three conditions winning team
March 8, 2019

The 3 Conditions for a Winning Team: Lessons from the Military in Leading Modern Work

By Jordan Staples | Director of Training at Workfront


Steven Ambrose’s book Band of Brothers tells the story of Lt. Winters and the 11 men of Easy Company from the 101st airborne division.

One week before the invasion on Normandy, the 101st airborne division was shipped to a camp where they were locked down. There they were briefed on the mission and learned the location of every building, bridge, and stronghold of the Germans where, as one soldier put it, “until they knew it cold.” Except for one—Brecourt Manor. The Germans had successfully camouflaged a battery of four 105mm howitzer cannons.

So, in the early hours of D-day, easy company flew 90 minutes across the south of England and crossed Cherbourg Peninsula and jumped into German anti-aircraft fire spewing from the ground. Many soldiers lost their gear on the way down and as one soldier described, all he had was his trench knife, canteen, and about 6 candy bars to fight the Germans.

Lt. Winter rallied his 11 men and was asked to take care of the artillery coming from over the hedgerow (Brecourt Manor). Winter took his 11 men and found that the howitzers were being camouflaged in trenches around the property. He split his unit into two teams with one providing cover with hand grenades while the other charged the first position. In the heat of battle Private Wynn saw an arm coming from a camouflaged tent holding a potato masher grenade. The german soldier dropped it next to Wynn who scrambled to get away when the blast went off wreaking havoc on the back side of his body. As Winter witnessed the moment, he remarked that Wynn didn’t holler out in pain or for help but hollered out that he was sorry, he had ‘goofed.’ Winter called the moment beautiful and a demonstration of how dedicated the men were to the company and each other.

Easy Company went on to overtake the 50 Germans and four howitzers at Brecourt Manor, fight for the liberation of Holland, hold the frontline against Germans in the Battle of the Bulge, and secured Hitler’s Eagle’s nest.

How the Ordinary Achieve Something Extraordinary

An incredible story that I know many of you have heard some or all of before. However, as I dug into the history of Lt. Winter and Easy Company and heard them tell their stories, I realized that most if not all of those men were civilians just two years prior to the invasion. So, what happened between their last day of civilian life and their first day in Normandy?

They became a team capable of extraordinary things. Let me explain.

James Kouzes and Barry Posner articulate a key principle in their book The Leadership Challenge:

“To achieve the extraordinary you have to be do things that have never been done before. [You] need to take risks with bold ideas. You can’t achieve anything new or extraordinary by doing things the way you have always done them. You have to test unproven strategies. You have to break out of the norms that box you in, venture beyond the limitations you usually place on yourself and others, try new things, and take chances.”

While this is not new to most of you reading this blog post, what we don’t often talk about or do deliberately as leaders is this (again from The Leadership Challenge):

“Leaders must take this one step further. Not only do they have to be willing to test bold ideas and take calculated risks, but they also have to get others to join them on these adventures in uncertainty. It’s one thing to set off alone into the unknown; its entirely another to get others to follow you into the darkness.”


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The 3 Conditions for a Winning Team

The difference between a leader who achieves something extraordinary and those who don’t are leaders who create conditions that build the conviction, capability, and chemistry of their team.

1. Conviction

To be a paratrooper in WW2 you had to volunteer. You had to sign up for to join an elite team that had a much higher risk of injury or death, but also paid quite a bit more. Some soldiers read the difficult requirements in Life magazine, saw it as a challenge and wanted to see if they could do it. Others, didn’t want to join the infantry, they refused to, if they were going to join the military they were going to be part of something elite and do something special.

Whatever the motivation or mission, you need conviction. You need a team that wants to be there, that wants to be part of the mission.

And you might be thinking, “yeah, my team seems happy and they are doing their job…” But let me share some research with you. According to a recent State of the Global Workplace report from Gallup, 85% of employees are not engaged or actively disengaged at work. The economic impact of this "norm" is around $7 trillion in lost productivity. There is 18% of that group who are actively disengaged in their work and workplace, with the 67% categorized as "not engaged."

This latter group makes up the majority of the workforce -- they are not your worst performers, but they are indifferent to your organization, your mission, and the work your team is doing. They give you their time, but not their best effort nor their best ideas. They likely come to work wanting to make a difference — but nobody has ever asked them to use their strengths, helping them do their best work.

Is this surprising to anybody? Do a quick evaluation of someone on your team. Are they wanting to make a difference? If not, they are actively disengaged. If yes, answer this: Are they committed to the organization and its goals? If not, They are not engaged. They are motivated to make a difference but don’t have the conviction to bring that next-level effort in their job at your organization. If you want a team with conviction you need people who want to be there. You will never do great work if your people are not doing their best work.

Here’s your first action item: Make work matter. Make it clear to each team member how their strengths will make a difference to the organization and its goals. You’ll know you’ve succeeded when they can answer these three questions with a yes:

  • Do they know their role?
  • Do they believe it matters?
  • Do they have the opportunity to be proud of their work?

2. Capability

Second, you need a team with capability. You have to have the right talent, skills, and experience to achieve the extraordinary. However, you are going to hire and inherit team members who have never done what you are about to ask them to do and that’s okay. Here’s why: The rate of innovation and change is faster than experience or education. Which means, you have to normalize risk-taking as part of your group culture. Give your team the space to try, fail, and learn…. Then reward them for it.

