Here’s some math that makes this obvious once you see it: you spend dozens, maybe hundreds of hours developing a strategy. You think through the problems, the options, the trade-offs, the execution paths. You live with it. You sleep on it. You iterate on it. You pressure-test it with other senior execs and your leadership team.

Then you spend a few hours communicating it. It’s a 30-45 minute explanation in all-hands. A Slack post. Maybe a follow-up Q&A. Then you’re surprised when people aren’t aligned, when they make decisions that don’t reflect the strategy, or when they ask questions you thought you’d already answered. This matters even more when the strategy isn’t incremental, like when you’re asking people to change how they fundamentally work, not just what they’re working on.

The uncomfortable truth is, as a leader, you’ll be sick of your own voice long before the message sticks. Most leaders stop repeating because they’re bored, not because they’re done. Repetition isn’t about persuasion. It’s about responsibility.

It’s not a failure of your people’s ability to understand and internalize change, it’s a reflection of the information asymmetry. It’s a failure to recognize that absorbing strategy takes repetition — often a lot more of it than we, as leaders, want it to take. Strategy isn’t strategy unless repeated.

Why One-and-Done Fails

Your people have day jobs. They’re deep in their day-to-day, shipping features, troubleshooting issues, managing their teams, sitting in their own meetings. They are still executing the last version of the strategy as they understand it. They are still working off the priorities that they know. When you present the (new) strategy, you’re asking them to context-switch into your world for an hour, absorb weeks or months of your thinking, follow your train of thought, and then go back to their work with (hopefully) perfect retention.

That’s not how brains work. It gets harder when you factor in that everyone comes with different context, different tenure, different experiences with past strategies that did or didn’t pan out, different abilities to internalize new information, different levels of trust in leadership, different baggage from previous companies, you get the idea. People are people. The person who’s been at the company for five years hears your strategy differently than the person who joined last month. The person who got burned by the last reorg hears it differently than the person who benefited from it.

A single communication gives people facts and opinions. It doesn’t give them understanding. And without understanding, you get compliance at best. People will mostly do what they’re told because that’s how the professional game is played and people want to do a good job. But compliance isn’t buy-in. Buy-in is when people bridge the gap between what you’re asking and what they already care about. That takes (much) more than one pass.

Strategy Delivery Should Be Multimodal

Repetition doesn’t mean sending the same email five times (or 3 times on email and twice on Slack). It means delivering the same core message through different channels, at different depths, in different contexts, and usually also from slightly different angles.

Here’s what this looks like in practice:

• Town Halls work for the macro view. Monthly, I cover the big strategic updates. These are things like: what’s changing, why it’s changing, what success looks like. This is the org-wide context that everyone needs to hear directly, not filtered through three layers of management. These should be happening weekly if you are in the thick of the changes.
• Weekly leadership syncs keep the cascade flowing. Every week, I make sure my staff has the latest context from the Senior Leadership Team so they can translate it for their teams. This isn’t about them parroting my words, it’s about them having enough context to answer questions and connect strategy to their team’s specific work. They know their people and how to talk to them. It’s also giving them the forum to deepen their understanding amongst their peers who likely have the same questions.
• One-on-ones are where the really deep understanding actually happens. This is where you find out if the message landed and can see where the translation gaps are. It’s where you can connect the abstract (“we’re shifting our focus to enterprise customers”) to the concrete (“here’s what that means for the project you’re working on”). It’s also where people feel safe asking the questions they didn’t want to ask in front of 250 people or 10 of their peers.
• Async updates handle the in-between like emails or Slack. Not everything can or should wait for the next Town Hall. When something important shifts, I send updates to the relevant levels of the org. This keeps people from being surprised and reinforces that communication is ongoing, not just a monthly event.

The point isn’t volume (although sometimes that helps). It’s that the same message, delivered through different formats at different depths, with different starting points, helps it to actually stick.

Same Strategy, Different Depths

Strategy means different things at different altitudes in your organization.

At the departmental or org level, people need the what and the why. What are we doing? Why are we doing it? What does success look like? This is the narrative. It’s the story that ties everything together.

At the team level, people need the so-what. How does this affect our roadmap? What should we prioritize differently? What does this mean for the project we’re halfway through?

At the individual level, people need the connection to their work. Why does what I’m doing matter to this strategy? How do I make decisions when I’m deep in the details and nobody’s watching?

You can’t skip levels. If you only communicate at the org level, people nod along but don’t change their behavior. If you only communicate at the team level, people don’t understand the bigger picture and can’t make judgment calls. The goal is for people to connect the dots between their day-to-day and the change in strategy. Part of that connection is helping them see how the strategy aligns with what they already care about– their growth, their team’s success, the problems they’ve been wanting to solve, whatever it is. That’s what generates real motivation. You have to help them make that connection at every level.

Problem Before Solution

You can’t give people everything at once. The temptation is to lay out the full picture: here’s the problem, here’s the solution, here’s the plan, here’s the timeline. People try to do all that in one comprehensive presentation. Resist that urge.

People need to understand the problem deeply before they can hold the solution. If you jump straight to the answer, you get two failure modes. First, people who didn’t fully grasp the problem can’t evaluate whether the solution makes sense. They’ll nod along and usually follow your logic, but they won’t be able to make judgment calls when they hit edge cases. Second, if the solution changes later, and it inevitably will, you have to re-educate from scratch because they were never afforded the opportunity to build the foundation. They learned “do X” without learning why X was the answer to begin with.

Start with the problem space, then the problem itself. Let that sit. Some people need the processing time that you already heard during the time you were building the strategy. The goal is to anchor them in the problem so deeply that when the solution evolves, they can follow why.

If you don’t have the whole solution figured out, say so. If you do have the full plan, you can share it, but spend more time ensuring people understand the problem than the solution. The solution is what they’ll execute, but the problem is what lets them adapt when execution gets messy.

