The first woman Commandant of the United States Military Academy talks leadership, grit and mentorship

The United States Military Academy from across the Hudson River

A few years ago, Brigadier General Diana Holland made history, if quietly, taking the reins as the first woman Commandant in the 216 year history of the United States Military Academy, West Point.

Connecting with Holland is challenging, because she hasn’t slowed down. We finally arrange a call adjusting time zones from Pacific Standard Time to her current station in Puerto Rico where she is working with the Army Corps of Engineers on disaster relief as Commander of the South Atlantic Division. I can’t imagine how overwhelming the devastation must be, how frustrating it would be to see the destruction and suffering.

“The crisis period lasted longer than we’ve seen anywhere else,” she admits. “It’s life and death engineering. They don’t have power yet. The electrical grid is so unstable, it’s going to take a long time. At some point they’re going to have to decide if we invest in more resiliency to natural disasters.”

Holland’s focus began early on as a young girl in Santa Barbara, California. An only child, she was also the daughter of a Marine and granddaughter to a Marine who had served in WWII, “I was just six years old when I told my dad I wanted to be a Marine,” she says. “When I was 8 and still talking about it, my dad told me I could do whatever I wanted to do. There were no limits. He never discouraged me, but he did say I should go to college, be an officer.”

Early focus

The young Holland had a set of encyclopedias in her room, and sat and read about the service academies. They had just opened to women.

She joined JROTC in high school, and “I was all in.”

But not everyone around her was supportive.

“I had a math teacher who was really outspoken about having been at Berkeley and part of the (Vietnam War) protests. One Thursday I came into class in my ROTC uniform and he asked “Why do you want to do this? Why do you want to kill babies?”

The antagonism did not deter Holland.

Despite her petite frame — as an adult she stands just over 5’1” — Holland stayed focused on her future.

“My dad installed a pull-up bar in the doorway to my room. He’d take me on runs and encourage me,” she recalls. “He told me that if I wanted to be in the military, I needed to be physically fit.”

Holland applied early to the United States Military Academy at West Point, and entered in 1986. It was the 10th class of women.

“It was pretty much what I’d expected,” she says. “I’d done so much reading on it, already memorized so much of what I would have to know.”

Still, it wasn’t easy. “Beast Barracks [Cadet Basic Training] that summer was very hard. I definitely had some growing to do. There were some times I wondered: is this what I signed up for four years? Then before I knew it we were issued books and the academic year was underway.”

Holland as a cadet in Beast Barracks

Athletic from the beginning, Holland took her years in community sports and high school basketball to the lacrosse field.

“Like anything else in the Army, West Point is all about the team. I had an incredible roommate who is one of my best friends today,” Holland says.

“My challenges had more to do with being short than anything else. There were advantages and disadvantages to being a woman. I’ve found the Army very welcoming. There’s a way to contribute even if it’s not in the way you thought you would have.”

Later she would have younger women ask her if she felt that she had to prove herself.

“My personal philosophy is always do your best,” she says. “Sometimes that will exceed the standard, and sometimes it meets the standard. Sometimes I think some of this pressure [to work harder than men] is self-inflicted. I encourage young women to not put so much pressure on themselves.”

Holland continues with what she sees as guiding principles. “Be grounded in what is right. Even today I continually ask myself, are we all doing the right thing? If you do that, you can always look yourself in the mirror.”

Her wisdom comes from hard earned experience. I ask her about her hardest lessons in her decades in uniform.

“When I was a 1st lieutenant, single, all in and all about the mission, I was a company executive officer. I had a sergeant first class who worked for me. He was really good. Then there was a gradual decline in performance. I only saw it as a decline in performance, and didn’t recognize that there was something else going on. I found out later — after I’d left and written a negative performance review — that he had just found out his wife had left him.

I didn’t ask enough questions. I didn’t know better.

Over the years, young soldiers have taken their lives. “As a brigade commander, I had three soldiers commit suicide, two soldiers hanging themselves in the barracks in one week. It was devastating for our team. As in every case when something goes wrong, I asked myself what I could have done differently.”

Holland as a major on deployment to Iraq

The Army is a people business,” she says. “People are what make things happen. So, while mission accomplishment is essential in our profession, it is only possible if your people make it so. When I was a major I started to see how being overly focused on execution can negatively impact the organizational culture. That lesson helped me be a different sort of leader.”

It was her first return to West Point as a teacher that helped to translate the lessons about people into action.

