Necessary Endings (25 page)

It might . . .” And we stay stuck.

Self-selection for yourself works the same way. Set the standard: “If the business has not turned a profit by the end of this year, I shut it down.” Or

“If I have not found the job I want by June 1, I wil cal it quits and move.” I live in L.A. and know many people who are trying to make it in the entertainment or music industry. Some of them have been trying for a while. When to quit? In my opinion, the smart ones have a date out there somewhere. “If I am not making a living at this by , I wil give it up and go back to grad school.”

Some people have a problem with such an approach, saying they might be sel ing themselves short. But I did not say the time period had to be short. I just said that it is a good idea to know how much of your life or resources you want to spend on something before you lose them al . What matters is that you are in charge, and sometimes having a standard to self-select against takes the decision out of your head and makes it objective, similar to Jack Welch’s “Be number one or two in the market, or fix it, sel it, or shut it down.”

Having the Conversation: Strategies for Ending Things Well

H
ave you talked to him yet?” I asked Lori, a leader in an advertising firm.

I was referring to Jeff, her direct report who had been heading a substantial division of their business and was responsible for working with various media platforms. Lori had just been recruited to another company, much larger and with much greater opportunity. She was going to be able to build her new team at the new company, and everyone assumed that Jeff would fol ow her wherever she went. Jeff had been her number-one person for seven years. They were pretty tight for a number of reasons.

First, Jeff was extremely competent in the math of it al . He could build models that used complicated formulas to find the best media buys and coordinate releases in a way that maximized returns for their clients. That meant lots of continued business and better bottom-line returns.

Second, Jeff was a bit of an eccentric character and did not let many people into his confidence. He kept them at a distance with an exterior that came off as arrogant and condescending. But Lori had an extreme gift in emotional intel igence (I told her many times she should have been a shrink if she had not been such a good executive) and because of that had won Jeff’s trust over the years. She was one of the few people he had let into his life. As a result, she had gotten a lot of benefits over the last several years, not only from their friendship, but also from his incredible brain.

What they had accomplished was superior. And there was a great deal of loyalty shared between the two of them.

But she had paid a price for that accomplishment. Jeff had two worlds inside the organization: those he treated wel and those he treated despicably. He was one of those people that psychologists would describe as using a lot of
splitting
as a defense against his insecurity. He would divide the world into good guys and bad guys and treat them accordingly. If you had ever offended him or gotten on his bad side for any reason, forget it. There was little chance that you could get back in.

Over the years, Jeff’s behavior had created a culture that was often fractured, making some projects difficult to navigate, and many people thought he was a real jerk. More often than she would like to admit, Lori found herself in the position of smoothing over situations with the people Jeff had offended. Too often she felt more like a therapist than an executive, and as good as Jeff was, she came to resent it. In addition, sometimes even with her, his “paranoia,” as she cal ed it would get aroused if his feelings were hurt or he felt slighted, and she would have to spend time and energy wooing him back.

After a lot of coaching conversations and soul searching, Lori reached a conclusion. Though Jeff was talented and smart, she was not going to take him with her to the new company. When she real y got honest with herself, she admitted she was tired of having to deal with al of the col ateral damage that Jeff caused, and al of the time and energy that she spent dancing around his issues. She had a vision of having a new deputy who was easier to work with, or at least someone who created less drama. Once she saw this vision of the future, she felt “like a weight has been lifted,”

she said. Until . . .

“No, I haven’t told him,” she replied. “No . . .” The last
no
came with a heavy sigh and a look into the distance.

“Why?” I asked her.

“I don’t know. I mean, I do know. It is going to be a nightmare tel ing him. He is not going to take this wel at al . And I understand. After al , he has been my right arm for a long time. But he real y has little clue how hard it has been for me, so he is just going to interpret this as me screwing him over, and it wil reinforce his view that the world is not trustworthy,” she went on. “I am dreading it.”

As a coach, I have had that same conversation with scores of other people, as they stal ed out in either a personal or professional context. Why did the ending stal ? After al the deciding had been done, and they were
certain
that they needed to go forward, they stil 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 tel me it is the conversation itself, as wel 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 al 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 al the difference in the world. It can provide the confidence and the skil s needed to final y pul 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 usual y 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 wil tel 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” al 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 al the back-and-forth a mil ion times. But something about getting to that moment of actual y 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 wil cal the police.

