June 8, 2025

Organize Around Long-Term Planning Cycles: Interview with Anne Marie Dougherty, CEO of the Bob Woodruff Foundation

My conversation with Anne Marie Dougherty, CEO of the Bob Woodruff Foundation
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Adam Mendler

Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here?

Anne Marie: I grew up in a military family. My grandfather and father both served. I saw early on the sacrifices families like mine made every day to support those who put on the uniform. I got involved with the foundation back in 2008. Back then, it was more of a “kitchen table operation” with a lot of ideas and a lot of energy behind our cause – driven all by Bob and Lee Woodruff and his extraordinary story and what would soon become a lifelong commitment to those who serve. 

I may not have described it this way at the time. But looking back, it’s clear to me that supporting veterans and our military families was something of a calling. As a journalism student, I was inspired by Bob’s story. I cared about what our foundation’s success meant for families like mine and those serving alongside my husband, an active-duty Marine at the time. My life experiences, what I was living, what inspired me, it all came together. Not everyone is fortunate enough to be able to say that. Fast forward to today, and we’ve gotten $170 million into proven programs that help the veteran, the spouse, and the military child at the community level. We may have grown from the kitchen table, but the same spirit and sense of urgency are still very much there. 

Adam: What experiences, failures, setbacks, or challenges have been most instrumental to your growth? 

Anne Marie: Covid changed everything for everyone. We all know that. But as a small team that has to operate efficiently with donor dollars making up our entire budget, I was worried what it would mean for our ability to keep getting money into the hands of local service providers whose needs didn’t magically go away during the pandemic. We had veterans still needing housing and legal help, some even needing food assistance or emergency shelter. Lots needed help finding work. Even more needing some mental health care. So, candidly, I was worried we would be stuck between shrinking corporate donations from companies scaling back during the pandemic, and the growing needs of veterans also stuck in the Covid economy. 

We learned a ton about ourselves and our partners as a result. We got leaner in some places. We got more efficient and flexed in different directions in others. We got closer to our corporate partners. We relied even more on the data and expertise that guides who and what we fund. Covid was the most uncertain time we’ve had as an organization. But with a big sigh of relief, I can tell you today that we are stronger now than we were the day before the pandemic hit. 

Adam: What are the best leadership lessons you have learned from leading a non-profit organization? 

Anne Marie: It’s important to organize around long-term planning cycles, even as you fight the smaller day-to-day fires that you deal with in getting any organization off the ground. Or as one of my greatest mentors and leaders I’ve ever known, General Martin Dempsey, 18th Chairman of the Joint Chiefs of Staff, always pushed me to answer, “What’s over the horizon?” Every non-profit must be built brick by brick, but you have to plan for the organization you want to be a year down the road, two years out, five years out. If you don’t do this, you will always be scrambling to try and meet the evolving moment, and you’ll usually find yourself just behind where you need to be. Longer-term planning allows you to prepare for and meet challenges before they’re a threat to your growth. This applies to budgeting, donor relationships, how you grow your staff and expertise – all of it. Our instinct is to live day to day just to keep our head above water, especially when you’re new and small. But a good part of your planning energy must look further downfield than that. 

Adam: What are your best tips for fellow leaders of non-profit organizations? 

Anne Marie: Most non-profits need to fundraise, including us. Donations are always the result of trust. Trust is a commodity, and building it takes time. Investing time in relationships is hard and can come at a real cost to the rest of your responsibilities. Designing a thoughtful way to prioritize these connections and mitigate the other costs of this heavy human investment will be a much more effective fundraising strategy than constantly relying on an entirely new group of donors each year. Very few non-profit leaders get into this work because we enjoy fundraising. So, I get it. A focus like I’m describing isn’t instinctual to most of us. It takes discipline.   

Adam: In your experience, what are the defining qualities of an effective leader?  

Anne Marie: Humility and courage. No matter how talented or inspirational, it’s very hard to follow someone leading a mission who isn’t humble and who isn’t courageous. At some point, the mission will fail because the people will bail. It’s our job as the boss to support the people who work for us, not the other way around.   

Adam: What is your best advice on building, leading, and managing teams? 

Anne Marie: It’s really important for teams to leverage a wide variety of perspectives in making decisions. Whether it’s personal backgrounds or professional skills, teams that approach problems with the same experiences, biases, and worldviews will always have limited growth potential. They’ll always be too narrow and static in how they map issues and execute. No one teammate has a truly comprehensive vantage point on everything in life, no matter how skilled or dedicated they are. It’s on you as the boss to make sure the people at the table, together, give you as close to a 360-degree view of something as you can have. Building teams that way forces you to fight against the ‘fit-in’ approach to culture and management. When we see high-profile examples of teams failing in business or government or in the non-profit world, very often they failed because someone allowed for one perspective or one type of person to be the only voice in the room. And remember, credit is free. Give it often, publicly, and with genuine recognition and appreciation. It matters a lot more than you think. 

Adam: What can anyone do to pay it forward? 

Anne Marie: Everyone understands the value of mentorship. But I think it can be an intimidating word to both the mentor and the mentee. It sounds like a big, weighty relationship that in the real world, most people just don’t have the bandwidth to take on. I try and think about it in a different way. Mentorship is moments, large and small. It’s taking the coffee or Zoom chat with someone navigating a tough professional situation. It’s being a reference for someone applying for a job. It’s talking someone out of a bad decision. It can be lots of things! And when we think about it like that, it makes it less daunting and far more meaningful to both sides of the equation. When we’re talking about paying it forward, I urge people to deconstruct what mentorship means and offer it more frequently and in smaller doses than we assume is required. Like when someone pays for your coffee ahead of you in line, a small act of kindness, the gift of time, however much it is, can be the best gift of all.   

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Adam Mendler

Adam Mendler is a nationally recognized authority on leadership and is the creator and host of Thirty Minute Mentors, where he regularly elicits insights from America's top CEOs, founders, athletes, celebrities, and political and military leaders. Adam draws upon his unique background and lessons learned from time spent with America’s top leaders in delivering perspective-shifting insights as a keynote speaker to businesses, universities, and non-profit organizations. A Los Angeles native and lifelong Angels fan, Adam teaches graduate-level courses on leadership at UCLA and is an advisor to numerous companies and leaders.

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