How To Have Difficult Conversations With Employees

If you’re a manager, business leader, or HR professional, you’ve likely had to engage in difficult conversations with team members from time to time. While not always pleasant, having difficult conversations with employees is often inevitable. When workplace challenges arise, addressing problems directly can help resolve issues promptly—rather than waiting until the situation gets worse to schedule a conversation.

Having challenging conversations with employees requires thoughtful preparation. Given increased adoption of remote and hybrid work, ensuring you have the right process and approach is more important than ever, because reading body language and other nonverbal cues can be more challenging during a video meeting or when using another form of virtual communications.

Whether you’re looking to improve how you personally manage these conversations or are seeking training and techniques for managing challenging conversations at your organization, this guide can help. Learn how to effectively carry out these conversations, manage negative reactions, and ensure effective follow-up.

How to have difficult employee conversations

The exact process for completing tough conversations with employees may vary depending on your organization’s size, workplace policies, reporting structure, and other criteria, but the overall steps are often the same across companies.

Here are the steps to the process:

1. Prepare
2. Conduct the conversation
3. Recap and follow up

1. Prepare

While having difficult conversations with employees can seem daunting, proper preparation can help. Do your homework to ease some of the stress associated with these discussions, ensure you’ve gathered all important details ahead of time, and help avoid missteps.

Consider the following steps to prepare for a difficult conversation:

• Define the problem or issue. Difficult conversations may arise for a variety of reasons. Some may include poor performance, conflicts between workers, company policy violations, unprofessional behavior, and layoffs or terminations. As a first step to prepare for a difficult conversation with a team member, determine the exact problem you’re looking to address and focus on the issue itself rather than the person.
• Conduct a root cause analysis. Once you identify the problem, determine any underlying conditions that may have led to the issue. For example, a worker may be underperforming due to unclear expectations, a lack of training, or the individual’s hesitation to ask for help. While the worker may share their perspective on the root cause of the issue during the conversation, outlining possible contributing factors beforehand can be helpful.
• Outline talking points. When you develop talking points, include any necessary documentation related to the discussion, as well as relevant company policies. Keep in mind, while talking points are helpful to stay on topic and have a constructive conversation, try to avoid reading from a script. The discussion is meant to be a two-way conversation and reading word-for-word from a script may come across as less genuine, empathetic, or engaged in the conversation.
• Determine the right timing for the meeting. Try to schedule the discussion as soon as possible once an issue arises and at a time that will minimize disruptions to the worker and the broader team. For example, you may want to avoid having the conversation right before a team meeting, presentation, or client call. Consider extending the worker’s regular check-in meeting or scheduling the conversation at the end of the day.
• Maintain confidentiality. Keeping difficult conversations confidential can help establish trust, avoid violating workplace policies, and minimize potential gossip among team members. If your team works in a physical office, book a conference room. If your team works remotely, suggest the individual find a private, quiet place for the conversation. Also make sure any documents related to the conversation aren’t stored in shared team folders and that only those directly involved have access.
• Invite an HR representative if necessary. If you’re discussing a serious or sensitive topic, consider inviting a team member from your human resources department to join the meeting. An HR team member can serve as a neutral witness to hear both sides of the discussion, ensure the conversation adheres to company policies, and provide proper documentation.
• Think about the worker’s perspective. As you prepare for a tough conversation, you may have all the necessary facts gathered and a desired outcome. However, taking the worker’s perspective into consideration is also important so the conversation isn’t one-sided. Plan to join the meeting with an open mind and willingness to hear the individual’s point of view.

2. Conduct the conversation

Once you’ve scheduled the meeting and adequately prepared, the next step is conducting the conversation. Taking the right approach can increase the likelihood of positive outcomes following the discussion.

