7 Difficult Discussion Tips for School Leaders

difficult discussions at school

Whether you’re a principal, deputy, department head or in business admin support, as a school leader, difficult discussions with teachers, parents, colleagues or kids, tend to crop up on a monotonously regular basis, one after the other.

Resolving your way through touchy topics – troubling incidents or behaviours, difficult feedback, distressing news, unkept commitments, or things that’ve gone wrong or aren’t up to scratch – is something you’d probably prefer not to have to deal with. But they’re a critical part of your role, and how you handle them can impact you and others across the school community in so many, often far-reaching ways… 

teacher stress

The prospect of a difficult discussion can be daunting and anxiety-raising for you, and the person you’re addressing. If defensiveness kicks in and heats up the conversational temperature, we either go one of two major ways – we retreat or retaliate.

While there’s no silver bullets or bunches of garlic to hang over your door, our Difficult Discussions Clinic has conversational scaffolding, tools and tips, to make tackling tough talks more constructive and a little less painful.  Here’s a sampling of some of them that I cover in this clinic…

TIP #1: Plan it - don't Wing it

It’s not always possible but avoid if you can, having difficult discussions on the spur of the moment. This may disappoint the impetuously spontaneous amongst us, who relish a bit of improvisation, but think carefully through a few of these do’s and don’ts beforehand:

  • Do make a few notes about what you’re going to say, how you’re going to say it, and how to bring it up to start with. This is not a pre-set script to stick to – just some mental anchors you might want to drop into your conversational ocean at some point.
  • Do list any incidences, facts, key points or related information you may want to refer to during the discussion (school policies, pedagogical practices, standards, values) but don’t hit them with the “rule-book’ straight up.
  • Don’t act lawyer-like and assemble an iron-clad-case-full of evidence to solely support your position and squash theirs. This means your oppositional mind’s already made up.
  • Don’t think of preparation as a way to get the upper-hand on them or establish control. This puts you on an adversarial footing straightaway.
  • Do think about and mentally square away any questions you might ask to find out more – and keep them open, not closed.
  • Do think about what their perspective might be on this and how they might see it.

“One of the most critical capacities school leaders need to build trust and authenticity is the ability and willingness to engage in challenging, difficult, and sensitive conversations…” Ontario Ministry of Education 2013

TIP #2: Sort out your own Sentiments before you start

The more prepared you are, the more likely it is you’ll stay balanced, fair-minded, and even-tempered and not let your emotional nerves get the better of you.

A looming difficult discussion raises all sorts of sentiments you should try to settle before you start. For example:

  • How do you feel about what this person seems to have done?
  • What concerns you most about bringing this up?
  • What emotions are likely to come up for both of you?
  • What emotions are likely to derail you in this conversation?
  • What is your position and where do both of your stories differ?
  • How do you want to show up for this conversation?
  • What would be a good outcome for both of you?
  • How might this conversation get out of hand?
  • What do you ultimately want out of this conversation?

“Thoughts and feelings you bring into a tough talk belong to you, so don’t blame them. If you don’t manage the emotions that come up for you, the unruly ones can take over and start doing the talking for you….”

TIP #3: Listen first, don’t lead

Predictably, the person you’re talking with probably expects that you will kick-off the conversation, especially since you initiated it. That’s fine. By all means, set up the conversation but be brief (20 seconds or so). Here’s a few more do’s and don’ts again:

  • Do treat this conversation like the most essential one you’ll ever have with this person. This means focus as much of your attentional energy on it as you can muster.
  • Do shut your laptop. Move away from your computer, out from behind your desk. Sit yourself down beside them. Silence your phone and ask not to be disturbed. You can’t give this discussion your dutiful attention if you’re distracted.
  • Do make yourself present and clear your mind so you can really listen to what someone else is saying (not just the words, but the emotion and intent behind them)
  • Do start by briefly describing the issue from a neutral point of view – not from your own, then invite them to tell you how they see it first.
  • Don’t take the floor in full flight first, and lay out your position, resolutions or why they’re at fault. This is a controlling conversation and, feeling condemned without a hearing, they’re going to defend themselves and insist on being heard first anyway.
  • Do pause to explore their side of the story first and ask open-ended questions (sparingly) to find out more about their view of what happened. You may discover things you’d otherwise miss if you just stick to your “right” version of what happened and shut your ears to theirs.
  • Do listen mindfully to what they are saying. If you’re mentally planning what to say next or thinking solution while they’re talking, you aren’t really listening openly.
  • Don’t interrupt, correct or try to talk over the top of them even if that’s what they do to you. If they see that you’re tuned in to listening to them, they may do the same (but don’t count on it).

