e.g. “fix this bug ticket and submit a PR before lunch”). As the person learns and grows, they are better equipped to handle situations on their own, drawing on their own professional experience to solve new problems. Move high enough into the leadership ranks, and a person may have one goal to accomplish in a year or two…but that goal is huge and extremely vague (e.g. “increase our NPS score at least 20 points by next year”). What does this have to do with a crisis? Leaders are FAR more comfortable making decisions with imperfect or ambiguous information than the people they lead. This must be recognized quickly and addressed through frequent candid conversations in order to stem the flow of Fear, Uncertainty, and Doubt (FUD).


Effective communication takes work during the best of times. It does not come naturally, doesn’t get easier with experience, and is flat out exhausting in a crisis. But it must be done, or the wheels will come off your wagon quicker than you could ever imagine. How should you communicate? It depends on your leadership style, the organization you lead, and the situation you’re in. But, here are a few things that have worked for me.

  • Oversharing - I’ve touched on this before, but I think this is absolutely vital during crisis communications with your team. Your team needs to know that you’re human (with similar hopes and fears), you’re one of them, you’re all in this together, and you’re all going to come through this just fine, as a team. If you had not been oversharing before the crisis, you’re going to have to work twice as hard to earn their trust now…there are no shortcuts here.
  • Repetition - Whatever the message is, you need to repeat it, often. Don’t just say the same things over and over…change how you say it. Expound. Summarize. Provide detail. Change your medium (email, chat, phone calls, in person, whatever you can). Whatever it takes to get the message across, that’s what you need to do.
  • Listening - You need to talk a lot, but you need to listen a lot, too. As I mentioned earlier, your perspectives are different. The team has different concerns than you, because they naturally see things from a different point of view. Learn from this perspective and don’t dismiss it, or they won’t bother to tell you anything else.
  • Candid conversation - Don’t wing it. Bad information is almost as bad as no information. If you don’t know something, promise to find out, and then follow up. This is what you expect from them when you ask them questions, right? It works both ways.
  • Probe for concerns - This is almost an art form, or a variant of social engineering. Be mindful of how you request input, because you absolutely do convey your true intentions when you say things like: “ok if there aren’t any questions we can all get out of here.” Instead try something like “I know you have all been thinking about this, so what are your concerns?” If nobody speaks up, don’t be afraid to put someone on the spot with something like “hey yesterday I was asked a great question by X, so I talked to my boss and then her boss and here’s what I found out.” This shows that you’re not afraid to ask questions, you’re open to people approaching you with their questions, and you will do what it takes to get them an answer. That’s the kind of thing that builds trust.

Model Behavior

Confidence is contagious. If you’ve been communicating effectively, then you should now be on the same page with your team. Explain the challenges you’re facing together, explain how you think things are going to shake out, and then get to work. If they trust you, they’ll do the same, right behind you. Conversely, if your team sees you panicking and updating your LinkedIn profile, they ironically will probably land a new gig quicker than you. Then you’re in real trouble. It’s easier to just be who you want them to be.

We Can Do This

I’m sure after reading the above you’ve been re-living past crises with fresh perspective. Maybe you’re recalling how poorly a manager reacted to a breach. Or maybe you’re thinking back to triumph as a team with “the best boss ever.” Whatever it was, learn from it, and apply those lessons as we move forward with COVID-19. These next weeks are going to be tough, and your people are counting on you. You’re more ready than you think, and we can do this.