“I learned what mentorship really was. I’d never had a mentor, but these young people were so hungry for that. They really wanted to know about our profession and what they were getting into.”

Evolving as a leader

How did all of this change her as a leader over the years?

“As a battalion and brigade commander, my priorities were more about readiness as it pertains to good order and discipline, conduct, and organizational health. Trying to prevent things like misuse of alcohol, sexual assault and suicide as part of leadership and readiness instead of something we talk about separately.”

Holland concedes that she looks at her subordinate leaders differently as a result of her own understanding.

“You might have a great executor working for you, and he is very effective at getting the mission done, But does he or she have a healthy organization? How do you know? First off, pay attention to the anonymous surveys. Second, visit your units. Don’t just follow along with what subordinate leaders what to show you. Find other ways to get information. You can’t be afraid of hosting a town hall or sensing session where you might be a target of criticism. You don’t have to have formal events, either. Walk to the motor pool and talk to a specialist.

A leader has to make people feel safe telling you anything.”

One of greatest assignments I’ve had was serving as the commander of the 92nd Engineer Battalion, the Black Diamonds, at Fort Stewart, GA and in Afghanistan. Command is a privilege unmatched by any other Army experience. Command in a combat zone is even more extraordinary. It’s what we signed up to do. It’s what we trained for. It brings out the best in people — and it can bring out the worst. I saw the best of the best in the 92nd in Afghanistan that year. We always talk about how leaders are supposed to inspire people. In 2010–2011, the Black Diamonds inspired me. Even under the most challenging conditions and austere living conditions, our Soldiers remained positive. They would say, “Send me. We can do this. We came here to make a difference.” Sometimes their spirit and enthusiasm would leave me speechless.

I ask her to elaborate.

What you learn from deployment

“One of the anxieties of junior Army officers is that they will show up at their first units and be the only person without a combat patch. The NCOs and Soldiers they lead will have had one or several deployments under their belts but their lieutenant won’t carry that credibility. It’s a reasonable concern, but I tell them not to worry. The strenuous deployment cycles are not ending anytime soon. Furthermore, their soldiers are only superficially taking note of the lack of a combat patch. What a soldier really cares about is whether their lieutenant is a good leader, cares about them, sets the standard, enforces standards, trains them, and treats them fairly. A leader can be authorized to wear 16 combat patches, but those pieces of cloth don’t mean a thing to their soldiers if the officer doesn’t meet their expectations in the things that matter.

My first deployment occurred in my 15th year of service when I deployed to Iraq as a major with the 3rd Infantry Division in January 2005. I remember thinking that it was about time! It was very professionally rewarding, demanding, and tested my endurance in several ways. I spent the first six months as a plans officer in the HQs. I learned how to employ combat forces and enablers across the battlefield. I came to appreciate the power and might of an Army division. I also learned that you’ll never have enough time in those situations to come to the 100% solution. You have to do your best for the sake of the soldiers on the ground who execute and are in harm’s way.

I also learned that everyone brings something to the table, sometimes when you least expect it. Because I was the only engineer officer in the plans shop, no matter what else I was doing, I was always responsible for the terrain brief and the geospatial support that went with every plan. In one very crucial briefing to the Commanding General, it was the terrain briefing that reversed a decision on a bold combat operation. The plan was 90% decided. Units were preparing to execute. In preparation for the briefing, I looked at how a little bit of rain (expected during the operation and considered an advantage to friendly forces in this scenario) was going to result in conditions that would present many obstacles to our equipment and soldiers and increased risk to the force. Displaying that in a way that was easily understood and with credibility was important. I was alone in the view that the timing wasn’t right for the plan. Ultimately, the Commanding General shelved the plan and we didn’t discuss it again while I was in the job.

Halfway through the 2005 deployment, I moved across Camp Victory to join the 92nd Engineer Battalion where I served as the S-3 until our redeployment in January 2006. I was almost overwhelmed with excitement. This was going to be the ultimate job — operations officer of an engineer battalion in combat. I wasn’t sure what to expect, but I felt I had reached the pinnacle. It was the most rewarding thing I had experienced in my career to that point. The battalion was a great team and was all over the battlefield improving remote patrol bases, repairing roads following IED blasts, constructing security towers, expanding existing infrastructure, and improving the lives of Soldiers. The Black Diamonds were well known by US units in the Baghdad area. I loved every minute of my time with the 92nd and worked hard to balance my time between being with soldiers in harm’s way and guiding future efforts and resourcing in the battalion headquarters.