“Leaders need to avoid being ensnared by cognitive bias traps to avoid prejudice, judgementalism and fault-finding, which make the other person an opponent not a partner, and prevent them from taking a neutral, factual and even-minded stance necessary to successful resolution…”

TIP #4: Back-burner your Bias – be understanding

Rather than leap to conclusions and rush in with blame, judgement and various nefarious motives that race around in your head (of course you look calm and in control on the outside), it’s important to try and see the situation from their viewpoint and compare their story with yours. Once more, here’s some do’s and don’ts…

  • Do stay open-minded about what happened and how they see the situation. It doesn’t mean you need to agree but you do need to understand how they see it, rather than immediately prove to yourself that your version of events is all right, and theirs is all wrong.
  • Do be curious, don’t be critical. Listen to learn something about this you didn’t know Try to find out answers to questions such as:
    • Why might they have acted this way? Is this a one-off incident, out of character for them, or part of a pattern?
    • What facts, assumptions and intentions loom large in their mind?
    • What might be happening in their lives to lead them to do something like this?
    • How might this have been prevented? or
    • Did I contribute to this in some way I’m unaware of?

  • Don’t be judgemental. Sure, they’re perhaps in breach of school rules, classroom management practices, curriculum directions, codes of conduct, or your notion of good parenting. But look at the situation through their lens and the many complex factors that may have come into play for them, rather than get entangled in the emotions of the situation.
  • Do find the uncharitable story, prejudicial beliefs, or less-than-noble motives you may hold toward them (wanting to put them in their place, show them how wrong they are, stamp your authority all over them). See how the stories you make up about them are likely to make you think, feel and act.
  • Do tell yourself a different story. One that’s more understanding, empathetic, even minded or compassionate and less judgemental. This can help emotionally balance you before you even commence your conversation.

“Ground your difficult discussion in common concern and purpose. You may need to talk standards and expectations but before you do a course correction, check to see if they’re aware they’ve veered off it, whether they share your concern for the deviation and whether they knew what the correct course direction was in the first place…”

TIP #5: Be Neutral, Factual and Fair-minded

Staying the distance in a difficult discussion is more likely if you can. Here’s a couple more do’s and don’ts…

  • Don’t assume you have all the facts about this situation and avoid confusing facts with assumptions as we sometimes all do. The Ladder of Inference is a tool that can tell you a bit about this.
  • Do list down what facts you know but also remind yourself they may know facts you don’t, or that you may have discounted or overlooked. What facts do they know that may be different to yours? What facts do you have that may be different to theirs? Exchange stories and talk about these differences. You may find things they saw as important that you didn’t and vice-versa.
  • Do be fair-minded about what you want and open to what they may want to. This is about finding common ground and mutual purpose you can both adhere to. What matters to both of us that may bring us together? For example, is it: doing it right by the kids? Getting good learning outcomes? More engagement in the classroom or preserving the reputation of the school? This can lead to a better chance of reaching a resolution that works for everyone that you’re both accepting of.
  • Don’t get lured into advocating for your personal preferences or solutions if there are other avenues to explore. We often convince ourselves there are no other options when in reality there are. We just don’t want to go down those paths for whatever reason. This is being close-minded.

