By Simon Judkins

EDITION #7 – How do I cope with a challenge?

Published – 24th July 2019

Simon Judkins teaches at Camelot Rise Primary School


When we think about challenging conversations, our minds can often leap straight to a ‘worst-case scenario’ involving an angry or upset parent – many teachers have experienced an incident along these lines. But the truth is that challenging conversations come in many guises, and they can be some of the most rewarding things we do as teachers. This doesn’t mean they can’t still feel daunting, but there are some simple strategies we can use to help navigate the world of challenging conversations and maximise their potential for positive outcomes. Through this article we’ll explore the management of challenging conversations with students, parents and colleagues. We’ll consider ways to positively frame conversations, ask questions that support challenge, and the effective use of silence.



Challenging conversations often start because of something that seems negative. This could be something as simple as identifying an area for future growth within student work, or it could be a concern with a current direction or how something has been handled. In a world that often seems intent on focusing on the negative, it’s important to understand and iterate the value of a growth mindset. Our focus in these conversations should be on moving forward, not looking back. Ensuring our language is positive (but honest) is a good way of getting uptake from all those involved in the conversation.

It is difficult to get positive outcomes by focusing on what a student is doing wrong, even if it at the core there is something requiring improvement. It’s not just about saying nice things though. The challenge often comes in delivering meaningful feedback that leaves the student with a solid understanding of where they’re headed next. Saying something like, ‘I really like how you attempted… It could be improved even further by doing…,’ is far more positive than, ‘It doesn’t look like you fully understand this yet, so let’s practise more.’

One of our priorities as teachers is to help kids do more than they thought they could do. Pushing students to change and grow can be some of the most important and challenging conversations we have. Ensuring we positively frame that growth can be a great enabler.

When it comes to managing behaviour, schools may already have a behaviour management policy which includes strategies such as Restorative Practices or School Wide Positive Behaviour Support. Implementing a whole school system based on one of these types of frameworks can be particularly effective as they are designed around a consistent set of questions and procedures, removing the variable of designing your own.


A technique for you to try

Let the other person do a great deal of the talking is one of Dale Carnegie’s (2010) core principles, (Carnegie is the acclaimed author of ‘How to win friends & influence people’). It is a great technique for almost all challenging conversations – though it can look a little different depending on the situation.

When it comes to students, there are two main ingredients: the strength to stay silent, and good questions. The first point can take a while to adjust to; the idea of simply sitting and waiting for the student to talk without filling in the silence can be challenging…and the students know it. Students are often content to sit back and wait for the teacher to speak again, doing their work for them. But perseverance is key here. I still remember as a graduate teacher being involved in a challenging conversation with a student, with an experienced teacher beside me, feeling the need to speak into every awkward silence. My colleague pointed this out afterwards and since then deliberate waiting has been one of my most successful and frequently applied strategies.

The second part goes very much in hand with the first. Asking questions that cause the other party to reflect and evaluate can be integral to them taking responsibility and ownership over what comes next. ‘What do you think you did well?’ ‘What could you develop further?’ ‘What would you like to try next?’ ‘Why?’ When we take the time to ask questions, we can build on these things and it feels more like the student painting their own path forward than having one dictated to them.



With parents, the same ideas can apply. If they have a grievance, let them talk and express their feelings without intervening. Be a listener. When you respond, do so with questions such as, ‘What would you like to see next time?’. This way you’re not committing to anything, becoming defensive, or making the conversation more challenging than it already is. Remember, it’s not about ‘winning’ the conversation but allowing all parties to feel heard and valued. They may be approaching you with comments such as ‘my child is being bullied’ or ‘my child is bored in class’. Listen well to make sure you understand what is being shared.

If you’re the one initiating the conversation, let them know what you’ve seen, be it academic or behavioural, and then ask for their input. You might ask, ‘What have you noticed at home?’ or ‘What are your thoughts about this?’. Asking for parent input into the conversation can be a great way to foster connections, the importance of which is outlined in the second edition of this Graduate Teacher Learning Series. In addition, be sure to communicate with parents about positive things that happen to help foster strong and trusting relationships. The strength of these relationships can help make any difficult conversations much easier to approach.


A technique for you to try

Buying yourself time is a great technique when dealing with any challenging conversation and yet it’s often the first one we forget.

One of the reasons why certain conversations can feel challenging is because we’re being addressed with little or no warning about an issue, and yet we feel the need to respond capably on the spot. This isn’t required in most situations. That email you received at 11pm doesn’t need to be replied to immediately. You don’t need to be an instant fount of knowledge or be able to accommodate every unscheduled meeting on the spot. It’s not rude to let a parent know that you’re unable to discuss a matter right now. It is important to show that you are willing to schedule a time to do so. This provides you with the time necessary to wrap your head around the situation and get all the information you’ll need to manage the conversation. You could also use this time to apply other suggested strategies, like arranging a colleague to support you.

