How to handle difficult conversations as a leader

Nobody looks forward to difficult conversations. Here are some steps you can take to make the experience a little smoother for everyone involved.

Difficult conversations with employees are often avoided because they’re uncomfortable for all people involved. With that said, as a leader, handling these discussions in the right way is key for maintaining high performance and team standards. 

Having more effective and productive difficult conversations includes transparent processes supported by a candid and data-driven culture on your team. 

The foundations of tough conversations

The key to successful outcomes is awareness of your tone and approach. Giving the individual time to digest the conversation while still maintaining empathy is pivotal; the report involved is a human one, and we need to respect their feelings. 

Before the meeting, remove all biases – whether it’s similarity bias, recency bias, tenure in the organization bias, or favorable bias toward those who are in closer geographical proximity to the leader – and avoid distractions like emails, internal chats, etc. This shows that you are invested and clarifies your intent further to set the individual up for sustainable success.

During the discussion, maintain an assertive approach, balancing sensitivity and open-mindedness with seriousness and candor. The result is a productive conversation where both parties feel heard and learn new information, which leads to a deeper common understanding and action plan. 

Effective preparation before sitting down with your report is paramount. Below is a four-step approach that can help prepare for the conversation.

Step 1: Build empathy

Empathy is the cornerstone of effective leadership, and it is even more so when handling a difficult conversation. Empathy allows the parties involved to be more open to understanding each other’s points of view and perspectives. 

The leader may feel the conversation is necessary based on observations, team interactions across multiple situations within the business, and feedback from peers or stakeholders. However, your report might not share these same perspectives or experiences regarding the situation. Understanding the potential disconnect in perspectives will lead to a more productive outcome, opening the door to a two-way discourse that maintains a respectable and professional environment. 

Clearly stating the purpose of the conversation can make it more effective. I usually use phrases like, “I am invested in this discussion, and I am working in your best interest to ensure you’re set up for long-term sustainable success,” or “My goal is to help you build a self-owned career here, with coaching that will benefit you across roles and business units.” This reassures the individual that I have their best interests at heart.  

Step 2: Ensure a collaborative approach 

It’s a common trap to place all the onus on your report for the position they’re in. To avoid this, acknowledge your own role or external factors like limited access to resources or sudden shifts in priorities that may have led to this situation. 

Data shows that situations prompting difficult conversations rarely occur from a single issue. Instead, they are the outcome of a series of events and observations. As such, it is important to provide relevant examples of how the individual could have approached a situation differently, even if they were impacted by external factors. Examples include being more transparent with their leadership, escalating sooner, being more proactive, etc. This approach not only encourages reciprocity in acknowledgment but also sets a precedent for collaborative problem-solving. 

Leaders should model self-reflection and accountability to inspire similar behavior in others. Embracing this approach ensures that upcoming discussions are grounded in honesty, readiness to address personal contributions, and a willingness to apologize when appropriate, ultimately promoting growth and reconciliation within teams.

Step 3: Open the conversation with data, assertively 

In the realm of difficult conversations, the initial moments are pivotal for establishing a constructive dialogue. It’s essential to prepare your opening remarks to set a tone that is both assertive and collaborative. 

Start by clearly stating the context that prompted the conversation, using a concise format such as situation-behavior-impact (SBI) to frame the issue at hand. Next, outline the key points you intend to discuss, ensuring clarity and focus to avoid unnecessary deviations. Express your intentions for the conversation – aim for mutual understanding and proactive resolution while clarifying that it is important to stay respectful during the conversation. 

Additionally, it is important to make sure the other person is able to share their perspective early on, following the principle of seeking first to understand, then to be understood. Actively listen as they speak, allowing their insights to deepen your understanding and potentially reshape your viewpoint. This approach fosters a meaningful exchange of ideas and perspectives. 

Step 4: Stay balanced with your emotions

Despite a lot of preparation, unexpected disruptions can sometimes derail the dialogue. These disruptions can manifest as external disturbances like interruptions from others or notifications, which can divert attention and hinder focused communication. They can alternatively come from an internal place, such as personal biases, the impulse to assert dominance, or emotional reactions to the other person’s responses – whether silence, agitation, or tears – that can cloud judgment and impede productive discussion. 

It’s crucial to preemptively identify these distractions and create strategies to mitigate their impact. Maintaining composure, poise, and clarity amidst disruptions ensures that difficult conversations remain conducive to mutual understanding and resolution.

Difficult conversations can change people for the better

I once navigated a challenging situation where a team member I managed lacked clarity on their role expectations and how to elevate their performance within the organization. Ahead of our conversation, I gathered data to address their misunderstandings. First, I spoke with their previous manager to understand the team member’s past performance and check for any patterns. Next, I collected peer feedback to get a sense of their team interactions. Finally, I reviewed customer feedback trends. 

Timing the meeting to suit their availability, I initiated the discussion virtually, ensuring a neutral demeanor and assertive yet respectful tone. By providing context and revisiting past discussions, I fostered understanding and engaged them collaboratively, pausing to ensure comprehension and inviting questions. The result was transformative: clarity dawned, and a 45-day coaching plan was crafted. In a heartfelt email, after the coaching ended, they appreciated the transparency and operational insights, subsequently becoming a standout contributor who shared their newfound strategies, fostering a culture of high performance and teamwork.

Ultimately, using an assertive, collaborative approach in difficult conversations helps both parties reach a deeper understanding. This method increases the chances of creating a productive action plan that directly addresses the underlying issue.