Not Everyone is Cut Out to Thrive as a Rural Executive: Here's What It Really Takes
Thanks to decades of combined experience, we’re very familiar with challenges that leaders of rural organizations face. That knowledge is why we’ve come to be the experts you can trust among search firms with an emphasis on place. At Pierson Henry, our tried-and-true executive search process will help you pinpoint exactly what you’re looking for in a leader, and accompany your team on the journey to hiring someone who can see and understand the big picture. Firm co-founder, Katrina Pierson, shares how growing up in a small town shaped her understanding of leadership in a rural community, as well as the top qualities Pierson Henry looks for in each and every candidate considered for your position.
What makes rural leadership different?
Too often, the assumption is that leading in a smaller town or community is easier than leading in an urban area. The truth is: rural leadership isn’t easier or harder—it’s challenging in a different way.
Having been raised as the youngest (and wildest child) in a small northern Minnesota town where my mother was editor of the local newspaper, I couldn't get away with anything. Everyone knew who my Mom was and everything I did was ... visible. This is the same reality that rural executives face every day. Here are some of the most common questions we hear about rural leadership—and the answers we’ve learned from years of experience in rural leadership.
Isn’t leading in a rural community easier because organizations are smaller?
That’s the myth. While organizations may be smaller, the expectations are no lighter. Rural leaders often play multiple roles—CEO, community liaison, problem-solver, and sometimes even fundraiser-in-chief.
Unlike in a larger city, you can’t disappear into anonymity. As my partner Holly Kelsey-Henry will often say, "a foundation leader we place will run into grant applicants who they had to deny at the grocery store. They have to be ready for that." Your neighbor may also be your board member. Everyone knows you, so accountability is not only constant but at times can feel very personal.
Biggest challenges for rural executives
Accessibility: You can’t hide behind the walls of an office—your work and your reputation are visible and there are few protective layers between you and your stakeholders. In short, rural leaders are often more accessible.
Resource Gaps: You’re expected to do more with less—less funding, fewer staff, tighter budgets.
Isolation: Professional networks can feel sparse, and the nearest peer might be 200 miles away.
Integration: In rural communities, the “personal” and “professional” blur—your role isn’t just about an organization, it’s about the whole community ecosystem.
Qualities that lead to a thriving rural leader
Relational Trust-Building: In small communities, relationships are currency. A rural executive needs to listen deeply, show up consistently, and honor commitments—because reputations travel fast.
Adaptability & Versatility: With fewer staff and resources, leaders often wear many hats. The ability to shift from strategic visioning to hands-on problem solving (sometimes in the same day) is crucial.
Community Visibility & Presence: You can’t be a “closed door” leader. Grocery store conversations, Friday night football games, or even funeral luncheons are part of the role. Honing presence means being approachable, authentic, and consistent wherever you are seen.
Resourcefulness & Creativity: Budget constraints and workforce shortages demand inventive solutions. Leaders must learn to leverage partnerships, grants, and unconventional collaborations.
Resilience & Emotional Balance: The pressures are personal—when challenges arise, everyone feels it. Leaders need to manage stress, maintain perspective, and not let community criticism erode confidence.
Rootedness & Cultural Awareness: Honing a genuine love for place, history, and local culture. A successful rural executive learns how things get done here—respecting traditions while also challenging unhealthy narratives with grace and introducing new ideas.
Storytelling & Communication: Whether it’s rallying donors, speaking to a county commission, or updating a board, strong communication is essential. Storytelling helps connect the mission to the identity of the community.
What is one truth every prospective rural leader should know?
Not everyone is cut out to be a rural executive. But for the right person, it’s the most rewarding leadership role you’ll ever have—because you’re not just leading an organization, you’re shaping the future of a community. And yes—you should be ready to have just as many conversations in the produce aisle as in the boardroom.
Join the Conversation
What qualities do you think make someone shine in a rural executive role? If you’re currently seeking a rural search firm to guide the search for your organization, the experience at Pierson Henry is truly unmatched. If you’d like to talk more about how we can put our knowledge and expertise to work for your next rural search, give us a phone call at (715)-580-0479. You’re also welcome to connect via email at info@piersonhenry.com. The team at Pierson Henry Executive Search is excited to connect with you to discuss how we can work together and find the next best leader for your rural organization.