Here are some tips to keep in mind during difficult conversations:

• Be clear and concise. The talking points you prepared in advance can help you address the issue or problem in a clear and concise manner. If you use vague terms rather than discussing the problem and its impact directly, this approach may only lead to confusion and miscommunication. Aim to present fact-based, specific examples, along with any data points related to the issue. Also avoid using subjective language, such as “I think” or “In my opinion,” or sandwiching constructive feedback in between positive feedback, as doing so may diminish the importance of the points you’re sharing.
• Display empathy. Similar to thinking about the worker’s perspective ahead of time, be empathetic when the worker shares their point of view. For example, a team member’s performance may have slipped due to a stressor in their personal life or because they’re struggling to learn a new skill. Without letting emotions disrupt the conversation, acknowledge that you understand the worker’s perspective and want to work together toward a solution.  
• Engage in active listening. As the individual shares thoughts, questions, or concerns, you can show that their points are valued by engaging in active listening. Active steps you can take include repeating their statements in your own words to clarify key points, asking follow-up questions, and taking notes.
• Collaborate to determine a solution or plan of action. After discussing the issue and hearing the team member’s perspective, work together to identify a solution based on the conversation. If the individual is involved in brainstorming the solution, they will likely feel more empowered and motivated than if they were dictated next steps without the opportunity for personal input. As you work together on a solution or plan of action, consider the individual’s goals and needs, as well as solutions that will best serve the broader team and company as a whole.
• Keep a record of the conversation. Take notes throughout the discussion so you can refer to key points in any follow-up communication. Depending on your organization or workplace policies, you may need to complete specific forms and add them to the team member’s personal file.

3. Recap and follow up

Many points are covered during a difficult conversation and effective follow-up is essential for avoiding misunderstanding and miscommunication. Recapping and following up on the meeting can help ensure all parties are aligned and understand next steps.

Steps to take as you wrap up the meeting and immediately following include:

• Reiterating key points, action items, and follow-ups verbally at the end of the meeting
• Sending an email to thank the worker for their time, document the discussion, and share any next steps
• Scheduling a follow-up meeting to answer any questions that may arise after the initial conversation and restate the solution or plan of action

Tips for handling negative reactions

Difficult conversations can quickly veer off topic or become uncomfortable if the worker you’re addressing has a negative reaction. The reaction can vary depending on the conversation topic and may include disagreeing with your feedback, sharing negative feedback of their own, denying certain actions, making excuses, placing the blame on others, or questioning the validity of points made during the discussion.

While handling negative reactions can be unpleasant, consider the following tips to maintain focus and ensure a smooth conversation:

• Stay calm, objective, and professional
• Reiterate facts and data related to the issue
• Acknowledge and validate the worker's feelings
• Address inappropriate behavior as needed
• Refocus on the issue at hand
• Engage an HR representative if the team member’s reaction violates company policies

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Next steps after a difficult conversation

In addition to the initial recap and documentation shared at the end of a difficult workplace conversation, setting a long-term plan in place can help hold workers accountable for ongoing improvement. As a manager or leader, identifying next steps can also ensure you’re providing the support needed for the team member to address the issue discussed. A long-term plan can help you improve your communication and workplace conflict resolution skills.

A long-term talent development plan is particularly relevant if the difficult conversation was related to a team member’s performance issues. In the event of workplace policy violations or the departure of an individual from the company, next steps will likely be more immediate.
The following steps can help you outline an action plan to improve performance following a difficult conversation with a team member.

1. Set clear expectations and goals

When outlining expectations and establishing goals, consider using the SMART framework to ensure goals are specific, measurable, attainable, relevant, and time-bound. This can help ensure workers have a clear understanding and action plan to achieve goals.

A SMART goal for an underperforming team member may be to take an online skills development course by the end of the quarter and achieve a passing score on the assessment at the end of the course. Once the course is complete, the worker can also meet with their manager to discuss how they’ll apply key learnings to improve in their role.

When you set SMART goals, make sure the team member fully understands the overall objectives and specific metrics and discuss initial actions they may take to work toward the goal. Resolving any questions or concerns up front can help avoid another potential difficult conversation in the future.

2. Check in and provide ongoing support

Once expectations and goals are defined, discuss progress on a regular basis during one-on-one check-ins. Meeting cadence may vary depending on your team size and business processes; one-on-ones often take place weekly, biweekly, or monthly.

During recurring meetings, touch base on goals, document updates in writing, and create a safe space for individuals to share feedback, ask questions, and request additional support, if needed.

