Does Your Team Actually Know What Winning Looks Like?

Leadership teams put a lot of effort into creating alignment. We develop the strategy, set priorities, define KPIs, brief managers, hold town halls and communicate the plan across the organization. After all of that work, it is easy to believe everyone understands where we are going and what matters most.

But try something.

Walk a few levels down in your organization and ask five people, from different functions and at different levels, one question:

What are the three most important things this organization needs to accomplish right now?

One person might say growth. Another says margin. Someone else says customer experience, while another points to a transformation program or operational stability. The interesting part is that none of them may necessarily be wrong. Each person may be describing something that genuinely matters.

That’s the problem.

An organization can have smart, capable people working incredibly hard toward legitimate objectives and still lack strategic alignment. Alignment isn’t demonstrated by whether people have heard the strategy or can repeat the priorities from the last town hall. It is demonstrated by whether they understand what winning looks like well enough to make decisions consistent with it when senior leadership isn’t in the room.

The Strategy You Say Versus the Strategy People See

I saw this play out during my time at 1st Canadian Division.

At the broader Canadian Armed Forces level, there were several things we needed to be prepared to do. There was a desire for the CAF to become more engaged in another part of the world, while 1st Canadian Division also needed to remain prepared to establish a new CAF operation if required. At the same time, we maintained responsibilities related to non-combatant evacuation operations and humanitarian assistance.

Those requirements all mattered. Inside the Division, however, our commander’s focus was clear: divisional-level warfare.

As that emphasis became increasingly dominant, the organization naturally began to follow it. Our training focused heavily on warfare. Our international engagements followed that focus, as did staff effort and attention. The more energy the organization put behind that priority, the harder it became to protect the planning and engagement required for the other tasks we were still mandated to perform.

I saw that tension directly because some of those other responsibilities sat with my team. I did what I could to protect their focus and keep them working on our mandated tasks while still balancing the pull toward the Division’s dominant priority. But there was only so much capacity available, and leadership emphasis creates a kind of organizational gravity. People, resources, meetings, training and attention naturally begin moving toward what senior leaders consistently demonstrate matters most.

The problem wasn’t that divisional warfare was unimportant. It absolutely mattered, and there were very good reasons for us to maintain that capability. The problem was that it wasn’t the only thing that mattered. We still had other mandated responsibilities, and as more of the Division’s attention shifted in one direction, maintaining the focus required for those other responsibilities became increasingly difficult.

From what I understand, some of that balance was restored after I left the Division. But the experience reinforced something that has stayed with me ever since: your people don’t determine your priorities solely from what is written in your strategy. They watch what you do.

They pay attention to where resources go, what gets discussed repeatedly in meetings, what gets exercised, what gets measured and what senior leaders continually ask about. Over time, those signals become far more influential than whatever was written on the original strategy slide. Whether we intend it or not, our behaviour teaches the organization what actually matters.

Hearing the Strategy Is Only the Beginning

When I think about strategic alignment now, I see it as a progression through four levels:

1. Heard it. People have been exposed to the strategy and know what leadership has said is important.
2. Understood it. They can explain what the organization is trying to accomplish and why it matters in their own words.
3. Can prioritize with it. They can use that understanding to determine what deserves attention and what does not.
4. Can decide with it. They can make difficult trade-offs consistent with leadership’s intent without waiting for someone senior to tell them what to do.

Most organizations are pretty good at the first level. We know how to communicate through town halls, strategy decks, internal communications and management briefings. Many get to the second level as well, particularly when managers take the time to translate the strategy for their teams.

The real challenge begins with levels three and four because that is where knowing something has to turn into judgment.

Someone being able to repeat your priorities doesn’t tell you what they will do when two legitimate demands collide. What happens when an opportunity increases revenue but compresses margin? What happens when releasing a product faster increases operational risk? Do you move people toward a new strategic priority or protect an existing commitment?

These are the decisions through which strategy actually comes to life. I think of them as Tuesday afternoon decisions because they rarely arrive in a perfectly packaged strategy session. They happen during normal operations when someone has competing demands, limited resources and incomplete information, and a decision still has to be made.

There won’t be a town hall before each one, nor should senior leadership have to adjudicate every decision. Your people need to understand your intent well enough to determine which choice best supports what the organization is trying to accomplish.

If your people cannot use your strategy to resolve competing demands, you don’t have alignment. You have awareness.

Your Behaviour Is Part of the Strategy

This is where leaders can unintentionally create the very misalignment they later complain about.

We might publish three strategic priorities but consistently ask questions about only one. We tell people innovation matters but punish every experiment that fails. We say developing people is important but promote the leader who hits the numbers while burning out everyone around them. We announce a major transformation but refuse to stop existing projects to create the capacity required to deliver it.

Then we wonder why the organization isn’t behaving according to the strategy.

People are reading the signals we’re sending them, and those signals aren’t limited to what we say. That was part of what I experienced at 1st Division. Nobody needed to announce every morning that divisional warfare was the priority. The organization’s behaviour was already communicating it through our training, international engagement, senior leader attention and where we invested our finite staff capacity.

I’m seeing this lesson from a very different perspective now as I transition from the military into my role with Arcanus. I’m entering an organization with significant opportunities in front of it, and opportunity creates its own leadership challenge. When multiple promising directions are available, the temptation is to chase all of them because each one can make sense on its own.

But saying yes to an opportunity isn’t just a business development decision. It consumes engineering capacity, leadership attention, money, time and organizational energy. Enough individually good decisions can eventually pull an organization away from what it originally said mattered most.

