Having the Conversation: How to End a Job or Relationship

In this excerpt from his new book Necessary Endings, author Henry Cloud discusses the trouble people have while ending a relationship or even a job. It’s all about preparing for that difficult discussion.

Necessary Endings

As a coach, I have had that same conversation with scores of other people, as they stalled out in either a personal or professional context. Why did the ending stall? After all the deciding had been done, and they were certain that they needed to go forward, they still sat on it. Not because they were unsure or were afraid of the future. Not because they second-guessed their decisions or their mental maps prevented them from making it. The reason?


They dreaded the conversation.

They tell me it is the conversation itself, as well as the potential aftermath with the person in some instances, that stops them cold.

They say that they play it over and over in their heads, and see it going badly, imagining all the worst scenarios. Add that to some of the mental maps we discussed before–endings are personal failures; endings make you mean; endings hurt other people–and you can see the appeal of not going through with a necessary ending.

What gets them through it? One key ingredient is to be prepared for the conversation itself. That preparation can make all the difference in the world. It can provide the confidence and the skills needed to finally pull the trigger. Let’s look at how you can be prepared for the difficult conversation of a necessary ending.

Begin with the End in Mind

With the more difficult endings, there are usually a few issues that sidetrack the conversation. People may get off-mission in the midst of the endings conversation. They go into it thinking that they will tell someone that “it’s over,” whatever “it” is, but once they get in there, one of two things happens. They may get sidetracked by their attachment to the person or whatever else is the issue; then they “refeel” all of their love for the person or the project. They feel how fond they are of the person or the good sides of the business, and somehow they get engaged in talking about those, which invariably leads to the familiar wish: “Can’t we find a way to make this work somehow?”

Then the conversation goes down the path of finding a way to “work it out.” Never mind that the person doing the ending has spent months or more getting sure about the ending, having obsessed over all the back-and-forth a million times. But something about getting to that moment of actually making it happen makes people squishy once again. I remember one time when a board sent a CEO to fire someone and he came back having extended the person’s contract! I said to him, “You went to break up, and you came back engaged! Not good!” But it happens.


The other thing that often happens in the ending conversation is that the ender runs into resistance from the endee and loses the verbal joust. Being more adept at the conversational dance, the endee talks the ender out of the ending.
Neither of these derailments is good, but both can be prevented with a little advance work and training. The work consists first of “beginning with the end in mind.” Before you have the conversation, make sure you are clear in your head what you want the result of the conversation to be. Have specific goals for the conversation.

Here are some examples:

  • I want to leave the conversation with zero confusion, complete confidence that this is over.
  • I want to leave the conversation having said that I care about the person.
  • I want to leave the conversation letting the person know that although this is over, I want to keep in touch in case another opportunity opens up.
  • I want to leave the conversation with the person knowing that although the project is over, I want the relationship to continue.
  • I want to leave the conversation having said very clearly not only that it is over, but also why.
  • I want to leave the conversation having said that I want absolutely no further relationship or contact with the person.
  • I want to leave the conversation having said that if the person ever contacts me again, I will call the police.
  • I want to leave the conversation having said that I do not want the relationship to end at all. What I want to end is a pattern, but it is her choice whether or not she wants to continue, and if she does, she will have to fulfill certain requirements.

While there are other possibilities, you get the gist. These are difficult conversations to have, and if you are not clear in your own head what you want to make absolutely sure you have said when it is over, chances are you won’t say it. The results of that could be that you have no ending at all, only more ongoing confusion. Make a pact with yourself, “I promise I will not end the conversation until I have clarity on what I went there to say and do.”

Reprinted from the new book Necessary Endings: The Employees, Businesses, and Relationships That All of Us Have to Give Up in Order to Move Forward, by Dr. Henry Cloud. Excerpt courtesy of HarperCollins Publishers.