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Coping with the unexpected in hostile territory

An unexpected thing happened one night while I was on the road and it stopped me in my tracks — almost literally. I had joined a convoy that was escorting about five of our trucks and engineers from Camp Victory into southern Baghdad. The area is known as “the Fiyahs” because it is comprised of Mahmudiah, Lutifiyah, and Latifiyah. It was an area that had frequent enemy activity, a rural part of Iraq characterized by farmland, canals, dirt roads, and swaths of trees. Our mission was to travel to Lutifiyah to emplace new showers and latrines for the camp. Our engineers love these missions because they know what a difference they make for fellow soldiers living in austere conditions. Nighttime was considered the best time to move due to the threat. As soon as it was dusk, our convoy moved out. We were integrated into another unit that was providing escort. I was the senior person in the convoy but not the officer-in-charge.

Once we reached the dirt roads and farmland, it was pitch dark. It was unnerving because of the wide canals that promised to ruin our day, particularly our turret gunners, if any of our vehicles rolled into the water. It was slow-going because the tractor trailers that carried water tanks and custom-built plywood latrines had to carefully navigate the narrow roads and tight turns. I was reassured hearing the Apaches overhead, providing us a greater degree of security.

Holland as Brigade Commander in Afghanistan

I remember staring hard at the road and the big truck in front of us when there was an explosion next to me. Dirt sprayed over the hood of our HMMWV. For a split second I thought, “Why would someone detonate a training grenade out here?” That was the only type of explosion I had ever known until this moment. I quickly realized it was not a training grenade but an IED and it had detonated very close to our vehicle. I switched to the internal net and asked if everyone was OK. My driver said yes and so did our passenger in the back seat. Our gunner in the turret did not respond. I raised my voice and called to him by name. There was no response. I reached back, slapped his leg, and asked if he was all right. He responded that he was and that he was looking for anyone moving in the nearby field. Hearing the voices of everyone in our vehicle was the most reassuring thing I could have imagined. All of that happened within seconds, but it seemed like forever.

Meanwhile several things started to happen all at once. There was small arms fire in the distance. Our vehicle was sluggish and my driver struggled to maintain speed and control. The voices on the external net started to sound panicked. The pilots overhead then said something I will never forget.

“Get moving. You need to get out of the kill zone.”

I quickly switched to the external net and informed everyone that our vehicle was the one hit by the blast, that we were all OK and continuing on. I urged everyone to continue to move out but to be cautious because of the terrain. The chatter stopped. The convoy continued.

It was a good thing we could still move because we were in the middle of the convoy and on a very narrow stretch of dirt road. Had we been completely disabled, the tow truck could not have reached us. The vehicle in front of us was already well down the road and could not have hooked up to us without backing up on that treacherous road. Had we been disabled, we would have been stuck along with half the convoy that followed us.

“We continued to move but we had lost sight of the truck in front of us. The black-out lights had long disappeared. Our HMMWV was clearly struggling in the sand. I remember hearing a soldier over the radio imploring us to hurry up because we had lost the front half of the convoy and we were going to get lost. I spoke with the calmest voice possible, strained to see what I could in the space surrounding us, and kept tabs on my driver who was struggling with the steering wheel and searching for the correct turns in the dark. At one turn, we stalled because the sand was so loose due to the traffic that had already traversed the corner. SPC Harvey switched back and forth between drive and reverse to get enough momentum to keep going.

“At this point, in front of us, I noticed a wall with windows. Must have been the edge of a village. I remember expecting that I would see a curtain move and a person peer out at us. For a split second I wondered if we were about to be ambushed. And then the HMMWV started moving again and we were headed down the road. Shortly thereafter, we saw chem lights on wire and were entering the basecamp. There was no pause at the gate to confirm who we were. The camp was awake and ready to respond to our crisis — they had heard it all on the radio.

“We pulled into an open area and came to an awkward halt. I didn’t move. I was waiting to hear that the entire convoy was safe. Suddenly, my door was wrenched open and someone said, “Ma’am, are you all right?” I said yes. The voice said, “I’m surprised you made it. Your back tire is completely flat — you’re lucky you were able to keep going. Don’t worry, we have plenty of tires on hand. We’ll change it and get you back on the road.” I stepped out of the vehicle and noticed that my chest was tight and my ears were ringing from the IED. None of that mattered. I was grateful everyone was safe and among friends. We returned to Camp Victory a few hours later without incident.

