Steps to Managing Difficult Employee Conversations

6 Steps to Transform Difficult Conversations


Effective communication is crucial in any workplace, as it helps to align employees, build teamwork, and enhance performance. However, it’s not always easy to achieve. In fact, a staggering 86% of employees and executives identify poor communication as a primary cause of workplace failures.

 As a manager or leader, one of your main challenges is navigating difficult conversations with your employees. Whether you need to discuss a dip in performance with a top performer or address sensitive issues like burnout and disengagement, it’s essential to approach these conversations with empathy and understanding.

 Although these discussions can be tough for everyone involved, they are vital to ensuring your employees continue to excel in their roles. So, how can you approach complex conversations in a way that fosters understanding and promotes positive outcomes?


Step 1: Gather the Right Information

To ensure a successful conversation, preparation is key. The more information you have prior to the discussion, the better your chances of achieving mutual understanding. 

For instance, if you need to address performance issues with an employee, simply telling them they seem “distracted” might not yield the desired outcome. Negative feedback can often trigger a defensive response, with the employee dismissing the feedback as incorrect or irrelevant.

 However, if you come to the meeting armed with specific examples of missed deadlines, negative feedback from clients or cross-functional partners, or failure to meet objectives, your message is more likely to resonate. This approach also facilitates a deeper discussion about what may be causing the issues. For example, missed deadlines could be a sign of impending burnout, even if the quality of work remains high.


By taking the time to prepare and gather specific examples, you demonstrate your commitment to the employee’s success, while also making it clear that you take their concerns seriously. This paves the way for a more productive, collaborative conversation and usually leads to positive outcomes.

 Step 2: Set the Stage for a Valuable Discussion

Creating the right setting and plan can have a significant impact on the outcome of a complex conversation. When discussing difficult topics, it’s important to provide a private and confidential space that allows the employee to feel comfortable and open. Nobody wants to feel called out in front of their colleagues or peers, as this can lead to defensiveness and an unproductive conversation. 

Choosing a room or environment that feels welcoming and non-threatening can help to foster a positive atmosphere. You want to avoid making your employee feel like they’re being interrogated, which can quickly lead to a one-sided conversation that fails to address the underlying issues. To ensure a successful outcome, schedule the meeting at a time that works for both parties and allow enough time to have a detailed conversation.

Additionally, it’s worth letting your employee know what to expect in advance, so they can come prepared. Instead of saying “We need to discuss what happened in the last meeting,” try framing it in a way that encourages collaboration and problem-solving. For example, you could say, “I noticed you seemed less engaged than usual in the previous meeting. Let’s set up a time to discuss how we can work together to improve engagement going forward.”By creating a supportive and collaborative environment, you demonstrate your commitment to the employee’s success, while also encouraging open and honest communication. This sets the stage for a productive conversation that leads to positive outcomes for everyone involved. 

Step 3: Put Facts Before Feelings

During a complex conversation, emotions can easily become heightened. However, it’s important to maintain a level head and avoid letting emotions lead to unproductive arguments between staff. As a leader, it’s essential to demonstrate your leadership skills by taking an objective and logical approach.

 One effective strategy is to use the facts you gathered during the initial preparation stage to structure your conversation and prioritize logic. Start by introducing all of the key issues you want to address, along with any evidence and proof to support your claims. This approach will help to validate your concerns and set the tone for a productive conversation. Avoid using “I feel” statements and refrain from expressing disappointment or frustration. Instead, stay calm and objective by focusing on the facts. For example, instead of saying “I feel like you didn’t do your best on this project,” you can say, “Based on the facts, it’s clear that this project doesn’t reflect your best work. Can you help me understand what happened?”

By maintaining a logical and objective approach, you can avoid getting bogged down in emotions and keep the conversation focused on finding solutions. This not only helps to foster a more positive and productive discussion, but it also reinforces your role as a leader and trusted advisor to your employees.

Step 4: Stay Positive

In addition to maintaining an objective and logical viewpoint, it’s essential to cultivate a positive attitude when approaching a complex discussion with one of your team members. The goal is not to blame or demoralize your employee, but to work together on a solution to the problem at hand.

It’s crucial to demonstrate to your staff members that you’re approaching the situation with a positive mindset, which will encourage them to collaborate with you to resolve the issue. Rather than simply accusing your employee of being lazy or not working as hard as usual, ask them for their thoughts on what might be causing the issue. Use their feedback to provide constructive advice on how they can make positive changes. For example, if an employee is overwhelmed with too much work, you can suggest alternative scheduling strategies or ask if they’ve considered delegating some of their tasks. By adopting a collaborative and supportive approach, you’ll create a work environment where everyone is motivated to perform their best.

Step 5: Listen to Your Employee

To make a conversation productive, it’s important to foster an environment where both parties feel heard and valued. Remember, a conversation is not just about you expressing your views, it’s also about listening to the other person’s perspective. Instead of just presenting your evidence, give your employee a chance to share their thoughts on the situation. Ask open-ended questions that encourage them to share their views, and show that you’re willing to consider their perspective. This will help build trust and respect between you and your employee, and ultimately lead to a more positive outcome. By working collaboratively to find a solution, you’ll not only resolve the issue at hand but also create a more positive and productive work environment.

Step 6: Follow Up

To wrap up a complex conversation with your team member, it’s crucial to remember that the goal is to move forward and implement positive changes. You want to leave the conversation with a clear plan of action that you and your employee agree upon. Remember to follow up after the conversation to see how things are going and whether the agreed-upon plan is working. This will show your employee that you care about their progress and are invested in helping them improve.

If the initial plan doesn’t work out as expected, don’t hesitate to schedule another meeting to reassess the situation and come up with alternative solutions. This will demonstrate your commitment to supporting your staff member and helping them succeed. By approaching complex conversations with a positive and collaborative mindset, you can turn difficult situations into opportunities for growth and improvement for both yourself and your team.

 Difficult Conversations are Common 

By setting clear expectations during the hiring process and bringing on individuals who are open to communication, you can avoid many of the difficulties that come with complex conversations. However, even with the best hiring practices in place, it’s important to remember that discussions with your team can be challenging. Remember to approach the conversation with empathy and an open mind, and to choose a comfortable setting for your employee. Be objective, but also maintain a positive outlook, and don’t forget to actively listen to your employee’s perspective.

 By the end of the discussion, you should have a plan in place for moving forward and a strategy for following up with your employee to ensure that the resolution is effective. Remember, difficult conversations are an opportunity for growth and development for both you and your staff. With the right approach, you can navigate complex conversations and emerge with a stronger, more productive team.




Written by

Lileah Akiode


Lileah Akiode is the Managing Director of The Black Diamond Agency, a recruitment firm dedicated to connecting talented people with rewarding career opportunities. With a strong background in Talent Acquisition across different corporate retailers, Lileah brings a wealth of experience to ensure a seamless and positive candidate experience. In addition to corporate retail, Lileah also experience supporting the Financial Services and IT industries.


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