From left: At the Farmville Chamber awards ceremony, Den Cralle accepted the Business of the Year award on behalf of Green Front Furniture, the family-owned company he now leads as president; Sheri McGuire was honored with the Career Achievement Award for her lasting impact on the region to support small businesses; Ilsa Loeser of Letterpress Communications and Doug Stanley, Prince Edward County administrator, received the Citizen of the Year award for his commitment to fostering leadership. Courtesy of Ilsa Loeser.
From left: At the Farmville Chamber awards ceremony, Den Cralle, who accepted the Business of the Year award on behalf of Green Front Furniture, the family-owned company he now leads as president; Sheri McGuire, who was honored with the Career Achievement Award for her lasting impact on the region to support small businesses; Ilsa Loeser of Letterpress Communications; and Doug Stanley, Prince Edward County administrator, who received the Citizen of the Year award for his commitment to fostering leadership. Courtesy of Ilsa Loeser.

A wise woman from the Deep South once told me: “There’s nothing wrong with this town that a few funerals won’t solve.” 

It was 2016. We were in a Southern Virginia community, and she had been hired to bring change to an established organization. I was in my early 30s and had returned home to rural Virginia with big ideas that I wasn’t sure how to translate into action. I felt like everything was moving forward too slowly. 

In those moments, her remark — while a bit morbid — gave me hope. 

Challenges in rural leadership 

Like any region, rural Virginia needs leadership development in both business and civic organizations. However, we often lack the critical mass of young energy needed to bring change. This brain drain is caused by many things, including a lack of jobs, educational opportunities and potential life partners. But in its most insidious form, it is self-inflicted and self-perpetuated. 

With fewer leadership positions to go around, those who take on the roles tend to stay in them long-term, limiting opportunities for leaders-in-waiting. These less experienced leaders, who are passionate to make an impact and do good, find themselves facing a brick wall — with too few on their side to help them scale it. Too often, after a time of effort and strain, they leave exhausted and frustrated. I’ve seen this happen to peers raised in my own community. They served on boards and volunteered but ultimately moved elsewhere seeking better opportunities. 

But there is also a different — and perhaps more positive — narrative about rural leadership. 

Rural communities have been doing important work to address this problem. Regional and local collaborations, such as the think tank that economic development organization GO Virginia Region 3 recently hosted, have begun addressing the perceived leadership challenge in a broader way. The statewide network Lead Virginia, formed in 2005, involves established business and community leaders in experiential learning about innovation solutions being deployed across the Commonwealth. In doing so, Lead Virginia increases collaboration and builds capacity for leveraging social capital (instead of individual might). Another fantastic example is the collaborative partnership of the Virginia Rural Leadership Institute, a rural-focused approach that exposes developing leaders to new ideas, opportunities and learnings from other communities. 

In many rural areas, businesses have become one of our primary leadership development tools.

As one example, in my hometown of Farmville, Virginia state senator and YakAttack owner Luther Cifers shared the story of a young man he hired with only a semester of college under his belt and no engineering experience. Luther recognized his natural ability. Over the past 10 years, he’s gone from production worker to apprenticing in engineering to now directing all engineering and product development for the industry leader in kayak fishing accessories. 

My own company, Letterpress Communications, invests in its employees’ professional development, training and peer support. In our labor market, this is not only an ethical move, but also an economical one. When facing the additional pressures of workforce recruitment, the best businesses survive by developing leadership internally. 

Business-led leadership development: Succession planning 

Over time, I have learned that a successful business leader is not one who is indispensable. Instead, it is a person who has empowered a team to work independently. This is much like successful parenthood. The goal is not to raise a child who lives in your basement; it’s to nurture one who is self-sufficient. 

What if our established rural leaders viewed succession the same way? 

In leadership conversations, we tend to look at young, energetic hopefuls and tell them to work harder or learn more. We focus solutions on supporting their growth and development. However, raising up young leaders is not enough. There is another root issue we need to take seriously. 

It’s time for those in the establishment to do the hard work of gracefully stepping into their next phase of impact. In doing so, they must provide mentorship, allowing young leaders to learn through experience (and perhaps also through failure). 

This is, admittedly, a challenge for many leaders. It took me nearly a decade — and many hard-earned lessons in delegating responsibility and trusting others — but I am in the process of transitioning the company I founded in 2015 into the hands of two highly capable women who have never before held the roles of CEO and COO. In doing so, not only has Letterpress gained capable leaders, but so too have the places these women call home. 

