Entrepreneurs and managers: four questions that can transform the way you lead your team or company

Four strategic questions that every boss, manager or entrepreneur should ask to make clearer, more ethical and effective decisions in times of constant crisis and rapid change.

Businessmen, gerentes, coordinators, supervisors and other professionals with decision-making power face a new type of scenario. Instead of dealing with occasional crises, as was common in the past, many today operate in a reality of constant crisis.

These are geopolitical changes, climate shocks, rapid technological advances — all at the same time. Every month, a new challenge. Every week, an uncertainty.

In this scenario, decisions based on old formulas lose their validity.

What worked before may fail now. And that's precisely why, Asking good questions before acting has become one of the main leadership tools.

This article presents fundamental questions that every boss, manager, entrepreneur or professional in a decision-making position should ask in times of uncertainty.

They don't offer magic answers, but they help to clear your thinking, see hidden risks and act with more confidence even in the midst of instability.

Old methods are no longer enough

For a long time, leaders and managers have been trained to reduce ambiguity. Focus on return on investment. Set timelines. Plan based on history.

These questions work well in predictable environments.

But when everything is changing all the time, they start to limit their vision. They get stuck in what has already been done. And they don't allow us to see the new.

Furthermore, in times of crisis, the instinct is to seek Safety.

As a result, many leaders end up trying to repeat old formulas. But this can create a false sense of control — and with it, the risk of making bad decisions.

Therefore, the first step is to change the way of thinking. Instead of quick answers, the focus should be ask strategic questions that open paths.

Will this decision still make sense a year from now?

Company leaders and managers are under pressure to achieve quick results.

In difficult times, this intensifies: cost cuts, process changes, project cancellations. But will these measures stand the test of time?

This question forces the leader to think beyond the current quarter.

And it helps to maintain focus on lasting choices, aligned with the business values ​​and the company's real objectives.

Imagine a practical scenario is that of an executive at a global consumer brand.

After a poor quarter, your team suggested cutting sustainability initiatives.

It was a simple measure, with guaranteed savings and minimal operational impact.

But when you ask yourself “Will this decision still make sense a year from now?”, the manager realizes something bigger.

Sustainability was a central part of the brand image, especially for younger consumers, who valued environmental and social actions.

Cutting this program could generate immediate savings — but it would hurt the company’s reputation in the long run.

Therefore, she decided to keep the most visible and important projects. She restructured the others. And she communicated the decision transparently to her employees.

This shows that the company remains committed to the future, even when facing limitations in the present.

This simple question helps to avoid a reactive decision, reinforcing the company's strategic positioning.

If this decision is remembered a year from now, what will it say about us?

Leadership is also an example. It is not enough to decide — it is necessary show what is valued, how to act and what is the ethical standard that guides the business.

That’s why this question is so powerful. Instead of focusing solely on the outcome, it prompts the leader to reflect on the legacy of the choice.

How will the team view this decision in the future? What about the customers? What about the market?

Raj, a vice president at a technology company, faced this dilemma. He was leading the launch of an innovative but risky product.

A staff member raised concerns about the protection of user data. It wasn’t illegal — but there was a gray area.

Launching on time would please investors. Delaying it, not so much.

That's when Raj asked himself, “If this decision is remembered a year from now, what will it say about us as a company and as a leadership team?"

The answer came quickly: that they prioritize ethics and safety.

He chose to delay the launch by two weeks. He adjusted the system. And he openly communicated the reasons.

The company missed the deadline. But it gained respect. Internally and externally. A year later, this decision is still remembered as an example of responsible leadership.

What if it's not a bad phase, what if it's the new normal?

Bosses and entrepreneurs often see crises as something temporary. A “storm” to be overcome. But what if that is not the case? What if the current scenario — unstable, challenging — is permanent?

This question shifts the focus from survival to adaptation. It challenges the instinct to wait things out.”return to normal”. And it encourages planning based on the current reality, however difficult it may be.

Darryl, the COO of a consumer goods company, had just such a shock. A key supplier started failing. Delays. Quality issues. Yet he insisted on keeping the partner, hoping things would get better.

During a meeting, a colleague asked him: “What if it's not the storm, what if it's the weather?"

The question turned the tide. Darryl realized that the supplier could no longer handle the company’s expansion. The problem was not temporary. It was structural.

He then created a plan to bring on a new supplier without immediately abandoning the old one. He set performance targets for both.

And prepared the company for the transition.

The result was a more robust and reliable supply chain. It all started with a question that exposed the root of the problem.

What is the cost of waiting?

Waiting seems safe. Waiting for more data. Waiting for the market to stabilize. But in times of high volatility, waiting can be very costly.

This question invites leaders—business owners, managers, supervisors—to look at the risks of not acting.

What will be lost if the decision is postponed? What is the impact of hesitation?

Monica, the chief strategy officer at a financial firm, found herself in this situation. She needed to hire a marketing director. But the economic climate was not helping. The temptation to postpone the decision was strong.

It was then that she asked: “What is the cost of waiting?"

The team identified concrete risks: losing good talent that was available now. Wasting time in promoting new products.

Losing market share and, internally, losing the rhythm that the team had been building.

The decision was made: they hired the new director. And they adjusted the remuneration policy to attract even more quality.

The question didn’t bring certainty. But it did reveal that the biggest risk wasn’t taking action—it was waiting too long.

Ask to see what the eyes cannot see

None of the questions mentioned have ready answers. But they all have the same effect: broaden the vision of bosses and managers.

They help you see beyond the obvious. They reveal hidden risks. And they show opportunities that routine can hide.

These questions are not a script. They are tools. They should be used when decisions seem too difficult. When the pressure is great. When the outlook is unstable.

Leading is deciding. But it is also reflecting.

Leadership in difficult times requires more than courage. It requires clarity. And that clarity starts with asking good questions.

The examples show that thinking differently leads to different results.

Instead of repeating patterns, they looked for another way. And they found stronger, more responsible solutions that were more aligned with what their companies really needed.

These cases show that, for those who run companies, teams or projects, the right questions are worth more than hasty decisions.

The new role of the manager in uncertain times

Business leaders, managers, coordinators and entrepreneurs don’t need to have all the answers. But they do need to create space for the right questions.

Instead of acting on impulse, it’s worth stopping and reflecting:

• Will this choice still be valid in the future?
• What does it say about our leadership style?
• Are we waiting for a crisis to pass or adapting our business to reality?
• What's the harm in doing nothing now?

These four questions do not eliminate risk. But they help us better understand the challenges. And to act with more consistency, ethics and vision.

In today's world of constant change, leaders need more than fixed plans. They need the ability to adapt.

Of reading the scenario. And of humility to ask good questions before making important decisions.

Bosses, managers, and entrepreneurs should not seek total control. They should seek clarity. They should embrace uncertainty, and still act. And, whenever possible, use the right questions to avoid the most common mistakes—those born of fear, haste, or repeating the past.

With information from Harvard Business Review.