Spanx founder, Sara Blakely tells an amazing story about how her father did this for her all growing up. She recounts that every night around the dinner table her dad would ask her what she failed at that day and praise her for it. Sara’s dad normalized the process of figuring things out… of stepping into the unknown and learning from it.

Workfront interviewed Mark McGinnis (former NAVY SEAL commander) for our book Done Right, and he gave this advice:

“Ensure that the purpose and parameters of the mission are clearly understood, then trust your team to deliver the actions to get you there.”

Again, give your team the opportunity to test, try, fail, and learn… and be deliberate about it. A significant part of the military training for paratroopers is to normalize calculated risk-taking. Here’s how they approach it.

  • Week 1: Ground week

    • The first things soldiers are taught is about the parachute and harness. They practice jumping out of mock doors four inches off the ground, teaching them how to make an individual exit out a plane. They learn how to land properly sliding on a zip line four feet off the ground. They learn how to load onto an aircraft, what to do while on the aircraft, and how to exit the aircraft. This training isn’t in a classroom but outside in what looks like a playground built to roughly resemble the dimensions of the plane. Once they have the basics they progress to 34 feet. The tower is where they get their first real taste of what lies ahead. This is key: It’s the first time the soldiers are really at a height and where they are taught to rely on their training to do this “unnatural act” of jumping off a tower.

  • Week 2: Tower week

    • The training progresses where they are strapped into a harness with an open parachute hoisted up and released at 250+ feet to experience what descent and landing are like strapped to a parachute and to practice their technique. If you were watching this unfold, their instructor would be on the ground with a megaphone, coaching them through the experience.

  • Week 3: Jump week

    • As you can imagine this is where the soldiers actually jump from a plane. They do five jumps that week, the final being at night, in the dark, so they are prepared to do what paratroopers most often do in combat, insertion behind enemy lines at night.  

This paratrooper training is what happens today and is what happened to prepare Easy Company for the invasion at Normandy. But before that ever happened, when those soldiers were in Toccoa, Georgia standing on the 34ft tower the only thing they could think about with this unnatural act of jumping that platform. They weren’t nervous about Normandy, they were nervous about Georgia.

Here’s your second action item: Encourage the extraordinary by creating momentum toward uncertainty. You can do this by understanding their are 4 types of goals:

  • Clear goals: something you / your team can confidently do today.
  • Stretch goals: something you / your team can do if they push themselves to their limits.
  • Extraordinary goals: something at the edge of you and your teams headlights, meaning they believe in what is trying to be accomplished and that it can be done but requires everyone to change the way you do things as a team.
  • Pipe dreams: The only distinction between the extraordinary and a pipe dream is that one has a team of people with belief and the potential to make it happen while the latter does not.

You will create momentum toward the extraordinary when your team knows they can handle the low risk, that their leader has their back, and they have a team who will sacrifice blood, sweat, and tears to keep them safe.

That leads us to our last topic...

3. Chemistry

Trusting and leveraging your team members for help begins well before your pursuit of extraordinary. As Simon Sinek writes, “We call them leaders because they take the risk before anybody else does. We call them leaders because they will choose to sacrifice so that their people may be safe and protected and so their people may gain, and when we do, the natural response is that our people will sacrifice for us. They will give us their blood and sweat and tears to see that their leader's vision comes to life, and when we ask them, "Why would you do that? Why would you give your blood and sweat and tears for that person?" they all say the same thing: "Because they would have done it for me."

That chemistry is built well before you and your team execute the extraordinary. Shifty Powers if Easy Company said of his team, “You know these people that you are in service with. You know those people better than you will ever know anybody in your life and you will know them right down to the final thing. That comes when you start your training, while that progresses.” In other words, as you build the capability of your team to do the extraordinary they will learn to come together, rely on each other, and serve the needs of those they work with.

But today’s reality is a workforce who are skeptical of their colleagues’ work—and rate co-workers on average a 3.7 stars out of 5. The most common source of conflict with other departments or teams:

  • Conflicting priorities (57%)
  • Lack of communication (56%)
  • Lack of understanding of urgency (47%)

If you want a team with chemistry you have to give up your time or even opportunities to make sure they gain and succeed in their clear and stretch goals.

Here’s your third and final action item: Give for their gain. Win their loyalty to your mission and to each other. You can do this by reviewing the projects your team members are working on, find out what they need and personally make it happen. Give them your time and enable their win.

Conclusion: Learn to Lead the Extraordinary

For any of us to to lead a team to do extraordinary things we have to have the courage to do something different or new—we have to figure out how to be a leader of extraordinary achievements by doing things to become better leaders.

This is not easy or painless. You have to be willing to step into the darkness just like Easy Company. But if you create the right conditions your team will develop:

  • Conviction: Make work matter by helping them know their role, believe that it matters, and have the opportunity to be proud of their work.

  • Capability: Encourage the extraordinary by creating momentum from clear to stretch to extraordinary goals.

  • Chemistry: Give for their gain. Give your blood, sweat, and tears to ensure your team members win.

To wrap things up, I'll quote from Theodore Roosevelt's "Man in the Arena" speech:

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”

What a perfect encapsulation of what it takes to lead.


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