5 Tips for Having Tough Conversations with Your Employees


When you become a leader, you learn quite quickly that your job comes with its fair share of conflict, challenges, and difficulty. And working through the maze of your everyday responsibilities while paying attention to how you communicate in every situation can be daunting, especially in a remote work environment.

The most challenging form of communication for many leaders is the one-on-one conversation, particularly when that conversation is an uncomfortable or difficult one. As a leader, you absolutely cannot avoid these conversations or continuously procrastinate on acting. It is a challenge you must overcome by finding an approach that aligns with your style of leadership.

Avoiding Conflict Compromises the Bottom Line

Here’s the thing: Avoiding difficult conversations can never lead to positive outcomes. So why it is that we see so many leaders continue to sidestep conflict? We are only human, and for most of us, we would rather live and work in a conflict-free environment and it’s only natural that we seek to avoid difficult interactions.

However, your role as a leader requires you to lead by example and deal with conflict and difficulty head on. If you don’t engage with your employees during both the positive and challenging times, you run the risk of creating employee disengagement and losing respect from your employees as a result of your lack of action 

Here are a few simple tips to help you crack the code on tough conversations.  

#1 — Embrace and Activate Your Empathy

It’s important to understand that when an individual in your workplace is failing to live up to expectations, it doesn’t mean they’re a bad employee. The failure could be caused by several different factors that may or may not have anything to do with their work responsibilities. Put yourself in your employee’s shoes and seek to understand what is happening and how you can help support them before addressing the gap in performance. Your employees will appreciate your kindness and compassion and that will accelerate realigning expectations in performance. 

#2 — Lead with the Coaching Style of Leadership

When you label a conversation as “difficult” before you engage, you are setting yourself up for stress and negativity. Instead, treat your conversation as a “normal” coaching conversation that facilitates open discussion while working to a collaborative conclusion. Lead with the right questions that will help you uncover the issue, then ask additional leading questions and guide them on self-identifying what the issue is. Overall, be patient and actively listen, without interruption and create a safe space for them to share what is happening in their world.

#3 — Ensure Your Facts Are Correct

Are you very clear on what the issue is and how it is impacting the employee’s performance? Write down the reasons why you need to have the conversation and determine what you want the outcome to be. Be prepared to support your case with data and facts. If necessary, make sure you use language appropriate to the task, and do not over dramatize what has occurred. Ground yourself with facts vs. assumptions and judgment. 

#4 — Proactive vs. Reactive Response

Practice choice by taking a pause before you react. Being reactive can exacerbate the issue and cause you to do or say things that you may regret later. Prepare yourself with positive intentions, focus on creating a positive outcome and choose to be calm and levelheaded. This demeanor that will allow you to show up in a powerful and inspirational way.  Leverage your self-awareness and EQ muscles to create a safe environment where your employees will not fear telling you the truth. Relationships are all about trust, and your employees need to know that you have their back, no matter the circumstances.

#5 — Reflect and Revisit

Once your difficult conversation has concluded, it’s important to debrief with yourself. What went well? What could you have done differently? Could you have been more compassionate? Additionally, you need to understand that every single conversation is part of a larger, ongoing coaching dialogue. Then revisit the issue with your employee to make sure they are on the right track and understand what’s expected of them and ensure they know they can count on your support. 

How to Handle Workplace Conflict

You can’t avoid conflict or difficult conversations within your organization, but you can always improve your ability to handle them. If you are challenged with having difficult conversations, I’d be happy to deliver insights and best practices that will help you re-engineer your approach. Please reach out to me at joanne.trotta@leadersedgeinc.ca so we can explore this topic together. I’m looking forward to hearing from you!

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