5 Questions Every Manager Needs to Ask Their Direct Reports

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If you’re worried that your employees are eyeing the door, it’s time to start having some important career-defining conversations. In this piece, executive coach Susan Peppercorn outlines five questions to start asking your direct reports so that you can get a better sense of how they’re feeling about their positions: 1) How would you like to grow within this organization? 2) Do you feel a sense of purpose in your job? 3) What do you need from me to do your best work? 4) What are we currently not doing as a company that you feel we should do? 5) Do you have the opportunity to do what you do best every day? When managers make checking in with these five questions a regular part of how they interact with their employees, it helps ensure that people feel seen and valued. And when managers help individuals on their teams feel that way, they’re more likely to be rewarded by employees who become advocates for the department and organization, no matter how long they stay.

Sara, a departing employee, sat across from her company’s HR leader for an exit interview. As a marketing executive for a financial services company, she was resigning after five years to take a CMO role at a fintech startup.

When the HR director asked Sara, “Is there anything else we could have done to keep you here?” Sara paused. “Yes. I wish there had been conversations about my career goals and opportunities for growth,” she said.

This is just one of the discussions that often takes place too late, after top talent is already on the way out the door.

As the number of workers quitting their jobs continues to swell amid the Great Resignation, soon-to-be-former employees are finding themselves in exit interviews with HR representatives who hope to gain a clearer sense of what’s happening inside the company — and who often learn — after the fact — things that management was unaware of. Exit interviews provide “a way to find out what is happening, or what has happened, that may be motivating this employee… to leave,” according to Yuletta Pringle, knowledge advisor at the Society for Human Resources Management.

Yet as the above dialogue illustrates, these conversations may be too little too late. 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.

Before asking questions as a manager, though, it’s critical to know what motivates employees to stay with an organization and why. Gallup research shows 12 needs managers can meet to improve employee engagement, including:

  • Prioritizing employee development
  • Facilitating a sense of purpose
  • Caring about employees
  • Considering employee opinions
  • Focusing on employee strengths

These five measures map closely with research recently published by HBR on strategies to boost retention. With these five needs in mind, consider incorporating the questions below into routine check-ins with your direct reports, so that you can ask employees the questions they want to hear before they’re gone:

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

Career development is the most critical of the elements identified by Gallup, and two-thirds of people — regardless of their level — leave their company because of a lack of career-development opportunities. With this in mind, it’s important to figure out what growth opportunities each employee needs for optimum development, whether through sponsorship, coaching, mentoring, visibility, or challenging work assignments.

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?

For the five years that Sara worked for the financial services company that she was resigning from, she never felt that her work impacted people’s lives in a meaningful way. By joining a fintech company committed to improving the accessibility and affordability of financial services for underserved populations, she was excited that her marketing efforts could make a difference in the lives of people who needed access to capital. Her employer and manager missed an opportunity to tap into Sara’s sense of passion and purpose in her marketing role.

Managers can play a meaningful role in helping employees understand how their roles contribute to the organization’s broader mission. 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.

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

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.

As you explore what your employees need to do their best work, you might also ask, “What is your biggest frustration, and what action can I take to help you deal with it? What have you been trying to tell me that I’ve not been hearing? How would you like to be recognized?”

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

The best managers let workers know that their opinions count by promoting open dialogue and providing honest feedback on employees’ opinions and suggestions, supporting good ideas and addressing unfeasible ones. 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?

When Sara was in her marketing role, her concentration was on data analytics. Although she learned how to master analyzing customer use data, she never considered it one of her strengths. Her new role will allow her to concentrate on branding and audience acquisition, areas that she enjoys and excels in. Once again, her former employer missed an opportunity to harness the best of Sara’s talents before she took them to a new organization.

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?”

When managers make checking in with these five questions a regular part of how they interact with their employees, it helps ensure that people feel seen and valued. And when managers help individuals on their teams feel that way, they’re more likely to be rewarded by employees who become advocates for the department and organization, no matter how long they stay.

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