Just why is this conversation SO difficult?

When we run workshops on Difficult Conversations, one thing always surprises people…the list of reasons a conversation can feel difficult is much longer than they expect.

At The Conversation Lab, we define a Difficult Conversation simply as one where something makes it harder than normal to achieve the outcome you want. And it isn’t always the subject.

• It can be the person.

• The situation.

• What is at stake.

• How confident you feel.

• What you think the other person might do.

Or just how clear you are about what you want from the conversation.

And that is just for starters. It’s usually the point in the workshop where people start recognising their own conversations. The one they have been putting off or they one that they keep rehearsing in the shower.

In this post, we’re going to look at what makes conversations difficult, what can complicate them, what can happen when they go badly or are avoided, and some practical ways to think about them before you start talking.

Sometimes it isn’t just about how you feel about the conversation.

The situation itself can make it much more complicated. Think about challenging a colleague about something, then imagine having exactly the same conversation with your boss. The issue may not have changed, but the context has. There may now be a power imbalance, more at stake, a greater dependency on the relationship, or more concern about the consequences. Add in things like history between the two people, a lack of trust, strong emotions, conflicting interests, time pressure or incomplete information, and the conversation can quickly become much harder to navigate.

When we explore this in workshops, people often realise they have been focusing on what they need to say without really thinking about everything else that could affect how the conversation plays out.This is also why some of the usual advice about Difficult Conversations can feel a bit unhelpful. “stay calm”, “listen” and “be assertive” are all useful, but being assertive with your boss can feel very different from being assertive with a peer. Before you think about how to approach a Difficult Conversation, it is worth understanding what is making this particular situation more complicated.

There’s another part of this that often gets less attention: what happens if the conversation doesn’t happen at all?

Most people naturally focus on the immediate risk of having the conversation. They worry about how the other person will react, whether the relationship might be damaged, whether they’ll get the outcome they want, or whether they could make things worse.Those concerns are valid. But avoiding the conversation carries its own risks too. The issue may continue or escalate. Trust can be affected. Someone may disengage. A customer problem can become harder to resolve. A poor decision may go unchallenged. And quite often, the longer something is left, the harder the eventual conversation becomes. That doesn’t mean every Difficult Conversation should happen immediately. There are times when you need more information, when the timing isn’t right, or when waiting is genuinely the sensible thing to do. But it is worth thinking about both sides of the decision: 

• What could happen if I have this conversation? 

• What could happen if I don’t?

• The second question is often the one people spend less time considering.

There is a big difference between choosing to wait and simply avoiding the conversation.

And what about our Mindset?

One of the shifts we encourage people to make is to stop thinking about a potential conversation as “Difficult” before it has even happened. That label can shape how you go into it. You start anticipating resistance, conflict or a bad reaction, and before long you are preparing yourself for a battle rather than a conversation.

We prefer to think about having a Clear Conversation.

That means being clear about what needs to be said, what you need the other person to understand, what you want to understand from them, and what you are trying to achieve together.

The conversation may still be uncomfortable. There may still be emotion, disagreement or a response you were not expecting. But your mindset is different because you are not walking in focused on how difficult it might be.

You are focused on being clear.

For us, that is a much more useful place to start.

Not “How do I get through this Difficult Conversation?”

More “How do I have this conversation clearly?”

If you want to help your managers have Clearer Conversations, get in touch.