Ryan Daly (kneeling first row, center/right) with his team, the 2nd Platoon, Alpha Company, 3rd Battalion, 7th Infantry Regiment, 4th Brigade Combat Team, 3rd Infantry Division of the US Army in 2008. Today, Ryan is the Director of Partner Operations at Jet.com.

Lessons in Leadership from Four Fallen Heroes

By Ryan Daly, Director of Partner Operations

Memorial Day is a time to honor the fallen, to spend with family and friends, and for veterans in particular, it’s a time for reflection. It also falls within a week of an unforgettable night eight years ago that forever changed my life.

On May 22, 2008, I was serving as a Lieutenant for the US Army in Iraq when my team was ambushed. While that wasn’t an uncommon occurrence given our assignment, that night proved life-changing. The attack took the life of one of my youngest soldiers, Kyle Norris, who was just 22 years old at the time. I was barely older than him at 23.

That night kicked off a series of events that taught me the meaning of teamwork at a very young age. I lost four men in fifteen months, each of whom stepped up to fill a gap left by the teammate before.

So this week, I’d like to honor four incredible soldiers I’ll never forget — Kyle Norris, Darris Dawson, Wesley Durbin, and Ronald Phillips. Sharing their stories solidifies the lessons they taught me by honoring their sacrifice — and I hope inspires others leading teams on the battlefield and off.

1. Raise Your Expectations For What You And Your Team Can Achieve

Army Spc Kyle P. Norris of Zanesville, Ohio.

Kyle Norris was a great soldier on my team who enlisted right out of high school and worked on the headquarters team when we first deployed. He was eager to become part of a tight-knit unit and energetically joined my team as soon as the opportunity came up. His task was to build a working relationship between our team and the local Iraqi Army and Police. It proved to be a particularly difficult assignment, as Kyle had to earn trust, span the cultural divide, and build genuine connections in a highly tense and violent operating environment.

Rather than accepting that it was too hard, Kyle dedicated his limited free time to learning Arabic language skills and forming bonds that ultimately saved lives and built trust. One day, we received an emergency call from the local Iraqi community, but learned that our interpreter would be delayed to assist. Kyle was able to leverage his language skills to assess the immediate threat, get a local family to safety, and thwart a possible enemy attack on the community.

Through Kyle’s work, I learned that when you come upon a task that seems too hard, take one step forward and do one small thing to chip away at it. The greatest gains start with the smallest step.

Unfortunately, Kyle’s time ended too soon. On the night of May 22, 2008 he was driving a lead vehicle on patrol when a roadside bomb detonated under his vehicle. Our team worked hard to treat and evacuate him, but he passed away late in the night at the hospital.

2. Dig Deep To Achieve Big Outcomes

Army Staff Sgt. Darris J. Dawson of Pensacola, Florida.

Darris Dawson joined my platoon following the IED attack that took Kyle’s life and wounded three other teammates. At a time when our team was feeling empty after the loss of Kyle, Darris brought his style of grit and determination to the team. He raised the team’s morale by driving us to reach near impossible outcomes.

Darris always inspired his team to tackle all aspects of a problem and arrive at a much larger scale of impact. He was adept at using “hard” tactics such as patrols and intelligence-driven operations, but invested just as aggressively in relationship-building and social impact with the local people. He leveraged his relationships to earn trust with locals by leading projects that improved two local schools and resolved multiple water delivery and treatment issues. By tackling all aspects and motivating his team, he arrived at huge gains when the odds were stacked against him.

From Darris, I learned to embrace grit. Stay scrappy. Be hungry. Be resilient. When you feel like you are out of gas, dig down and lean on each other. Through resilience, mental toughness, and a “battle mindset,” you can drive yourself and others to true gains.

3. Be True To Yourself And Play To Your Strengths

Army Sgt. Wesley R. Durbin of Hurst, Texas.

Wesley Durbin was a former Marine. He shifted to the Army and was assigned as a leader on my team throughout our deployment. In contrast to the Army’s loud, hard-charging culture, Wes had a much more thoughtful and measured style. He was approachable, a coach and mentor, and always remained calm under pressure. He didn’t try to “fit in” by being aggressive, as he knew it wouldn’t come across as genuine. Rather, he played to his strengths, and his team admired his ability to build connections with locals due to his patient demeanor.

On one occasion, Wes was tasked with leading his team to train the local Iraqi Army unit on various objectives. As his team became frustrated with the Iraqi soldiers who couldn’t keep up with the pace of training, he calmed and reassured them of their mission. He overcame the initial challenge, chatted with the Iraqi Sergeant, and ensured the training was of the highest possible quality. He could have allowed his soldiers to become stressed, but instead Wes took a step back, assessed, and ultimately drove synergy between the teams.

As you seek to improve your leadership skills, remember there is no one-size-fits-all model. Relentlessly work to get better by building on your strengths and improving your weaknesses.

Tragically, on the night of September 14, 2008, both Darris and Wes were shot and killed on the patrol base and passed away en route to medical help.

4. Never Quit

Army Staff Sgt. Ronald Phillips Jr. of of Conway, South Carolina.

After the tragic deaths of Darris and Wes, Ronald Phillips returned to our team. That’s right. Returned.

Ronald had previously led us for over two years, and after losing Darris and Wes, we needed him. And he knew it too. With a beautiful wife and children at home, he sacrificed a safe assignment in order to support our team.

Through his leadership, our team bounced back. But tragically, Ronald was killed just two weeks after his return. Just two weeks after coming back, and for the sake of helping us after losing so many men, he lost his own life too.

After losing Ron, the team was burned out. But knew we had to honor him by finishing our mission. We carried out our remaining three months, and ultimately established peace in a previously perilous region in Ron’s honor.

The lesson from Ron is the one that I carry with me every single day.

Never quit on your team. Ever.

We finished our mission, and those of us who were able to return home to our families were able to do so because of Ronald, Darris, Wes, and Kyle. Not one of them quit on us.

What Would You Do For Your Team?

Sharing these stories is not easy for me. It brings back a lot of emotions about leadership, life, and loss.

I’ve found that vulnerability and humility can be powerful tools as a leader, especially in the face of adversity. It helps the team persevere. The more I’ve let others into these experiences and lessons, the more I’ve been able to give as a team leader — and the more I’ve gained in return.

I challenge you to think about the people around you. Actively learn from each other, appreciate one another, and push yourselves to be better people. I encourage managers and team members alike to find meaning in the good they can bring for those around them.

When things get tough, or simply uncertain, truly ask the question: “How far would you go for your team?”

My hope is that in that moment, you’ll draw inspiration from the lessons of Kyle, Darris, Wes and Ronald — four ordinary men who found themselves in extraordinary situations. Step up when there’s a need. And never, ever quit on your team.

In the photo on the left, Ryan Daly (kneeling on the far right) with his Platoon in December 2008. In the photo on the right, Ryan and the Jet.com team at HQ on the site’s launch day in July 2015.

Ryan Daly is the Director of Partner Operations at Jet.com, leading a team of 24 (and growing) employees who provide technical and operational support to retail partners selling on Jet . Ryan served in the military for 5 years, spending fifteen months in Iraq. In the Army, he led a platoon of 40 soldiers, and managed teams as large as 200. Ryan holds a BS in International and Strategic History / Engineering from the United States Military Academy at West Point and an MBA from The Wharton School at the University of Pennsylvania.

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