Consider asking the following questions to guide the conversation during check-ins:

• Can you share an update on progress you’ve made toward agreed-upon goals?
• Which changes or improvements have you found to be most successful since our conversation?
• Are you facing any roadblocks that may impact your ability to meet expectations?  
• How can I offer more support or coaching?
• What additional resources do you need to deliver required business outcomes?
• Do we need to consider any changes or updates to goals based on your progress to date?
• What next steps do you have planned to continue working toward goals?

3. Offer access to talent development resources

One of the reasons workers may fall short of expectations is that they need to improve their existing skills or develop new ones to deliver positive business outcomes. Based on the goals you’ve outlined, you may want to offer access to talent development resources to help team members build the skills they need to succeed.

Talent development resources may include, but aren’t limited to:

• Online learning platform access
• Stipends for professional development events and courses
• Skill and talent assessment tools
• Stretch assignments and experiential learning
• Formal coaching and mentoring opportunities

Identifying the most effective talent development strategies and resources requires time and thoughtful planning. Rather than approaching the process on your own, consider engaging an independent training and development professional. A skilled independent professional can share their expertise and help you build or improve talent development efforts at your organization.

4. Celebrate successes

Difficult conversations can sometimes have a negative impact on worker motivation and productivity. As workers reach milestones or achieve goals, recognizing their efforts can help boost motivation. In fact, a survey of 2,000 U.S. workers from Bonusly found that 65% of respondents would work harder if they felt like their contributions would be noticed by management.

Some ways to celebrate successes include:

• Saying thank you in an email, direct message, or meeting
• Calling out direct, positive feedback on a specific project
• Highlighting achievements and milestones during team meetings
• Giving praise to an individual or several workers on a team email or chat channel
• Passing along compliments about an individual to another manager or leader on the team
• Sharing positive feedback from customers, managers, and peers

5. Address setbacks and new issues

Similar to discussing the initial issue as soon as possible, continue to address any setbacks or new problems that emerge following a difficult conversation. Addressing issues as they arise can help you identify solutions to help the team member get back on track with goals and expectations.

If the team member continues to face setbacks, you may need to reiterate expectations or implement a performance improvement plan, which is a formal document outlining specific development opportunities for an individual. A performance improvement plan also features more detailed goals, expectations, and actionable next steps for a team member to make changes or improvements.

6. Improve difficult conversations in the future

In addition to pursuing any follow-up with individual team members after difficult conversations, you, as a manager or leader, can also benefit. Each conversation offers an opportunity for you to reflect, determine what went well, and identify areas of improvement for future challenging discussions.

Consider answering the following questions, either as a self-reflection exercise or during a recap meeting with you own manager or an HR representative:

• How  prepared was I for the conversations?
• What steps could I have taken to be better prepared?
• How well did the worker understand the reasoning behind and need for the conversation?
• How did the team member react to the problem or issue?
• If the team member reacted negatively, how did I respond?
• How well did I listen to the individual’s perspective and show empathy?
• How can I improve active listening in future conversations?
• Which aspects of the conversation were the most successful?
• How well did the conversation lead to an effective solution or plan of action?
• Which aspects of the conversation require improvement?
• What coaching or additional training do I need to improve future difficult conversations?

Difficult conversations can lead to long-term improvement

Having difficult conversations with employees can be challenging. However, addressing issues sooner rather than later can lead to long-term improvement that will benefit team members and your business as a whole. On the other hand, avoiding difficult conversations can cause problems to build over time, which may have a negative impact on the work environment, team morale, productivity, and overall business outcomes.  

By preparing in advance, conducting a clear and concise discussion, working together toward a solution, and identifying next steps following the meeting, you can alleviate some of the stress often associated with difficult conversations. Each time you have a challenging conversation, you’ll also learn from the experience, which will help make the process smoother in the future.

For additional support, consider engaging an independent performance management professional to help train your team on best practices for effective difficult conversations.

Experienced performance management specialists are available through Project Catalog™, offering one-on-one consultations and fixed-price projects. Simply book a consultation or select a project that aligns with your business needs and begin working with an expert right away. Get started—browse available performance management services on Project Catalog.