Different organization, very different environment, but the leadership challenge remains remarkably similar. What we repeatedly give our attention to eventually tells the organization what matters, regardless of what we say our priorities are.

Your calendar, budget, questions, recognition and promotions all reinforce that message. So do the decisions leaders make about what gets funded, paused or rejected. Those actions repeat the strategy far more effectively than showing the same slides again because they demonstrate how priorities are supposed to work when choices become real.

Perhaps one of the strongest signals of all is what you are willing to stop doing. If leadership announces a new strategic priority but refuses to take anything else off the organization’s plate, people quickly learn that the new priority isn’t really a priority. It is simply another task.

Try the Five-Person Test

You don’t need a massive employee survey to get an initial sense of whether your strategy is actually travelling through the organization. Start with five conversations.

Pick five people from different levels and functions. Don’t brief them beforehand or send them the strategy deck as a refresher. Ask each person the same five questions:

1. What are the three most important things this organization needs to accomplish right now?
2. Why do those three things matter?
3. What are we deliberately not prioritizing right now?
4. When two priorities conflict, which one wins?
5. What decision have you made recently because of those priorities?

You’re not looking for five identical answers. In fact, you probably shouldn’t get them. Someone in Finance will naturally see the organization through a different lens than someone in Sales, Operations or HR, and a frontline employee won’t describe the strategy with the same context as an executive.

What you’re looking for is whether those different answers still point toward the same destination.

The language can be different. The examples can be different. Even the emphasis can be different depending on someone’s role. But underneath those differences, you should be able to recognize the same organizational priorities, the same broad understanding of the trade-offs, and the same picture of what winning looks like.

That’s the distinction between alignment and uniformity. Alignment doesn’t require everyone to think the same way. It requires people to make sense of their part of the organization in a way that still supports the whole.

The fifth question is particularly important because it moves the conversation from understanding into behaviour. If everyone can explain the strategy but nobody can identify a decision that changed because of it, then the strategy probably hasn’t travelled as far into the organization as leadership thinks.

If their answers are inconsistent, resist the temptation to conclude that employees weren’t listening. Instead, ask a much more uncomfortable leadership question:

What have we been teaching them to believe matters?

The Five-Person Test isn’t really an employee test. It’s a leadership diagnostic. Their answers tell you something about the environment you and your leadership team have created for decision-making.

What If the Answers Are All Over the Place?

If the Five-Person Test exposes a problem, your first response shouldn’t be another town hall or a new version of the strategy deck. Start by looking at three things.

Your priorities. Have you actually made the trade-offs clear? Naming five or six things that matter isn’t the same as telling people which one takes precedence when they collide.

Your signals. Look at where leadership spends its time, where resources go, what gets measured and what gets rewarded. Do those signals reinforce the priorities you say matter, or are they teaching the organization something different?

Your decision boundaries. Do people know where they can exercise judgment? Do they understand which risks they can accept, which decisions require escalation and what wins when two legitimate priorities conflict?

This isn’t about eliminating every difference of opinion. It’s about identifying why reasonable people, acting in good faith, might be making decisions that pull the organization in different directions.

Make the Choices Before Your People Have To

This is where leadership has to do some uncomfortable work.

Strategy requires choice, and meaningful choices require saying no. What aren’t we doing this quarter? Which project are we willing to pause? Which opportunity aren’t we pursuing right now?

Those conversations are difficult because most of the things competing for resources have value. Nobody is fighting passionately to protect a useless project. The hard decisions happen when two worthwhile things are competing for the same time, money or people.

If senior leaders avoid making those choices, the trade-off doesn’t disappear. It simply moves further down the organization, where someone with less context eventually has to make it.

The same applies to decision boundaries. Senior leaders cannot anticipate every situation their people will face, nor should they try. What they can do is provide enough clarity for capable people to exercise judgment. If growth and margin collide, which one takes precedence right now? If speed and reliability conflict, which matters more? Where can teams accept additional risk, and which decisions genuinely require escalation?

I’ve always believed that one of the clearest measures of leadership is what happens when the leader isn’t there. If every difficult decision continues to come back to you, you might have control, but you don’t necessarily have alignment.

When the priorities, trade-offs and boundaries are clear, the question changes from “What would the boss want me to do?” to “What decision best supports what we’re trying to accomplish?”

That’s a far more capable organization.

Does Your Team Know What Winning Looks Like?

Go back to those five people.

Ask them what the three most important things your organization needs to accomplish right now are. Ask what you are deliberately not prioritizing, what happens when two priorities collide, and what decision they have made recently because of the strategy.

Then stop talking and listen.

If their answers surprise you, don’t immediately ask why they failed to understand the strategy. Look first at the signals your leadership team has been sending. Where are you spending your time? Where are the resources going? What are you continually asking about? What gets rewarded? What have you called a priority while refusing to stop something else to make room for it?

Your strategy isn’t ultimately defined by what leadership writes down. It is defined by the decisions people make when leadership isn’t in the room.

That’s the real test of alignment.

If you’re a senior leader who keeps finding yourself pulled into decisions your capable people should be able to make without you, the issue may not be their capability. It may be the clarity surrounding them.

That’s the kind of organizational leadership challenge I work through with senior leaders. If this article has you wondering whether your strategy is actually travelling through your organization, a Leadership Clarity Call is a good place to start.

Lead. Don’t Boss.