13 Questions to Help You Prep for Difficult Conversations

I don’t know many people who relish delivering bad news or confronting someone. It’s certainly not my favorite thing to do! However, I’ve learned that taking the time to shift my mindset and look at the situation from the other person’s perspective helps me prepare.

This approach helps me consider what may be important to the other person. I can reflect on why they may have a different point of view and think through how I can respond to their questions or arguments.

Going through my process of answering the questions below enables me to be more objective – it neutralizes my emotions about the topic.

Here is my go-to list of questions:

  1. What will the other person be thinking about this situation?
  2. Is this situation creating a change for them?
  3. Is there a reason it could seem unfair to them?
  4. What does this person value?
  5. Is there something I can offer that is important to them?
  6. Will this be distressing for them because of their values?
  7. What will this person say to me when I present the situation?
  8. What will this person say to others about the situation?
  9. What might this person hear from me? (This helps me carefully consider the specific words I use when communicating the situation. I want to avoid misinterpretation as much as possible.)
  10. What might this person fear?
  11. What frustrations might this person experience?
  12. What obstacles could be in the way of resolving this situation?
  13. What is the upside if this conversation goes well?

These questions foster empathy with the other person. Empathy brings value to teams and generates an environment where creativity and productivity abounds! I also like using these questions to prepare for a negotiation.

Here’s the other thing I love about these questions … all can be applied in your personal life as well as at work. Just think of all the opportunities to practice!

Martha Duesterhoft is a Partner with PeopleResults. Follow her on Twitter @mduesterhoft or connect via email at mduesterhoft@people-results.com.

 

Martha Duesterhoft