Probing Questions to Get Beneath the Surface

Last updated: September 30, 2021
Estimated reading time: 1.5 min

When you’re invested in a project or assignment (as the manager, a direct report, or a colleague) but are slightly removed from it, it can be hard to feel fully tapped into what’s going on. Probing questions are a handy tool for getting beneath the surface to really understand how a project is progressing.

Probing questions serve three main purposes:

  1. Information. At the most basic level, asking good questions gets you more information that can help you identify looming obstacles, opportunities to leverage, and foreshadow outcomes.
  2. Relationship-building. Expressing genuine curiosity about someone else’s work demonstrates interest and investment in them. Digging deeper helps you better understand your colleague’s thinking and approach so that you can work better together.
  3. Results. Making time to get aligned, anticipate challenges, and discuss approaches and decision-making adds more rigor to the process, which ultimately leads to better results.

Here are some questions that can help you get beneath the surface. Most of them can be used in any “direction”—that is, you can use these questions not just with a direct report, but also with a colleague or a manager (in fact, we encourage you to!).

General questions

  • What indicators are you looking at to see if things are on or off track?
  • How are you handling X [a specific element]?
  • What seems to be working well? Why?
  • How is this impacting you, your work, or your relationships with colleagues/partners/members?

Getting aligned

  • Can you help me understand what X means to you?
  • When you say Y, I’m picturing ABC [impact, steps, etc]. How do you see it?

Anticipating challenges

  • What could go wrong? What do you have the most concerns about?
  • Have you thought about what you’ll do if Y happens?
  • What are some pitfalls you’ve seen in projects like this in the past? How have you dealt with them?
  • Do you anticipate any disparate impacts based on identity?
    • How do you plan to mitigate them?
    • Do you have any suggestions for how to mitigate them?

Strategy and approach

  • What led you to make that decision? How are you making sure that the process and outcome will be equitable?
  • Can you share your thinking about this? What else did you consider/are you considering?
  • Are there any new approaches or tactics you’re trying out?
  • Of all these potential approaches, which do you think might be most effective?
  • Is there any bigger picture context I should keep in mind as I work on this?

Your role

  • How else can I best support you with this?
  • What else do you need (from me) to make that work?
  • Is there anything you’d like me to do differently to support you?

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