The 5 biggest questions every manager needs to ask

If you’re not asking your direct reports these questions, you may lose your best team members

Kate Mulcrone

By Kate Mulcrone

a manager leads a brainstorming session

According to a top workplace experct, there are five questions every manager needs to ask their direct reports.

Whether you’re a brand-new manager or have led a team for decades, it can still be hard to have a sense of how each of your team members is doing, even if your organization has periodic review processes.

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Writing in the Harvard Business Review, Susan Peppercorn, an executive career transition coach and author of Ditch Your Inner Critic at Work: Evidence-Based Strategies to Thrive in Your Career, enumerates five key questions managers need to ask their direct reports.

As an expert in career transitions, Peppercorn has spoken to hundreds of employees across industries and at all levels of their careers about what really matters to them – and it’s not necessarily what you think!

“In a recent Gallup study, more than half of employees surveyed said that no one — including their manager — had talked to them about how they were feeling in their role in their last three months before they quit. And 52% of exiting employees stressed that their manager or organization could have done something to prevent them from leaving their job. Having coached hundreds of employees in career transition for more than a decade, I can validate these findings. Countless clients have told me they wished their employer had asked them questions to encourage their growth before they resigned. They wanted these questions to come from their manager proactively, rather than retroactively from HR.”

workers sit in a meeting discussing a project

So just what are these burning questions? Here are Peppercorn’s top five questions that managers should ask their current direct reports, preferably in a casual one-on-one talk rather than as part of a formal review.

1. How would you like to grow within this organization?

This question might sound like an interview question, but managers need to recognize that a current employee will have a very different, nuanced response compared to an outsider who is going through your organization’s recruitment process.

This question not only sets the stage for the rest of the discussion, but it lets the employee focus on their own needs.

If your direct report is drawing a blank, Peppercorn suggests a more open-ended phrasing. “To get at the answer, you might also ask, ‘What role would love to do (whether it exists or not), and what can I do as your manager to encourage your development in this company?’”

2. Do you feel a sense of purpose in your job?

“Managers can play a meaningful role in helping employees understand how their roles contribute to the organization’s broader mission,” Peppercorn says. “But helping employees feel a sense of purpose must go deeper than this to tap into what’s purposeful to employees about their job and connects with their own values.”

Before you ask this thorny question, make sure that your employee understands that you’re concerned about their wellbeing and personal sense of purpose, not their performance! Also, make sure you have a plan for how to proceed it the answer is no. Focus on what you can do as a manager to make your employee feel more engaged with their values at work. If you can’t fix the issue yourself, it’s worth raising your employee’s concerns with your manager, as long as you don’t reveal which of your direct reports is feeling disconnected at the moment.

3. What do you need from me to do your best work?

Good managers know when to lean in and offer assistance and when to back off and let a direct report focus on their most important tasks. That said, your employees may not feel comfortable speaking up about a lack of resources or a clash of work styles.

“The most effective managers respect and care about their employees by knowing them as individuals, acknowledging their achievements, having performance conversations, and conducting formal reviews. These supportive behaviors build a work environment where employees feel safe experimenting with new ideas, sharing information, exploring development opportunities, and supporting each other,” says Peppercorn.

4. What are we currently not doing as a company that you feel we should do?

You never know where the big idea is going to come from! Although many companies encourage employees to communicate their ideas to upper management, not everyone is going to be comfortable doing so.

As a manager, you have an opportunity to act as a bridge between your team and company decision-makers. Peppercorn stresses the importance of the right approach with this question, since it can make employees feel they are being put on the spot.

“By asking individual team members what they feel the company could be doing better, what market opportunities the organization might be overlooking, and how to leverage company resources more effectively, you’re validating that their thoughts matter. You might also ask things like, ‘Are you satisfied with our current work from home/hybrid policy? If not, what do you think needs to change? How satisfied are you with the tools you use to communicate with your colleagues when working remotely?’”

5. Do you have the opportunity to do what you do best every day?

Although this question is fairly similar to question three, in this case you’re inviting your direct reports to open up about truly any issue that is a hurdle for them.

You want your employees to spend most of their time on the specific tasks that fall under their mandate, but there may be obstacles that are keeping them from being able to focus on what’s important.

A woman wearing a red veil and a white long sleeved shirt is holding a blue folder. Behind her is a table of men and women having a meeting

“To determine whether your employees are focusing on their strengths, you might also ask, ‘What is the best part of your job? Which of your talents are you not using in your current role? What part of your job would you eliminate if you could?,’” says Peppercorn.

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Kate Mulcrone

Kate Mulcrone

Kate Mulcrone has more than 10 years’ experience writing about travel, tech, and the workplace for a variety of publications.