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How Are You?

While you may be tempted to get right down to business—especially if you’re under pressure to finish a project or in back-to-back meetings—take the time to pause and gauge how your direct report is feeling, both about work and outside of it.

“At the very start of a meeting, there should be a personal vibe,” Knight says. “You want to know how they’re doing as a person and what’s going on in their lives.”

2. Do You Have Any Updates From Our Last Meeting?

Before diving into new topics, Rock suggests tying up any loose ends from the previous session. “Get those updates out of the way so you can then focus on what’s most pressing based on deadlines and urgency, or the areas where the most support may be needed,” she says.

3. What Are You Focusing on Now?

Employees should be encouraged to share priorities and top projects in order to manage expectations on both sides. As a boss, you can also use this question to make sure someone’s work is aligned with the goals you have set together, and that they are on track to achieve them (whether it’s developing a new skill or contributing to a specific project).

“This way you’re making sure they’re growing and getting the skills they need so they’re not in that role forever and can move on to something bigger and better,” Rock says.

4. How Are You Feeling About Your Workload?

Nowadays it’s easy to get caught up in the work-from-home hustle and spend all day at the computer—so anything you can do as a boss to show compassion is recommended.

“We’re all burning the candle on both ends, and there are people who can perform at a high level but are essentially dying inside because the work is stressful or overwhelming,” says Rock. “So it’s important for managers to see whether their staff needs more support or a lighter workload.”

5. How Are You Feeling in Your Role?

Although it may be tempting to leave this question for annual performance reviews, it’s a critical one to ask on an ongoing basis because it may uncover problem areas earlier on.

“It’s necessary to make sure you’re getting a pulse on how someone is feeling about their role and the progress they’re making so you can look out for opportunities that may be good for their development,” Rock says.

6. Where Do You See the Team Falling Short?

According to Rock, direct reports often have a better line of vision into how their team is actually functioning whereas the manager may be more removed. “Asking for the employee’s perspective on how we can be more collaborative or what can we do to get better results for the organization enables them to give valuable input and feel empowered,” she says.

7. Do You Have Any Questions About [Insert Company News/Project/Etc. Here]?

A one-on-one meeting is a good opportunity to see if direct reports need more information about any big-picture issues relating to the company. Maybe someone on the team was recently laid off, or there’s a new COO or other high-level executive, or perhaps HR has announced updated diversity initiatives. Regardless of the topic, “the questions should be framed in an open-ended way coming from a place of curiosity,” Knight says.

8. Is This Format Working for You?

Even if you think your one-on-ones are successful, your direct report may be feeling otherwise—so it’s crucial to occasionally check in and determine whether the current structure is mutually beneficial. “And if not, you can follow up by asking, ‘what can we change about this to revitalize it?” Knight says.