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?