Leadership Means Giving Up Your Admin Privileges - Lessons from Band of Brothers

A few weeks ago, I found myself driving through the Netherlands with an extra day on my hands. I had been invited to speak at a cybersecurity conference in Amsterdam, and when planning the trip I realized I could stay an extra day, rent a car and visit one of the major battlefields of World War II. If you've ever heard the phrase "a bridge too far," that was where I was headed: Arnhem and the surrounding battlefields of Operation Market Garden.

What I hadn't fully appreciated was how close I would be to several locations connected to Easy Company of the 101st Airborne, the men portrayed in Band of Brothers. The landing zones are still there, although today some are simply farm fields. I drove portions of Hell's Highway near Veghel and eventually found myself in the Betuwe, an area the soldiers called "The Island." It is also the setting for one of my favorite Band of Brothersepisodes, Crossroads.

I've watched the episode several times over the years. On the surface, it is about combat and one of Easy Company's most successful actions of the war. Watching it again after visiting the area, though, I realized there is another story running underneath it. Crossroads is really about leadership and, more specifically, what happens when a leader is promoted beyond the job that made him successful.

At the beginning of the episode, Captain Dick Winters is doing what we've watched him do throughout the series. He's leading from the front. During a German counterattack in Holland, Winters races toward a dike, discovers a much larger German force and leads Easy Company in an aggressive attack. It's classic Winters: decisive, calm under pressure and technically excellent at his profession. He's at the point of execution, making decisions and leading his men directly.

Actual site of the battle

Shortly afterward, Colonel Sink rewards him with a promotion. Winters becomes executive officer of the 2nd Battalion, and Lieutenant "Moose" Heyliger takes command of Easy Company. On paper, it's unquestionably a step forward in Winters' career. In practice, however, something fundamental has changed. Winters is no longer supposed to run toward every fight. Someone else is.

I think this is one of the hardest lessons to learn as a leader.

The Promotion Paradox

We tend to think of promotions in terms of what we gain: a new title, more responsibility, greater authority and hopefully more compensation. What we don't talk about nearly enough is what a promotion requires us to give up. This is particularly difficult in technology because the skills that get someone promoted are often exactly the skills they need to stop using every day once they become a leader.

You become a technical lead because you're technically good. You solve difficult problems, earn certifications and develop expertise. When something breaks, people come to you because you've built a reputation as the person who knows how things work. If you do that successfully for long enough, eventually someone decides you should manage the team.

That's where I made one of my early leadership mistakes.

When I moved into management, I accepted all of the management responsibilities, but I didn't give up the technical ones. I still wanted to troubleshoot the difficult problems. I wanted administrative access. If something wasn't going the way I thought it should, my instinct was to jump in and fix it.

In my mind, I was helping the team. I had spent years developing these skills and had the certifications to prove it. If I could solve a problem in twenty minutes that might take someone else two hours, why wouldn't I help?

Eventually, one of my coworkers gave me some advice I didn't particularly enjoy hearing. He told me I needed to "remove my admin privileges, trust the team to do the day-to-day work and focus on what's on the horizon."

My initial reaction was, well, not positive. My ego was bruised because being technically capable had become part of my professional identity. I had spent years becoming good at something and now someone was telling me that one of the best things I could do for my team was stop doing it.

After a day or two, it sank in. He was right.

Your Team Can't Grow While You're Doing Their Jobs

The problem wasn't that my technical knowledge had suddenly become worthless. In fact, I think technical knowledge becomes even more valuable as you move into leadership. What has to change is how you use it.

There is an enormous difference between saying, "I know how to do this, so I'll do it," and saying, "I know how to do this, so I can help you learn to do it."

The first approach often feels more efficient. A problem appears, you know the answer and you fix it. The technical problem is solved and everyone moves on. The problem is that while you may have solved the technical issue, you may have created a leadership problem in its place.

The person on your team didn't develop the skill. They didn't work through the problem, experience the consequences of their decisions or develop the confidence that comes from solving something difficult. More importantly, they may have learned that when a problem becomes sufficiently challenging, the boss will eventually step in and take over.

