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?