'I Was Tougher Than I Had Previously Given Myself Credit For'

Brittany Masalosalo was crushed.

She had just completed basic training and was set to move on to her next Army assignment — but a bureaucratic holdup meant she was going to have to remain at Fort Jackson for an extra three months.

“I was falling to pieces about it,” she said. “I was hard-charging and a high performer and wanted to move on.”

It was in that moment that a drill sergeant gave her a message she still thinks about.

“Private, this is not going to be the biggest inconvenience of your career,” he said. “If it is, you better count yourself blessed.” 

Masalosalo has since navigated far more complicated hurdles while serving two tours of duty in Iraq, working for NATO and the Pentagon, and briefing the Vice President as a senior National Security advisor.

She’s currently the chief public policy officer at HP Inc.

The Daily Coach spoke to Masalosalo about lessons from the military, overcoming the anxiety of being in the White House, and what she considers her “Chicken Little” moments. 

This interview has been edited and condensed for clarity.

Brittany, thanks a lot for doing this. Tell us a little about your childhood and some key lessons from it.

I’m originally from Denver. I grew up in a pretty poor family. My mom had some challenges, and I got caught up in the foster-care system. Me and my sisters spent about seven or eight years in it. I was the oldest and was catapulted into a role of responsibility, which I’m grateful for looking back on.

My mom, being a true model of resiliency, was able to help our family reunify. 

I got my first job when I was 15 years old scooping ice cream at Baskin-Robbins. My mom was very adamant about prioritizing education. If my grades were slipping, she had no problem saying, “You can’t work if you can’t balance both.”

What appealed to you about the Army and what were your initial impressions of it?

I got into one of the top engineering schools in Colorado, the Colorado School of Mines, in Golden. I dropped out after one year to join the Army because I knew I needed to get the heck out of the area. 

My family had no money. There was no option for me to leave the state and go to college. But my dad had served in the military for a few years, and he had talked about the stability it brought to his life. I thought that could be my train ticket out.

I fell in love with the Army early on. There were some aspects of it that were a little bit of an awakening for me, but it gave me exposure to other cultures, people, ways of life and thinking. I saw some people fall apart in the face of authority and physical or mental stress, but I found out I was tougher than I had previously given myself credit for because of where I had grown up.

There’s a motto in the Army that “Training isn’t something we do. Training is what we do.” It’s embedded in the core of how the Army functions, and one of the things that made it a good fit for me was that I was instantly able to find a community of mentors and people who were culturally invested in developing new leaders.

You end up doing two combat tours in Iraq, the second as a sergeant. What type of leader were you and is there any retrospective advice you’d give yourself?

My second deployment, I had some rank on my shoulders. It was a totally different mindset. Before, I was following orders, executing, just trying to do my best every day and stay alive. Now, I was doing all of those things, but leading a team of 17, 18, 19-year-olds whose parents had entrusted the U.S. government with their lives. I had to help them cope with the mental strain of being deployed, the physical stress your body endures, the emotional stress of being at war.

I wish I could come to you with an ego and say I knocked it out of the park right out of the gate, but that would be a total lie. I struggled with basic fundamentals. I struggled with not spending enough time getting to know the people I was leading. I struggled early on with not getting a collective buy in and trust. I paid the price for it, but I learned a lot of lessons coming out.

I’m grateful to have had those experiences early in my career because they helped me come into my own and become more seasoned as a leader. You want to deliver, and you want to deliver excellence. The way to find that balance is you have to prioritize connecting with your people. You have to practice seeing the humanity in everybody and not just viewing them as a resource. You can have the best software engineer on your team, but if you only see them as a software engineer and only connect with them through that, you’re going to struggle. The team I have now, I can tell you about their kids, they can tell you about my kids, their families, where they went on vacation.

We all want to be heard, seen and loved. We all want to be valued. That’s how you’re going to drive the best performance. That’s how you’re going to drive the trust for people to respect your authority and your position of leadership.

You’ve had a pretty remarkable career since and went on to serve as a senior National Security advisor. I heard you say in another interview you felt some anxiety being in some of the rooms you were in. How did you overcome that?  

It could be quite intimidating. Imagine being 28 years old, I’m the only person who looks like me, and I’m going to brief the Vice President of the United States and members of his team. 

I moved past it by No. 1, grounding myself on a fact I learned early in my military career: It’s O.K. if they don’t like you. It’s O.K. because I remind myself I don’t like everybody I meet.

No. 2, I remind myself I’m capable and I’m confident. My credentials are evidence of that.

I also have a small group of personal confidants I can call and talk to and say I may be having a crisis of confidence. They’ll remind me of a time I really nailed it to move past that anxiety.

The last thing I do is I just shift my focus and think, “Who else might be feeling the same way?” Maybe if I can pull them along, we can help each other at the same time.

I have to think there were lots of instances where you were an expert and knew more about a specific subject matter than the person you were briefing. What’s the key to delivering an effective, condensed message in that scenario?

If I get 10 seconds, what is the No. 1 thing I want you to walk away knowing?

I can’t tell you how many times I start briefing or presenting and it gets cut short. But what is the most important thing this person needs to know? I filter out all of the backstory, all of the history and come up with two or three sentences that capture the most important thing and go from there. 

The other thing is, at the top, I’ll give them my three points and ask, “Is there some place you prefer I start?” They may not have the level of understanding to know, in which case I’ll do my own prioritization. Getting the elevator pitch down on your level of expertise is essential.

There must’ve also been plenty of people who maybe didn’t fully embrace what you were saying or were glossing over your information. What’s the key to persuading a skeptical audience in your eyes?

I call those my “Chicken Little” moments. The easiest way to overcome those are to pull in additional stakeholders. Who else is this issue important to? Who else can amplify my message? Typically, if I’m at a place where what I’m saying is not being recognized or acknowledged, it’s a reflection of a lack of credibility I have with that audience. That’s something that comes with time.

The first thing I do is turn to some of the more credible voices to give amplification to my message. If that doesn’t work, then I also do a perspective check. Let me make sure I’m grounded in reality and not being chicken little. Is this really an issue that deserves the level of attention I’m giving it.  

Never be afraid to let new evidence change your mind.

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