Leadership vision that actually works doesn’t die in translation.
It dies in repetition.
I spent years thinking the problem was clarity. I needed simpler language. Better frameworks. One sentence instead of sixty slides.
And I was right. Compression matters.
But I missed something bigger: The moment I got tired of saying the same thing over and over, my team started drifting. Not because they forgot. Because I stopped reminding them.
Here’s what nobody tells you about vision. The hardest part isn’t creating it. It’s saying it again tomorrow when you’re bored of hearing yourself.
The Drift Starts With You
Your team isn’t wandering because they don’t understand where you’re going.
They’re wandering because you stopped pointing.
I watched this pattern repeat with every mid-career leader I worked with. Clear vision at launch. Momentum in quarter one. And then somewhere around month four, the leader stops talking about it.
Not consciously. They just assume everyone already knows. They said it in January. Why repeat it in April?
Because your team is working. You’re thinking.
While they’re executing toward point A, you’re already considering point B. You’ve mentally moved on. They haven’t. And when you stop reinforcing the destination, they start drifting.
The work continues. Meetings happen. Emails get answered. But nobody’s certain anymore if they’re still headed where they thought they were going.
That’s not a team problem. That’s a leader problem.
When Boredom Becomes Chaos
Here’s the uncomfortable truth about leadership vision that actually works: You’ll be sick of saying it long before your team is sick of hearing it.
You’ve been thinking about this direction for months. Maybe years. You’ve processed it. Wrestled with it. Refined it until it finally compressed into something simple enough to remember.
And now you have to say it. Again. And again. And again.
In the all-hands. In one-on-ones. In planning meetings. In hallway conversations. In Slack threads.
The same sentence. The same direction. The same first step.
You’ll want to add nuance. Context. Strategic layers that make it feel fresh to you.
Don’t.
The moment you start varying the message because you’re bored, you’re creating confusion. What sounds like helpful clarification to you sounds like a direction change to them.
They’re wondering: Did we misunderstand the first time? Is this a pivot? Are we still doing what we thought we were doing?
Meanwhile, you’re just trying not to sound robotic.
What Compression Actually Costs
Everyone talks about compressing vision into one sentence.
Nobody talks about what you lose when you do it.
When I finally compressed my vision to something my team could repeat, three of my senior leaders pushed back. Hard.
“That’s reductive.”
“We’re losing important nuance.”
“What about the strategic complexity?”
They weren’t wrong. Compression does remove nuance. It does simplify complexity.
That’s the point.
But here’s what I learned: The leaders who resist compression aren’t worried about losing strategic depth. They’re worried about looking less strategic.
A one-sentence vision doesn’t feel sophisticated. It doesn’t showcase the thinking that went into it. It doesn’t prove you’ve considered all the angles.
And that discomfort is exactly why it works.
The Trade You Have To Make
Leadership vision that actually works trades sophistication for repeatability.
Your leadership team might need the full context. They might benefit from understanding the strategic reasoning behind the direction.
Your frontline doesn’t.
They need to know: Where are we going? What’s my next step? Can I make this decision without asking permission?
If your vision requires them to understand the full strategic rationale, they can’t move without you.
And if they can’t move without you, you’re not leading. You’re bottlenecking.
I had to make this trade three times before I accepted it. Every time I compressed vision, I felt like I was over simplifying it. Every time I added back complexity, my team stopped moving.
The vision that moves people isn’t the one that proves you’re smart. It’s the one they can use when you’re not in the room.
From Here to There
The best vision I ever cast fit in five words.
Not because I was trying to be memorable. Because I finally understood what vision actually does.
Vision doesn’t explain everything. It points somewhere.
From here to there. Point A to point B. Current state to future state.
That’s it.
If someone on my team can tell me where “there” is and what the first step toward it looks like, the vision is working.
If they need to check the strategy deck, I haven’t clarified it yet.
Here’s the test I use now: I ask three people at different levels of the organization where we’re headed. If I get three different answers, the vision isn’t clear. If I get three versions of the same answer, we’re aligned.
Not perfect alignment. Not word-for-word repetition. But directional agreement.
They all know where “there” is. They might describe the path differently, but they’re pointing at the same destination.
That’s enough.
The Annual Revisit
Leadership vision that actually works doesn’t mean the vision never changes.
It means you don’t change it without telling anyone.
Every year, I sit with the same question: Where are we taking this team?
Sometimes the answer is the same. Sometimes it shifts.
But when it shifts, I don’t quietly update my thinking and assume everyone will catch on. I announce it. I explain why. I give people time to reorient.
Because the fastest way to create organizational chaos is to change direction without changing your communication.
Your team will keep executing toward the old destination while you’re already planning for the new one. And six months later, you’ll wonder why everything feels misaligned.
That’s not their failure to keep up. That’s your failure to communicate the change.
The Repetition Nobody Warns You About
Leadership vision that actually works requires you to become a broken record.
Same sentence. Same direction. Same first step.
In every meeting. Every email. Every conversation.
Not because your team is slow. Because you’re competing with noise.
Every day, your team is processing dozens of inputs. Customer requests. Operational fires. Strategic pivots from other departments. The vision you cast three months ago is buried under ninety days of urgent.
If you’re not constantly bringing them back to the destination, they’ll default to whatever feels most urgent.
And urgency doesn’t care about vision. It cares about now.
So you say it again. And again. And again.
Even when you’re bored of hearing yourself. Especially when you’re bored of hearing yourself.
Because the moment you stop saying it is the moment they start drifting.
What Actually Sticks
Leadership vision that actually works survives three tests.
The breakroom test: Can someone explain where we’re going while getting coffee?
The commute test: Can someone describe our direction while driving home?
The hallway test: Can someone make a decision aligned with vision without asking permission?
If the answer to any of these is no, the vision isn’t compressed enough yet.
Not because your team isn’t smart. Because vision that requires notes to remember isn’t vision.
It’s a document about vision.
And documents don’t survive Monday morning.
Start Here
If you’re reading this and thinking your vision still feels too complicated, here’s where to start.
Sit with one question: If your team could only remember one sentence about where you’re going, what would it be?
Not the full strategy. Not the supporting rationale. Not the five-year plan.
One sentence.
From here to there. Point A to point B.
Write it. Test it with three people. If they can repeat it back without checking notes, you’re close.
If they hedge or qualify or need clarification, keep compressing.
And once you have it? Say it tomorrow. And the day after. And the day after that.
Even when you’re bored.
Especially when you’re bored.
Because leadership vision that actually works doesn’t die in translation. It dies the moment you stop repeating it.
Every Tuesday I send what I’m learning about leadership, clarity, and sustainable growth. No fluff. Just frameworks that work. Free at toddmckeever.com/newsletter