Challenging Conversations

This blog post is based on a #LeadMeet online presentation I gave for Haberdashers’ Aske’s Schools – the Boys’ and Girls’ schools – on Monday 9th November 2020.  Many thanks to James Bown for asking me to be involved in the event.

“Across my 30 year career, in both academic and pastoral leadership roles, I held a significant number of challenging conversations and, looking back, some went better than others! 

I’m going to suggest:

How you might best prepare

How you need to conduct yourself in the conversation itself, and

How you could follow up

I want to start by saying that we may be called upon to hold challenging conversations with many different people as we fulfil our professional roles: students (such as predicted grades conversations), staff (for example, following a parental complaint), parents (to whom we, inevitably, sometimes have to communicate messages they really don’t want to hear), leaders across the school (I remember liaising between the Heads of PE, Drama & Music when they are all demanding the time of the same talented pupil), governors (with whom we need to work closely in the best interests of the school but with whom we may not always be completely in alignment), and members of the wider community beyond the school gates. (Conversations with neighbours about parent parking were always a particular highlight for me…)

Whatever your role in your school – whether you’re teaching or support staff, whether you’re a leader at any level, whatever your area of responsibility – you are all crucial to the smooth working of the school and part of this may involve defusing tension, and managing sensitive, demanding dialogue at times.

At the moment, as we navigate the particular challenges 2020 has brought, emotions are running high, and we are, inevitably, called upon to find the best way forward when members of our wider school community, including our parents, are fearful, anxious, frustrated, angry – and often, and we’ve certainly seen this played out in recent months, people are looking for someone to blame.  Schools can, too easily, fulfil this role, when life doesn’t go as people wish it to.  So I think this may be a particularly fitting time to talk about how we can work together to resolve some very tough problems, and to find the most positive, constructive outcomes.

Whatever the circumstances of a challenging conversation, there are strategies we can use to ensure that, as far as we possibly can, we move towards some kind of resolution.  And that’s what we want – be clear at the outset what it is you’re hoping for.  This is never about winning an argument.  It’s about, ideally, both parties feeling more positive at the end than they did at the beginning and the way forward looking clearer and brighter for everyone concerned. 

Sometimes you may go into the conversation knowing exactly what you think the way forward should be.  Sometimes you will get there a different way from the one you anticipated because you’ve responded to the suggestions of others, you’ve listened, you’ve thought, you’ve understood their perspective and you’ve arrived at new insights.  Ideally that’s an even better conclusion.  The most important thing is that there’s a constructive outcome which will move you all on.

How you might best prepare

Build the most positive relationships you can, with all members of the wider school community, before issues arise.  Ensure there are members of staff who have positive, constructive dialogue, for example, with every new parent, so that the first time someone from the school has to contact a parent to talk about their child, it isn’t because there has been a problem.  Communicate well with parents, listen to them and show you value their perspective and their opinions, before you hit stormy weather.

Build mutual trust in your dealings, too, with colleagues – if there is trust, that’s a much more positive beginning when you do have an issue to address together.  Focus on developing the leadership skills of all leaders across the school so that they understand their responsibilities as leaders and are credible and capable in their leadership role – support staff managers as well as teaching staff leaders. 

Trust is key in your relationships with students, too – they need to be confident that you care, and that you are committed to doing all you can to ensure they are supported and challenged to be their best, within and beyond the classroom. 

Work to generate the most effective relationship with your governors so that they know the school and the staff, and that the staff, and ideally parents too, know something about them.  Look for opportunities to get the school’s neighbours onside by building positive community links.

All these things are important and key to the successful operation of our schools.  We should do this because it’s the right thing to do, but it’s also an especially strong framework within which we can navigate the challenges which inevitably arise. Because even if you’ve managed all that, there will still be tricky conversations from time to time.  And when they arise, step up, don’t step aside.  Putting things off can mean that problems fester & people feel worse – more frustrated and angry over time.  Eat the frog.

The advice I’m going to offer won’t of course cover every eventuality, but I’m going to focus on what you may need to do when faced with the most challenging conversations.  Take from this whatever is useful to you.

Prepare fully.  Ensure you have all the info you need.  Don’t be derailed by someone saying, ‘I don’t know what you’re talking about. There isn’t a problem’.  Be sure of your ground.  Have your facts clear and at your fingertips.

And practise.  Sit with someone you trust and try out the words: if you have difficult words to say, you don’t want the first time you say them to be in the conversation itself.  Hear what they sound like.  Practise being concise – don’t ramble, and don’t talk too much.  Be clear.  Be calm.  Seek feedback from whoever you’re trying it out with and act on their advice.  You may then feel more confident and assured when you step into the meeting.

