5 questions managers should ask their teams quarterly

As a manager, it’s important to keep the lines of communication open and to gather information that will help you be more effective. There are some general questions managers should ask about direct reports’ well-being and job effectiveness, but the frequency you bring up these questions matters.

You should be asking these sorts of questions only about once a quarter, because it gives your reports a chance to look across the last several months and provide responses that are not just a reflection of the last few days of work.

Asking questions, though, brings with it a responsibility to do something with this information. Employees are unlikely to continue to want to provide honest answers to questions if they feel like their manager does not do anything with the responses.

With that in mind, here are five questions managers should ask every quarter. If you have a quarterly team meeting, you can embed versions of these questions in that meeting. Otherwise, make a note on your calendar and discuss these issues in individual meetings with your supervisees.

How are you doing?

We often ask people how they’re doing as a follow-up to saying hello. This kind of social grease gets conversations going, but all too often we don’t really want a detailed answer. Consequently, people develop stock answers to this question like “Hanging in there.”

Periodically, though, it is important to ask your direct reports how they’re doing when you actually want the full answer. The answer you get back should reflect how people are doing overall, work, health, home, family, and work-life balance.

When someone is struggling with some phase of their life, express some empathy, and ask whether there is anything you can do to help. It’s important to get a sense of people’s well-being, partly because there may be something you or your organization can do to be of service.

Even if there isn’t anything you can do, being aware of issues people are dealing with may help you to better understand their work performance or even to shift certain responsibilities away from people temporarily to give them the time to address any struggles they may experience.

What’s your big goal?

You’d also like to have a good sense of the big things that your supervisees want to accomplish. Managers should ask this question because it goes above-and-beyond the business goals that you have probably set with a direct report. It’s important to know what is motivating them at this moment.

Understanding what drives your reports is valuable, because if you can help them to achieve their goals, then they are likely to continue to enjoy their work and bring their best efforts.

These conversations can also be helpful to set realistic expectations. A lot of people who are new to the workplace are often hoping to be promoted quickly. That’s not always an option. Giving employees a clear sense of the typical career path and how long it takes to reach key milestones can help to avoid frustration from employees who have a vision of a fast rise in an organization.

What’s your big obstacle?

Work would be easy to do if you just came in, put in some effort, and projects moved forward on a straight line forward. As you know, that’s rarely the case. Instead, a crucial part of success is identifying what’s preventing a project from advancing and then fixing those problems.

A key role you need to play as a manager is to help your team to identify obstacles and to provide strategies and support to move beyond them. Your experience is likely to be valuable to help your team members to see aspects of situations that hinder them. You can then mentor them to be better able to recognize those obstacles in the future and to have strategies to address them.

At times, the obstacles that prevent progress on a project involve people or resources. In those cases, you, as a manager, may be in a better position to address those obstacles than your direct report.

What do you need to know?

As a manager, you’re also at the front lines of creating a culture of learning. Developing your team members is an important part of your role. A focus on development starts by asking your supervisees what they would like to know.

At times, the things your team members should learn requires taking a training or getting a microcredential. Make sure that your reports use whatever education benefits the organization provides to learn something new each year. Use these conversations to help plan that educational path.

Often, though, there are things that you can incorporate into the work day that also promote acquisition of new knowledge and skills. You might bring your supervisees on “ride-along” meetings where they get to see how you handle situations they might not encounter in their normal work. You might coach your team members through problems to help them learn to solve them alone in the future. This informal mentoring is enhanced by knowing about the things your supervisees want to learn.

What do you see that I don’t?

As you move into management, you start to step away from the day-to-day engagement with specific tasks that move the business forward. You may engage less often with customers and clients, or be less engaged with creating content, writing programs, or manufacturing products. Instead, you are focused on strategy and on getting the most out of the people who work for you.

That means that you lose sight of the positive and negative things that are going on in the front lines of your company. That is where your supervisees can be your eyes and ears. You want to find out how the work looks to them.

This feedback is valuable because it can provide an early-warning system for things that might take a long time to show up on lagging indicators of problems like lost sales, product returns, or employee turnover. In addition, the strategic decisions that managers make may have unexpected consequences. Often, running potential decisions by a few of your employees can bring to light problems that may arise from a course of action being considered. Even if you move forward with that particular option, you are aware of the problems it may cause and can be prepared for them.