Feeling like sit-downs with your employee are going nowhere? Read on for three questions that will help foster productive meetings and stop wasting your staff’s time!

By: Sandra Sears

July 7th, 2023

Sandra is the owner and founder of Staffworks. Follow along and read more insights every Friday on her LinkedIn.

Regular one-on-ones with your direct-reports have the potential to be useful, insightful, encouraging, and purposeful.

They can also be a total waste of time.

If you’re leaving every sit-down with your team leaders feeling no further ahead, then it’s time to change that. Take the initiative and prepare a few questions that get the conversation flowing. I saw an article in HBR recently that inspired me to list a few questions I like to ask my managers. The discussions that follow ensure I’m working in harmony with my team, and that our strategies and targets are in sync. Here are a few things I like to ask when we sit down together.

Question #1: What are your top 3 big-picture priorities?

When speaking with an employee, I encourage them to share their work priorities with me. In turn, I share mine with them. We see if they sync up—and if they don’t, together we iron out the details and reprioritize together.

Question #2: What’s keeping you up at night?

You can’t effectively support your team if you don’t know what’s on their minds.  That’s why I make sure to give my employee the opening to share the deep-seated challenges standing in the way of their objectives. It’s amazing what can come out and get cleared up in the context of this discussion.

Question #3: What potential challenges do you see coming our/your way?

Volunteer your own observations, and ask your employee for their opinion on the subject. Maybe there’s a particular technology or trend in your industry that’s worrying. This can be a great opportunity to parse real threats from perceived and prepare solutions in advance.

More Ideas to Stop Wasting Your Staff’s Time

What are some questions you wish you could ask your boss (or wish your boss would ask you!) in a one-on-one? I’m always looking for new ways to connect with my staff—please share! Follow me on LinkedIn and let me know what you think.