Preparing for a Challenging Conversation

thoughtful womanThink back to the last challenging conversation you had. Were you prepared? If not, how well did it go? Chances are it didn’t go as well as you hoped it would.

Most challenging conversations are more effective when we take the time to prepare for them. I’d like to suggest five things you can do to be better prepared to guide your next challenging conversation to a successful outcome.

Gather the relevant information.

First of all, collect the relevant information pertaining to the topic of the conversation—the who, what, and why. Ask yourself:

  • Who do I need to talk to?
  • What is the problem?
  • Why might this problem be occurring?

Envision the desired outcome.

Imagine the best possible outcome. If the conversation goes well, what will be the result? Be specific as you visualize this. Being keenly aware of your intentions will make preparation easier—and keeping those intentions in mind will guide the conversation in the direction you want it to go.

Anticipate the other person’s reactions and your response.

Think about ways the other person might react to the conversation to guard against the possibility of being blindsided by their words or actions. If you have considered their probable reactions and determined how you will best respond , you will be ahead of the game. Remember, though, that you can’t predict every reaction—even from someone you know well.

Pay attention to logistical issues.

The environment surrounding a difficult conversation can affect its outcome. A bit of forethought and preparation can have a significant positive impact. Here are some best practices for handling the logistics of the conversation.

  • Schedule more than enough time – 30 minutes more than you expect.
  • Hold the conversation in a private, safe, neutral location if possible.
  • Make sure you will not be interrupted.
  • Turn all phones and devices off.
  • Have tissue available if tears are a possibility.
  • Have a glass or bottle of water handy.
  • If the conversation is with a direct report, be prepared to give the person the rest of the day off if needed—and do not have the conversation at the end of the day on Friday.

Decide if the conversation is worth having.

Note that I put the decision about actually having the conversation last.  Sometimes you find that the conversation itself is not as important as the deliberations you went through to prepare for it. What you really needed was to sort out your own thoughts and feelings. After all of your preparation, if you determine that you don’t need to have the conversation, you will lose nothing by changing your mind.

What other ideas do you have for preparing for challenging conversations?

About the author:

John Hester is a senior consulting partner with The Ken Blanchard Companies who specializes in performance and self-leadership.  You can read John’s posts on the second Thursday of each month.

12 thoughts on “Preparing for a Challenging Conversation

  1. Excellent advice, John. I had a difficult conversation today, and I was glad I had read your post beforehand. Your specific advice around logistical issues were particularly helpful, especially the advice to schedule more time than I anticipated I would need. You were right. It is worth taking the time needed to bring the conversation to a good closing point.

  2. Even after 24 years of marriage I find your approach the best. Be prepared. Like many re-married couples we carry baggage from previous marriages into this one, especially about money and how it’s handled. Our conversations have to be carefully managed so that we reach the goal of communicating effectively so we understand each others point of view. Don’t want hurt feelings to arise out if misunderstanding what was said.

    • I found the post to be timely for any subject matter. I enjoyed your comment Rebecca. I’m also remarried and one thing packed in our luggage was an issue with how money is handled. It feels good to know you’re not alone and it’s a wonderful reminder to tame our tongue by thinking before we speak.

    • Good reminder. There are some challenging conversations where we want to let the person know in advance that we want to have this conversation, give them the subject matter, and then give them time to prepare. Just don’t make the invitation on a Friday for a Monday meeting. You’ve just ruined their weekend 🙂

  3. Dear John,
    Preparing for a challenging conversation is something that challenges those who dont know how to engage in conversation either official or other wise, they delibertely act in such a way to put any organised law out any meaning full conversation, so many of them are out there.
    Well for me i believe in organised world, that is why so many men are animals with this crinimals either men or women, because many men the way they behave or act, i thank God i am a christain.
    So John help.

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  5. John, I noticed there wasn’t a section on listening. The practice of mindful inquiry is helpful in challenging conversations, as it provides the opportunity for both conversation partners to process and reflect on what the issues are, to make sure that what is being heard is what is actually being meant.
    – Kehaulani

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  7. Thanks John – great points.
    I would add – if I am initiating the conversation – figure out the shortest way to make it clear what I want to talk about.
    ALSO – be prepared to be surprised if you really try to understand the other person’s point of view.

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