How to make those difficult conversations a little bit easier

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How to make those difficult conversations a little bit easier

By Michael Bungay Stanier


Michael Bungay Stanier is a keynote speaker at the upcoming CPCO Conference 2017. To register for the conference, visit our website.


As a Principal, you’re likely used to having conversations of all kinds with students and fellow employees, but having to tackle a difficult discussion with a parent is another feat altogether.

I’m sure many Principals can recall a difficult conversation (or two, or three) they’ve had to have with a parent. Maybe the parent was unwilling to listen, maybe they weren’t supportive, maybe they were overly concerned or all around confused. We’ve all been there — in that awkward, difficult-conversation twilight zone, where everything seems to spiral downwards.

Luckily, there are a few ways to make your next difficult conversation a little easier, and it all essentially comes down to improving communication.

Practice mindful communication

This really is just a fancy way to refer to the art of listening and thinking before responding. This kind of communication is all about consciousness — being mindful of your words, speaking with kindness and being aware.

Ask questions

Let’s look at the example of a conversation where a Principal needs to tell a parent that their child is acting out and not doing well in class. This will likely be an emotional conversation that could escalate quickly, depending on the way the message is communicated and how it is received. Saying something like “Your kid is really difficult to teach” versus “I’m a little concerned about how your child is doing” will elicit different responses.

Mindful communication tells us to listen, to think, and to be aware and kind when communicating. Using questions to get to the heart of an issue — rather than jumping in with advice — can be part of that practice.

You’d be surprised at how much valuable information comes from asking a simple question (and how much more help you might be by asking more and saying less).

Choose the right questions

Asking the lazy question of “How can I help?” might just open the lines of communication and get to the bottom of things — all without plummeting into an unnecessarily tough discussion.

Another strategy/approach (which works well with parents, as well as students) is asking “And what else? (AWE)” as a follow-up question. In most situations, the first answer is never the only answer and is rarely the best. Asking the AWE question will draw more from the person you’re speaking with and hopefully lead to the best possible answer you can then consider together.


Michael Bungay Stanier
Michael Bungay Stanier

Michael is the Senior Partner at Box of Crayons, a company that teaches 10-minute coaching so that busy managers can build stronger teams and get better results. His most recent book, The Coaching Habit, has sold a quarter of a million copies. Michael is a Rhodes Scholar and was recently recognized as the #3 Global Guru in coaching. Visit Box of Crayons for more information.

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