We Need to Talk: Preparing for Difficult Conversations

The day is etched into my memory forever. I had recently been promoted to director of admission and financial aid – a career move I had been aspiring to for years. As an internal hire, I was no stranger to the office’s working dynamics. Still, I was optimistic and excited about all that lay ahead. Then two weeks into this leadership journey, I faced my first real test. I needed to have a difficult conversation with a former peer and now direct report. 

The specifics of that conversation do not matter. It was and has remained one of my greatest leadership lessons. 

I entered the conversation with trepidation and nervousness. My heart was beating hard, and my mind was racing. I did what I thought I needed to do. I focused on myself. I considered what I needed to convey, and how I wanted to present myself as the new leader. And then I started talking. 

Within moments, the conversation took a turn for the worse. Emotions escalated, and tensions flared. I found myself grasping to find the right words. Everything I said was vague and lacked depth and clarity. I thought a broad approach would be enough to get through this conversation. I didn’t get into specifics believing that the words I spoke would convey my message. The discussion ended with chaos and confusion on both of our parts.

I thought I knew what I needed to do in having this conversation. I quickly realized that I, in fact, did not know what I was doing. 

Leadership was about to get the best of me only two weeks in. 

The intensity of the experience was undeniable. Immediately looking back, I questioned the choices I made in that moment and their impact on the relationship. What I know now that I didn’t know then was that difficult conversations require preparation. 

School leaders often face difficult conversations. Things come up constantly – student issues, interactions with colleagues or direct reports, and conversations with parents. In my work with school leaders, it’s not surprising that difficult conversations are a frequent theme.

Our work in schools is deeply rooted in community. Our communities are made up of the individuals who contribute to their unique essence. Not every interaction in our communities is flawless. We are human after all. However, our commitment to nurturing our communities demands we lean into the more challenging aspects of our work. This includes difficult conversations.  

I have found it helpful in my work with educators to reframe difficult conversations as feedback conversations. While feedback is part of the everyday experience with students in our schools, adults may find these kinds of conversations create a range of emotions. Many times, it can feel easier to avoid initiating these conversations. Our inclination to avoid may also stem from a desire to preserve a relationship and prevent other problems. However, avoiding these conversations doesn’t make them disappear; it often makes the situation worse. 

Brené Brown has said “Clear is kind. Unclear is unkind.” Her work reinforces the notion that avoiding difficult conversations may seem compassionate but ultimately it can be detrimental. Therefore, engaging in open and honest discussions, even when difficult, is essential for fostering mutual understanding and growth in relationships.

More importantly, people want feedback, even when it is critical. Research shows that people underestimate others’ desire for feedback. “Not recognizing others’ desire for constructive feedback may lead people to provide less feedback, potentially hurting others’ outcomes.” A McKinsey & Company survey of over 12,000 managers revealed that managers consider “candid, insightful feedback” extremely important to their career development. Research by Gallup shows 80% of employees who say they have received meaningful feedback in the past week are fully engaged. Avoidance is not the answer to creating the kind of communities we desire. If leaning into these moments is good for individuals and organizations, what can we do to improve how we approach difficult conversations? 

We can prepare.

Preparation is the important first step in navigating difficult conversations – a step that is often overlooked. It involves a deep understanding of  the issue you want to discuss, establishing clear goals, and a thoughtful approach to the conversation. Preparation is where you anticipate challenges, objections, and emotions that might arise. Preparation gives you the tools needed to respond effectively. It allows you to deliver your message with clarity, empathy, and purpose. Reflecting on my first difficult conversation, I realized that without preparation, a constructive conversation was nearly impossible. 

There are many books on the subject of difficult conversations. Radical Candor by Kim Scott and Difficult Conversations: How to Discuss What Matters Most by Douglas Stone, Bruce Patton, and Sheila Heen are two that sit on my bookshelf. Years ago, a mentor handed me Fierce Conversations by Susan Scott. My copy is dog-eared with tabbed sections I’ve returned to time and again. Scott says, “The conversation is the relationship.” In Fierce Conversations, she talks about the transformative power of conversations in shaping and defining the dynamics between individuals. She encourages readers to recognize that the quality of their relationships is intricately tied to the quality of their conversations and urges approaching conversations with authenticity, courage, and a commitment to fostering meaningful connections. All of that requires preparation.

