How and why to have tough conversations

We have all had this sinking feeling when we realize that there is something that we need to talk to someone about. Maybe you are leaving work, going into a meeting, or you wake up with it, but whatever the location, the feeling is almost always accompanied by the dreaded “should” statement that we often use against ourselves.

“I should really talk to him about that.”

Other times, a tough conversation happens to us. We are minding our own business, innocent, knocking off things on our list, when all of the sudden, someone upsets our apple cart.

“Why is she bringing this up now?”

Why are those tough conversations necessary, and how can we get better at them?

What is a “tough conversation”?

In short, a tough conversation stems from an unsolved – and sometimes unspoken – conflict. It may be conflict that hasn’t actually taken place, although you may have seen sparks, or it is a regular conflict that one or both of you wants to settle.

The conflict could come from opposing ideas, beliefs, needs or desires. Tough conversations aren’t limited to certain categories, and certainly not limited by the context of your relationship with the other person – meaning sometimes a tough conversation at work is about things that aren’t exactly about work. ¹

The relative position on the business org chart (official or unofficial) of two people having a tough conversation doesn’t make a tough conversation any easier, and anyone who has spent more than two consecutive days as part of a team at work knows this.

The things we complain about to other people outside of work indicate that a tough conversation is necessary or might happen at work. Think about statements that start with:

“I like him, but . . . . “

“If she thinks that I’m going to . . . .”

“Obviously, his behavior is bad for the team, but . . . .”

The desire to have a tough conversation – no matter how much anxiety it produces – is almost always reflective of the desire to make a situation better, to reach a resolution, to solve a problem, or to at least make something less bad.

Why tough conversations are tough, but important

Here are some of the things that make a tough conversation, well, tough:

It disrupts the social equilibrium that we all hold on to, and even those of us who take pride in mimicking a bull in a china shop value equilibrium.
We don’t want to face the other person’s thoughts and feelings –a different point of view or conclusions, maybe anger, disappointment, resentment, or shame.
We don’t want to face the possibility that we might be contributing to the situation that the conversation is supposed to address and solve. The extreme fear: we could be wrong. (Judas, let’s stay away from that at all costs.)
We might lose control of our emotions, or even of our ability to understand whats happening. It’s natural to avoid those two things, and without having the talk, the other person is wrong and you are right (usually). Opening up the discussion would mean there would be a period of time where you’re both trying to figure out what the truth is, and that can be nerve-wracking.

Carl Jung – for all his faults – linked the ideas of terror and enlightenment: when someone faces fears (terror) voluntarily, he or she adapts and learns (enlightenment). ² This idea is reflected in the many myths, but King Arthur and the Knights of the Roundtable is one of the more popular and well-known. In short, we tend to hide or avoid things that are uncomfortable, but progress (enlightenment) is contained in voluntarily facing the uncomfortable fear (terror). That’s where we get expressions like “there is no progress without challenge” and “everything good is on the other side of hard.”

That’s what Jung and King Arthur have to do with tough conversations: they are challenging, hard, uncomfortable, and sometimes terrifying, but willfully having tough conversations brings further understanding, deeper connection, a better social environment, (and possibly enlightenment).

In some ways, difficult conversations define the relationship between two people. While it’s true that it wouldn’t be much fun if the entire relationship was only tough conversations, a true connection between two people cannot exist without recognizing, respecting and discussing different ideas, points of views, and conclusions.

In fact, how well both of you succeed in your tough conversations determines the depth and quality of your relationship. Do you always “just fight about politics” every time it comes up and then fake maturity by “agreeing to disagree”? Or do you embrace your differences, respectively, and truly learn from each other’s position?

Conflict is inevitable and productive

It is a fallacy that team or individual relationships are devoid of conflict. Good teams, personal, and work relationships all require some sort of friction between people in order to discuss, learn and progress. Different points of view, desires and conclusions help you examine yours, and the difference between someone else’s perspective and yours serves as a necessary contrast that enables you to find places you can improve or change. (Those who know already that either they are perfect or the other person is clearly and completely wrong are free to skip to the next section.)

