Every year, I know less and less about more and more.

Assumptions, Truth-Tellers, and Life at the Edge of the Big Boss Table

Every year, I know less and less about more and more.

It sounds like a joke - and maybe it is - but it’s also uncomfortably true. And it brings me to a lesson I picked up early in my career, one that keeps getting reinforced as the years go by:

Never assume your boss knows… well, anything.

Now, don’t take that the wrong way. This isn’t about taking cheap shots at people in charge. What I learned early - from a seat near the Big Boss Table (usually somewhere on the sidelines of the conference room) - is that most leaders are smart, committed, and genuinely trying to do the right thing. But they’re also human. They’re navigating complex issues, juggling priorities, managing crises, and constantly switching context. And the further up you go, the less direct contact you have with the day-to-day realities of the work.

It’s not that leaders don’t care or aren’t qualified. It’s that the system of leadership often creates distance - a kind of well-intentioned disconnect between decision-makers and the people doing the real work. The information reaching leaders is often delayed, filtered, or incomplete. And the people who do know what’s going on may be hesitant (or afraid) to speak up, may not feel heard, or might not even be in the room.

So here’s the hard truth: you can’t assume your boss knows…

• What you’re actually working on

• When you’re stuck, frustrated, or need help

• How the team feels about the latest reorg or vision statement

• When a project is veering off track

• When the context has changed and the plan needs a rethink

• What should happen next

Making those assumptions - on either side of the leadership equation - is a recipe for disappointment. What helps? A few things that are simple to say and really hard to practice: open communication, initiative, empathy, candor, and a touch of humility — from everyone involved.

I had the good fortune to grow up in a high-pressure, high-performing technical culture — the kind where mistakes matter and feedback is constant. I started as a front-line supervisor and eventually found myself in executive roles. And somewhere along the way, I hit that classic leadership milestone: the moment when you go from leading people who know you personally, to managing a large team of people who don’t.

That’s when things really change. Your messages are delivered through layers. Your intentions are interpreted, paraphrased, or sometimes lost. And when people don’t know you, they’re a lot less likely to give you the benefit of the doubt — or ask clarifying questions when they’re confused or skeptical. And they don’t easily forgive your mistakes.

One of the best pieces of advice I ever got from a management course: surround yourself with truth-tellers. Sounds good in theory. But it takes deliberate effort — and vulnerability — to make it happen in real life.

I started having quiet, one-on-one conversations with people I trusted. I’d say something like:

“I took this job because I think I can help. I’ll always try to do what’s right for the people and the mission. I need you to tell me when I’m wrong, misinformed, or headed off-course. I promise to listen, and I’ll always respect your honesty. But please understand: I can’t always act on your advice exactly the way you’d like. I have to balance technical solutions with available resources, policy, politics, and execution realities. But I need your truth anyway.”

In my little corner of the NSA leadership world, finding people willing to speak truth was never the issue. The tougher challenge was finding those who truly understood - and could embrace - the two-way nature of that relationship. Honest feedback is only useful when both sides respect the complexity of leadership decisions.

We often talk about “leading down,” but leading up is just as important. Healthy organizations depend on people at every level taking responsibility for communication — not just when things are going well, but especially when they aren’t. And if you’re the person in charge, your job is to create space for others to speak up, share reality, and tell you what you might not want to hear.

Whether you sit at the head of the table or on one of the chairs along the wall, remember this: assumptions are the enemy of good leadership. Listening, clarity, trust — and yes, a few truth-tellers — are what keep things running when the pressure is on.