Difficult Conversations Can Strengthen School Values

When employees aren't meeting expectations, leaders must initiate what might be a difficult conversation. Doing so with courageous authenticity will help leaders have clear, honest and direct communication that can solve

Jun 18, 2019

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It’s often difficult to start these conversations. Obstacles include aversion to conflict, fear of where the conversation will lead, issue avoidance, imposter syndrome and lack of time. But preparation, careful execution and follow-up will help foster good communication.

Here are four ways to prepare for a critical conversation:

  • Write a letter in advance and document what you want to say.
  • Match your language with language that in school documents, e.g., handbooks and position descriptions.
  • Conduct a “pre-mortem” by asking a colleague to poke holes in your messaging.
  • Role play the conversation by playing the person with whom you’ll be speaking.

During the conversation it’s important to show genuine care for the person and confidence that they can incorporate and grow from the feedback. Focus on the impact of a person’s behavior rather than their intent. Be non-threatening by asking questions. Have another person in the room with you; an employee may be less defensive if there is a second person with whom they have had a positive experience.

When the meeting is over, document the discussion. Email is fine if the level of concern isn’t high, but in some cases a formal letter works better. Put the employee’s feedback into the written summary, and identify clear action steps and a timeline. Indicate a time period for a follow-up discussion.

For more on this topic, consult the presentation materials, including an executive summary, in the 2019 NBOA Annual Meeting archive.


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