Taking Conversations from Difficult to Doable

At some point you will have to have a difficult conversation at work. There’s just no way around it. Whether you’re giving not-so-positive feedback to an employee, broaching a sensitive issue with a coworker, or even confronting a moody employee, there will come a time when you need to bite the proverbial bullet and just say what needs saying.

Holding a tough conversation is not a task for the timid. There’s an art to doing it well (i.e., in a way that doesn’t make the other person cry, explode, or tune out what you’re saying). But if you haven’t yet mastered that art, you’ll likely do okay if you focus on this key phrase: Seek to complete, not compete.

People tend to enter tough conversations from a place of competing—they’re dead-set on proving themselves right and the other person wrong. The other person will focus on your tone and demeanor, not your message, and you end up harming the relationship.

But approach the conversation from a place of ‘Okay, I’m seeking more information to complete my understanding,’ and it will go much more smoothly. And it’s much more likely that what you need to happen will happen.

Instead of setting up a blame/defensiveness cycle, you want to help the other person. You’re looking for a win/win outcome, not a situation in which someone has to lose if you win. You’re not looking to punish, embarrass, or put the person ‘in their place.’ If this is your mindset, the conversation absolutely will fail.

Here are three tips to help you complete, not compete:

Ease into it.

When you need to have a difficult conversation, it’s often wise to “ease” into the tough topic. Talk about something positive or neutral so that the other person feels at ease and is not immediately put on the defensive. When people feel that they have been “attacked out of nowhere,” they don’t do their best listening or thinking—which will impair your efforts to “complete.”

Say, “Yes, and…” instead of, “Yes, but…”

You’ll find it’s much more productive to have a tough conversation if you use the Yes, and syntax. Consider, “Suzy, you’re doing a great job learning that new task, BUT you’d finish more quickly if you changed the sequence of steps a little.” The BUT diminishes the compliment with which the sentence started.

Doesn’t this sound more positive? ‘Suzy, you’re doing a great job learning that new task, AND I think you’d be even more successful if you change the sequence of steps a little. “When I am training leaders on how to master tough conversations, I remind them to keep the BUTs out of the conversation!”

Speak respectfully, especially when disagreeing. 

Trust is essential in navigating difficult conversations (not to mention creating the kind of culture that leads to business success). Trust and respect are closely tied, and both are necessary for “completion” to take place. It’s important to hold up the mirror during difficult conversations and, if necessary, adjust your behavior to create a safe, respectful environment.

Let the Golden Rule be your guide. Ask yourself, How would I feel if someone else talked to me this way? Would I be motivated to work toward resolution, or would I feel the need to defend myself?

It can be especially tricky to keep the conversation respectful if you find that you must disagree with the other person. In this case, say, ‘I hear what you’re saying. I’d like to respectfully disagree with your conclusion or the process you are suggesting.’ That’s so much more positive than attacking, yelling, screaming, or stomping out of a meeting…or even simply sitting and seething.

These three tips will help you create a safe environment. That’s important, because trust, respect, and safety are three legs of a stool that must be in balance to master tough conversations.

If you can create a safe environment, you can talk with almost anyone about almost anything. People will feel safe when they think you respect them and you care about them. Not coincidentally, when respect and care are present, you have the raw materials for a vibrant, growth-oriented culture and an incredibly successful company.