The Squad Behind Enemy Lines: How Charles Allen Found His Leadership Community

Charles Allen leads a 153-year-old faith-based tourism destination that serves 80,000 guests annually. He manages 250 employees across two hotels, oversees a downtown business district, and reports to two boards. Yet despite all the people around him, he faced a dangerous reality that plagues leaders at every level: profound isolation.

"As leaders, we insulate ourselves from a lot of different areas," Allen explains. "Who can I talk to that I can trust? What community do I build around myself that can help me process a business idea before I take it to the board or a staffing issue before I deal with HR or legal? You're in a dangerous spot when you're your own counsel."

As President and CEO of The Lakeside Association in Ohio, Allen runs what he calls "a multi-generational family experience better than anybody else in the world." The historic Chautauqua community offers vacation programming built around four pillars: religion, education, arts and entertainment, and recreation. It's a vacation where you don't have to turn your brain off from learning.

But leading at this level created gaps Allen couldn't fill alone — gaps in business wisdom, family presence, and spiritual depth.

The Isolation at the Top

Allen's struggle reveals a tension familiar to Christian leaders: the higher you climb, the fewer people understand the view. "I can only talk so much to my senior staff," he says. "And I have two boards. When you're leading at that level, you begin to isolate yourself."

The isolation wasn't just professional. It was spiritual. "Working for God doesn't bring you closer to God," Allen observes — a lesson he learned from his years training pastors and ministry leaders. "In a lot of cases, it will separate you from God because we get so busy doing, we forget to be with God and sit with God."

Allen needed a space that addressed leadership not as a compartmentalized skill set, but as an integrated whole — business decisions, family presence, and spiritual formation woven together. He found it in Kingdom Factor peer advisory groups.

Finding the Squad

Allen describes an old mentor's wisdom that shaped how he thinks about leadership community: "In a leadership position, you find your squad. You look for people who have the same insignia as yours. He always used the analogy of being dropped behind enemy lines. Your first mission was not to do the mission, but to find your squad so you can do the mission together."

That's what Kingdom Factor is — finding a squad of people who are on the same mission to do it together.

The decision to join wasn't about adding another meeting to his calendar. It was about finding a well-rounded place where he wouldn't feel isolated — "a community of people who understand leadership at the level I'm leading, who also understand leadership in the context of ministry and family."

The Test of Real Leadership

The value of that community showed up when Allen faced a critical decision. His board was excited about an opportunity that would impact every property owner in the community. Allen knew it wasn't the right time. "I had a large share of the community there," he recalls. The pressure was immense.

In his Kingdom Factor group, Allen received what isolated leaders rarely get: godly counsel on how to present his case, how to ensure his decision wasn't just emotional, and how to align his conviction with the organization's best interests. "When you bring an issue to the group and there are two or three other people dealing with the same situation or who have already gone beyond that — man, life comes into it."

The transformation went deeper than one decision. Allen's participation in Kingdom Factor exposed a low trust threshold that was limiting his leadership. "I didn't really trust my senior leadership to do certain things. I figured if I wasn't involved in it or I wasn't doing it, then it wouldn't get done."

Kingdom Factor helped me build my trust — one, in God more, and two, in the leadership that God has put around me.

The shift was measurable: "Now I feel like I'm in a season where I don't have to work in it as much as I have to work on it."

The Intentionality Requirement

Allen doesn't sugarcoat the challenge. "A four-hour block with all that we have going on is really hard." Monthly meetings. Lesson preparation. Reflection questions. It requires discipline most leaders struggle to maintain.

But Allen learned something from his wife that changed how he approaches commitment: "Nothing good comes unless you're intentional about it. You can't have a good marriage unless you're intentional. Your relationship with God cannot be good unless there's intention."

He brings that same intentionality to Kingdom Factor — reviewing lessons ahead of time, coming prepared, engaging fully. "When I make the commitment, that is when I get the most out of those meetings. And quite honestly, it's when God uses me the most in those meetings as well."

The Wisdom in Diversity

Allen's advice to Christian business leaders considering Kingdom Factor is rooted in Scripture: "The Bible says there's wisdom in the multitude of counsel. But that's not necessarily about the amount of people — it's the diversity of the people you have around you."

If you only talk to people who think like you, in the same industry as you, you'll always get the same advice — your advice. "But when you get yourself in a community of people who are biblically grounded, seeking God, yet diverse in their experiences, their tenure, their age — that's where you get wisdom in the multitude of counsel."

Since joining Kingdom Factor, Allen has introduced others to the community. One member recently told him it transformed his way of doing business. "For me, man, it's like — yeah, it's definitely met and exceeded expectations."

As You Grow, the Organization Grows

Allen's transformation as a leader has rippled through The Lakeside Association. "As I grow as a person, the organization grows and those around me who are reporting to me grow."

It's the kind of integrated growth that can't happen in isolation — where spiritual formation shapes business decisions, where trust in God translates to trust in your team, where being becomes as important as doing.

"If you only surround yourself with people who think like you," Allen challenges, "you're always going to get your advice back." But when you find your squad — people with the same mission but different perspectives, the same faith but diverse experiences — you find the wisdom isolated leaders desperately need.

The question isn't whether you can afford the time investment. The question is whether you can afford to keep leading alone.