The Biggest Mistake Leaders Make When Having Difficult Conversations and How to Avoid It

What makes difficult conversations so difficult?

If you’re the boss in your workplace, you have the ability (and the responsibility) to sometimes pull rank, call the shots, and make tough decisions. This is an absolutely appropriate way to deal with certain difficult situations, assuming it’s done in a way that doesn’t shut people down.

If “taking a stand” is your default leadership style, however, you’ll probably run into trouble pretty quickly because the bottom line is that your people’s needs aren’t getting met. And this isn’t the best long-term team-building strategy for you.

So let me let you in on a little secret… the biggest mistake that leaders make in difficult conversations is that they waste their time arguing about positions instead of dialoguing about underlying needs.

This is because many leaders don’t really understand how to have difficult conversations in a way that enables them to get their needs met, while at the same time meeting the needs of the people they lead.

Let’s break it down…

If you’re managing a team that’s leading a big project, you may prefer to have everyone update the project plan on a weekly basis. Perhaps you need this information to keep your boss appraised of progress, concerns, questions, etc.

Breaking this down into positions and needs:

Your position: Team members update the project plan once a week

Your underlying need: Information

Now perhaps Sally is on your team, and Sally prefers to update the project plan at the end of each month. She finds that this is the most efficient way for her to work given her natural preferences and time constraints.

Sally’s solution: Update the project plan every month

Sally’s underlying need: Efficiency

You and Sally could argue for days about whether the project plan should be updated every week or every month and get nowhere. But as soon as you shift the conversation to a dialogue about how to meet both of your underlying needs (i.e., information and efficiency), you have a solid foundation to come up with options that actually work for both of you.

A conversation about “How do we meet both of our needs?” could lead to options like:

  • Sally shares her updates at weekly team meetings.
  • You ask Sally when you need information about the project and she proactively raises issues with you.
  • Sally updates you at your weekly individual check-in meetings.
  • Joe (a co-worker) takes a small task off Sally’s plate, freeing up time which she will use to update the project plan every week.

And the list goes on. The point is that now you’re working towards a resolution that you both can buy into! And this is how you get your needs met, while meeting the needs of others.

Quick Tip: A position is nothing more than a person’s preferred solution for meeting their needs. The way to distinguish between positions and needs is that positions can only be satisfied in one way (or very few ways), whereas underlying needs can be met in many different ways.

How to Avoid the Biggest Mistake

The problem with most difficult conversations is that the underlying needs of each individual remain below the surface in the conversation, or in other words, they are left unsaid. So it’s no wonder that we find ourselves spinning our wheels!

Underlying needs are kind of like the roots of a tree – we don’t see them but they play a crucial role. They anchor the tree to the soil, provide it with nutrients, give it support for its structure, etc. A person’s underlying needs are often based on their goals, their desires, their values, etc. In other words, all of the things that make up who they are as an individual.

Your mission, if you choose to accept it, is to hone your open-ended questioning skills so that you can help surface the underlying needs of others when you’re faced with a difficult conversation. Questions like the ones below will help you do this:

  • Walk me through your thought-process here.
  • Tell me what’s most pressing for you in all of this?
  • What’s your biggest concern right now?

This approach can be challenging when you’re feeling frustrated, but it opens up the possibility of having a deeper and more meaningful conversation that actually resolves the issue at hand.

And keep in mind that in most situations there are usually key joint needs that both people share, such as running a successful project. You may have different ideas about how to get there, but keeping these key shared needs in mind is incredibly helpful… especially if the conversation starts to become heated.

You can use joint-needs to refocus the discussion if things escalate, for example: “Hey, I know we both really want to ensure that this project is a success. We just have different ideas about how to get there but our end goal is the same. Let’s get back to talking about options that might work for both of us. Say more about why [xxx] is important to you…”

Working towards win-win resolutions may take a more time in the short-term, but building this type of goodwill with your employees will pay off in spades in the long run.