How to Have Difficult Conversations

Let’s face it: if you are alive, you are going to have difficult conversations from time to time. Leaders have to confront poor performance. Parents have to challenge their grown children. You will have disagreements with your spouse, significant other or a good friend.

Whenever you must have a difficult conversation with someone you care about, the potential for conflict with that person can be debilitating because you don’t want to risk the relationship. I don’t know anyone who just loves to make their friends angry, enjoys the negative reaction from a relative, or wants to upset a coworker. The better you are as a person – the more empathetic, caring and relational you are, the more upsetting a difficult conversation can be.

There are two reasons a conversation can be difficult for you:

  1. The possibility of conflict.

You imagine that the other person is going to react badly. They are going to become angry and yell, swear, criticize you, and vow to sever your relationship. Or they are going to be sad and cry, withdraw, shrink, and take it personally. You believe they are going to be defensive, aggressive, offended or hurt.

And ultimately you think that your relationship with the person is going to be negatively affected because of what you need to say.

If the possibility of conflict makes you nervous (afraid, anxious, etc), then your tendency will be to avoid the conversation altogether, delay the interaction until issues build up to a crisis, or handle things with passive aggression because you just cannot bring yourself to directly say what you want to say.

  1. You try to manage someone else’s emotions and reactions.

When you hate conflict but are forced to have the conversation anyway, the result is often an attempt to control the situation by managing the other person’s emotions and reactions. Before talking to the person, you run a lot of scenarios in your head and make plans to either ensure they don’t happen, or if they do, you know what you’re going to say in order to keep the peace.

“Oh, I love you and you’re such a joy to have in my life!”

“You’ve been with us for a long time and you are a valued member of the team!”

“We are good friends!”

“I see that you are very angry – nevermind; it’s not a big deal.”

“I know I’ve got my own problems too and here is how I behave just like you…”

And so on.

When you feel you must massage someone’s ego and manipulate the conversation so that their emotions and reactions are in check, then that becomes the outcome. Rather than clearing the air and expressing yourself so that resolution and agreement can happen, you’ve moved the interaction into a different arena where the best possible outcome is that the other person is confused by what you had to say (but she feels better!), and the worst possible outcome is that you didn’t say anything at all that needed to be said and you must have the conversation again at some point in the future.

You must face and accept that: “I cannot manage other people’s emotions; I will not even try.”

Managing someone else’s emotions requires a lot of babysitting and amateurish psychology that requires them to be a victim and you to be the hero. Your relationship is built on unequal terms where they need you to “parent” them.

But that’s not what you want, is it? You want an adult-to-adult, equal relationship where both you and they accept responsibility for your own lives.

So if you are a leader, and if you value your own sanity and well-being, then you must face and embrace that confronting and challenging is your responsibility and you must be willing to express yourself even if the result is someone becoming triggered or unhappy.

Here is how a leader conducts “difficult” conversations:

  1. Have the conversation sooner rather than later.

As soon as you become aware that a conversation must take place, schedule it.

Fearing conflict, many people make the mistake of putting off their confrontational meetings until later. Managers wait for the formal review, leaders wait until a future evaluation, parents wait until they reach boiling point, friends wait until they feel that the conversation is not needed at all.

But this is a mistake because you are wired to hold your grievances internally until they can be fully expressed and released. When you delay expressing and releasing what bothers you, other things come along and stick to that thing, and you begin to accumulate all kinds of important, unexpressed issues that trouble you. Which produces feelings that are not expressed and released. Which builds up within you until you begin to feel the effects: anxiety, irritation, anger, resentment, and so on.

Do yourself a favor and have the conversation as soon as possible.

  1. Say it to express yourself, not to change them.

Much of what we say to other people is intended to make them change. The reality is that nothing you do or say can change another person.

If they want to do something – like stay disorganized, be late to work, talk about you behind your back, or break their agreements – then they are going to continue to do those things regardless of what you say to them. And if they don’t want to do something – like help you with the dishes, work faster, take on extra responsibility, or clean up their room – then your impassioned pleas will have no effect.

When you try to change someone, two things happen: they can get angry and defensive, and you get unhappy. They resent that you think you know them better than they know them, and you become frustrated because they cannot see things your way. The surest way to be unhappy is to try to change what you cannot change or control what you cannot control.

Instead try this: speak to reveal yourself rather than to change them.

Fully expressing yourself is what you really want, isn’t it? You can live with disagreement, but you’re conflicted when you know you aren’t understood. So give them the chance: let them hear you express what you’re thinking, what you’re feeling, and your deepest desire for them and the situation.

Speaking to reveal yourself requires a different mindset and set of skills that you will develop with practice and time, but here are the top three mindset-changers for you to consider and adopt:

  1. Explore the opposite.

Here’s the scenario: A coworker arrives late to the meeting yet again. You notice and think that she is disorganized and careless. You assigned a motive to her action, which is you trying to make sense of the situation. Your mind goes into overdrive imagining why she did it, what she was thinking, her attitude, her reasoning, and whatever else helps you to try and understand. In short, you’ve told yourself a story about her and the situation.