When I shared my succession plans with a fellow rural business leader, he was excited. He said, “I wish the established leaders in my community were willing to do the same thing. They keep asking where the young people are and why they won’t step up. But few have taken real, consistent steps to make room for the next wave of leaders.” 

I’ve spoken with leaders from that same community who are proud of their work in leadership development. But perhaps they have not considered the fact that you cannot just develop leaders. You also must make room for them.

No one can step up if the ladder is already full. 

Leadership transitions: The challenges of letting go 

My heart goes out to our established leaders. For many of us, the companies and organizations we help lead are our lifeblood — our identity. My own marketing firm has created a positive impact across my community and the commonwealth in ways I could not have imagined when I started. And, as I was reminded by a fellow founder, no one will ever be as passionate about Letterpress as I was in those early years. 

And yet: Making room for new leaders offers stability and a way forward for our rural regions. 

An established economic development leader (as well as a friend and mentor of mine), Liz Povar has worked across the commonwealth, leaving an indelible mark as an opportunist of all that rural communities can be. Eager to help elevate those with less experience, she noted that “no one is actively teaching us how to do this. How to lift up young leaders. How to let go and do succession planning.” 

Alexandra Veatch, the woman that I named Letterpress’ new CEO, has so much more professional experience than I did when I started. Yet, there are lessons she’ll only be able to learn as I did — through hard-won experience. I know that she will take a fresh perspective and do things differently. And I want her to! Because that is the way of growth and life and flourishing. My goal is to be there as her coach and supporter. After all, the less I am the linchpin, the more stable Letterpress will be. 

As I transition my business into Alex’s hands, I realize that successful leadership is not about the impact you make individually. It’s about multiplying your impact. It’s about the number of people who can fill your seat and take an organization — and a community — to the next level. 

Our rural superpower 

What we are really talking about here is scaling. 

Rural regions need to start by developing the established leaders at the top. For businesses to scale, these leaders must constantly delegate and elevate others, adding new layers of support and implementation. 

Returning to our parent-child analogy: For children to become independent adults, they must learn to walk without holding anyone’s hand, even if that means falling down. They must get a learner’s permit. They must be allowed to cook on the stove — even if they may start a fire. Recently, there has been much ridicule of a new level of helicopter parents who attend their children’s college admissions interviews — or even job interviews. But how different are business and civic leaders who think they are the only ones who can set the course? Are established leaders hovering over younger leaders and questioning their approaches rather than celebrating their successes and providing a safe space to adapt from failures? 

In my own entrepreneurial journey, I was lucky to encounter supportive mentors. When I was a reporter making $12 an hour, a former dean of Longwood University’s MBA program set aside time for beers at a local brewery. He shared his time and wisdom. Others offered knowledge, resources and encouragement. Some were even Letterpress’ earliest clients. When I was overwhelmed and thought about shutting my business down, they listened, giving me room to vent and choose my own path. Ultimately, even after Letterpress found the success it is now enjoying, these mentors empowered me to let go and put the company into the hands of a new leader. They encouraged me to think about where I could make my next impact, even if that meant stepping away from the company I started. 

This is a superpower of rural communities. With a low population density, we all know each other. We connect. We may have fewer people, but we have more proximity. When established leaders build up those around them, this empowers others to create new visions. We scale through our powers of relationship-building, passing down our learnings and creating space for the next generation to take the lead. 

I encourage rural communities to find meaningful ways to celebrate and support established leaders as they step forward into their next phase of impact. Organizations can adopt best practices like setting term limits on boards, integrating succession planning into their strategic vision, and developing board nomination plans that encourage senior members to mentor emerging leaders. But beyond individual organizations, it’s time to expand our regional efforts. In addition to cultivating new leadership talent, we must also create exit and sustainability strategies for established leaders, potentially through facilitated sessions or peer support groups. We could start simply by asking current leaders directly what support they might need to feel comfortable building redundancy and making room for new blood. 

Then, when we have a funeral, we are not scrambling to fill a hole in our leadership. Instead, we are celebrating the legacy of leadership passed down to those who are already here and well-prepared to fill the role.

Ilsa Loeser is the founder of Letterpress Communications in Farmville.

Ilsa Loeser is the founder of Letterpress Communications in Farmville.