How to have a difficult conversation

Written by: John Rutter | Published:
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Difficult conversations are a frequent reality for many school leaders – whether they be with parents, teachers or middle leaders. John Rutter advises on handling these situations

Not many people relish confrontation. Teachers are no exception. We are generally nice people who shy away from difficult conversations and arguments.

Undoubtedly there will be some power-mad leaders among us who want to exert their authority over others but, for most, this is anathema to our view of a caring profession.

But as a senior leader, the difficult conversation – while not exactly your bread and butter – will be a staple of your working life. It can take many forms and be with many different people. There are the parents who believe their children are incapable of poor behaviour or hold the school responsible for their lack of achievement; there are the teachers who show a lack of recognition when confronted with a complaint from a parent of unfair treatment of their child; and there are the principal teachers who defend their own staff in the wake of evidence of poor performance.

These conversations will undoubtedly bring conflict on some level, but they are often necessary and need to be approached with the same degree of professionalism that you would use to carry out any of the other 264 things you have to do in the course of a day’s work.

From what I remember of my headteacher qualification there was very little training in how to have a difficult conversation with someone. I already had some experience as a principal teacher and a depute but all of this came on-the-job. In other parts of the world the skill is embedded in the core capacities of leadership.

The Ontario Leadership Framework specifically states that educational leadership development involves “engaging in courageous conversations (which are about) challenging current practices and fostering improvement and growth through conversation, listening to and acting on feedback”.

The focus of all such conversations – whether in the context of performance appraisal, mentoring or coaching – is ultimately to find a way towards improving student achievement and wellbeing. Furthermore: “Individuals are encouraged to express their views openly and truthfully, rather than defensively or with the purpose of laying blame.”

The Ontario framework goes on to outline the two main types of conversation people engage in:

  • Dialogue occurs when people try to understand each other’s viewpoints. It is a reflective process for participants as they try to come to a new (and shared) understanding or meaning – although this may not necessarily be the right answer or the best solution.
  • Discussion occurs when two or more people talk in order to come to some kind of decision or, at least, some agreement.

In my experience, there have been a number of courageous conversations which result in neither agreement, shared understanding or any kind of reflection whatsoever. Certainly no solutions or right answers.

In these situations, it is important not to have had too many pre-conceptions about how you wanted the conversation to end. Advice on courageous conversations often includes an instruction to know what you want the outcomes to be, but you need to be prepared to abandon your desires if the conversation does not go the way you expect.

In this respect the most important thing you can do in preparation for a difficult conversation is to have worked really hard beforehand on building up relationships to a point where people trust you to only carry out these conversations when absolutely necessary.

Whether they have personal experience of you or only know of you by reputation, people will feel more secure – and there is more likely to be a successful outcome, if they believe you to be unstintingly fair and honest.

So, how do we handle a difficult conversation? Almost inevitably, you will be anxious when the situation arises and with good reason. The implications for it going wrong may include increased hostility, resentment or detachment for the other participant/s and may result in a highly emotional reaction including tears, anger, raised voices and counter-accusations.

Fear of these implications leads to a different option – that of avoidance. This route, however, inevitably leads to a deterioration in the situation and, perhaps, an irrecoverable loss of trust from those who rely on you.

Psychologist and motivational speaker Dr Michelle Rozen has outlined some questions you may want to ask yourself in order to figure out whether a courageous conversation needs to take place:

  • How severe is the situation that I am looking to address?
  • What are my possible risks?
  • What are my possible gains?
  • Who is my recipient? What is their personality like? How are they likely to respond?

The final questions here can be all-important to how successful your approach will be. On the whole, teachers are overwhelmingly reflective and self-critical and constantly strive to improve. This makes it even more surprising, therefore, when you come across those who show little realisation that they may be the cause of a problem which is obvious to everyone else. In these circumstances the success of a conversation may depend entirely how direct the approach is.

Being overly anxious about the reaction to what is being said can result in what psychologists call “avoidant communication”. So while the conversation takes place the message is delivered in such an obscure fashion that what has to be said is unclear and the recipient is left not really getting it. To avoid this make sure that everything you are going to say is accurate and backed up by facts. Try not to repeat yourself or be out of control in your use of adjectives. You could practise what you are going to say in advance but be prepared that things may not go the way you foresee.

Other tips from leadership training professionals on how to engage in a successful conversation focus mainly on your abilities as an effective listener and organiser.

Make sure, after you have outlined the initial incident or area of concern (backed up by the facts) that you allow the person to have their say. This may be a recognition of what went wrong or it could well be a justification for their actions and an attack on the failure of others (including you).

How you proceed will depend completely on how this pans out. Do not be so focused on the plan you have for what you have to say that you fail to listen to the other person’s side of the argument or even, perhaps, fail to hear that they are agreeing with you.
Listen carefully and look for the positives. Does the other person recognise there is a problem? If so, what support can you give to help them fix it? Look for anything in the discussion that can help you to work towards a successful outcome.

Finally, the most important thing to remember is that your own behaviour will determine the direction of the conversation. Your ego will be all-important. You do not have to win and if you focus on being right instead of searching for truth then it is likely you will end up with conflict and ill-feeling.

Remember you are seeking a resolution that benefits relationships across the school rather than on an individual basis. Be prepared for discomfort. If you are not then you will skirt around the subject to avoid confrontation rather than getting to the heart of the matter.

And, finally, remember it is you who will set the emotional tone for the conversation. Remain calm even as others get increasingly agitated. Nobody gives their best when upset. Sometimes it may be best just to call it a day and agree to discuss things again at some point in the near future.

Courageous conversations are a frequent, although hopefully not daily, aspect of any school leader’s job. They are all different. Nobody can lay down a format that works with them all. Just remember to establish a reputation that you are someone who can be trusted to carry them out fairly and be true to your conviction that they are ultimately taking place for the good of the pupils in your school.

  • John Rutter is headteacher of Inverness High School. Read his previous articles for SecEd at


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