TIP #6: Empathise don’t escalate

Rather than detach and distance yourself, engage them. Your emotional demeanour, as well as the actual words you use during the conversation, matter because they can calm and connect, or incense and disconnect. Some more dos and don’ts’ – as if you hadn’t guessed…

  • Do stay connected. Otherwise, little will be achieved. They’ll either go to rage or disengage, retreat or retaliate. Either way, these emotional states disconnect and create defensiveness that works against resolution. You need to make the other person part of the solution rather than a piece of your problem.
  • Do speak in measured and respectful tones. Don’t raise your voice or adopt more commanding tones. Naturally, you know sounding belligerent, threatening or even yelling is unprofessional and off the table, even if they indulge in it. It shuts down the conversation.
  • Do watch your words – they carry an emotional load. As you get emotional, your word choices may get more inflammatory.
  • Don’t start using “blaming you’s”, spiced with ‘always’ and ‘nevers’, or labelling words like “inappropriate”, “unprofessional” or “unacceptable”. Maybe they are? But the chance of your message being heard and the conversation staying on course, plummets as their defences focus on being told off, attacked, talked down to, criticised or lectured at.
  • Don’t ramp up feelings through accusation, criticism or frustration. It only serves to increase defensiveness, entrench positions and lead to argument. The more you do, the less chance there is of restoring relationships and reaching resolution.
  • Don’t try to ban feelings from the conversation. You can’t, no matter how much you might like to. Feelings are inherently a substantial part of what makes a difficult discussion difficult, and often until people process their feelings, little will change.
  • Do take a calmer, more composed and connective approach that begins with listening mindfully to understand their side of the situation and comes from a place of caring, not criticism or contradiction.

TIP #7: Optionalise and Solution-find

Compromises can work if they don’t water down the effectiveness of a solution. But often they represent a lazy or expedient way out. So, try some of these dos and don’ts instead for finding a way forward:

  • Don’t go for the easiest solution just to get this pesky discussion out of the way quickly. There’s a rule of Systems Thinking that says, “the easy way out always leads us back in to the problem”.
  • Do optionalise. Really ask each other “What other options do we have?” and really think expansively. This includes asking, ”What else might we have both missed? or “Is there a middle ground that might work or a novel approach to this?”
  • Do be specific about suggestions. Difficult conversation that never get round to con sidering ways to solve the situation are frustrating. If you’re talking about poor performance for example, explain why it’s below par, and specify what a good performance looks like and what they need to work on to make theirs better.
  • Do stay focused on a mutual outcome you both want and finding a way forward but never wade into a difficult discussion from the start with this. You need to work through some other important things we’ve mentioned above before you can do this.
  • Don’t think you can fast-forward the conversation by suggesting your own solution up-front. The person may feel compelled to have to go along with you because you’re in charge but remain uncommitted or resistant to making a solution work because you have imposed it on them.
  • Do be clear on any boundaries that have to be taken into account. Are there any strict guidelines, policies or other boundaries – as opposed to flexibilities you can explore. It’s not much use looking at options that may fall outside of them. Be clear on what you can and can’t do, even what you will or won’t do or what you are prepared to accept or not. This is not a matter of “putting your foot down” so much as observing limitations that may be outside or your control.
  • Do translate solutions into specific action plans and commitments. Difficult discussions often flounder here because we don’t spend the extra time (or have another meeting) to clarify what they will specifically do and what you will do too to support them.

“While baby-boomers tend to proffer performance expectations as tactful suggestions and encouragements, many millennials don’t mind a more up-front approach of just saying what the boundaries, non-negotiables and requirements are…”

In Closing...

One last thing. Remember to take care of yourself as a priority in all this.

  • Difficult conversations can be very stressful and slowly build up to exert bad effects on us over time.
  • You may certainly need to unwind with a walk or a bit of mindful breathing or debrief with a confidante to wind down

It’s also fine to take time out from a difficult discussion to cool off – go get a cuppa, do something else to distract you – but don’t let this become a way of letting the conversation slip out of sight. Agree to return to the conversation later to continue talking over things.

By the way, many difficult conversations are not the subject of a single discussion – they’ll more often be a series of talks. And of course, sometimes, you may just have to let it go. There’ll be some situations, personalities or behaviours that you just can’t do much about – and that’s OK too.
What’s important to retrieve in this is that you tried. You’ll still walk away knowing you did the best you could with what you had at the time.

“If you don’t feel fitted-out to have difficult discussions, it can be daunting and anxiety-creating. Equipping yourself with the tools you need to successfully navigate their conversational swells with a bit more balance can make all the difference.”

Our 2-day Dealing with Difficult Discussions clinic and 1-day Tackling Tough Talks fast-track alternative show you tools and formulas to help apply these kinds of tips in your conversations, to build better understanding and hopefully achieve more constructive and mutually agreeable resolutions.

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