Who’s in Your Corner? Navigating Trusted Relationships as a CEO

When you’re a CEO, the weight of responsibility can feel immeasurable. The decisions you make ripple across your organization, impacting employees, clients, and stakeholders alike. But while the role comes with great authority, it also comes with a sense of isolation. CEOs are tasked with navigating critical decisions, driving organizational success, and shouldering the complexities of a position that few truly understand. Leadership at the top demands more than strategic thinking and decision-making—it requires a network of trusted relationships, both within and beyond the organization, to thrive.

Who does a CEO turn to for advice, perspective, or simply to talk things through? While the executive team, board, and trusted advisors are invaluable partners, the weight of leadership often brings challenges that require an additional kind of support. At the top, it’s not about a lack of connection—it’s about finding the right spaces and relationships that allow for open dialogue, fresh perspectives, and shared experiences that truly resonate with the unique demands of the role.

Who Does a CEO Turn to?

The unique demands of a CEO’s role often call for more than just a capable team or a supportive board. While the executive team, board members, and external advisors are invaluable, there’s a deeper layer of connection that many leaders crave.

It’s not about a lack of resources; it’s about finding the right spaces for open dialogue, fresh perspectives, and shared experiences. CEOs need trusted relationships where they can navigate the personal complexities of leadership, gain clarity, and develop solutions to challenges that demand both expertise and empathy.

The Unique Challenge of Leading at the Top

As a CEO, you’re not just responsible for your company’s bottom line but also for its vision, culture, and future. That level of accountability is both exhilarating and daunting.

However, the role’s inherent isolation can make it challenging to share the burden. Whether managing a merger, steering through a crisis, or driving innovation, the confidentiality and expertise required often limit the people a CEO can turn to.

While executive teams drive the company forward, board members provide oversight, and advisors offer technical expertise, these relationships often come with boundaries. For many CEOs, the missing element is a space where vulnerability and candor can thrive—a space where the pressures of leadership can be understood and shared.

Richard E. Mastrocola, CEO of Tonneson + Co, knows that leadership cannot exist in isolation. Beyond cultivating his own network of trusted advisors, Richard has prioritized empowering the next generation of strategic thinkers within his firm. One of his most impactful initiatives has been the creation of a diverse group of rising leaders called THRIVE to engage in meaningful conversations about business and leadership.

“True leadership isn’t about holding onto authority—it’s about creating space for others to grow into it,” Richard explains. “By empowering rising leaders, we’re investing in the future of our firm while ensuring that our decision-making reflects a broad range of perspectives,” says Mastrocola.

Who’s in Your Corner?

As a CEO, your success relies on a mix of internal and external advisors to navigate the complexities of leadership. Consider these key relationships:

• Executive Team: Your immediate team is essential for executing strategy and providing operational insights. Building trust and fostering open communication with them is foundational.
• Board Members: While they provide governance and strategic guidance, they may not always be accessible for day-to-day challenges.
• Legal and Financial Advisors: These professionals are invaluable for ensuring compliance, navigating transactions, and managing fiscal health.
• Leadership Mentors or Coaches: A mentor can offer long-term perspective and wisdom, while coaches provide structure and focus for personal and professional growth.
• Operational Advisors: Specialized advisors in HR, IT, marketing, or supply chain can bring clarity to complex areas of the business.

These relationships are critical, but they don’t always address the personal side of leadership—the challenges, tough calls, and unique pressures that come with being at the helm.

The Power of Peer Connections

For many CEOs, the most valuable insights often come from peers who have walked in their shoes. Conversations with other CEOs can provide an unspoken understanding of the challenges, fears, and triumphs that come with leadership.

Peer groups—whether formal or informal—offer a safe space to share ideas, seek advice, and gain fresh perspectives. Richard E. Mastrocola reflects on the importance of these connections:

“Early in my role as CEO, I made it a priority to connect with other leaders in similar positions. Sharing ideas and discussing challenges with those who truly understand the dynamics of leadership has been incredibly rewarding. These conversations often lead to solutions I might not have arrived at on my own.”

At Tonneson + Co, Richard has created a similar environment within the firm through the THRIVE group—a diverse leadership cohort that bridges perspectives and fosters strategic growth. This internal peer network ensures that the firm’s leadership reflects the needs and aspirations of its entire team.

“Having trusted voices within the firm—people I can collaborate with as equals—is one of the most fulfilling aspects of leadership,”

Richard says.

“It’s a reminder that leadership isn’t about going it alone but about building a team that grows and succeeds together.”

Building Your Own Circle of Trust

If you don’t already have a network of peers to lean on, now is the time to build one. Here are some ways to get started:

• Join an Existing Group: Consider joining CEO peer groups or industry cohorts. Richard emphasizes the value of connecting with other leaders, noting, “There’s an unspoken understanding among peers who have faced similar challenges. It’s not just about advice; it’s about sharing experiences and realizing you’re not alone.”
• Start a Local Cohort: Invite trusted peers from non-competing industries to meet regularly and discuss challenges in a confidential setting.
• Diversify Your Network: Seek mentors or advisors from outside your industry to gain fresh perspectives. Engage with specialists in areas like HR, IT, or marketing for
• clarity on specific challenges. While going outside of your industry could work, also try going to different venues within your organization. Groups like THRIVE serve as a circle of trust, where leaders collaborate to share experiences, exchange ideas, and support one another in a confidential and empowering environment.
• Be Intentional: Build transparency and trust with those closest to you—whether it’s your executive team, board members, or external advisors.

A New Kind of Leadership

The notion that CEOs must “go it alone” is a myth. The most successful leaders understand the power of collaboration and connection. By surrounding themselves with trusted advisors, mentors, and peers, they create a dynamic support system that fosters growth, innovation, and resilience.

Whether you’re a current CEO or aspiring to the role, investing in meaningful relationships can be transformative. The right connections provide fresh perspectives, guidance, and shared experiences to navigate the complexities of leadership—and build a legacy of success.