Do that often enough and you haven't built a strong team. You've built a team that depends upon you.

That's not leadership. That's a bottleneck with a management title.

Looking back, I realized I wasn't helping my team move forward by remaining deeply involved in the technical execution. In some cases, I was actually holding them back. My role had changed, but my behavior hadn't.

The View Changes

This is one of the reasons Crossroads resonates with me.

Winters knows Easy Company extraordinarily well. He knows the men, understands how they operate and knows how he would lead them. But they're no longer his company. His responsibility is now larger than the individual action occurring directly in front of him.

The episode repeatedly confronts him with this change. Easy Company participates in Operation Pegasus, helping rescue more than 100 British paratroopers trapped across the river. Heyliger leads the company. Later, Heyliger is badly wounded in a friendly-fire incident. Winters remains close enough to see what's happening and certainly has opinions about how things should be done, but his role has changed. He now has to provide leadership across the battalion rather than personally execute every mission.

That's what happens as leadership scales. As a technical lead, your horizon might be today's incident or this week's project. As a manager, it might be the quarter. As a senior leader, it could be next year or even several years beyond that. Eventually your job becomes less about solving the problem directly in front of you and more about identifying the problem nobody else is looking at yet.

That's what my coworker meant when he told me to focus on the horizon.

I needed to learn new skills. Business skills, strategy, budgeting, hiring, coaching and organizational dynamics became more important. Perhaps hardest of all, I needed to become comfortable watching someone solve a problem differently than I would have solved it.

Sometimes they would even fail.

That was part of the job too.

People need room to fail intelligently and learn from those failures. If you remove every opportunity for someone to make a mistake, you also remove many of the opportunities for them to grow. The leader's responsibility isn't to eliminate failure. It's to create an environment where people can fail smartly without putting the organization at unacceptable risk.

Remove Your Admin Privileges

Years later, I still think about the advice to remove my admin privileges. It sounds like cybersecurity advice, and given my profession perhaps that's why it stuck with me, but it was really leadership advice.

Administrator privileges give you the ability to change almost anything in a system. Good security practice says you shouldn't use those privileges simply because you have them. You use them when they're actually required. Leadership, I've come to believe, works much the same way.

As a leader, you often retain the ability to jump in. You can take over the meeting, rewrite the presentation, fix the configuration, call the customer or make the technical decision yourself. You have the authority and, in many cases, you still have the skills.

The harder question is whether you should use them.

Sometimes the answer is absolutely yes. Leadership doesn't mean standing by while the building burns down because you're committed to delegation. There are moments when experience matters and a leader needs to step forward. But those moments should become the exception rather than the default.

The objective is no longer to demonstrate that you can do the work. The objective is to build a team capable of doing the work without you. That's a very different measure of success.

The Hardest Promotion

There is a reason I think Crossroads means something different to me today than when I first watched it years ago. Earlier in my career, the exciting part was Winters running toward the dike. It was the action, the decision-making and the example of a leader at the front.

Today, I notice what happens afterward.

Winters gets promoted and suddenly leadership requires something different from him. He has to trust someone else with Easy Company. He has to think beyond the fight directly in front of him and let go of something he was exceptionally good at doing so he can become effective at something larger.

Most of us will never have to learn that lesson on a battlefield, but most leaders eventually encounter their own version of it. It's the engineer who needs to stop writing every important piece of code, the salesperson who needs to stop closing every major deal, the security architect who needs to stop designing every solution or the manager who needs to stop solving every employee's problem.

For me, the lesson came from a coworker telling me to remove my admin privileges. For Dick Winters, it came somewhere in Holland. The circumstances could hardly be more different, but the leadership problem is remarkably similar.

The skills that make us successful are difficult to let go of because they're part of how we define ourselves. Yet sometimes the next step in leadership isn't learning what else you can do. It's recognizing what you need to stop doing so someone else has the opportunity to grow.

What are you still doing today that someone on your team needs you to let go of?