What is it about difficult conversations?

What is it about difficult conversations? I mean, what’s so difficult?

Not every conversation we have should or will be easy. To have conversations is to exchange ideas, to learn together. Learning isn’t always easy. And any conversation worth having requires some effort.

I recently had an executive client declare that he wanted to learn how to have difficult conversations. I challenged him. There are only two types of conversations: the ones we are having and the ones we are not having. Together, we looked at what made it possible for him to have the conversations that he was having and what made it not possible to have the ones that he was calling “difficult”.

I’ll cut to the chase. What we discovered is that it’s the health of the working relationship you have—how you relate to one another from your roles and expectations—that predicts the level of ease or difficulty of your conversations. Improve the health of your relationship and you can have more of the conversations you used to call “difficult”. Ironically, what my client had been looking for was a conversational structure, a recipe to follow, to solve for the difficulties he was anticipating.

We cannot superimpose a structure or recipe for how to have a difficult conversation over top of the same.

These are outside-in solutions to what is really an inside-out challenge. The difficulty of a conversation isn’t some uncontrollable external circumstance like the weather. There is no law of physics, no scientific axiom that establishes the difficulty of a conversation. You construct a conversation as “difficult” by thinking and behaving as if it will be so.

What is the inside-out solution to this inside-out challenge?

Design and develop each of your working relationships so that you can have whatever conversations you need to have in order to transact your business as required.

Where to start? I think love—in the form of compassion—is the place to start. I know that, for some of you, talking about this will trigger your aversion to “soft skills”. Bear with me.

If you have enough compassion for yourself to believe that your point of view, ideas, priorities, intentions and aspirations are worthy of being known and understood by the other person just on their own merits AND if you have enough compassion for the other person to acknowledge that their point of view, ideas, priorities, intentions and aspirations are worthy of being known and understood by you just on their own merits, then you have the beginning of a conversation. This makes it possible to have a conversation in which both parties can learn together from each other. Where ideas and possibilities won’t just add up—they will multiply. Think exponential “collective wisdom”.

It is not that easy, you say. The other person is a jerk. Or the difficulty is with your boss and you don’t want to lose your job. I get it.

The thing is if you can talk with the other party and come to an agreement about how you’ll talk with one another, you may be able to have whatever conversations you need to have—efficiently and effectively—to transact your business in a more fulfilling way.

Let’s be realistic. You will have your differences. Understand that when you bring two intelligent, deeply committed people together who have different responsibilities, different priorities and different ways of looking at the world and interpreting what they see, those differences may become a source of difficulty. Acknowledge this as the norm and prepare yourself ahead of time by discussing how you will stay in the conversation when this happens.

That’s what I mean by designing your relationship. Setting yourselves up to have your differences be a source of learning and innovation—instead of a potential source of difficulty.

This may still feel difficult. But it is a lot less so than not having conversations to get our work done together.