Preparing for a difficult conversation requires self-reflection, offering an opportunity to deepen self-awareness and achieve clarity. Starting with a clear understanding of why you need to have a difficult conversation is crucial. Simon Sinek’s Golden Circle Model on beginning with “why” comes to mind here. While Sinek’s framework doesn’t directly address difficult conversations, defining the purpose behind such conversations is like mapping out the journey ahead. Understanding your ‘why’ is just a starting point. It’s equally important to consider other aspects of the conversation to ensure a well-rounded approach and engage in a meaningful dialogue. 

Carefully consider what it is you are looking to address. What is the conversation you want to have? What are the facts? This is an opportunity to consider what outcomes you may hope to achieve in coming together with the other person. Additionally, consider your role. How have you contributed to the situation? For example, you may be an equal player, or you may need to take responsibility for not bringing this to the other person’s attention earlier. This is also a moment to check your assumptions and biases. You may feel a certain way, but don’t assume the other person’s intention. This allows you to enter the conversation with curiosity and a desire to understand. 

It is easy to underestimate how emotions can affect a conversation.

Emotions run deep and can impact your thoughts, words, and actions. They have the power to significantly shape the course and outcome of a conversation. Without preparation, emotions easily take over in a conversation. When you take time to consider your emotions and your role, you are better prepared to navigate your emotions and enter the conversation from a place of empathy. Acknowledging the emotions involved sets the stage for a more compassionate and considerate exchange. 

Self-reflection is also a chance to consider the other person’s perspective and anticipate how might they respond or react during the conversation. If you have ever been on the receiving end of a difficult conversation, processing what is happening can be challenging. How might you request the conversation without it feeling confrontational? Ask yourself how you would want to be treated if someone was having this conversation with you. By considering this in advance, you can enter the conversation with empathy.

Finally, it’s crucial to ask yourself: “Do I need to have this conversation?” Sometimes, what initially appears as a necessary discussion may actually stem from a desire to prove a point rather than address genuine concerns. If you find yourself in this situation, it’s valuable to take a step back and explore your feelings more. 

Writing serves as a powerful tool in the self-reflection process enabling you to not only organize your thoughts but also gain perspective and enhance your readiness. You foster insights into your perspective and give yourself room to process your thoughts and feelings before you are in the middle of the conversation. You have the chance to clarify what you want to say and to separate emotions from facts. Additionally, your notes will help you remember what you want to say in the middle of the conversation. 

When I first began a self-reflective practice before engaging in another challenging conversation, I was amazed by its impact in helping me understand what I had previously overlooked. It made me long to redo some past difficult conversations, especially that first one. 

Meaningful connections often come from moments of discomfort. Preparation is the key to navigating those moments successfully. It provides you with the tools and confidence needed to tackle the uncertainty ahead. Looking back, it’s clear that preparation is the lesson I wish I had learned earlier in my leadership journey.

Susanne Carpenter is the principal and founder of Carpenter Leadership Consulting, a leadership consulting and executive coaching firm focused on helping leaders and leadership teams become high-performing and strategy-focused. Channeling her own experience as a leader, Susanne empowers others to unlock their full potential, fostering confidence, effectiveness, and success. Her goal is to help her clients reach their fullest potential and lead with impact. She believes that when leaders are at their best, their organizations thrive. Previously, Susanne served in three Massachusetts independent schools as assistant head of school at Walnut Hill School for the Arts and director of admission at Nashoba Brooks School and Worcester Academy. She is a graduate of Westover School and Wheaton College. She is an Associate Certified Coach (ACC) through the International Coaching Federation and is also a Gallup Certified Strengths Coach. She is currently the treasurer for the board of trustees at Westover School. Susanne lives with her family in the Boston area.