How to Lead During the Tough Conversations in School

Some topics are uncomfortable, emotional, and messy. As an educational leader, it is your responsibility to not only facilitate positive conversations and initiatives but also to find ways to overcome and deal with the challenging situations. If you avoid them, they will fester, and the community will lose trust in your ability to solve problems. So, how do we approach difficult conversations? Let’s explore some tried and true strategies.

Present the Facts

When you are approaching a difficult conversation, it is important to leave your emotions out of the equation. Let the other party know that this is not a judgment of their value as a person, but rather a conversation about their work or behavior. Simply present the issue(s) that the conversation is meant to discuss, instead of using phrases like “you always,” or “everyone is complaining.” You want to keep the focus on the work at hand as much as possible, instead of bringing up negative emotions that won’t help to solve the issue.

Additionally, you need to be clear about the reason for the conversation. Don’t let the message get lost by sugar-coating. This doesn’t mean you need to be harsh and critical, but rather, you need to be straight-forward about the problem. The other party will come to appreciate it, and it will reduce the emotions present in the conversation. It’s fine to begin the conversation by letting the other person know that you are supportive and you only want to work together to find a solution to the problem but don’t let them walk away wondering why the meeting happened in the first place.


They say to never walk into a meeting unprepared – the same goes for tough conversations. You can’t begin a dialogue about a difficult subject without emotional preparation, as well as preparing the delivery of the issue. Act out different scenarios of how the conversation may go based on your past experiences with the other party, and consider how you will respond. Have specific instances of the issue that you can provide, and if possible, have documentation that can support it. Preparation will help make the conversation go smoother, and it will be more likely to end with a positive outcome.

Embrace the Silence

When conversations get uncomfortable or awkward, it’s natural to want to fill in the silences. Sometimes, though, these silences are necessary. For one, if you talk only to fill in the gaps in the conversation, you may say something that you did not plan, and it could derail the entire conversation. Additionally, the other person may be silent because they are simply processing the information. You need to give them the time and space to think through what they are hearing, organize their thoughts, and put their emotions aside. If you push for a response or keep repeating points that bring on negative emotions, you may encourage resistance to the feedback you are providing.

In the classroom, delivering consequences to students feels natural, and is critical to their growth. Yet, when we have to approach these subjects with our peers, it can be difficult and uncomfortable. A good leader knows how to handle these situations with professionalism, and can structure them so that there is an opportunity for a positive change and growth. Use these strategies to help, and your next difficult conversation may go easier than expected.

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