“Over the next 24 hours, my chest loosened up and my ears stopped ringing. I contemplated what had occurred. The IED had been initiated by someone watching our convoy, otherwise it would have gone off on one of the vehicles in front of us. Someone chose to disable a vehicle in the middle of the convoy. Thankfully, the angle of the platform was at the wrong angle or had been initiated too late, thus only striking our tire. It was eerie to think he had chosen us.

In the grand scheme of things, this was a “non-event.” No one was hurt. No one was lost. Damage to equipment was a flat tire. The mission was executed as planned. Even so, I re-learned important lessons. First, if you’re going to join another unit in an operation, spend time to get to know them and rehearse with them, even if the mission is as simple as a logistics movement. Otherwise, be able to move your units independently and only join others when you have to. I applied this lesson in 2010 when I commanded the 92nd Engineer Battalion in Afghanistan. We worked hard to make our platoons independent and confident on the roads. For the most part, we would not require external ground security to move to our project sites. Second, remaining calm at the most stressful moments really is the most important thing a leader can demonstrate. Not only does it calm the unit, but it calms you as well. Finally, train hard on executing missions within stressful scenarios. For us that night in 2005, the IED explosion was only one small part of the crisis. It was the cascade of other developments that presented the greatest risk.”

Holland as battalion commander

“Deployments, whether to Iraq, Afghanistan, or Puerto Rico, are incredibly rewarding personally and professionally. But as a leader who has to make daily decisions about putting Soldiers in harm’s way, particularly in the combat deployments, it takes a toll. I spent much of my time as a battalion commander in Afghanistan ensuring we were mitigating risk, getting our Soldiers everything they needed to handle anything they might face. My command sergeant major and I were pretty tough about safety, wearing protective gear, ensuring leaders performed pre-combat checks and inspections. I rode with the missions frequently, though not so often that subordinate leaders might think I didn’t trust them. Like most leaders though, I wanted to be present if something bad happened because I had put them in harm’s way — I was responsible. On the days when I didn’t go on the missions and when messages would come in to the operations center reporting attacks on our vehicles or construction sites, I would hold my breath. Thankfully, despite several engagements with the enemy and countless miles on the dangerous roads of eastern Afghanistan, the 92nd Engineer Battalion brought everyone home safe and sound. That means every Black Diamond family hugged their smiling soldier at the welcome home ceremony. It doesn’t get any better than that.”

Taking the helm at West Point

Finally we come to her selection for and days at West Point as the commandant.

“I don’t know how I became the commandant — it had never crossed my mind,” Holland says.

Just being a general was something I never expected. I was assigned as deputy commanding general for support at Ft. Drum. I learned about the assignment in an unusual way. I’d been at the Pentagon in the E-Ring, the headquarters of the Army. It was an incredible vantage point to watch the most senior officials of our service.

There was a meeting three times a week where the Chief of Staff of the Army was briefed. I was the executive officer to the Director of the Army Staff so I sat in the back of the room with all the other XOs. At one meeting, General Odierno walked into the room, we all stood, and he came straight up to me stating he needed to speak with me. Everyone stared at me. I didn’t hear anything at that meeting — I was busy worrying about what I had done to get the Chief’s attention.

I waited for him in the hallway, and when he came out of the room we started walking. He’s about ten feet tall and I remember straining my neck to look him in the eye.

“Hey, I’ve decided I need you to go to Ft. Drum to be a deputy commanding general and you have to be there in thirty days.” he says. “Do you have a problem with that?”

My mind started racing. I didn’t think I heard correctly. Luckily, my training kicked in and I automatically responded that I had no problem with it.

I wondered how I was going to do that. Be the deputy commanding general of a division, especially a light infantry division?

We got to his office and paused, and he asked if I had any questions.

I didn’t even say “Sir.” I just blurted, ‘Are you serious?’” He simply answered, “Yes,” turned around and walked through his door.

After her time at Ft. Drum, Holland headed back to her alma mater.

“The opportunity to interact with all those great young Americans with all that energy,” she says. “They just wore me out.” I can almost hear her smiling on the other end of the call.

“It was so special. I love the history of that place, the symbolism, and the opportunity to make a difference in the development of future officers. I still follow them now.”

Holland integrated more modern social media into the role of Commandant, too.

Brigadier General Holland with West Point cadets

“A recently-graduated lieutenant told me I had to have an Instagram account because Facebook was for ‘people his mom’s age.’ Of course, I’m his mom’s age! Anyway, social media became a way to highlight cadets and brag about what they’re doing.”