Every one of us is imperfect, and we grow over time. What we think or agree with changes as we learn more and become more experienced in life. Additionally, we have strong similarities between us, but we don’t always have the same preferences or the same cultural background. So there will be differences between how we think, what we want, what is valuable to us and how to proceed in life.

That means conflict between us is inevitable, and when we work together, tough conversations are necessary to resolve that conflict.

In order for tough conversations to be productive, we need to face the conversation voluntarily. Even when you aren’t the person who has initiated the conversation, you still have the option to either participate or defend. Participating is not agreeing – participation is listening, restating, and being open to understanding what the other person is saying. Defending is saying and doing things that indicate simply that the other person is wrong (sometimes indirectly and cleverly) and won’t allow a bridge to be formed between you.

Indeed, how you have tough conversations and defuse conflict is a critical part of how well your relationship functions. A cooperative – even if it’s uncomfortable – tough conversation has the ability to strengthen both your connection with the other person, but also allows a better version of the disputed subject to emerge.

The consequences of avoidance

If you avoid a tough conversation, the problem or conflict gets bigger. What you don’t attend to grows, festers, and begins to affect more aspects of your work and – very quickly – your physical and mental health.

Something else takes place when you avoid tough conversations: we adapt our behavior to compensate for the problem.³ We steer clear of certain people, certain topics, or parts of work. We may “just” take care of things that “somebody else” should be doing, we even change strategy or give others different work in order to stay away from the conversation we dread.

Most tough conversations – even the challenging ones – are often not as bad as the movie script in our head, and we create the emotional exaggeration that makes much of our resistance to having them. It is almost always also true that the tough conversation you are pondering right now would have been a little less tough had you started it the first time the thought of it crossed your mind.

What all tough conversations have in common

The excellent book Difficult Conversations outlines three common tough conversations, and it’s worth noting the similarities in them to help a leader navigate what’s happening. Tough conversations have some element of all three in them, even if you don’t address a part out loud.

“What’s happening” – disagreement or tension over the facts of a situation (or at least what we consider the facts), and it usually entails what you’re right about, now, then, and in the future plus the idea of “fault.”
“Feelings” – how both of you are feeling about what’s happening. Some feelings may be rationally connected to what’s happening, but we still have the power – and responsibility – to behave well, despite how we feel.
“Identity” – what is at stake in the results of this tough conversation? Will where we end up affect my job, position in the business, or ability to work?

What to do

Before you start a tough conversation (or before you start responding to one), take a breath, step back, and ask yourself what you would like as a resolution. Is your intended result a winner-take-all result, where the only logical possibility is that the other person recant his or her position, completely and permanently change their behavior, plus pay a reasonable tax-free annuity to you as restitution for having such an outlandish opinion in the first place?

That may be how we feel sometimes, but it’s not what will happen, and taking that approach will prevent a solution.

If so, maybe the first tough conversation you need to have is with yourself. Here is a mental checklist to guide you:

Be upfront. Be clear, so that the other person has the best chance to understand what you are saying.
Be kind. The tough conversation is tough for both people, and person you are talking to feels the same way you do. Respect and courtesy goes a long way towards achieving peace.
Focus on the problem, not the person. This is tricky, because emotions are high and how both of you feel is important. Acknowledge feelings, but stick to the problem at hand.
Listen and repeat – an old technique, but it has survived in our culture because it works.
Be curious, even if you find the other person’s position near the limit of what you can bear. We all have a lot to learn, and we don’t learn much from people who already agree with us.
Detach from your ego. Notice everything you feel because it’s information. But it’s not justification for action.
Who are you speaking for? If you are a leader, you are speaking for the business as well as yourself. Don’t forget that.
Practice makes permanent. If you regularly engage in tough conversations when you become aware of them, it will be easier to do so in the future.
Be realistic. Instead of the winner-take-all outcome above, consider what is logically and realistically possible as an outcome of the conflict. Do not use your leadership position for retribution or corrective penalties.

If you are a leader in business, the power differential between you and your employees makes it less likely that they will expose their differences to you readily, so you have a responsibility to create an environment between you and them to make it easier for them to have tough conversations with you, and for tough conversation to be productive and helpful.

That’s the goal for tough conversations: productive, helpful to both of you, and it should pave the way for a better future.

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