Probing Questions to Get Beneath the Surface

You’ve probably had the experience of asking a staff member, manager, or colleague 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, manager, or colleague in avoiding them. Here are some questions that can help you get beneath the surface.

Probing questions you can ask your staff:

  • 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?
  • How might that strategy differently impact our volunteers, members, or constituents who are more marginalized? [Some dimensions of identity/experience to consider: race, ethnicity, gender/gender identity, class, ability, sexual orientation, religious affiliation, age]
  • How might identity impact the way that might resonate?
  • What makes you say that?
  • What kind of data do we have to inform how that’s working?
  • What’s your timeline for that? Roughly how much of your time are you spending on that?
  • Can we take one specific example and talk through how you’re approaching it?
  • Can we role-play what that might look like?
  • Can I see what you put together / wrote?
  • What does your agenda for that look like?
  • What other options did/might you consider?
  • How else can I best support you with this?
  • What else do you need (from me) to make that work?
  • How is this work impacting you / your other work?
  • Is there anything I’m doing in this process that’s not working for you?
  • What one or two things would make this week a success for you?

Probing questions you can ask your manager or colleague:

  • When you’ve dealt with this challenge in the past, how have you handled it?
  • Do you have any concerns about this plan / draft? What are your concerns?
  • What’s the bigger picture context I should be keeping in mind as I work on this?
  • What are some pitfalls you’ve seen in projects like this in the past?
  • Can you say a bit more about that?
  • Can you help me understand what X means to you?
  • When you say _____, I’m picturing _____. How do you see it?
  • Of all these potential approaches, which do you think might be most effective?
  • When you saw me do X, what do you think worked best? What didn’t work so well?
  • I think I could have done better at x. Is there anything else I should keep in mind for next time?

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