Podcast: How Letting Teams Fail Can Help Them Succeed
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Leadership Jan 25, 2023

Podcast: How Letting Teams Fail Can Help Them Succeed

It can be tempting for leaders to swoop in to solve problems. On this episode of The Insightful Leader, we hear from a U.S. Army colonel about why doing so is a disservice.

Based on insights from

Fredric Maddox

Listening: How Letting Teams Fail Can Help Them Succeed
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For a leader, there’s a fine line between helping people and doing their job. When a mistake carries high costs, that line can get blurry.

Still, it’s important to step back and allow your team to fly—and even fall—says Colonel Fredric Maddox, an assistant professor at the U.S. Army War College and Chief of Staff of the Army senior fellow at the Kellogg School.

If you don’t, he says, “you’re actually pulling back all the opportunities that you can give your team to actually succeed and prove that they’re capable.”

In this episode of The Insightful Leader, Maddox explains how to loosen your grip on the wheel and trust your team more.

Podcast Transcript

Laura PAVIN: If you’re a leader, it’s probably because people see you as someone they can rely on to get a job done. The problem comes in when you start feeling like you’re the only one who can do it. So then you start doing it for everyone else.

Fredric MADDOX: If you’re focused on doing the tasks they’re doing, you probably aren’t seeing the other issues that are out there that would help you resource them better, as well as prepare the organization.

PAVIN: That’s Fredric Maddox. He’s a colonel in the Army, where he was awarded the Defense Superior Service medal for his work overseeing operations at the Defense Logistics Agency. He teaches leadership at the U.S. Army War College in Pennsylvania. And he’s also the U.S. Army Chief of Staff Senior Fellow here at Kellogg.

So he knows as well as anyone that the temptation to swoop in, help, and micromanage your team is sometimes really hard to resist.

But Maddox says getting too into-the-weeds with your team’s day-to-day just ends up hurting everyone.

MADDOX: You’re actually pulling back all the opportunities that you can give your team to actually succeed and prove that they’re capable—and more capable than what you have.

PAVIN: You’re listening to The Insightful Leader. I’m Laura Pavin. This episode, we’ll look at three solid steps you can take to get better at stepping back. You’ll want to consider the unique abilities of each person on your team, give them the training they’ll need to succeed, and finally, give them the opportunity to fail—as safely as possible. That’s next.


PAVIN: Maddox remembers a time when he was observing a meeting between the higher level staff on a team. There was a general officer who was tasked with fixing a problem on a deployment in Afghanistan: The problem was that service members weren’t getting the support they needed in a timely and efficient manner.

MADDOX: So the general officer walks the entire staff through his thought process of what needs to occur. And then to everyone’s surprise, he says, “we’ll conclude the meeting, and then I will be at this location to begin the mapping process.”

PAVIN: So the general officer goes into the field to watch how people and equipment were moving throughout the system, how well paperwork was filled out, and how much time it took to do all of this. And he comes back to the meeting with instructions on what should change. Then, he went out again and came back with more instructions. And all this time, Maddox is watching this happen.

MADDOX: The first thought was, “wow, I can’t believe he took the time to do that. That is amazing.” And then in hindsight, after a little bit of time passed, I was like, “wow ... he took all of that time to do that...”

PAVIN: There were officers in the room who could have told this general officer what was happening on the ground, Maddox said—particularly if they knew exactly the kind of information he was looking for. Not letting them go into the field and report back themselves was unwise, and honestly kind of embarrassing.

MADDOX: As the senior leader, his responsibility is to see the bigger picture.

PAVIN: And that’s the first lesson Maddox wants to get across to managers who tend to want to do everything for everyone: step back and consider the expertise in the room. What’s everyone’s responsibility, and how do they fit into the overall picture of your organization? Knowing this allows you to delegate and have more time to plan around your team’s bigger-picture goals.

But failing to delegate not only hurts your ability to drive the team forward, it also hurts your team’s morale.

Maddox brings it back to the general officer and his team.

MADDOX: Now they all lost trust in their own abilities because it takes a general officer to do the tactical work of figuring this out. And I was like, “I would really not want to be a member of the staff because you’re doing my job.”

PAVIN: So if you want to get better at stepping back, know your team’s capabilities and then, well, step back.

