Who Supports the Leader? Finding Clarity at the Top

Starting a new job is always nerve-wracking. You don’t know the people, and you don’t know the processes. Usually, though, you have a manager—someone who met you during the hiring process and can help guide you through those early days. You also have peers—colleagues you can turn to with questions as you find your footing.

But what happens when you are the leader?

When you step into a top leadership role—especially in smaller organizations—the onboarding experience looks different. You don’t really have a manager; you likely report to a board that meets periodically and isn’t involved in day-to-day operations. And you don’t have true peers, because most people around you, in some way, report up to you.

This creates a unique and often invisible challenge: where do you go for support when you’re the one expected to have the answers?

The Weight of Uncertainty

I remember stepping into a senior leadership role for the first time and asking my board, “What does success look like over the next three to six months?” The response? Silence—or worse, vague platitudes.

At the same time, my direct reports were looking to me for clarity. Where are we going? What’s the plan? What’s expected of us? I didn’t have a satisfying answer for them yet. And that’s an unsettling place to be as a leader.

In the absence of clear direction from above, I did what many leaders do—I created one. I drafted a short-term business plan and submitted it to the board. I informed them that until I heard otherwise, we would proceed as though this was the approved plan. My hope was simple: if I was wildly off course, they would step in with corrections.

This plan wasn’t meant to be a long-term strategy; it was a six-month to one-year holding pattern to stabilize operations while waiting for some major strategic decisions to unfold. For the most part, my team was relieved to have some direction. Even a short-term plan helped them communicate a cohesive narrative to employees and provided a sense of structure. But at the leadership table, the future remained a big, unanswered question. Some of my senior team members recognized that this was only a temporary roadmap, and their questions continued: What comes next? Where are we heading?

At times, it felt like I was playing two roles—Chief Stabilization Officer for the present, and Chief Visionary Officer for a future I couldn’t quite see yet. I also felt the weight of being a leader. It isn’t in the daily decisions alone; it’s in the quiet moments when you realize that the next choice you make could change the trajectory of the organization—and the lives of the people within it.

The Leadership Isolation Trap

One of the realities of senior leadership is how isolating it can be.

I had an open and supportive board. But when I approached them with big-picture, exploratory questions—seeking a sounding board to help me think through complex issues—I often received narrow directives instead. Rather than engaging in generative brainstorming, conversations turned to tactical solutions or, worse, decisions made in isolation without fully exploring the implications.

Over time, I found myself going to the board less and less, feeling increasingly isolated. While I could sometimes explore ideas with my leadership team, many of the most sensitive challenges weren’t ready for broad discussion—or they directly involved members of that team. I didn’t want to be seen as complaining or gossiping about my direct reports, but I desperately needed a place to work out those leadership challenges safely and confidentially.

I remember the moment when I realized the decision before me wasn’t simply operational—it was existential. I was weighing options that included whether the organization should be sold or shut down. These weren’t everyday leadership questions. These were legacy-defining decisions with far-reaching consequences.

The board had requested that I not share with the leadership team what was being explored, and while I respected their reasons, it created a heavy and lonely burden. My leadership team was experienced—some had been through mergers and acquisitions before—and I knew they could have offered valuable insights. But instead, I found myself in a position where their direct questions—“How are the deliberations going? Is a sale or shutdown imminent?”—had to be met with vague responses.

It felt dishonest. Inauthentic. And it went against every instinct I had about transparent leadership. As the due diligence process unfolded, I was required to ask for information from my leadership team and was finally able to let them know that a potential sale was in the works. Even then, the timeline kept shifting, and uncertainty lingered.

When the final decision was made, I wasn’t able to share it with employees until the day the purchase went through. They were blindsided—many had recently made major financial commitments or turned down other job opportunities, unaware of what was coming. Delivering that news—seeing the shock and betrayal on their faces—remains one of the hardest moments of my career.

And yet, there was nowhere I felt safe saying, “I don’t know how to manage this. I’ve never faced a decision like this before.” This wasn’t just a strategic leadership challenge; it was a personal one.

The Support I Needed—And What I Now Offer

I didn’t need a decision-making framework. I needed someone to talk to—someone outside the boardroom and beyond my immediate team. Someone who could hold space for the uncertainty, ask me the hard questions I was avoiding, and help me sort through the noise to find what really mattered.

That’s the kind of moment where leadership coaching—not the prescriptive, answer-driven kind, but the exploratory, thought-partnering kind—could have made all the difference. Not to provide easy answers, but to create space for the hard questions. Not to tell me what to do, but to help me think more clearly about what mattered most.

If I could go back, I wouldn’t ask for someone to hand me a plan. I’d ask for a safe, neutral space to say the messy, half-formed things out loud. A space where it was okay to admit, “I have no idea what I’m doing here, and no one to talk to.”

I believe that all leaders need spaces like this. A space where no one expects you to have the answers yet. A space where you’re met with powerful questions instead of judgment. A space where the goal isn’t immediate solutions, but deeper clarity.

If you’re standing at that crossroads now—or can feel it approaching—know that you don’t have to navigate it alone. That’s why I created Leadership Clarity Circles™—a dedicated space for senior leaders to pause, reflect, and find clarity in the middle of complexity. It’s not about having the right answers; it’s about asking the right questions in a space where honesty, uncertainty, and vulnerability are welcome.

When the decisions feel high-stakes and the path ahead is unclear, this is where you can think out loud, explore the hard questions, and regain your footing, without judgment or pressure. Because sometimes, the most powerful thing a leader can say is, “I don’t know… yet.”