Five Conversations That Reveal How Your Team Thinks About Strategy

These will tell you more about your strategy than any business review ever has.

You do not need a strategy offsite to find out whether your strategy is working. You need five conversations.

Each one takes less than 15 minutes. Each one uses a single question. And the answers will tell you more about the real state of your strategy than any business review, any engagement survey, or any consultant’s diagnostic ever has.

Here is what makes these conversations different from the ones you are already having: they are not about performance. They are about orientation. They test whether the people executing your strategy understand what it is, where it is going, and why their work matters to it.

This is important: if your team cannot answer these questions clearly, your strategy exists only in leadership’s minds, nowhere else. And these five conversations will show you exactly where the gap is.

Let’s go through them.

Conversation 1: “What is changing in the world that will affect our customers in five years?”

This is the most revealing question you can ask.

Listen carefully to the answer.

If your employee describes a specific structural change, such as the shift to electric vehicles, the ageing of the population, or the automation of supply chains, and can connect it to your customers, your strategy has landed. That person understands why the firm is moving in the direction it is moving.

If they say something vague (”everything is changing,” “AI is going to be huge,” “the market is uncertain”), your strategy has not given them a framework for understanding the external world. They know things are changing. They do not know which changes matter to your firm or why.

If they describe internal priorities (”we’re focused on growing revenue in EMEA” or “we need to improve our NPS scores”), your strategy is organised around operational targets, and your team has absorbed that orientation. They are looking inward because the strategy is looking inward.

Remember: my research across 8,430 companies found that the firms which captured dominant profit share were the ones whose leadership teams paid disproportionate attention to external changes. The firms that lost market share paid disproportionate attention to internal operations. This question tests which orientation your team has absorbed.

Conversation 2: “Which of our current investments would you not make if you were starting today?”

This one is uncomfortable.

Every firm carries legacy investments: products, projects, partnerships, and processes that made sense when they were started but no longer serve where the firm is heading. Your team knows which ones these are. They work on them every day. The question is whether they feel safe enough to say it.

If they can name specific investments and explain why those investments no longer fit the strategic direction, two things are true. They understand the direction, and the culture allows them to challenge it constructively. Both are good signs.

If they say “everything we’re doing is important,” they either do not understand the direction well enough to evaluate against it, or they do not feel safe naming the misalignment. Either way, you have a problem. Strategy requires exclusion. If your team cannot identify what should be excluded, the strategy is not constraining decisions, which means it is not organising them.

You might be thinking, “I can’t ask people to criticise existing investments. It will create anxiety.” The opposite is true. People who can see misalignment but are not allowed to name it are already anxious. Giving them a structured way to raise it reduces anxiety. Silence is what creates the fear culture that destroyed Nokia.

Conversation 3: “If we could only build around three external changes for the next decade, what would they be?”

This forces a different type of thinking. Not “what should we do?” but “what is happening in the world that is important enough to organise around for ten years?”

Most people have never been asked this question. That is the point. The quality of their answers tells you whether your strategy has taught them to think about long-term structural change, or whether their mental model of strategy is limited to annual plans and competitive responses.

Let’s be very clear: you are not looking for the right answer. You are looking for the quality of the thinking. Can they distinguish between a structural shift and a passing trend? Do they think in terms of years rather than quarters? Can they articulate why one change matters more than another?

If your team can do this, your strategy has done something most strategies fail to do. It has changed how people think, not just what they do. That is the difference between a strategy that survives your leadership and one that disappears when you leave.

Conversation 4: “How does your work connect to the direction we are heading?”

This is the retention question. The one your best people are asking themselves even if they never ask you.

If an employee can draw a clear line from their daily work to the firm’s strategic direction, they have something that compensation cannot provide: a sense of trajectory. They are building skills that will be more valuable as the world changes. They are contributing to something larger than this quarter’s target. That is what keeps talented people.

If they cannot draw that line, their work feels disconnected from anything larger. It does not feel like it is going anywhere. And people who feel that way leave.

The answer also tells you something about your communication. A strategy that is clear at the top but invisible at the middle is a strategy that has not been translated into a narrative that reaches every audience. If the connection is missing, the story is missing.

Conversation 5: “What would you do differently if you had the authority?”

This one requires trust. But the answers are extraordinarily valuable.

Your team sees things you do not. They are closer to the customers, closer to the operations, closer to the failures. When you ask what they would change, you are testing two things at once: whether they understand the strategic direction well enough to propose improvements to it, and whether the ownership architecture gives them enough authority to act on what they see.

If they have specific, strategically aligned suggestions, promote them. Seriously. These are the people who understand the direction and can see how to accelerate it. They are exactly the talent you cannot afford to lose.

If they have suggestions that are disconnected from the strategic direction, the direction has not landed clearly enough for them to contribute to it. That is a communication problem, and it is fixable.

If they say “nothing, everything is fine,” the culture is not safe enough for honest answers, and you have a bigger problem than strategy.

How to run them

Do not do all five in one sitting. Spread them across two weeks. Pick different people at different levels and in different functions. Do not announce it as a diagnostic or a programme. Just have the conversations. Listen more than you talk. Take notes afterwards, not during.

Remember: you are not looking for consensus. You are looking for patterns. If three people in different parts of the firm give you the same answer to Conversation 1, that answer is your strategy’s real orientation, whether or not it matches what the leadership team intended.

And here is the hard part: if the patterns reveal a gap between what you think the strategy is and what your team has absorbed, the problem sits with the strategy or how it has been communicated. Not with your team.

What next?

You now have five conversations you can use.

Run them. Write down what you hear. Compare it to what you intended.

The gap between those two things is the most important strategic information you will collect. And unlike most strategic information, collecting it costs you nothing but the willingness to listen to the answers.

Start tomorrow.