You Have to Be Comfortable with Some Cognitive Dissonance: Interview with Ross Dickman, CEO of Hire Heroes USA
I recently went one-on-one with Ross Dickman, CEO of Hire Heroes USA.
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? What experiences, failures, setbacks, or challenges have been most instrumental to your growth?
Ross: I grew up in an Army family—my dad was in the Infantry—and experiencing that world was a pivotal part of my upbringing. It set the stage for me to pursue a service-oriented career, first in the military and then in the nonprofit sector. But growing up in a military family had its challenges. We moved about every two years, often starting over at a new school in a new state halfway through the school year. That experience was key to my development; I learned so much about navigating change, building relationships, starting fresh, and being resilient.
My time at West Point was instrumental as well. I finished high school at a small Department of Defense school in England, with a graduating class of about 40 students—a big fish in a small pond. Then I ended up at West Point, surrounded by multi-sport athletes, class valedictorians, Rhodes Scholars, and Marshall Scholars. It was eye-opening, realizing you can’t always be number one; there’s always someone faster, smarter, better. That experience taught me a lot about humility, failure, and growth.
Adam: What are the best leadership lessons you have learned from your time in the Army?
Ross: The first, and probably most important, lesson I learned is that people will work hard for someone who works hard. I’m not talking about a “grind culture” mentality but rather about leaders who are willing to put their back into the work and get into the details to add real value. I used to say, “Nobody is too important to make a fresh pot of coffee,” and that applies to every task.
Another key lesson is that you can’t outwork a broken process. With enough effort, you can temporarily cover for process inefficiencies, but it’s ultimately unsustainable. If you have a team of go-getters giving it their all but they’re stuck with flawed processes, systems, or tools, there’s only so far you can go. Ensuring that those foundations are right is crucial to support any hardworking team.
A final lesson that stands out is this: if your soldiers include you in the joke, you’re doing something right. Soldiers have a tough job, and good-natured pranks are one way they blow off steam and build camaraderie. Being the subject of a prank can be a bit of a test—how you handle it speaks volumes. I’ve seen highly competent leaders lose their team’s respect simply by overreacting to a harmless prank, like finding their folders replaced with children’s notebooks. Being in on the joke is a powerful way to build trust and credibility as a leader.
Adam: What are the best leadership lessons you have learned from leading a non-profit organization?
Ross: The number one lesson I’ve learned from leading in the social impact sector is that a team’s attachment to the mission is the most powerful force you have to inspire commitment and positive energy. That attachment must be respected, reinforced, and treated as the most valuable asset in your organization’s culture. If you take it for granted or over-leverage it, you risk losing the cultural buy-in that fuels your team. This mission-driven commitment can uplift other areas where resources may be limited, but if you lose it, you risk losing the heart of the organization itself.
Adam: What are your best tips for fellow leaders of non-profit organizations?
Ross: To run a successful nonprofit—meaning an organization that genuinely makes an impact in its focus area—you have to be comfortable with some cognitive dissonance. On one hand, you need to operate the organization like a business: lean, focused, and disciplined, with strong attention to detail, process, and measurable outcomes in your impact area. On the other hand, you must also embrace what sets the nonprofit sector apart: a high degree of accountability, transparency, and public disclosure of data, including fundraising, expenses, and performance metrics. Doing this well requires a clear understanding of what your organization truly is and does, along with a commitment to integrity and a disciplined focus on your theory of change.
Adam: In your experience, what are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level?
Ross: The best leaders I’ve worked with share a few key qualities: they’re authentic, focused, action-oriented, and genuinely care about others. Authenticity is often talked about, but many managers just “cosplay” at being authentic. Real authenticity is an art—it’s about lowering barriers so your team understands how you think, operate, and what you stand for.
When it comes to focus, I think the “rise and grind” mentality has convinced people they need to juggle multiple priorities, but I believe in the Ron Swanson approach: “Don’t half-ass two things, whole-ass one thing.” Focus on where you uniquely add value and be excellent in that area.
Great leaders also have a bias toward action. As a leader, there comes a time when people are waiting on you to make a decision, even if you don’t have all the information. That decision will have consequences, so make a play and commit to it.
Lastly, empathy is an incredibly powerful leadership tool. It’s really about listening—being present and accessible to hear what your team needs you to hear. It’s not always about problem-solving; often, it’s just about showing that you’re there for them.
Adam: What are your three best tips applicable to entrepreneurs, executives, and civic leaders?
Ross:
Define the difference you want to make. Start with a clear vision of the impact you want to achieve.
Understand the landscape. Fully grasp the world surrounding the problem before committing to a solution. The best solutions come from a well-rounded perspective.
Protect the space for critical thinking. Keep room to challenge your assumptions and stay open to hearing the information you may not want but absolutely need.
Adam: What is your best advice on building, leading, and managing teams?
Ross: Patience, trust, and clarity are essential when building and leading a team. You can’t rush through the stages of group formation, nor can you avoid the necessary confrontations that arise when people are working closely on a shared mission. Patience is key; use every opportunity to encourage collaboration and build trust.
In team building, you earn trust by giving it, and as a leader, that’s especially true. Finally, clear, consistent communication about the team’s direction and your expectations should be a core part of your leadership approach.
Adam: What is the single best piece of advice you have ever received?
Ross: The best advice I’ve ever received is that nobody will ever care as much about your career as you need to. It’s sometimes hard to hear, but it’s crucial advice. An organization can define career pathways and outline the traits and competencies expected for each role, but ultimately, you’re the only one with the ownership and authority to shape your career.
Adam: What can anyone do to pay it forward?
Ross: Invest in what you care about. This might mean a monetary donation, especially if you’re in a position to give. But for many of us, paying it forward is about using our time and talents to help others. Just a few hours a year can make a significant difference for someone.
Adam Mendler is an entrepreneur, writer, speaker, educator, and nationally recognized authority on leadership. Adam is the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one-on-one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal-winning athletes, political and military leaders - for intimate half-hour conversations each week. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities, and non-profit organizations. Adam has written extensively on leadership and related topics, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. Adam teaches graduate-level courses on leadership at UCLA and is an advisor to numerous companies and leaders. A Los Angeles native, Adam is a lifelong Angels fan and an avid backgammon player.
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