But the story you told yourself is just that – a story. Anaïs Nin said, “We don’t see the world as it is, we see the world as we are.” Which is another way to say that you project onto the situation and the other person what is already inside yourself. And that means that the story you’re telling yourself about them is made up. It’s not really true.

So when you told yourself that she is lazy and irresponsible because she was late to the meeting again, you were projecting your own values and experience onto her. You cannot imagine any other reason for her tardiness because you would never (rarely?) show up late to a meeting, and you’ve witnessed laziness and irresponsibility in yourself and others when they are late. So that must be the explanation here.

The problem with believing the story you tell yourself is that the story becomes a conclusion within you. You are convinced that you are right, she is wrong, and you must go about proving your right-ness to her and everybody else you talk to about the situation. She is lazy, disorganized and careless.

But is she?

What if she’s not? What if there is some other explanation of which you are completely unaware? If there is the possibility of another version of the story, could you consider that also? If you could allow yourself to explore the exact opposite of what you believe, wouldn’t that free you from the angst and tension and conflict and drama that is already gathering inside of you?

In her book, The Work, Katie Byron extensively shows how to free yourself from anxiety and turmoil that is self-generated when you believe the stories you tell yourself about someone or about a situation. Almost all of the “difficulty” of a conversation can evaporate before the conversation is even had if the participants would enter it without having to defend a story they told themselves prior.

  1. Speak unarguably.

If you want to reveal yourself and not change them, learn to speak so that there can be no argument about what you say.

If you are trying to change them, you are going to use language like: You always. You never. You are. This is language that is directed at them, defending what you believe (your story), with the intent of getting them to change. Which, as we’ve seen, never works and creates conflict and drama.

Instead, speak from yourself rather than to them. Here is an example of what that looks like:

  • “Lisa, you were late to the meeting again. [a statement of unarguable fact]
  • “I am feeling frustrated as we’ve talked about this before. [a statement of how you feel]
  • “The story I’m telling myself is that you just don’t care. [acknowledging that “you don’t care” is something you made up]
  • “Would you like to tell me what happened?”

Speaking unarguably means that you state facts (the way a video camera would record them – without interpretation), reveal your feelings, and let them know about the thoughts you have about the situation (always acknowledging that your thoughts are the stories you’ve told yourself and that you are not attached to them).

When you can speak in a way that is unarguable, then, well there can be no arguing! The other person will also be encouraged to express themselves in honest, unarguable ways, and the conversation has much more potential for resolution as a result.

  1. Balance care and candor.

When leaders are not equally committed to both care and candor, conversations can be difficult.

You care about someone a great deal. Their friendship, family relationship, or working relationship is very important to you and the last thing you want to do is rock that boat with confrontation. What they think about you and feel for you is far more important than anything else. That’s why you avoid uncomfortable interactions altogether.

Or,

You just love to speak your mind and let the chips fall where they may. It doesn’t matter who the other person is or what they think of you, truth matters and – watch out! – I’m going to tell them what I think!

The most effective leaders find ways to balance care and candor in their interactions with others. John Maxwell has written much about leadership, and here is what he has to say about balancing care and candor:

  • Care values the person; candor values the person’s potential.
  • Caring establishes the relationship. Candor grows the relationship.
  • Caring should never suppress candor. Candor should never replace caring.
  • Just as much as you care for the person, you should be 100% committed to the candor.
  1. Listen deeply.

All the good you intend to accomplish will be undone if you don’t listen to and understand the other person. While they are talking, many of us are guilty of thinking of what we are going to say next, refuting them in our heads, or letting our minds wander to something else entirely.

You can make a conversation much less difficult if you commit to listening deeply as the other person speaks. That means acknowledging and being aware of at least three things:

What are they saying?

Try repeating back what you heard and in your own words to see if they agree that that’s what they said.

What are they feeling?

As they speak, try to identify what they are feeling in that moment. Is it fear? Sadness? Anger? It’s not important that you tell them what you think they are feeling, nor is it necessary that you are correct in your assessment, but it is critical that you empathize with the emotions behind their words.

What is their deepest, core desire?

They may be talking about something, feeling something else, and want something else entirely. This is true because most people are not practiced in speaking directly and candidly, so they talk around what they really want, hoping that you’ll get it. That’s why it’s important to ask yourself, what do they really want in this situation? Understanding this will enable you to deal directly with what’s at the core of the issue.

  1. Forge an agreement.

The reason for the conversation in the first place is to come to an agreement that both of you can commit to. Everything else leads up to the agreement; without an agreement, the conversation served neither of you.

Most conversations fail because we only talk about what’s wrong and air our grievances. We think that by complaining and whining about all the things we don’t like, we’ll be able to wear the other person down so that they change. Kind of ridiculous when we put it that way, right?

Effective leaders know that they must move the conversation away from what’s wrong and toward what both people want. That’s the only way to progress. And the way to do that is by insisting on an agreement at the end of the conversation.

Be very clear about:

  • What will they do?
  • What will you do?
  • By when?

Forge an agreement and then hold each other accountable for it. Whether or not the conversation was “difficult,” an agreement at the end is the payoff reward for the effort.

No conversation has to be difficult. When you change your mindset from “this is going to be difficult” (which is motivated by control and fear) to “this is an opportunity” (to reveal, understand and agree), any conversation can be had with ease.

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