How to Have Tough Conversations with Employees & Teammates

You can’t be an effective leader without skillfully handling tough conversations.

Delivering feedback. Addressing underperformance. Resolving conflicts.

Learning how to constructively navigate these talks can help you build trust while upgrading your team’s performance.

But let’s be honest: Nobody looks forward to these moments. It’s human nature to want to put off these discussions, or come in with defensiveness. 

Avoiding these conversations only makes matters worse. Not to mention, the more tough conversations you’re willing to have, the better off your career will be.

Learn how to have tough conversations with employees and teammates with skill and empathy.

Why Tough Conversations Matter

Tough conversations, when handled well, help you clarify expectations, strengthen relationships, and improve your team’s performance.

The best leaders face challenges head-on, using them as moments to coach and uplift their teams​.

Unaddressed issues, however, can fester, leading to resentment, decreased productivity, and voluntary turnover. 

In fact, 95% of employees say they fully trust leaders who communicate clearly and openly.

Step 1: Prepare Thoughtfully

Don’t rush into a difficult conversation. Here’s how to get started:

Identify the Topic

Before the talk, get clear on what you want to talk about. Is it about performance, a role shift, or something else entirely? Clarify the issue and its impact on the team, project, or individual.

Set Clear Goals

Determine the outcome you’re seeking. Are you aiming to improve performance, resolve a conflict, or clarify expectations? Be ready to share this with your discussion partner.

Plan the Logistics

Think about when and where the conversation will take place. Choose a private and neutral setting to ensure everyone feels comfortable. 

Think about whether you want to have this talk in a regularly scheduled meeting, or if you want to schedule a specific meeting to talk about it. Share the topic of discussion with your teammate as you send the invite, and clarify that your #1 priority is to support them.

Visualize Success

Mental preparation is vital. Imagine the conversation going well — visualizing your tone, body language, and words to stay calm and collected​. Be ready to be open and vulnerable.

Talks like these can understandably bring up anxiety. If you’re feeling nervous, practice a few rounds of calming breathwork before your conversation to make sure you go in open and grounded.

Step 2: How to Start a Tough Conversation

The way you open this conversation sets the tone for the entire discussion. Start with empathy and clarity:

Be Direct, but Compassionate

Begin by clearly speaking to the issue at hand. For example: “I’d like to talk about your recent performance on [specific task].”

Express Your Intentions

Assure the other person that your goal is to support them. Say something like, “My intention here is to find a solution together.” Make sure your discussion partner knows that you’re "on their team."

Invite Teamwork

Use open-ended questions such as, “What challenges are you facing?” or “How can we work together to improve this?”

Step 3: Keep the Talk Constructive

Staying composed and focused during the conversation is essential. Here are some tips:

Invite Teamwork

Practice Active Listening

Give the other person space to share their perspective without interruption. This builds trust and shows you value their input.

Focus on Behavior, not Personality Traits

Frame feedback around specific actions rather than making it personal. For instance, instead of saying, “You’re unreliable,” try, “I’ve noticed delays in your deliverables recently. When this happens, it has xyz impact on our team.”

Stay Solution-Oriented

Frame the conversation toward actionable steps, rather than dwelling on the issue. For example: “How can we ensure the deadlines are met going forward?” “What support do you need from me?”

Remember, tough conversations can be emotionally charged. Techniques like deep breathing and body scans can help you stay calm and present during these moments​.

Step 4: How to Follow Up After a Tough Conversation

The work doesn’t end once the conversation is over. Follow-up actions are crucial to ensure progress and demonstrate commitment.

Reflect and Review

Take a moment to evaluate how the conversation went:

• What went well?
• Did it align with how you prepared?
• How did the other person respond, and what could you improve next time?

Celebrate Vulnerability

Regardless of the outcome, recognize your courage in addressing the issue — and your team member’s vulnerability during the conversation. Tough conversations are a sign of strong leadership and emotional intelligence.

Plan Next Steps

Collaboratively set clear goals and check-in points to ensure accountability. Following up shows that you are invested in the other person’s success.

Final Thoughts

Having tough conversations with employees or teammates isn’t easy, but it's an essential part of strong leadership.

By approaching these moments with preparation, empathy, and a solution-focused mindset, you can turn them into opportunities for growth — for both you and your team.

The more comfortable you become with navigating difficult discussions, the better equipped you’ll be to foster an environment where everyone feels supported and valued. 

To take your team’s trust and performance to the next level, look into Exos’ Human Performance Coaching for Organizations.