Then, when you come back to them, in the next Town Hall, the next leadership sync, the next async update, use the questions you collected to fill more of the gaps between problem and solution. Remind them of the foundation before you rush to build on it. The old writing advice applies: tell them what you’re going to tell them, tell them, tell them what you told them. But the real point isn’t repetition for its own sake. It’s that each pass adds depth to a structure they already hold.

Restating From Their Perspective

The challenge that’s less obvious is getting everyone to believe that you understand the problems from their perspective. You see the path clearly. You’ve been thinking about this for months. You know the problems, you’ve mapped as many of the solutions as possible and you see how the pieces fit together. But your people see their corner of it. They see the problems as they experience them — the frustrating process, the unclear priorities, the thing that’s been broken for six months that nobody seems to care about.

Just because you see it doesn’t mean they know you see it. Most of the time, this is about restating the same problem with a different perspective. Not new information, new framing. When you describe the problem the way they experience it, you go from only trying to convey that, “leadership has a plan” to, “leadership actually gets it.” That’s when the nodding stops being performative and people really buy in.

The questions people ask along the way are how you learn their perspective. Pay attention to what’s coming up repeatedly in 1:1s, in Slack threads, in the Q&A after Town Hall, or through the grapevine. Those patterns are telling you three things at once: where your communication has gaps, where their understanding has gaps, and where your strategy itself might have gaps. That third one is easy to miss — especially when you’ve been thinking about this non-stop for weeks or months and started to drink your own koolaid. The questions aren’t just revealing what people don’t understand, they’re revealing what you might have gotten wrong or left unconsidered. The people closest to the work often see things you don’t.

When you take those questions and weave the answers into your next communication, you’re not just filling gaps. You’re demonstrating that you’re listening, that you heard them, that their perspective shaped the conversation, and that the strategy is a living thing that incorporates input from across the org. That’s what makes repetition feel like dialogue instead of broadcast.

Making Strategy Stick

All of this repetition has a goal beyond alignment: getting people back to a state where the new strategy is their normal.

Change requires a different kind of energy than execution. During transformation, people operate in high-alert mode because they are processing new information, questioning old assumptions, adapting workflows, and finding a new normal. That’s cognitively expensive. Some people thrive in it briefly, but nobody thrives in it indefinitely, even the highly motivated ones. People can be productive in crisis mode, but they’re more consistent when they’re back to business as usual. The sooner you get them there, the more easily work flows from all levels of the organization.

The goal isn’t perpetual communication about the strategy. It’s reaching the point where people stop thinking about the change because the change has become the default. That’s when you get sustained output. That’s when people have headspace to be creative within the new model rather than spending their energy just understanding it and adjusting to it.

Visibility of progress accelerates this transition. If you’re in the thick of transformation, weekly updates like company-wide Town Halls are reasonable. You reinforce the information, build on it, and add nuance where relevant. At a minimum, there should be monthly communication about what’s shipped and what impact it’s had. People need to see valuable work coming out of the organization, even work that doesn’t touch their team directly. This is especially powerful through the lens of the new strategic direction. It creates stability during periods of change and signals that business as usual is still occurring, even while things are shifting.

Repetition is how strategy becomes culture.

Your Posture Matters

How you show up matters as much as what you say. There are two important things to get right here.

First, be honest about what you don’t know. It’s okay to say “here’s what we’re confident about, here’s what we’re still figuring out.” This isn’t weakness, it’s honesty; and it’s the kind of honesty that builds trust and leaves room for people to contribute. You’re reminding people that they’re not just executing orders. They’re in the positions they’re in and part of your organization because they can contribute, spot problems, and ask hard questions. Being genuine about uncertainty creates the conditions for people to actually speak up when something doesn’t make sense. If you perform total confidence, you’ll get compliance and silence. If you’re honest about the edges of the plan, you’ll get engagement.

This connects to something bigger: you want people to believe that you’re in this together. The strategy will never be perfect. Moving forward as a group, testing assumptions, changing course when needed, that only works if people have the psychological safety to raise concerns and everyone’s willing to engage honestly. Your willingness to say “I don’t know” models that it’s safe for them to say it too.

Second, manage your own excitement. If you’re genuinely energized by the strategy — and hopefully you are — the temptation is to share too much, too quickly. You want to brain-dump for hours, get them as fired up as you are, and show them the whole vision in all its glorious detail. Resist that urge. Your enthusiasm can work against you if it floods people before they’re ready. When you give them everything — the problem, the solution, the implementation details, the long-term possibilities — you crowd out their own thinking. They become executors of your ideas instead of contributors to the strategy.

Show the excitement. That kind of energy is contagious and necessary in moments where you’re trying to bring people along. Let them see that you believe in this. But hold back on every single detail until they’ve had time to hear the core message a few times, digest it, and start forming their own ideas. The goal isn’t just to transfer your vision into their heads. It’s to create enough space that they can add to it.

A Cadence You Can Steal

If you’re looking for a starting point, here’s a simple communication cadence:

• Monthly: Town Hall covering macro updates (repeating prior context while adding new layers), progress on strategic initiatives, and visible wins from across the org. These should be weekly during the more intense periods of change.
• Weekly: Leadership sync where your direct reports get the latest strategic context so they can cascade it, prioritize it and tie it in appropriately.
• Ongoing: One-on-ones that explicitly connect individual work to strategy, not just status updates and career conversations.
• As-needed: Async updates when something important changes and can’t wait for the next scheduled touchpoint.

The work isn’t done when you’ve communicated the strategy. It’s done when the strategy changes how people decide without you in the room. If you’re tired of hearing yourself say it, you’re probably halfway there. Until then, keep repeating. Until then, keep repeating.