• I want to leave the conversation having said that I do not want the relationship to end at al . 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 wil have to fulfil 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 al , only more ongoing confusion. Make a pact with yourself, “I promise I wil not end the conversation until I have clarity on what I went there to say and do.”

Integrate Care and Truth Inside Yourself

If the reason that you are hesitant about the conversation is that you are afraid of hurting someone, as is often the case, the best preparation you can have is to “get integrated” inside yourself before the conversation. Your sense of concern for the person must be integrated with the truth of what you need to say.

Usual y, when someone cares about how a person feels, there is the temptation to go squishy on the truth, because the truth hurts. So we tend to get a bit codependent in these kinds of conversations, not saying al that needs to be said for fear of hurting the person. The truth suffers, and often the ending gets flimsy.

On the other hand, if you are insensitive to people and just interested in the “truth” and dealing with reality, you might real y hurt someone needlessly. Even if you don’t care, it is stil to your advantage to get this right and begin to care, because if you don’t, it has a much greater chance of going bad.

So before you begin the conversation, get in touch with both sides, your concern for the other person and for the truth. Remind yourself that you care about the person and truly want the best for him. Feel your caring and empathize with how hard the truth may be for him to hear. As you do that, understand that the truth is always our guide. If something is not right for one party, it is not right for the other one, either. If it is not best for a team to keep someone on, it is real y not the best place for that person, either. It is a mismatch. The truth is painful but best in the end.

If the reason for the ending is that the person is not performing wel , you do a person no favor by giving her a position she does not deserve or not being honest with her about her shortcomings. You are robbing her of the chance to get better. So if you care, you wil want to have the conversation truthful y as an expression not only of the truth, but also of that very caring. Think Simon Cowel plus some TLC.

Just as in pul ing a tooth, quickly and thoroughly is usual y best. Commit yourself to being honest and clear, and don’t drag it out through a labyrinth of explanations, excuses, and less-than-honest patronization. Plan to just be nice and tel it the way it is, with a lot of compassion. Kind but true.

If you can get clear inside about your caring and the need for the truth, then you wil do a much better job, which wil al ow you to go forward with less resistance. Feeling your concern wil actual y make you less afraid to speak truthful y, as you wil know that you are not doing anything mean.

And your truth wil help you to be clear and helpful in what you say, and satisfy the need inside of you and the situation itself. It is like sharpening a knife to do the best surgery possible.

Practice and Role-Play If Necessary

It may seem cheesy, but practice can be very helpful. Ask someone you trust, someone who wil give you honest feedback, to help you rehearse the conversation. It wil help you to prepare, to be clear, and to be less shaky in the moment.

It may help you to write out your comments beforehand. Script exactly what you want to go over, and at least have a list to refer to. There is nothing wrong with referring to the list if you need it. Most people do not need this, but I have met many who find it helpful to at least know that if they get flustered in a very difficult scenario, they wil have their cheat sheet. In the conversation, they say something like, “I have a list here of the things I wanted to make sure we covered.” There is nothing weird about that.

Get the Tone Right

The importance of getting the tone right in a conversation like this cannot be overestimated. It is crucial that your tone be one that displays care and respect for the person. Because of the way the brain works, the other person’s emotional reactions wil be greatly affected by the tone of your voice in your communication. If your tone is soft and caring, fewer fight-or-flight reactions get triggered in the other person, and more rational responses are likely to be evoked. If you are not angry, harsh, or shaming, the other person wil be able to receive your message better. So monitor your tone as you speak. You wil be glad you did, and it wil be better for him or her.

Closely akin to tone is your perceived emotional presence. The other person wil unconsciously feel supported and “held” through a difficult ending if he senses that you are real y “there” with him. Empathize with him and validate how it must feel for him. If you do, he wil have a better chance of taking that care with him and a greater likelihood of hearing the constructive aspects of what you are tel ing him. Remember that there is probably a lot that you have to say that could prove helpful if he can hear it, and your emotional presence wil help that to occur.