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How to Have a Difficult Conversation

Updated: Apr 24, 2023



Ask Open Questions Throughout the Conversation ● Difficult conversations often require a negotiation to come to an agreeable outcome for both parties. Skilled negotiators ask twice as many questions as average negotiators.

● You can use questions throughout the conversation to: ○ Gather information about the other party’s position and interests ○ Manage the discussion and keep the other party engaged ○ Avoid direct disagreements and gain thinking time while the other party responds ○ Break up pro/con debates and enhance the possibility of creative solutions



Illuminate Meaning and Expand the Discussion ● Create a window into where they are coming from by asking what their definition is of a key term ○ E.g., “We need to discuss why you are always late to work.” “What? I don’t think I’m always late; how do you define being late for work?” “Cases start at 7a, so you need to be in the PACU by 6:30 a.m. at the latest.” “Oh! I don’t remember hearing that during my onboarding. At my last job, 6:50 a.m. was acceptable, now I know the expected start time and will arrive then!”

● Expand the discussion by exploring the larger context. This will make the other party’s interests more visible and allow the two parties to build trust and foster understanding. ○ e.g., “We need to discuss why you are always late to work.” “Yes, I’m sorry about that. My nanny is always late; I told her she can’t be!” “It’s okay; that’s why we are here to have a discussion and find a solution. You are a great clinician, and we wanted to know if there were ways that we can support you.” “I’ve talked to her over and over again about being on time, but I don’t feel comfortable interviewing and possibly switching nannies during the pandemic.” “I understand the position you are in, and I have a few ideas. There’s a daycare at the hospital that you could check out, or you could temporarily switch to a later start resource shift until the pandemic calms down and you can find another sitter.”

References and Further Reading:

  1. Putnam, L. L. (2005, March). Are You Asking the Right Questions? Negotiation.

  2. Tannen, D. (1995, September-October). The Power of Talk: Who Gets Heard and Why. Harvard Business Review OnPoint.


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