A Practical Guide to Mastering Difficult Conversations

Difficult conversations are an inevitable part of workplace dynamics, especially for leaders in education who are managing constant change, finances, and community expectations.

Whether it's providing constructive feedback, addressing budget issues, or resolving conflicts, these conversations can be challenging. For instance, you might have to discuss a significant overspend of a department budget, or you might have to address conflicts among staff members. Navigating these conversations effectively requires preparation, presence, and staying focused on the problem.

Preparation and Clarity

Before initiating a difficult conversation, it's crucial to prepare thoroughly. Start by clarifying your main goal for the conversation. Determine what you hope to achieve—whether it's resolving a conflict, providing feedback, or finding a solution to a problem. Having a clear objective can help guide the conversation. You can further outline the key points you need to address but be sure to focus on specific facts and behaviors rather than judgements and accusations.

During your preparation also consider how the other person might feel and what their possible concerns could be. Understanding their perspective and emotions can help you approach the conversation with empathy and address their needs effectively. Anticipate their reactions and prepare for different scenarios. This can help you stay calm and respond appropriately, no matter how the conversation unfolds. Be sure to also consider your own possible reactions and feelings that might come up during the conversation. This will help you stay calm and focused, rather than becoming reactionary.

Presence and Empathy

Give the other person your undivided attention by turning off your phone, closing your computer, and removing any other distraction. You can ask them to do the same. This shows your commitment to them and the conversation. Stay focused on the present conversation rather than dwelling on past issues or worrying about future outcomes. This can help you stay grounded and attentive.

You can be curious about their experience by asking them open-ended questions that require more than a yes or no answer. For example, you might ask, "Can you tell me more about that?" or "How did you feel when that happened?" This can help the other person feel understood and shows you are empathetic to the situation. Plus, these questions can help you uncover underlying issues that lead to collaborative problem-solving.

Problem vs Person

Focus on the problem, not the person or people involved. Keep the conversation centered on the issue at hand and avoid making it confrontational and creating defensiveness by using blame, finger-pointing, or attacking personal traits.

Identify areas where you both agree to create a foundation for brainstorming and building solutions together. Periodically summarize what has been discussed to ensure mutual understanding and clarify any points of confusion. A common pitfall is concentrating on assigning blame, finger-pointing, or personal attacks. This only creates a negative atmosphere, resentment, and no solution.

When you focus on collaborative problem-solving you build trust, improve relationships, and get buy-in for the solutions that have grown out of a problem.

Personal Anecdote

Many years ago, Diamond6 was running a workshop with a very large inner city school district. During a conversation with the group about how and why to stay curious as an adult a teacher told us a stunning story that really hit home.

She said that one of her students was late to school frequently and was then being pulled into the principal’s office for disciplinary action. Still, the situation did not improve, and the problem continued. This student was quiet and mostly kept to himself and he had not provided an explanation for being late so often.

The teacher became curious and pulled the student aside for a private conversation. She came down to his level and exhibited genuine curiosity by asking him why he was late every morning and whether there was anything she could do to help.

The student admitted quietly that his family was living in a shelter, and he was responsible for helping his little brother get ready for school in the morning. Each child only had one change of clothes and very limited access to a washer and dryer. So, many mornings, their clothes would still be damp, and they would have to wait for them to dry.

By being curious and asking questions the teacher became the champion of a solution that then benefitted many other children in the schools. She helped raise money to bring washers and dryers into some of the schools for students to use. Not only did she help the affected students, but it also helped the school and district in their mission – to educate all students in their community.

How does this apply to you?

School business officials often face difficult conversations related to budget constraints and resource allocation. For example, you might have to address a significant overspend in your district’s technology budget with the IT director.

You can prepare by gathering detailed financial reports to help illustrate the issue and take some time to consider the department head’s enthusiasm for their program. Outline the specific reasons for the cuts and consider their potential concerns.

During the conversation you can show curiosity and empathy by asking about the program, what their goals are for the program, and challenges they might be facing. With this information you can focus on the budget cut problem (rather than their proclivity to overspend, perhaps?) and work together to find creative solutions, such as seeking alternative funding sources or prioritizing program expenses.

Implementing these strategies can help turn difficult conversations into opportunities for growth, build your confidence as a leader, improve your working relationships, and accomplish your organization’s mission in education.

Tanya McCausland is the Co-Founder and Chief Executive Officer of Diamond6 Leadership & Strategy, headquartered in Carlisle, PA. With a passion for empowering leaders at all levels, Tanya and her team bring innovative leadership programs and workshops to public school educators and administrators across the country.

From Conflict to Cooperation