Probing Questions to Get Beneath the Surface

You’ve probably had the experience of asking a staff member how a project is going and receiving a simple “good” in response. Where do you go from there in order to get beneath the surface and understand what’s really happening?

If you simply run down a list of projects without digging deeper, you’re likely to miss important information about what obstacles might be looming and how you might be a resource to your staff in avoiding them. Here are some questions that can help you 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?  What are you most worried about?
  • Have you thought about what you’ll do if Y happens?
  • What’s most important out of all those things?
  • What makes you say that?
  • 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 does your agenda for that look like?
  • What other options did you consider?