How to Have Difficult Conversations with Employees

By Mariah Collins, SHRM-CP on Mar 15, 2023
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As a manager or business owner, it's inevitable you will need to have difficult conversations with employees from time to time. These conversations can be about a range of issues such as poor performance, personal behavior or disciplinary action. While it's never easy to have these kinds of conversations, it's important to approach them in a professional and constructive manner. Here are some tips on how to have difficult conversations with employees.

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At a Glance: Preparing for a Difficult Conversation

  • Call your Axcet HR Consultant/consult with your business’ HR expert. 
  • Be prepared with documentation and policies, when possible.
  • Leave your emotions at the door.
  • Be consistent. How have you handled this situation/similar situations in the past?
  • Schedule plenty of time for the conversation.
  • Come from a place of support and positivity.
  • Be prepared to listen – not just talk.
  • Be prepared with an action plan for the resolution of the issue.

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Is It Time to Have a Conversation?

Knowing when it’s time to have a difficult conversation with an employee is important to ensure that issues are addressed in a timely and constructive manner. Answering these questions will help guide you:

What is the issue?

Has the issue happened before? How severe is the issue? What IS the issue? Is the employee not meeting expectations/going against company policy? Analyzing these questions first can help you make the decision on having the difficult conversation – and determine whether or not this is a coaching opportunity, or something more severe that warrants a performance management approach. Each conversation will likely be “difficult” but determining the issue and the severity can help determine how to approach the conversation.

Is the issue pervasive? 

Is it affecting your team/organization? Are objectives not being met? Determine the impact of the issue at hand.

Is there a lack of improvement?

Has feedback/opportunity for improvement been given in the past? Are you seeing improvement? If not, it may be time for a difficult conversation.

Are you still unsure?

If you’re unsure about whether or not you need to have a difficult conversation with an employee, please reach out to your HR consultant.

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In-Depth: Having Difficult Conversations with Employees

Having difficult conversations with employees can be challenging, but there are steps you can take to make the process smoother. Here’s a deep dive to help set you up for success.

1. Don’t Jump to Conclusions

Investigate the situation thoroughly prior to deciding whether or not it is appropriate to have a difficult conversation.

2. Be Prepared

Before you have a difficult conversation with an employee, take time to prepare. Clarify the issue at hand, gather evidence or specific, factual examples, such as employee performance reviews and policies, and identify the key points you want to make. 

Consider the outcome you want to achieve and how you can best communicate your message. Remember, clear and honest feedback is always the best. 

Here’s what to consider as you prepare:

  • Think through what you want to say and what the employee might say or questions they may ask.
  • Consider how you will control your own emotions during the conversation, as well as mitigate negative emotions from the employee. Try to put yourself in the employee’s shoes to understand their emotions/thoughts/reactions to the difficult discussion.
  • Be prepared with possible solutions to the issue. What is the end goal? What are you trying to achieve as the employee’s manager?
  • Be prepared with an objective, factual statement surrounding the discussion. For example, what seems to be happening, how has it impacted the team/organization and what is the goal for improvement?

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3. Be Timely 

Don’t wait until the problem has really “reared its head” to address it with an employee.

4. Be Consistent 

Hold all employees accountable to the same performance expectations.

5. Put Thought into the Meeting Title

Address/schedule the conversation/meeting as something like a “quick conversation” or “quick touch base” versus “Performance Improvement Meeting” or “Disciplinary Action Meeting”.

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6. Time & Location

Ensure you schedule ample time for the conversation and have a private, confidential meeting area for the conversation to take place.

7. Be Present & Listen

Be present for the conversation – do not allow for outside distractions (phones, computers, etc). Be flexible and listen to the employee’s responses and concerns surrounding the difficult conversation. Address any concerns they have or follow up with them if you’re unable to address specific concerns during the conversation.

8. Be Positive

Relax and act naturally. If you are nervous or stressed, the employee will pick up on your energy. Ultimately, you want to make the employee feel comfortable. Positive energy, care and level-headedness go a long way in achieving this.

  • Show you care 

Again, be positive throughout the conversation. We don’t want to take the conversation from the standpoint of “you’re in trouble”, but rather “here’s the issue, but we’re going to fix it together” standpoint.

  • Remain level-headed

If the conversation/discussion seems strained or is escalated by the employee’s attitude or emotions surrounding the conversation – it is okay to pause the conversation and continue it at a later time. It is pertinent to move through the conversation as soon as possible – so this should really be a last-ditch option – but it is always okay to press “pause” and come back to the discussion once the employee has calmed down.

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9. Provide Opportunities for Improvement

Provide specific opportunities/expectations for improvement, where possible. Be positive about the things they can do to improve. Don’t simply tell the employee what they are doing wrong; provide them with the tools, guidance and support necessary for improvement.

10. Reassure the Employee

Reassure the employee of their opportunity for improvement – take the conversation from a “positive” approach versus a negative one. Reiterate your support, as their manager, and that you are here to help guide them to a positive future outlook surrounding the issue.

Sample: See the Script for an Actual Difficult Conversation >>

Follow Up

Follow up with the employee the next day. Take a moment to have a face-to-face conversation with the employee, thank them for their time during your meeting and offer further support and guidance as they move forward. Additionally, offer the chance for the employee to ask any follow-up questions or gain clarity on anything following the difficult conversation. This is key in making sure the employee feels heard and supported following the conversation.

After the initial follow-up, make it a point to check in regularly with the employee on the action items/expectations discussed in your initial meeting. Follow up on any expectations that are being met for positive reinforcement, and provide reminders about further expectations that may not be being met yet. A good setting for this would be touching base during regularly scheduled 1:1 meetings.

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When the Difficult Discussion Doesn’t have the Desired Impact

Following the difficult discussion, you should be having regular, documented follow-ups with the employee to discuss the issue/performance and steps being taken to rectify it. During these meetings, you should offer support, provide guidance and further clarify the steps needed to continue on the path of rectification.

If the employee is not responsive/putting forth the effort to rectify the issue, further discussion may be needed to clarify the issue and the path forward. This may warrant a verbal or written warning(s) or progressive discipline. If the employee is blatantly disregarding the issue and not working toward a resolution, progressive discipline may be warranted.

In severe circumstances where the employee may not be putting effort into rectifying the issue, you’ve had documented conversations and made effort to engage the employee in correcting their behavior/issue – termination may be your final answer. Prior to termination, we do encourage you to reach out to your HR Consultant at Axcet to discuss the nuances and risks that could ensue from the termination of an employee following a difficult conversation/conversations.


Difficult conversations should be initiated when an employee's performance, behavior, or actions are negatively impacting their work or the work of others. It's important to approach these conversations with empathy, clarity, and a focus on finding solutions. By addressing issues proactively, you can help create a positive and productive work environment for all team members. 

Do you still need guidance on having difficult conversations with employees? Axcet’s team of employee relations experts has been helping small and mid-sized business owners work through issues like this since 1988. Reach out to us today.

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