There is something that happens as you climb that nobody prepares you for.
I have talked about this before. How feedback gets softer. Pushback begins to disappear. Candid conversations become rarer. And the information that reaches you has often been filtered through several layers before it arrives.
But there is another dimension to this that gets talked about even less.
The higher you go, the fewer people exist at your level. And with fewer peers comes fewer outlets for the conversations that you want to have. The sensitive strategic question you cannot ask your team. The self-doubt you cannot show your board. The decision keeping you up at night that you have nobody safe to think through out loud.
The circle of people you can be genuinely honest with keeps shrinking. And most leaders never see it happening until they are already inside it.
The leaders who navigate this best are the ones who build deliberate structures around honest conversation. Who actively seek out the person willing to say something uncomfortable. Who notices when a room gets too agreeable and treat it as a warning signal rather than a win.
This is also where your personal board of directors becomes essential. The trusted circle of peers and friends inside and beyond your organization who know you, know your goals, and will support and challenge you in equal measure at exactly the right moments.
It can feel lonely at the top. It doesn’t have to be.