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Management-Kits Difficult Conversations Blog

Responsible for overseeing various facets of school operations, middle leaders in schools often find themselves at the crossroads of student, parent, and colleague concerns. From managing student disciplinary issues to handling disheartened parents and even addressing challenging colleagues, it requires juggling a lot of tasks at once. At times, it may seem like you’re trying to change the tide, only to realize some waves are harder to redirect than others.

Consider following example: You have a colleague, perhaps someone who’s been with the institution for a long while. They seem resistant to change and often challenge new learning principles, having a negative effect on everyone around them, including students. Conversations with them are difficult; they oppose, deflect, or ignore what was said once they leave the room. You want to address this for the improvement of the school, but the road looks thorny, with potential backlashes that could even expose the school to claims or litigation.

So, how do you handle such unpredictable situations without escalating things to a point of no return?


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Here are 4 steps for middle leaders in schools on how to handle difficult conversations

1. Prepare for the conversation

Before diving into the discussion, lay the groundwork. Ask yourself what your true intentions are and what outcome you want to achieve. Use a framework that combines empathy with honesty (discover the Management Kits framework from our difficult conversation tool). Address their concerns, acknowledge their viewpoints, and slowly bring in the issues that need attention. Remember, a spoonful of sugar helps the medicine go down. What you should be aiming for is creating common ground where both parties can build on.


2. Understand the context

It’s essential to first gauge the environment. Understanding the following factors helps to build a positive ground before getting to the real issue, set the tone of the conversation and prepare you for potential outcomes.

To achieve an impactful and positive conversation, consider:

  • Have there been difficult conversations with this person before?
  • How do other leaders on various levels assess the situation?
  • What do you believe are the reasons behind the person’s behavior (motivation, past experiences, opinions etc.)?

There is always the possibility that things don’t work out as planned despite your will to find a solution. This may sound tough – but reality shows that such conversations can also put you at risk if you don't achieve a full understanding of the situation. Therefore, also think about:

  • Does your school have a works council that could intervene?
  • How restrictive are the labor laws in your country?


3. Rope in senior leadership

Before you take the plunge, inform your senior leaders about the situation to let them support you. Their experience and understanding of the broader context will offer valuable insights. Walk them through what you intend to do as well as what you want to get out of it in the end. They can guide you on potential pitfalls, back you up with more authority, or help you consider specific aspects such as work councils or other regulatory bodies.

Additionally, don’t forget to keep senior and other middle leaders updated. Not only does this ensure they're in the loop, but it also means you have an ally in case things don't go as planned. You’ll also be able to discuss what worked and what didn’t to decide on your next steps. With limited formal authority as a middle leader, it’s vital to have senior leadership buy-in early-on and throughout the process.


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4. Embrace reality

It’s disheartening but true - some battles can't be won. There are cases where, despite your best efforts, certain colleagues continue to be a stumbling block. Due to stringent labor laws, you might not be able to make drastic changes. Here, resilience is key. Learn to adapt and manage, keeping the larger goal of student development in mind. Acknowledge all the progress (even the small) you are making against the things that bother you. From our experience guiding many clients that deal with resistance, a key aspect to success is to shift your focus away from the most resisting, as effective change comes from convincing “the middle”. After all, your energy is valuable, so remember pick your battles wisely.


It takes patience, preparation and the right support

In conclusion, being a middle leader in a school is akin to being the captain of a ship navigating through turbulent waters. With patience, preparation, and the right support, you can steer your ship safely to progress. Remember, every challenging conversation you engage in is a step closer to creating an encouraging learning environment for the young minds that look up to you.


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