Mastering the art of difficult conversations: a step-by-step guide for leaders

Organizational Leadership

If you’ve been a leader for even a few months, you know that difficult conversations are inevitable. Whether it’s someone being disruptive during meetings, someone underperforming and regularly failing to meet goals, or someone who mistreated a client, hard conversations are par for the course.

You also probably know that these conversations are called “difficult” for a reason. Being the leader who has to deliver tough news or give tough criticism can cause a great deal of stress and anxiety. Fortunately, there are steps you can take to make difficult conversations more manageable and less stressful.

If you spend some time on the front end working on mastering the art of difficult conversations, you’ll be able to avoid many of the pitfalls that can doom them. Read on to learn some of the best advice for having a successful difficult conversation. 

At the end of the article you’ll find a case study that applies this basic step-by-step process. 

You should also know that our coaches are here to help you prepare and think through how to approach these difficult conversations. Set up a free consultation and see if professional leadership coaching is for you!

Step 1: Preparation

Define the purpose of the conversation

Why are you having this difficult conversation? Be specific and explicit. If you struggle in this stage to articulate why you’re entering this conversation, it’s going to be impossible when you’re actually sitting in front of the direct report you’re having the conversation with.

Gather information and facts

Write a timeline of events using emails, messages, previous performance reviews, etc. You want to make it clear that this isn’t just you having a bad day and wanting to vent. This must be substantiated and objective.

Getting clear facts laid out ahead of time will help you avoid the fundamental attribution error.

Identify potential emotions that could come up

What emotions are you bringing into this conversation? You’re not a blank slate. If you’re not aware of entering the room in an emotionally charged state, you may see it unexpectedly come out. 

If, however, you take note of the frustration you’re feeling with your direct report ahead of time, you can have time to work through it before bringing it into the room.

Set goals for the conversation

What outcome are you hoping for? Why are you having this conversation? What do you want the individual to do in response? Write this out and be prepared to share it. Make sure it is a SMART goal, not some nebulous idea like, “Just be better!”

Create a script or outline

Think through, in detail, how you want this conversation to go. What are you going to say? How? 

What specific examples will you provide of the behavior you’re correcting? What goals will you hold them accountable to? 

What if they react in a hostile manner? What if they cry? It’s helpful to consider responses ahead of time, but don’t get bogged down with every possible reaction.

Step 2: Execution

Start the conversation on a positive note

Your direct report surely has some positive things you can take note of, or else you should be having a firing conversation, not merely one that is aimed at performance improvement. 

What is praiseworthy that they have done recently? How are they contributing to the success of your team? If you have to, you can think of past months or past projects.

Starting off on a positive note can be helpful in avoiding your direct report feeling like this meeting was purely an attack on their character.

Use active listening and empathy

The importance of good active listening and practicing empathy in this kind of conversation cannot be overstated. This is why we’ve devoted so much space to tackling these topics in previous articles.

We have an article describing the importance of active listening skills for leaders and how to develop powerful active listening skills.

We have an in-depth article providing practical tips on improving emotional intelligence and empathy

Speak clearly and assertively

You want to avoid coming across as rambling and uncertain, even in the face of a strong emotional response from your direct report. Carefully articulate your points, and try not to be overly defensive or make your passion become aggression.

Make sure the direct report knows that their behavior or attitude is the reason changes have to be made, not because you have a personal vendetta against them. 

Don’t be a jerk, but you should also avoid backing down when pressed. You did the work to document problems ahead of time precisely so you know you’re not coming into this on a whim. This is a well documented issue you’re addressing, so speak confidently.

Address emotions head-on

As a leader, you often have to take ownership of the emotional temperature of a conversation. If your direct report is getting defensive, hostile, or emotional, don’t shy away from it. Acknowledge it head-on. Validate their reaction and thank them for speaking up.

You can say, “I understand why you may be feeling frustrated. Let’s talk about it.” That’s an important first step to diffusing the tension and still addressing the issues at hand.

Vocalize an understanding of their position without validating their behavior. You can say phrases like, “It seems like this is very upsetting for you. Can you tell me why?” Or, “I understand that this may feel frustrating or embarrassing to have this conversation. However, I’ve laid out some of the specific instances where you’ve failed to meet performance goals, even when reminded of these goals multiple times.”

Stay focused on the goals of the conversation

In the face of being challenged or having to navigate emotion-packed conversations, it’s easy to get lost and derailed. You must stay on point and keep the conversation focused on the goals you set out to achieve in the preparation phase.

If you start to feel like you’re in a therapy session rather than a corrective conversation, firmly and politely bring the conversation back on track. Acknowledge emotions while reminding your direct report why you called them in.

