How to Boss Your Next Difficult Conversation


For weeks now your parents have been arguing after you've gone to bed and things seem to be getting worse. You want to know if they are about to split up but you don't know how to start the conversation.

You have a busy week coming up with play rehearsals, sports fixtures and it's your grandad's birthday on Saturday. You meant to get caught up on all your homework but time's got away from you and you know you're going to miss an essay deadline. You want to ask for an extension but your teacher is strict and you're scared about how he might respond.

One of your mates has been putting you down recently in front of your friendship group. It started out as a bit of fun but now it's hurtful and is starting to wind you up. You want to clear the air and ask them to stop but you're worried that you'll end up being teased more for not being able to take a joke. 

Difficult conversations like these are an inevitable part of growing up and so you'd think schools would have classes on how to express yourself, keep your cool and manage any fallout. After all, the chances are you'll need conflict management and conversational skills far more often than some of the stuff you have to cram for your exams, right?

Most of us muddled through our teen years and learned how to deal with tough talk the hard way. School presented us with plenty of opportunities, but the lessons we learned were by trial and error - not exactly the most effective strategy! Well, let's explore a few guidelines that you can apply right away to improve the quality of your trickier conversations.

Emotional hijack


Whenever we find ourselves in a situation which requires diplomacy or honest self-expression, we are likely to experience strong emotions. We are social beings and others' opinions, our social status and sense of belonging are strong triggers. If we are not able to manage our emotions, it can be all too easy to slip into 'Fight or Flight' mode and find ourselves hijacked by our amygdala (the oldest part of our brain which is focused on our physical and social survival). 

Before we know it we can be sweaty, trembling and saying things we will regret once we cool off again. Worse still, the very parts of our brain that deal with complex communication get shut down when our amygdala is in the driving seat, meaning that we can't seem to access the words we need to get the conversation back on track. Alternatively, we might choose flight over fight and just avoid the situation altogether. We might appease, suppress our feelings and pretend everything is fine, letting things fester. None of these outcomes is ideal.

So, the first rule of skilful conflict resolution is to recognise when we are becoming emotionally derailed and have some strategies to bring our higher order thinking back online. There is plenty of material elsewhere on 'Tests of Life' that will equip you with tricks and techniques you can use to dial down the stress response, so I won't repeat that in any detail here, but the key is to remember to breathe! There is a constant negotiation going on between your sympathetic nervous system (survival mode) and your parasympathetic nervous system (rest and recovery mode). Calm even breaths will help you to stay present and keep you emotionally in control, rather than just reactive. Good breath control keeps your options open and all of your critical faculties available!

Be prepared

If you have the time and space, being prepared ahead of a difficult conversation can make all the difference. Not only can you use this time to figure out what you want to achieve, but you can also anticipate the likely points of tension and plan around them. Here are some questions that can be really useful when you anticipate tough talk:

  • What is the issue I want to address and why is it important to me?
  • Is there any hidden agenda here?
  • What assumptions am I making about the other person's intentions?
  • Why might they feel justified in what they have said and done?
  • How might I have contributed to the situation?
  • What were my intentions and why do I feel justified in my position?
  • What outcome would I like to achieve from this conversation?
  • What am I willing to compromise and what is non-negotiable for me?
  • If we are not able to find a positive way forward, what is my next step?

Timing is everything

Having done the groundwork ahead of time, you need to think carefully about where and when you'd like to have the conversation. The last thing you want to do is blindside the other person by catching them on the back foot. That is a great way to throw them into their own survival loop and you want them to be rational, reasonable and creative rather than reptilian in their response! Ideally, you should give them the heads up that you'd like to talk and agree a time and place. Depending on the nature of the issue, you might want privacy or it could be wise to have an impartial third party there to help keep you both on track. Mediation is a key role in many high stakes conversations in the adult world and you might find that a tutor, counsellor or mutual friend can help hold a space in which you both feel safe to express yourselves.


Think carefully about who else is likely to be around, though. It can be difficult to have a vulnerable conversation if you have an audience - the interaction can become far more about maintaining your role in a social group if you find yourself performing rather than focusing on the other person and the specific issue in hand.

Try to also make sure you have given yourself enough time so the conversation doesn't feel rushed. I find it really challenging, for example, to discuss a potentially sensitive issue with a student if they approach me at the end of a lesson while my next class is queuing up outside my room. It may take a bit more planning, but it is far better to put aside some proper time - it also shows that you are taking the issue seriously. We don't always have the luxury of time and place but when possible, we should do what we can to make sure everyone feels safe, relaxed and respected and this should be reflected in the environment we choose.