Think also about timing, place, privacy.  Give some notice so that whoever you’re talking to can prepare themselves too, but not so much notice that they just have time to become increasingly anxious.

How you need to conduct yourself in the conversation itself

You’ve practised being succinct so that you don’t talk too much.  You have to give space for the other person.  Sometimes you need to let the silence do the heavy lifting – if you leave a pause and don’t leap to fill it, they have more time to think and they may well say more.  And you do need to be able to empathise and appreciate the perspective of whoever you’re talking to. 

In my experience when there is conflict, it often stems from fear and anxiety – even if it masks itself as aggression, or anger, apathy or arrogance, it can at root be about fear.  And there is a huge amount of displaced anxiety around at the moment – people appear to be upset about one thing, but their reaction to that can seem disproportionate.  Ask yourself what’s REALLY going on, here, and what fear may be driving them.  How can you support them as they deal with their fear? Letting them talk it out is part of this support.  And where parents are concerned, in my experience, in the vast majority of cases, they’re also motivated by love for their child.  It can help to bear that in mind.

I would often give a brief introduction and then give the floor to the other person – a disgruntled parent, or a member of staff who is upset, for example. I’d let them talk without interruption until they ran out of steam – they’d got it all out.  Even if they said something I felt to be wildly inaccurate, or even outrageous, I wouldn’t interrupt.  Let them speak. “Yes, but…” is never likely to be helpful!   

After they’d finished, I’d thank them and reassure them that I had been listening closely, I understood their point of view and could empathise. I might need to repeat the key messages I’d heard, to convince them of this.  If I didn’t feel I understood completely, I’d ask questions to check and clarify.  And then I’d give them my response, perhaps the school’s perspective if this was a conversation with a parent, ensuring the facts were accurate and clear, especially if there had been any misperception on their part.  And if they started to interrupt (“Yes, but…”) I’d say, politely, but assertively, ‘Please – I listened to you without interruption.  Let me finish, and then we’ll discuss it together.’

And you have to try to do all you can to stay composed, not to let strong emotion throw you.  Just as when we deal with pupils who are behaving badly and who may themselves be at the mercy of strong emotions, if we can’t control our own emotional response, we will struggle to make progress.  With a pupil, remember: you are the adult.  With a parent: you are the professional.  I know you will still feel the emotion, but work hard to keep it under control.  And I say that, absolutely understanding how hard it can be!

Try also to ensure there is a structure to the discussion, and make sure that towards the end you clarify, summarise, and agree next steps.  What needs to happen as a result of this conversation?  Who will do what, and by when?  How will the action be reported back?  Where do you all go next?

How you could follow up

After the event, do what you have promised.  Document everything clearly – I would often send an email or a letter straight after the conversation to confirm and clarify what was discussed and decided upon.  After that I’d log what action was taken, and what happened as a result.  You never know when you might need to refer back to this record, and remind people of what was said and committed to at the time. 

The follow up is just as important as the preparation and the meeting itself. The action taken needs to move you on.  It may not resolve the situation immediately – in fact, if this is a complex issue, this meeting may actually need to be one in a series, for example if you’re supporting a colleague to improve their practice or, if you’re constructively challenging a Middle Leader to hold their own tricky conversations and shoulder their leadership responsibility successfully.  This can’t be a quick fix.  But the direction of travel should be clear, and you should be taking perhaps small steps, but definitely steps in the right direction.

I hope the following resources may be helpful.

I was involved in a Teacher Development Trust online session with Kathryn Morgan on the subject of emotionally-loaded conversations specifically in the context of Covid in the summer.  I blogged about it afterwards.

See also this short video from Steve Munby, this blog post from Mark Anderson, and this book by Susan Scott.

Finally, make the most of your networks – within school, across schools and on social media.  You are not alone in dealing with your challenges.  A few years ago there was a Twitter #SLTchat session on the subject of ‘Managing difficult conversations’.  Between 8 and 8.30pm on a Sunday evening Senior Leaders shared advice, experiences, resources and debate.  I sat listening to it and thinking, “If anyone is going into school to eat a frog tomorrow, I can’t imagine any better preparation!”   

Many thanks for listening.”

4 thoughts on “Challenging Conversations

    1. Thanks, Christine! Hope it will be useful.

      And hope all is well with you!

      For interest, I’m currently developing ‘The Dresser’ to the length of a novella (30,000+ words). Would love to send it to you when it’s done to see what you think. Could you please send me a Facebook message sometime with your email address? Thanks. Sending love your way.


    1. Thanks, David – and please do! I write these pieces for people to share – am very happy if anything I’ve said is of use to others.

      I’ve also recorded a 20 minute session using this address for Mary Myatt’s ‘The Soak’ series of videos for educators, which I hope will also help to spread the advice.

      Best wishes.


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