Likewise, if you don’t know the full answer to a question, it’s okay to postpone your response. Saying something like, ‘That’s a really good question, I’ll go and find out for you’ can give you the time you need to collect all the facts. It can also reassure the parent that you’re looking after them. It’s just important to make sure you do actually get back to them in a timely manner.


Colleagues – a technique for you to try

Share your ideas openly. When I was a graduate, I initially found it difficult to understand why senior teachers would be interested in listening to my ideas, when they had so much experience already. Now, with the shoe on the other foot, it’s something I cherish so much – getting fresh ideas from fresh minds. So please have the confidence to speak up.

All schools will already have a strategic plan, looking to the future, with goals and directions the staff will be moving toward. So where do your ideas fit in? The answer is a simple one: everywhere. It might be difficult to speak up and suggest ideas, especially if you’ve tried before but had them dismissed. Try not to feel dejected; it’s not personal. If you disagree with a decision, you can always ask for clarification. Right away, in the middle of a meeting, might not be the appropriate time but afterwards ask your team leader or colleague to explain things in greater depth. Even though it might be a challenging conversation to have, you can learn so much from putting forward your thoughts respectfully. These conversations help you gain insights from the vast experience of others.


Two strategies to apply to all challenging conversations


You are not alone

It might sound like a simple thing, yet it’s surprising how often we forget; we are not alone. At no stage in our teaching career should we feel like we need to handle something on our own. We are a team. For graduates, your school will have appointed a mentor for you to connect with, but you will also have a team leader, leading teacher, learning specialist, and more – all of whom have experience and responsibility to assist and support you. You might even like to rehearse conversations with a colleague beforehand to prepare.

At times, we might think that if we’re not able or willing to handle a situation independently, then we’ll appear weak or incapable. But this simply isn’t true. The strategy of taking a colleague with you into a challenging conversation is used by even the most experienced of teachers. It is a smart move for a number of reasons.

The first of these is that it takes the pressure off you, helping you feel more confident. If things become a bit overwhelming, then your colleague is there to assist. If a curly question comes along, your colleague might be able to help. But another, often overlooked reason for having someone else with you is that it actually shows the other parties involved in the conversation that you’re taking them seriously, and the effect of this shouldn’t be underestimated. Throughout my teaching career, I’ve been accompanied by team leaders, leading teachers and even the assistant principal when going to a meeting where I have anticipated there might be a challenging conversation.

When it comes to students, it’s not just a good idea to have someone else nearby, you should view this as mandatory. Check the process in place at your school for managing this type of scenario.  Most of the time your challenging conversations will be academic in nature and completed during class when the rest of your students are present in the room. But if, for some reason, this is not the case, it’s vital to ensure you have a colleague in the room with you, even if they’re not involved in the conversation itself. If you need to address student behaviour or attitude, having another teacher with you can be helpful in case there is a misinterpretation in relaying information to parents.



Communication is key

Teachers are in the business of communication. Every day we communicate learning intentions and success criteria to dozens of young minds, collaborate with colleagues with varying experience and responsibilities, and connect with parents. Many challenging situations could be avoided altogether simply by communicating better in the beginning.

We often create challenging moments for ourselves by only entering into part of the required communication. We might talk to a student in the yard but forget to inform their classroom teacher. Or we have a challenging conversation with a student but neglect to pass on the relevant information to their parents. If something is worth a challenging conversation with a student, then it’s also worth communicating that with their teacher, parent or guardian. This can prevent miscommunication about the nature and purpose of the conversation, which itself might lead to further challenging conversations.

A lot of schools are employing apps like Seesaw and Dojo, or electronic platforms like Compass to provide a platform for greater communication between home and school but a simple email, phone call, or conversation at pick up can be plenty. Keeping those communication lines open is vital to a healthy teaching career.


A key takeaway

Don’t run away from challenging conversations. Embrace them. Challenging conversations, when handled in the right way, lead to growth.


Discussion with your mentor

  • Discuss a recent challenging conversation you had – which of the strategies discussed in this article did you use successfully? Which other strategies could you have used to assist in managing this conversation?
  • Consider your current communication strategies and whether there are any improvements to be made.
  • Discuss the importance of keeping records of challenging conversations. Your school might have a specific method for doing this.

Further Reading

Australian Institute for Teaching and School Leadership, 2017, Teacher Standards, viewed 01 March 2019,

Jennings, T. 2016, 7 tips for difficult parent conversations, Viewed 10 October 2018,

Rigby, K. 2010, Bullying interventions in schools: Six basic approaches., ACER, Camberwell.

Steen, M. 2017, The 6 Phases of a difficult conversation: A strategy guide for teachers. Viewed 10 October 2018,


Carnegie, D. 2010, How to win friends and influence people. Revised edition. Simon & Schuster, Inc, New York.