Step 3: Follow-up

Evaluate the outcome of the conversation

After the conversation, you should try to immediately debrief how it went.

Ask yourself questions like: did the actionable item that I wanted to set with this individual get set? Are there open questions or areas we need to work on? Is my direct report clear on what is expected of them going forward?

Analyzing conversations after they’re over gives you insights you can use in similar conversations moving forward.Specifically, make sure you reached the outcome you had identified earlier.

Reflect on areas for improvement

Then, consider how you might improve the next conversation.

In what ways could you have managed the conversation differently?

What areas can you improve on? Where did you struggle to stay focused or become too emotionally charged?

Write these down and refer back to them when preparing for the next conversation.

Address any unresolved issues

Are there lingering questions as a result of the conversation?

If they have identified anything they’d like to further discuss, provide a timeline for when those items can be addressed. 

Follow through on any actions or next steps

Did you identify anything that you will need to as a result of the conversation? If so, make sure you actually follow through.

Likewise, you must ensure that you hold your direct report accountable for what was agreed to.

Document the conversation

Finally, document all key points and decisions that came out of the conversation and email it to both yourself and the person you talked to.

Write down the actionable items and decisions, making sure you explicitly state what was addressed and what is expected moving forward. This is especially important if you’re dealing with a recurring issue or have to have follow-up conversations in the future.

A case study following the preparation, execution, follow-up framework

John is the manager of a team of software engineers at a technology company. One of his team members, Jane, has been consistently underperforming for several months. Despite John’s attempts to give her feedback and coaching, her performance has not improved. John knows that he needs to have a difficult conversation with Jane about her performance and potentially put her on a performance improvement plan.

Preparation:

  • Define the purpose of the conversation: to address Jane’s underperformance and create a plan for improvement
  • Gather information and facts: John reviews Jane’s performance metrics and collected feedback from her team members
  • Identify potential emotions and biases: John anticipates that Jane may feel defensive and upset during the conversation
  • Set goals for the conversation: John wants to have a productive conversation that results in a clear action plan for improvement
  • Create a script or outline: John creates an outline for the conversation that includes key points he wants to address and potential responses to any objections that Jane may have

Execution:

  • Start the conversation on a positive note: John starts the conversation by highlighting Jane’s strengths and contributions to the team. He then smoothly transitions into the reason for the meeting, the underperformance
  • Use active listening and empathy: John listens to Jane’s perspective and validates her feelings. He also acknowledges the challenges she’s been facing
  • Speak clearly and assertively: John explains the performance metrics and feedback that led him to the conclusion that her performance is below the team standards, He also sets clear expectations for what he expects from Jane going forward.
  • Address emotions and biases head-on: John validates Jane’s feelings and addresses her concerns. He also reassures her that the conversation is not about punishment, but rather about finding a solution and improving her performance.
  • Stay focused on the goals of the conversation: John keeps the conversation focused on finding a solution and creating a plan for improvement

Follow-up:

  • Evaluate the outcome of the conversation: John evaluates that the conversation was productive, and Jane seemed open to the feedback and action plan
  • Reflect on areas for improvement: John reflects on the conversation and identifies areas where he could have handled it better
  • Address any unresolved issues: John checks in with Jane regularly to ensure that she’s on track with her performance improvement plan and provide additional coaching if needed
  • Follow through on any actions or next steps: John implements the action plan and provides Jane with the necessary resources to improve her performance.

Lesson learned:

  • A difficult conversation can be productive if handled correctly.
  • It is important to set clear goals for the conversation and stay focused on them.
  • Active listening and empathy can help diffuse emotions and build trust.
  • Following up on the conversation and implementing a plan can ensure that the conversation was not only productive but also effective

Conclusion

Mastering the art of difficult conversations is important because it’s necessary to maintain a productive, healthy workplace environment. By following the preparation, execution, and follow-up steps outlined in this article, you’ll be able to navigate difficult conversations with ease, maintain a sense of composure, and ensure productive outcomes for all involved.

By preparing well for the conversations, you will be better poised to provide clear and direct feedback, stay focused on the goals of the conversation, and be prepared to lead the conversation well.

In executing the conversation while integrating these tips, you will be better able to manage any challenging emotions, misunderstandings, pushback, or other issues that may arise while still remaining focused on the goals of the conversation.

Finally, by following up on the conversation and implementing a plan, you will be able to ensure that the conversation was both productive and effective. Taking the time to reflect and address unresolved issues will also help ensure that any lingering issues are addressed and potential improvement areas are identified

All leaders must continuously improve their communication skills, especially when it comes to having difficult conversations. Challenge yourself to press into these conversations instead of avoiding them. It will transform you into a more effective, powerful leader.