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Handling Challenging Conversations

This one is for my leaders. The one thing you have to face as a leader is handling challenging conversation. I’d define a difficult conversation when it’s a discussion about layoffs, underperformance, or personal matters interfering with performance. We know these topics can be challenging and uncomfortable. I want to offer you ways to approach these difficult conversations while maintaining your servant leadership principles.

Layoffs: Balancing Empathy and Transparency

In my opinion layoffs are an unnecessary evil that only attempt to provide short-term shareholder benefits. While I personally don’t agree with the process of layoffs, I understand as a leader this is a reality I could face at some point. The first thing to keep in mind is that these are people, not numbers. We have to be sensitive to the impact layoffs have to the lives of everyone involved; this requires us to maintain our empathy and humanity as a leader. And while it doesn’t remedy the pain or frustration, sharing as much information with those affected can help them understand and reconcile the situation. When we are transparent with our teams and clearly communicate the “why” behind the “what” we let them know we care about them and want them to have a full understanding of everything going on. 

For effectively navigating this type of situation, I’d offer the following approaches as an example:

Open and Honest Communication: Be as open and forthcoming about the reasons behind the layoffs while maintaining confidentiality and sensitivity. Clearly communicate the decision-making process and provide necessary information to help affected employees navigate the transition. Honest communication could sound something like this: “Looking at the decline of our sales, our executive leaders have made the difficult decision to downsize the order fulfillment team. If they did not make this choice, then our company would be operating at a loss and there could be greater implications in the long term if we do not act now to address the change in our revenue.”

Empathy and Support: We want to have genuine empathy for the emotional impact of layoffs on individuals; put yourself in your shoes and think about what you would want or need to hear from your leader. Offer support and resources to assist employees in their job search or career transition. You could even consider providing recommendations, networking opportunities, or outplacement services. If I had to handle this conversation, I would attempt to empathize like this: “This is not a position I wanted to be in, and not an outcome I wanted to see for my team. While I cannot change the decisions, I will do my very best to support you all through this time. If you need time off to interview with another company, or need help finding resources until you can find another job, please come to me. We’ll get through this together.”

Underperformance: Nurturing Growth and Development

I need to say there is no telling why any employee is underperforming. A rock star employee could have a dip in their performance because of personal matters. A new hire could be struggling to adjust to the work and is lagging behind their expected performance scale. Whatever the case may be, when we see underperformance, it is an indicator that we need to address an issue and help nurture our teams so they can thrive. 

I’ll be the first to admit, addressing underperformance is uncomfortable, but it’s essential. Underperformance is felt by the entire team and if not resolved can cause issues in the entire teams dynamic and capabilities. If I put my servant leadership hat on, I’d try the following to address under performance:

Privacy and Respect: It would be best to hold a private conversation with the underperforming team member. This will create a safe space where they feel comfortable sharing their challenges and concerns with you. While it is a tough conversation, we also want to let them know it is intended to help them overcome any blockers so that they may continue to grow and excel at their work. I feel the conversation could start like this: “Thank you for making the time to meet with me. I noticed you’ve been struggling a bit, and I wanted to take some time to sit down with you and check in. This is an open conversation; I want to know what I can do to help you out. And if I’ve done anything to hinder you, please tell me so I can work on it!”

Active Listening and Feedback: When you set the tone for an open conversation, you have to hold that space for your team member. It’s tough, because we want to jump in and start fixing things right away. But people need time to express themselves and they want to be heard. Practice active listening to identify the root causes of their underperformance. As you listen, focus on identifying solutions and developing a plan for growth together. And when it’s appropriate, offer feedback or areas that need improvement. Because this one is all about listening, my advice to you is this: “...” Just don’t talk until they’ve explained everything!

Personal Matters: Balancing Care and Professionalism

I know people, me included, feel they do their best at separating personal matters from work. But we are all human, and sometimes it’s impossible to maintain separation. When personal matters affect the workplace, us leaders have to do our best to address the concerns. I’d like to define personal matters like hygiene issues, grief of loss, or financial issues; it’s anything that is not directly related to work, but as people they are things we have to balance between our work and home life. 

Tackling these issues is a delicate balance between care and professionalism. We can apply the principles of servant leadership in the following ways:

Confidential and Respectful: I don’t think it needs explaining why addressing personal matters needs to be a private conversation held with the utmost respect for the individual's dignity. Choose a suitable time and place for the conversation, ensuring privacy and minimizing embarrassment or discomfort. Let’s use personal hygiene as an example. I would start the conversation like this: “Thank you for finding time today. This meeting is not about your performance. It has come to my attention that you have been wearing the same clothes a few days in a row, and at times there is an odor others can smell. I wanted to ask if there was anything going on at home, if you are having a tough time outside work?”

Empathy and Support: It goes without saying, but I’ll keep saying it, empathy is the main ingredient to servant leadership. If you show empathy and understanding while discussing personal matters your team members will respect and trust you as someone they can turn to. So, acknowledge how people are affected by personal matters at work and offer support or resources, such as counseling or access to employee assistance programs, if necessary. A great example I think most people can understand is grief of loss: “I know you lost your mother earlier in the year, and we’ve talked about how you are still struggling. I wanted to let you know that I looked into it with HR and we have an employee assistance program. If you want to look into it, or talk about it with me, I’d be happy to help. They also have a contact line that is completely confidential and available 24/7 for you.”

Collaborative Problem-Solving: So, this one is like the approach of active listening and feedback, but because it’s not work related but more personal, we can tweak the intent and actions here. I’d recommend establishing the conversation as a collaborative problem-solving opportunity. Here you’d ask open-ended questions to understand the underlying causes and work together to identify potential solutions or support systems that can help the individual address the issue effectively. For this one specifically I want to focus on setting the tone of the conversation: “Thank you for trusting me with that personal information. I am so sorry to hear about your situation. Would it be helpful if we talked about it to see if there is anything I can do to help through resources, or come up with some solutions here at work to make things easier?”


It is tricky to handle challenging conversations, but if you address them with the principles of servant leadership you can build trust between you and your team. An effective approach to handling any situation will cultivate a supportive and thriving workplace environment where team members feel valued, heard, and empowered to grow.

I’d love to hear about times where a leader handled a difficult conversation with you, or you were the leader handling a difficult conversation. If it was good, bad, or downright ugly I think sharing our experiences can help each other grow as leaders. Thanks for reading!

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