Why Every Chief of Staff Needs a Coach: Unlocking Growth and Avoiding Blind Spots
When I first stepped into a Chief of Staff role, I felt a jolt of excitement mixed with a kind of weighty responsibility. My inbox exploded with details: scheduling leadership meetings, ironing out cross-functional miscommunications, and bridging knowledge gaps between execs and team leads. It was invigorating to have so much influence—until I realized how isolated I was becoming. Yes, I was in the room where decisions got made. Yes, I was trusted to guide the conversation. But who was guiding me?
That question came back again and again, especially in late-night moments after back-to-back 12-hour days. I saw how everyone relied on me to “keep the trains running.” I was a confidant, strategist, and occasional therapist. Yet I had no real counterpart to share my own uncertainties with—no one to challenge my blind spots or push me to develop my own leadership instincts. That’s when it clicked: a Chief of Staff can easily be the busiest person in the company while secretly having zero support for their own growth.
The Quiet Isolation of Being “The Go-To Person”
A Chief of Staff is often seen as the ultimate team player, but ironically, it can be one of the loneliest positions. There’s a misconception that because you’re close to the CEO or other executives, you automatically have access to their full mentorship and guidance. In reality, many of those leaders see you as the problem-solver, not the person with problems of your own. You become the hub of information for everyone else’s needs, concerns, and ideas—yet the moment you feel stuck or uneasy, you may not know where to turn.
Some Chiefs of Staff spend months or years in what I call “productive isolation.” On the surface, everything looks fine—projects are delivered on time, important decisions are logged, execs praise your ability to handle the chaos. But beneath that success, there’s often a nagging feeling of stagnation. If your day-to-day is consumed by orchestrating other people’s brilliance, when do you get to refine or expand your own?
I vividly remember a stretch where my CEO was making major strategic shifts. Teams were confused, investors were anxious, and morale dipped. In that swirl of chaos, all eyes turned to me for clarity. I worked tirelessly to align different stakeholders, calm fears, and salvage as many strained relationships as possible. We got through it, but the emotional toll on me was heavy. I was so busy maintaining everyone else’s momentum that I had no space to process my own doubts or get a broader perspective on the changes. That’s a classic scenario where an external, unbiased voice—a coach—can help you see beyond immediate fires and realize where you need to grow, not just where the company needs to go.
What Coaching Really Delivers: It’s Not Just Tactics
I initially assumed a coach would be a glorified consultant, someone to help me analyze data or optimize a workflow. But true coaching isn’t about handing you a template or telling you what to do. It’s about guiding you to discover your own answers, your own style of leadership, and your own capacity for critical thinking under pressure.
Picture a big product launch: you’ve spent weeks corralling engineering, marketing, and customer success to ensure everything lines up. As Chief of Staff, you see the entire battlefield—where tasks are lagging, who’s stressed, which priorities are urgent. Now imagine having a sounding board who doesn’t judge you for your worries or your half-formed ideas, but helps you refine them. A coach will ask the right questions—sometimes the ones you’re avoiding—and push you to think differently.
They’ll make you confront the real reasons your team might be struggling with execution (Hint: It’s often more cultural or relational than purely process-driven).
They’ll get you to articulate where you’re feeling insecure about your own leadership—like having to question the CEO’s assumptions or deliver tough feedback to a well-liked VP.
They’ll help you see that behind every “operational bottleneck” might be a deeper communication challenge that you, as Chief of Staff, can influence if you choose to.
This kind of introspection goes beyond swapping tactics or frameworks. It’s about unlocking a version of yourself that can handle the complexity of your role without sacrificing your own growth. Coaching cultivates a sense of agency, forcing you to take ownership of not just tasks and timelines, but your own development as a key leader in the company.
Stepping Into Your Own Leadership: The Power of an Unbiased Partner
One of the surprising truths about the Chief of Staff role is that, over time, you become integral to how your leadership team operates. But are you also stepping into your own leadership potential? A coach is the perfect foil here. They have no stake in whether your product launch hits its deadline. Their only stake is in you—your mindset, your blind spots, your capacity to push the organization further.
Unlike a mentor who might give you their playbook, a coach helps you craft your own. They listen deeply, observe patterns in how you make decisions or handle conflict, and reflect them back in a way that challenges you to grow. They don’t tiptoe around uncomfortable truths, nor do they try to shape you into a copy of themselves. Instead, they stand shoulder-to-shoulder with you, so you can see yourself and your situation more clearly than ever before.
What if you had that kind of ally while setting strategic priorities for the next quarter? Instead of just implementing whatever the CEO says, you could question assumptions and propose a different angle—backed by a coach’s guidance on how to frame the conversation. Or consider a recurring miscommunication with a certain exec. A coach could help you unravel the deeper dynamics at play, turning an ongoing point of friction into a breakthrough for collaboration.
That’s the real magic of coaching: it focuses on who you need to become, not just what you need to do. It elevates you from “trusted operator” to “trusted strategist.” You stop being the person who only orchestrates other people’s decisions and start shaping the decisions themselves. You learn to see obstacles—both external and internal—and address them proactively. It’s a shift from keeping the machine running to re-architecting how the machine itself could run better, which is the mark of a true leadership partner.
And here’s the best part: once you’ve engaged in this kind of transformative relationship, it has a ripple effect on the entire organization. Your own clarity and conviction in approaching challenges become contagious. You’re not just facilitating the meeting—you’re setting the tone for deeper, more honest dialogue at the highest levels of the company.
Final Thoughts
So many Chiefs of Staff operate under the assumption that they need to do it all alone, that their value is proven in how many fires they can extinguish on their own. But the truth is, the highest form of value you can bring isn’t about being a heroic fixer; it’s about evolving into the leader who can anticipate fires, challenge outdated assumptions, and guide the entire team toward smarter, more cohesive decisions.
A coach doesn’t remove the pressure of your role—if anything, they’ll help you lean into it. They’ll remind you that isolation doesn’t have to be the norm, and they’ll push you to claim your seat at the table with more authority and vision. If you’re tired of being in the thick of everyone else’s problems, maybe it’s time to invest in someone who’s solely focused on you. Because in the midst of driving the team forward, you deserve to grow, too.
Ready to talk more about how a coaching relationship can unlock your next level? Reach out if you want to dig deeper into how behavioral insights, frameworks, and honest reflection can transform not just your day-to-day effectiveness, but
