Preparing for and Handling Difficult Conversations at Work

Not many people like having difficult conversations. Yet, the reality is that, as leaders, we must be willing to sit with the difficult feelings involved and engage in hard conversations. From personal conflicts, misunderstandings, and feedback, to conversations about performance, poor behaviour, resource allocations, and the shifting of responsibilities within a team, we will need to navigate conflict and challenging situations.

When we leave things unaddressed or allow issues to persist, tension and conflict are likely to build. Avoiding difficult conversations entirely can lead to a breakdown in communication and trust. When we finally do engage in these conversations, we may find ourselves feeling ill-prepared or rushing through them because of discomfort. However, taking time to prepare and creating space for these difficult conversations is crucial for maintaining a productive work environment and fostering open communication within the team.

Three Keys to Productive Conversations

To support healthy conversations, understanding, and creative solutions, we can think about three principles when engaging in these conversations:

Communication: Both sides want to know why. Be honest and transparent about how you are feeling. Communication is a two-way street. It also requires listening to the other side.

Compassion: We are all human beings trying to navigate the situation in front of us. Work to understand the perspective and position of your colleague.

Compromise: We can’t always get everything we want. Consider options and try to find a middle ground that meets everybody’s needs—a win-win solution.

Using the Language of Compassion to Have Difficult Conversations

When potential conflict arises in our teams, it is helpful for us to get in touch with our own unmet needs and feelings and to consider what our colleagues may be needing as well. In this way, we are in a better position to balance the sometimes competing priorities of team performance and compassion for our team members.

Having a process to follow for these difficult conversations can be helpful for putting order to our thoughts and increasing our confidence. Nonviolent Communication (NVC), also known as the Language of Compassion, is an approach to effective communication developed by Dr. Marshall Rosenberg that supports empathetic dialogue and can contribute to a more inclusive and psychologically safe workplace.

The following four-step model is derived from Dr. Marshall Rosenberg’s work. I have provided an example of a team member working non-stop.

Step 1: What do I observe (with no judgment or criticism)?

Example: I notice that you are sending emails in the morning, throughout the day, and late at night.

Step 2: What am I feeling (hurt, uncomfortable, anxious, resistance, etc.)?

Example: I feel worried that you are not getting breaks and could be burning yourself out.

Step 3: What needs do I have (in relation to the feelings identified)?

Example: I need my team to have balance and breaks so they can stay well and be well.

Step 4: What requests can I make (in practical language that is not a demand)?

Example: Could you think about your boundaries with life and work and propose a flexible schedule for your availability, so you can get a break and also fulfill your tasks?

While every conversation will be different, this approach encourages us to be thoughtful about our perspectives and gives ideas for initiating the discussion in a caring way. Not only is it important for you to share your perspective in these conversations, but it is equally important to listen to your colleague. Try getting curious about what is happening with them so you can adapt your thoughts as you speak.

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Preparing for a Difficult Conversation

Before approaching a difficult conversation you know you need to have, I invite you to consider the following:

• What do I know that they do not know that might be relevant to the discussion?
• What conclusions and assumptions am I making?
• What information do I need to be sure to ask about?
• What emotions might I experience during the conversation and what can I do to manage them?
• What types of emotions might I elicit in the other person and how will I manage them?
• What can I say at the beginning to get the conversation started on the right foot?
• What is my end goal?

As much as it is helpful to be prepared, sometimes we can find ourselves in a difficult conversation by surprise. In these moments, it is important to keep in mind that while you may not be able to control the wants or needs of your colleague, you do have control over your own response. Oftentimes, it can be more productive to give both parties time and space to consider and revisit the discussion at a more appropriate time (whether that be an hour later or the following morning, for example).

Final Thoughts

All this is not to say that leaders always need to be the ones initiating all of these conversations. By making it clear that you are approachable, you encourage your team members to feel as though they can seek help and ask questions when needed. When you as the leader feel as though you lack the expertise or don’t feel equipped to have certain conversations, supporting team members by directing them to the information and resources they need can be helpful. Ultimately, we want to ensure that our team members feel heard and supported.

My hope is that the suggestions above help you to think about, and perhaps even reevaluate, how you are showing up for your teams and handling these difficult conversations. Sometimes, the most thoughtful and considerate action leaders can take is to go through difficult conversations rather than around them.