Management Questions

The Management Fix Tools for Busy Managers

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Hello friends,

We recently received this question from a reader:

I do regular check-ins with my staff members, but I don’t always feel like they help me understand what’s really going on and what problems might be on the horizon. For instance, today I was talking with an employee who’s working to launch a new training program. She says that all the planning is going fine, but how do I know that it really is?

Check-ins often won’t be nearly as helpful as they should if you don’t ask the right questions. What you want to do in these meetings isn’t just run down a list of project updates, but ask questions that will get beneath the surface so that you really understand what’s going on.

Here are the best questions that we’ve found to help do that.

The 3 Best Questions to Get Beneath the Surface

1. What makes you say that?

This is a good follow-up to all kind of statements — from “things are going fine” to “The venue seems like they’re not going to budge on the price.” The idea is that you don’t just want the surface statement — you want what lies behind the surface statement, and this question gets at that.

2. What do you think?

If a staff member isn’t sure how to handle a problem or move forward on a project, before you suggest a path to try, ask this question first. You might learn that your staff member suggests that solution herself — or a better one.

3. What are you most worried about?

This question can open to door to all kinds of information and concerns that you might never hear about otherwise. You might think that staff members will tell you their worries without being asked — but many won’t.

… And 15 – Yes, 15! – More

In addition to the three questions above, here are 15 more than you can use to get beneath the surface:

• What one or two things would make this week a success for you?
• How do you know you’re on track?
• How are you checking to make sure that’s working?
• How are you handling X [a specific element]? 
• What seems to be working well?  Why do you think that’s working?
• What could go wrong?
• Have you thought about what you’ll do if Y happens?
• What’s most important out of all those things?
• What kind of data do we have to inform how that’s working?
• Roughly how much of your time are you spending on that?
• What’s your timeline for that?
• Can you give me a specific example of that? 
• Can we take one specific instance and talk through how you’re approaching it?
• Can we role-play what that might look like?
• What other options did you consider?

Try some of these questions at your next check-in, and see if you don’t find the conversation more substantive and the meeting more useful.