Having a courageous conversation

It’s a scenario with which all Deputy Principals or school leads are familiar. A situation comes to your attention regarding a complaint and it lands on your desk for action. It may have passed through other layers of the school — but it’s now your responsibility to have what we might call a ‘courageous conversation’.

This is not usually an activity that any of us enjoy and the way we approach it is crucial. For example, consider this conversation in which Harry, a DP, tries to discuss the way a Head of Faculty, Tracey, is managing a member of her team:

Harry (DP): So, I wanted to have a chat about something…do you have a minute?

Tracey (Head of Faculty): Yes, sure, although I have to go and teach shortly.

Harry: Right, ok, well, it won’t take long. I heard that one of your team members, Joe, is needing a bit of extra support…?

Tracey: Ah, right, who mentioned that?

Harry: Oh, it was just in passing, but I was wondering….

Tracey: Yes, I have been meaning to have a chat about how he is managing his classes, although he is doing his best.

Harry: Absolutely, of course. I also have had a couple of emails from parents so perhaps we should have a chat about it?

Tracey: Oh, those parents. Always moaning. I don’t think it’s a massive issue but, look, I need to go and teach. I’ll have a think about it.

In this scenario, Harry is gently trying to raise his concerns but the way he chooses to approach the conversation means that Tracey does not take on his concerns. He does not pick an appropriate time, he is not clear about what he wants to see happen and he prioritises empathy over being clear about his point. In short, he lacks the courage to approach the conversation head on – and as a result, it is likely that there won’t be the action that is needed to resolve the situation with Joe and his classes.

How we react — and why we find it so difficult

Why would a school leader, who is otherwise a confident and pragmatic person, find it so difficult to tackle such a conversation? We have all been in situations where we know we need to address an issue head-on with a colleague or parent;  it can sometimes feel so stressful, it promotes a ‘fight or flight’ response.

Some leaders will take the ‘fight’ option and address a situation in uncompromising, perhaps even aggressive, tones. In this scenario, the person initiating the conversation may well be able to assert enough control (especially if they are in a powerful position) to get what they want, but at the cost of trampling over the needs and perspectives of the person they have spoken to. They might get compliance but probably not the long term goodwill required to take a team of people with them through the next initiative. By failing to listen to another person’s perspective, they might not actually get the resolution they were looking for.

The ‘flight’ response might lead us to avoid the conversation altogether or, more likely, have a conversation rather like the dialogue at the start of this piece. We fear hurting someone else’s feelings and work so hard to ensure they continue to like us, that the actual topic is never really discussed. We find ourselves hinting at the problem to be unpacked without ever really engaging with it in a way that will bring about change.

In either scenario, the problem we wish to resolve stays ‘live’ and drags on longer than it should — the poor teaching, the ineffective practice, the late deadlines, the disgruntled family — or we create an atmosphere of mistrust that will continue to ripple through future conversations for weeks to come….


This article was originally published in the ‘From the Deputy’s Desk’ column in LeadershipED NZ (Term 1 2019), published by EducationHQ. The opening of the article is published here with permission.

To read the rest, sign up to EducationHQ’s Hub; it’s free for schools. 

Image source: ‘Conversation’ by Stanislav CC BY-NC-SA 2.0

One thought on “Having a courageous conversation

  1. Thanks, good read. Courageous is a much better word than ‘difficult’ which was the standard term when I was an AP. In many ways Harry’s approach described in the scenario at the beginning is a bit like when you have a bit of loose wool sticking out of a jumper or a cardigan (My mum used to refer to this as a ‘pull’) If you just cut a small piece off at a time and don’t deal with it properly, soon there will be no jumper/cardigan left.


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