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October 17, 2022

Leadership Communication: 6 Steps to Handling Tough Conversations


It’s a given: Having tough conversations and communicating difficult topics is part of a leader’s job. But just like you plan for contingencies in your business, planning how you will communicate difficult messages can improve the ultimate outcome. It is seldom easy to share difficult news, but thinking through your approach in advance definitely can improve the process.

It’s human nature to avoid conflict; we’re wired in that way. I was talking with a leader recently about conflict and how he avoided conflict, which cost him time, energy, and negatively impacted relationships with others. The principle I shared was this: Go toward the conflict. Our natural tendency is to move away from it and avoid it. It’s only through what might feel like “rupture” that “repair” can happen. That’s the upside of conflict handled well – improved relationships and trust.

Handling Tough Conversations in the Best Way

Handling tough conversations involves two aspects: Crafting a clear message and having the conversation. Here are six steps to prepare:

Step 1: Identify the problem

What do you need to communicate? Are business results not where they should be? Do staffing changes need to be made? Are there undesired behaviors that need to change?

Step 2: Identify your desired outcome

What is your objective for the conversation? Are you trying to put business news in context for your employees? Do you need your team to understand the changes that are underway? Do you need desired behaviors to become the norm among your staff?

Step 3: Identify your audience

Who needs to hear this information? Do you need to inform your entire staff? Is it a small group? Is it one employee? And should they all hear the message at the same time, or should some people hear it before others?

Step 4: Structure your key messages/conversation

What do you want your audience(s) to know, feel and/or do?

  • Consider how they might feel and receive the information you want to share.
  • What concerns might they have and what perspective might they have?
  • What are their needs and fears, do you share common concerns?
  • How have you or they contributed to the problem and what would help it improve?

What will you say (in a calm, constructive way) to the employee(s) so that they understand the situation and your concerns?

  • Consider how to start the conversation.
  • Develop specific messages or even a script to deliver the key points.
  • Identify the questions you will ask (to seek input/check for understanding). For example, “Tell me how you feel about what I just said.”
  • Have stories or examples to share to illustrate your main point.
  • Outline specific actions being taken and/or that your employees need to take.

Step 5: Deliver your message

When it is time to deliver the message, select the right time and place to have a conversation with privacy and without distraction. Encourage dialogue so you can get real-time insight into how employees are receiving the information, what’s on their minds, and if they understand what you are saying. Allow for plenty of time to be sure they feel supported and listened to.

Step 6: Follow up

Be sure to make yourself available to answer questions – in front of a group as well as privately. Ask what’s on their minds and listen with empathy to people’s concerns. Confirm next steps or expectations and the timeline for completion, including any commitments you make to follow-up on their expressed concerns.

A Leadership Attitude

Tough conversations are perfect times to set a positive example as a leader. This includes understanding and managing your own assumptions and emotions, especially when dealing with sensitive topics. Assumptions can get in the way of productive dialogue, so keep an open mind and don’t assume you understand employees’ intentions or attitudes without specifically asking. Also, think about your own needs and fears and how they may contribute to your own emotions.

For the best outcome, enter the conversation with a positive attitude and listen carefully to what is said verbally as well as through body language.

However the conversation may progress, remain calm and view the discussion as objectively as possible, showing respect for employees’ positions and the challenges they face.

Are you ready for your next tough conversation?

—David Grossman

Map out your communication, whether it's to a colleague, your team, or your organization. Being more purposeful in your communications can take as little as five minutes.

Click below to download your free copy of the tool—Take 5™ Planning Template—today!

Click to download the free communication planning template - The Grossman Group

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