How to Have Difficult Conversations With Employees Like a Pro

January 31, 2025

Dreading a tough conversation with an employee? You’re not alone. Most people would rather avoid hard conversations at work—70% admit to steering clear of them, and more than half of employees avoid them. But sidestepping difficult conversations at work can lead to bigger problems down the road. With the right strategies, you can learn how to have difficult conversations with employees  and create opportunities for growth and connection.

Why difficult conversations at work are important

The way managers approach difficult conversations with employees can create a ripple effect across the entire workplace. Whether addressing performance issues, interpersonal conflicts, or personal challenges, your approach can significantly influence the outcome. Here’s why managing difficult conversations thoughtfully is so important:

• Morale - Poorly handled conversations can demotivate employees, while thoughtful conversations can reinforce their sense of value and direction.
• Productivity - Clear, direct communication helps resolve roadblocks and refocus efforts on key goals.
• Trust and relationships - Managing difficult conversations with empathy fosters mutual respect and psychological safety.
• Performance - Constructive feedback gives employees the insights they need to grow and improve.
• Team cohesion - Resolving interpersonal conflicts strengthens collaboration and teamwork.

How to have difficult conversations with employees

Having difficult conversations with employees is never easy, but they’re a chance to build trust and tackle important issues. Here’s how to prepare, engage, and follow up effectively. While many tips here are geared toward managers, several apply to any challenging discussion. For example, difficult conversations occur when employees discuss project challenges with each other, when employees speak with managers about workload support, or when managers address performance challenges with team members.

#1 Before the difficult conversation at work

Collect facts

Gather specific examples to illustrate your points (e.g., missed deadlines or a timeline of incidents).

Choose the best time and place

Set aside enough time for a meaningful discussion in a private, distraction-free space. For example, put phones or non-critical messaging platforms on do not disturb.

Practice your responses

Anticipate emotional reactions and rehearse calm, validating responses like, “It makes sense to me that you feel xyz—let's discuss how we can work together differently next time," rather than escalating with defensive or accusatory statements. 

Check your mindset

Before hard conversations with employees, reflect on your emotions and assumptions. Are you reacting to the situation at hand or bringing in unrelated stress? For example, if you’re upset about a team member’s tone in a meeting, consider whether it’s an isolated incident or part of a larger communication challenge. Reflecting on your mindset before the difficult conversation will help you approach the discussion with greater clarity.

Establish a culture of trust

Trust is the foundation for productive conversations. You can build trust by following through on commitments, admitting when you’ve made a mistake, asking for employees’ input on decisions, and showing appreciation for hard work.

#2 During the difficult conversation

Lead with empathy

Empathy and emotional intelligence are foundational skills when learning how to have tough conversations with employees. Start by acknowledging their perspective: “I've noticed some challenges, but first, how are things going for you?" 

Highlight strengths

Focus on strengths when giving feedback, such as: “Your ability to collaborate effectively is a great asset—your input really helps drive team success.” Avoid sandwiching constructive feedback between praise, as it can dilute the message and create confusion. Instead, keep strengths and areas for improvement separate. 

Focus on the issue, not the person

Avoid personal criticisms during difficult conversations at work. Stick to behaviors and outcomes, using recent examples and specific, observable facts (e.g., “Your last three deadlines were missed. Let’s discuss what got in the way and how we can improve the process so that  deadlines will be met moving forward”).

Keep your emotions in check

Giving feedback can feel overwhelming. Remember it’s important to stay calm and curious to keep the feedback discussion constructive. If you feel strong emotions arising, remember to pause before reacting. You can do this by pausing the conversation and scheduling more time. You can also use in-the-moment grounding techniques like deep breathing or focusing on your surroundings (e.g., noticing the feel of your feet on the floor) to stay calm.

Listen actively

Listening is as crucial as speaking when deciding how to have difficult conversations with employees. Show you’re fully present by maintaining eye contact, nodding, and acting clarifying questions. Avoid rushing to form a rebuttal while the other person is talking. Instead, focus on their message and ask clarifying questions. 

Collaborate on solutions 

Frame difficult conversations with employees as an opportunity to improve team dynamics. When challenges are viewed as growth opportunities, teams open the door to  innovative and effective resolutions that can lead to higher morale and performance. 

#3 After the difficult conversation

Following up after hard conversations with employees helps solidify progress, maintain trust, and address evolving challenges. Here's how you can continue supporting and guiding the employee:

Define next steps

Summarize action items and commit to follow-up. This can sound like, "Let's reconnect in a month to review progress." Documenting the action item and a time to follow up ensures both sides understand expectations and how progress will be tracked.

Foster open dialogue

After a difficult conversation at work, invite questions to clarify expectations and ensure alignment (e.g., "Is there anything you'd like to discuss further?").

Check in regularly 

Follow up to address lingering concerns and show ongoing support, such as, "How are you feeling about what we discussed last week?" This helps ensure that both parties are moving forward with a shared understanding.

Celebrate positive progress

Recognize improvements, no matter how small. You might say, "Thank you for implementing the new process we discussed last week—I can already see improvements in the quality and timeliness of your work.” Celebrating incremental progress helps the person feel valued and motivated to continue improving.

Discuss unresolved concerns

Not everything may be resolved after the first conversation, and that’s OK. Continue to check-in and raise challenges one at a time with the employee and stay patient as progress is made. If you don’t see improvements and aren’t sure how to move forward, don’t hesitate to reach out to HR. 

Offer continued support and resources

If the conversation involves behavioral or skill-related changes, check if the person needs any additional resources, training, or support. This shows that you’re invested in their growth and are willing to provide the tools they need to succeed.

Turn tough talks into opportunities

Difficult conversations don’t have to be something you dread—they can be a chance to strengthen relationships and inspire positive change. By normalizing these discussions, you create a culture where feedback is welcomed and issues are addressed proactively, preventing resentment from building. With the right preparation, empathy, and follow-through, even the toughest discussions can lead to productive and meaningful outcomes.