Of course, delegating doesn’t mean abdicating: you are still ultimately responsible for your team’s success. So just how close should you, as a leader, be to a problem in order to lead your team to a solution?

This will differ depending on the problem. For example, if failure could mean losing a client that’s very important to your organization, the situation might demand more of your attention.

But if you’re finding that every problem seems to require a lot of your attention, the real problem could be that you haven’t done enough work on the backend to ensure you do trust your team to handle whatever arises.

And that’s where step two comes in: train your team! It’s what Maddox did when he first went into battalion command, when he took over for a different commander.

MADDOX: Within the first month, I realized that there was an issue: I had leaders who were not being trained to lead their formations.

PAVIN: They had been trained on what to think, and not how to think, Maddox said. So he had them do exercises, and one of the key things they did was come up with a succession plan—figure out who would lead if something happened to the commander. And in those exercises, Maddox would have them determine the course of their own training. They would figure out where they were weak and how they wanted to address that, and based on their own insights, they would come back to Maddox and tell him what resources they needed to conduct this training. And Maddox would provide it!

MADDOX: I’d like to believe that every one of those commanders that left after being underneath me understood how to kind of walk in their autonomy. And I know it worked because in the last exercise we had, one of the companies said, “um, hey sir, look, we’ve been doing it this way the last couple of exercises. We want to break apart from the organization and do this for this exercise.” And I was so tempted to say “no.”

PAVIN: To set the stage, the exercise involved running a perimeter defense where the organization had to prepare for—and repel—attacks from all directions. And this particular company wanted to run its own perimeter separately from the rest of the battalion.

Maddox knew this was a bad idea because, in these scenarios, all units share the burden of this perimeter defense together. They can rely on all of the assets from the battalion to respond to attacks or issues in their area. Setting up separately would deprive the company of a lot of this support. And it would require individuals to take on the support roles that the battalion would have provided. On top of that, they would also have to defend their own perimeter themselves.

But even though Maddox knew it was a bad idea, he also knew that this company needed to realize that it was a bad idea on their own—and why.

So Maddox said ...

MADDOX: “Okay, give me your plan. We’ll run it and we’ll do it.” They briefed me. I said, “okay, you think it’s gonna work? Let’s do it.” They broke apart. We’re here; they’re there. It didn’t take long for them to understand why I wanted them to be a part of the group. I knew it would not work, but I had to allow them the opportunity.

PAVIN: And that’s the beauty of training! When you train your team, you can simulate really critical situations that they may one day encounter.

Maddox says you can turn almost any task, action or concern into a drill. For example, if a vendor calls and is unhappy with the service they received, you could create a drill that would talk the team through what should happen when the vendor calls. It would cover who is responsible for each task and how long it should all take. And then everyone would practice that.

This way, your team learns not just how to respond a certain way, but why they should respond a certain way. Because you gave them a safe environment to fail in.

And that’s our last step on our journey towards relinquishing control. Allow your team the chance to fail. We can learn really well from failure—at least when that failure is framed as situational, or part of the process of developing expertise, rather than a reflection of who we are as people.

MADDOX: What happens in that failure and how you treat the failure matters tremendously to what occurs next with the team. And so typically, if a team fails, good leaders will say, “okay, team, let’s look at what happened. Let’s identify the issue.” It should never be, “oh, you guys suck. You’re the team that failed me and that’s why I got to come in and do all the work.”

PAVIN: Reprimands aren’t great teachers—especially when they come without proper reflection. And it’s probably safe to say that using humiliation as a primary approach creates a pretty toxic workplace culture. So Maddox suggests creating opportunities for your team to fail in low-stakes scenarios. That way, they’re less likely to fall on their face when it really counts.

In the end, to lead a team successfully, you need to be able to step back from the smaller tasks so you can do more leading. So take the time to build a team that you can trust. It will be worth it: for them, for you, and for your organization.


PAVIN: This episode of The Insightful Leader was produced by Laura Pavin, Jessica Love, Emily Stone, Fred Schmalz, Maja Kos and Blake Goble. It was mixed by Andrew Meriwether. Special thanks to Fredric Maddox. Want more The Insightful Leader episodes? You can find us on iTunes, Spotify, or our website: insight.kellogg.northwestern.edu. We’ll be back in a couple weeks with another episode of The Insightful Leader Podcast.

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