Planning a Difficult Conversation? Start with the End

Posted Tuesday, October 2, 2012

Allen Slade

 You need to have a difficult conversation.

You know the conversation I mean. The conversation you keep putting off. You get butterflies just thinking about it. You know it will not be pleasant.

Your difficult conversation may be confronting someone about broken promises. It may be setting a boundary with someone who tramples over you or other people. You may be planning to share feedback that is unexpected and unwanted. Whatever the topic and whoever the other party, your difficult conversation feels like stepping into an emotional minefield.

As a leadership coach, I help clients hold the difficult conversation they have been putting off. To increase the odds of success, we work on two things: planning the conversation backwards and designing the conversation for maximum impact. Today, let’s think about how to plan your difficult conversation backwards. In other words, the best difficult conversations start with the end.

In planning a difficult conversation, always plan backward. Define a successful outcome for the difficult conversation before you hold it. 

What does success look like? What change would you like to see in the other person? It might be a change in behavior, such as an employee returning phone calls promptly. It might be a more subtle change in thinking, values, attitudes, beliefs or expectations. Sometimes your desired change is not in the cards – the other person does not share your motivation, your definition of success or your norms. Sometimes, the endgame is just not feasible.

Is it worth it? How much risk will you take? Some difficult conversations put your relationship at risk. While things may improve, you can also harm the relationship by opening emotional wounds. A difficult conversation can also harm your credibility with your wider circle of influence. You must decide if the probable pain is worth the potential gain.

Starting with the end will show you a lot of difficult conversations should not happen:

Don’t tilt at wind mills. Risking much with little odds of success is not a good bet. Don’t confront your boss during your performance review meeting, especially if you expect poor ratings. Don’t ask the CEO snide questions during the strategy rollout. Don’t voice complaints about the company on your last day of work. If you don’t have the standing to make a positive change, save your energy and your reputation.

Don’t do it to let off steam. Don’t hold a difficult conversation because you “have” to tell them something. If you are holding a difficult conversation to vent your frustration, punish the other person or get something off your chest, just don’t. Unless you can visualize a successful change in the other person, don’t start a difficult conversation. Talk to your therapist, write in your journal or yell in your private closet instead.

Don’t call out strangers. Grocery store parenting advice, barroom etiquette instruction and roadway driver’s ed rarely stick. Worse, strangers can react strangely with nasty expressions, verbal abuse or violence. Little upside and potentially grave downside make difficult conversations with strangers a bad bet.

By avoiding fruitless difficult conversations, you will be happier and healthier. You will also have more energy for the conversations that have the right end game. Then, with the proper planning, you can improve a relationship, change someone’s ineffective behavior or chart a new direction. You can have difficult conversations with the outcomes you seek, if you start with the end.

2 comments on “Planning a Difficult Conversation? Start with the End

  1. Nice one, Allen. I also suggest: Is it true? Is it helpful? Can it be said kindly? (although I think many people can use the last one to shy away from necessary difficult conversations. Must master the ability to speak truth with love.)

    • Allen Slade on said:

      Great advice, Sandy. Sometimes we act like bulldozers, focusing on the truth at the cost of the relationship. Sometimes we act like butterflies, flitting away at the first sign of conflict to save the relationship and avoid the truth. Speaking the truth in love should cause the bulldozers to tread lightly and the butterflies to gain traction.

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