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How to prepare for difficult conversations

Difficult conversations requires leaders to be prepared, to show the business case and to create an intention. Learn more about changing behavior through conversations.

5 min read


How to prepare for difficult conversations

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One of the most difficult conversations for a leader is talking about behavior change. Whether the behavior in question is dysfunctional, disruptive or divisive, what makes the conversation difficult depends on the context.

Here are some examples:

  • You allowed the behavior to continue for too long
  • You inherited the problem
  • The disruptive person is a high performer otherwise
  • You don’t know how to start the conversation
  • You tried to initiate a conversation and you failed
  • Your senior leaders won’t back your decision should you need to set a boundary

To successfully initiate conversations about behavior you must stop shooting from the hip. The difference between a successful conversation and a disaster is the preparation.

Here are some critical preparation steps to ensure a productive conversation about behavioral change.

Step No. 1: Define the problem behavior

The first step is to define the behavior that needs to change. Don’t start a conversation here. (Step No. 1 is only prep work.) The reason for the prep work is that if you start with the problem or start speaking without a plan, you’ll quickly get off course and create a bigger problem later.

What not to do: Don’t define the problem emotionally or judgmentally. When you say, “they don’t care” or “they are lazy,” it indicates you don’t clearly understand how to articulate the non-judgmental observable behavior.

What to do: Define only the observed behavior, working from facts instead of feelings. The question to ask yourself is, “What is happening that should not be happening?”

For example, Kim interrupts others during staff meetings. What should be happening is that Kim should take turns and wait until others are finished. It’s easier to ask for change if you can (in your preparation phase) clearly identify and articulate the problem behavior.

Step No. 2: Understand how the problem affects the business

Why is it important that Kim change behavior? If it’s only because it’s irritating to you, then the lesson is about expanding your conflict capacity. Let’s say that Kim’s behavior has contributed to internal conflict and, as a result, you almost lost an employee. Now you have a business case in favor of initiating a conversation.

What not to do: Don’t justify bad behavior in the name of performance or higher revenues.

What to do: Redefine performance so that behavior is included in how the employee is evaluated. If the employee works solo, there may not be a business case for changing behavior. If the role involves working with a team, then behavior matters.

Step No. 3: Define your desired outcome

Name your desired outcome. The desired outcome can be stated by clarifying what you want versus what you have. For example, “I want Kim to become a good listener to support the team.”

What not to do: Stop visualizing the worst possible outcome. Stop thinking about Chris crying, Daniel getting defensive and Raju getting resentful. These visions will erode your confidence and make you procrastinate.

What to do: Visualize the best outcome. For example, you see the employee working well with the team and learning skills to become a leadership candidate. When you have the end result clearly in mind, you have your starting place in the conversation.

Step No. 4: Create an intention

The intention is a statement that drives the conversation. Think of an intention as a goal with a soul. While a goal is all about achieving an intended outcome, intention also considers the process and the person.

What not to do: Don’t start the intention from a negative perspective. For example, don’t say. “Kim, my intention for this conversation is to get you to stop interrupting.”

What to do: Start the intention with a forward-moving, positive direction. For example, you might say, “Kim, my intention for this conversation is to talk about ways to improve our team meetings.”

Step No. 5: Put it all together

In this last phase of preparation, create an order to your conversation. Get a pen and paper to organize your outline.

What not to do: Don’t shoot from the hip without practicing. Don’t start with the problem or the business case.

What to do: Get the order correct before you initiate the conversation. Start with the intention, next state the observed behavior, followed by what you want — the desired end result.

It goes like this: “Kim, my intention for this conversation is to talk about how we can have more productive team meetings. What I’ve observed is that often you interrupt when you disagree. What I want is to create a culture where everyone feels heard and contributes.”


Conversations about behavior is difficult for most leaders. Most leaders fail to do the necessary preparation before the conversation, which leads to unnecessary conflict and wasted time. With some preparation and the right order, your conversations become more focused and productive.


Marlene Chism is a consultant, international speaker and the author of “Stop Workplace Drama” (Wiley, 2011), “No-Drama Leadership” (Bibliomotion, 2015) and the forthcoming book “From Conflict to Courage” (Berrett-Koehler, 2022). She is a recognized expert on the LinkedIn Global Learning platform. Connect with Chism via LinkedIn, or at

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