What was it like being the first woman commandant?

She doesn’t make a big deal about it.

“I think most people get it by now,” she demurs. “I suspect there were things said under the radar, but you do your best. You focus on the Cadets and what’s right for them and the institution. It was a very good 18 months.”

Holland reflects back over her years. “I wouldn’t change a day, an assignment, or an experience. I’ve had hard days, days that I would not care to repeat, but no bad days.”

Passion and grit

I have to ask, of course, about grit.

“The word grit is used a lot at West Point lately,” Holland says. “I think of it as a capability, a tool for certain circumstances. I don’t like it to describe a personality because it sounds abrasive. It is definitely appropriate for physical and mental trials, deployments, I’ve had to use it.”

She stops and thinks.

“I prefer the word passion. Passion leads to grit. I wouldn’t have the same level of resiliency if I wasn’t passionate. As I become more senior, resiliency became more critical when dealing with problems, making the right decisions in the face of opposition or controversy, and when really really tired. Sometimes it may mean remaining calm and patient. Forcing people to take a break. I’ve found in recent years that it is sometimes harder to do that than it is to inspire action.”

Everyone brings something to the table, sometimes when you least expect it.

It seems as a past commandant of West Point Holland would have good insights on developing grit.

“It’s got to start very young,” she says. “Scenarios that push people to their limits, pushing them out of their comfort zone. A lot of people have a lot more grit than they realize — they don’t recognize it until they are pushed.”

How can leaders be a part of developing that grit?

Helping others develop grit

“Practice, testing, then when they don’t pass, pull them back, and ask them what they’d do differently,” she says.

“Sometimes we get to 70% and move to the next task, but we don’t take time to figure out the 30%. Take time to help people grow who are in different places along the path to maturity.

A lot of it still comes back to your passion. When I’ve had a couple of jobs that might not have been what I wanted, it’s the people I’m working with who inspire me. The Army never leaves you alone. There are always other people. You won’t be making decisions all by yourself.”

Holland with the newest U.S. Army Rangers

Beyond the people, it’s challenge that interests Holland.

“Even if the role doesn’t interest me, the challenges are interesting,” she says. “It doesn’t matter what the job is if you do it well. Finding where you’re value added is important. There may be a different way to contribute, a place to play to your strengths you hadn’t expected.”

About women entering new roles in the Army, Holland explains “They’ve just instituted the occupational physical assessment test (OPAT). I’ll never be good at the long jump, but I’m a good sprinter. We can’t all be 100% at everything, and that’s OK because a team needs everybody’s strengths.”

It’s passion and wisdom that drives her forward now, but her success also seems tied to her positive attitude of contribution.

“When I walk into a new place, I wonder where I can contribute,” Holland says.

Her advice to new leaders comes from years of developing them.

Advice to new leaders

“Be yourself, but also be self-aware. Don’t change who you are, but it is important to appreciate how your behavior affects the organization. There are reasons we do peer assessments. Be aware of how you are being perceived, and consider changes if your actions or words are having a detrimental effect on the organization.”

Holland has a whole reading list for new leaders, and recommends four that we share in common as excellent sources for inspiration. Coach K’s book on Leading with the Heart, Good to Great, Unbroken, and Alison Levine’s On the Edge.(As a Blue Devil myself, I’m thrilled with her suggestions).

We return to talking about her current mission in Puerto Rico.

“You have to focus on the mission,” she says, something she’s learned from her decades in uniform. “By far the most challenging element is not the actual tasks, it is operating within the strategic environment. It’s important that we know where we fit in all of this. We in the Corps of Engineers are proud to be a part of the response — Puerto Rico will be better off than they were before Hurricane Maria.”

With all of her experience and focus, it’s a home base that keeps her grounded.

“I talk to my husband frequently,” she says. Her husband retired from the Army earlier and is back at their home in Alabama while she is in Puerto Rico. The Hollands plan to retire someday, along with two beloved Yorkshire Terriers, in Alabama. “It’s important to have the right people around you. I couldn’t do this without the support of my husband. He reminds me often, “just do your best.” One of the things that helps us cope with the challenges that come with military service is that we have our home where we plan to retire, on 36 acres, with a pond. It’s liberating to know our eventual end state.”


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Shannon H. Polson, Author, Veteran and Founder

LEADERSHIP. GRIT. PURPOSE. The Grit Factor AVAILABLE NOW: Founder: Committed to veterans and women in leadership.