Start with the end in mind

The chances are that when a difficult conversation is about to take place, both of you will be feeling some nerves and might not be coming from a place of trust. It's, therefore, a great idea to begin by making it clear what you want to talk about, why it is important to you and what outcome you are hoping to achieve. By laying your cards on the table like this, it can go a long way to setting the right tone for a successful discussion.

In doing this, try to avoid 'you' statements (which imply blame) but go with 'I' phrases instead. Keep this opening brief but use language that is respectful and segue to inviting the other person to have their say first. This step is really important and can be part of your preparation ahead of time.

Let's look at two examples - one that is 'on point' and the other which sets the conversation up for a nose dive! Can you figure out which is which?

"I want to talk about how you are always banging on about how much better than me you are at sports in front of our mates. It is really starting to wind me up and you need to sort it out - you got anything you wanna say to me?"

"Thanks for agreeing to meet. I want to talk about some of the banter we've been having recently about rugby. I've found some of the comments difficult and I am worried that it is starting to affect our friendship. I'd really like the chance to clear the air and figure out how we can move forward. Is this something you've been aware of too?

Don't worry if the model example seems a little artificial or uses language that wouldn't be natural for you. The word choices can be adapted of course - what's important is how one of these language patterns is toxic, while the other invites an honest and respectful conversation. This takes practice but is worth the investment of time and energy. If you set the right tone at the start, you're far more likely to get the outcome you are hoping for.

Seek first to understand

It can take a lot of self-discipline to invite the other person to have their say before you express your own thoughts and feelings. After all, you clearly feel some urgency or you wouldn't have asked for the meeting in the first place! It is, however, a golden rule of negotiation that we should seek first to understand and then to be understood. 


The other person is going to be far more likely to listen to your point of view once they have had a chance to express themselves. This step also means that you'll have more information which you can use in shaping your own response afterwards. The key here is to use active listening skills. Don't just wait impatiently for your chance to talk. Instead, gift the other person with your full attention. Become fascinated with their view of things. 

Some books on body language will suggest you occasionally nod or add little signs that you are following their ideas and thoughts - hmmm, I see - that kind of thing. For me, this always seems a little contrived - if you are genuinely trying to hear and understand them, the non-verbal communication will happen automatically. Nothing beats an authentic desire to connect to the other person - it's like conversational fairy dust and works wonders!

You can also use open questions to help them to fully express themselves. This can be any question which cannot be answered with a simple 'yes' or 'no'. You can use question stems such as these to help shape this part of the interaction:

  • I'm not sure I quite understand that.  Can you tell me a little more?
  • How does that make you feel?
  • Why do you think that might be the case?
  • Is there anything else that will help me understand your point of view here?

The nature of the issue will dictate how much of this kind of prompting you need. Asking a teacher how you can improve your effort grade ahead of the next assessment is very different from telling your best friend that you are concerned about how much they are drinking on the weekends. Asking why you have been dropped from a sports team will require different questions to broaching the fact that you've had suicidal thoughts with your counsellor. Human conversation is wonderfully diverse and so we need a flexible approach rather than a one-size-fits-all formula. If there are parts of this process that are mismatched to the specific conversation you face, ditch them. Think of the advice here as 'pick and mix' rather than a blueprint to be followed step by step.

Reflect Back

Once the other person has had a chance to get their thoughts and feelings off their chest, you have one last task before it's your turn. You should spend a little time to reflect back what you have heard and understood. This will make sure that you have not leapt to any false conclusions and will further settle their nerves. It tells them that you care and are invested in finding a solution which respects their position as well as your own. You can do this with phrases like:

  • So, if I have understood you correctly, you feel that...
  • Let me just make sure I have this right then. You...

If it turns out that you've not quite understood them, hand the reins of the conversation back to them and take a step backwards until you have clarity. 

Now it's your turn

In an ideal world, you've now both had your say and can now focus on a way forward that will meet both your needs. Often, however, you may need a little back and forth to iron out any remaining concerns or frustrations. This is where a conversation is more like Jazz than Classical composition. You may have to improvise, but stick to the golden rule of mutual respect and you won't go far wrong.


As soon as you can, focus the conversation on what you can both do now to arrive at a solution - one that is practical and works for both of you. Be prepared to give ground here - the nature of a negotiation is that you both may need to make compromises, but also remember what is non-negotiable for you. An agreement that is not aligned with your values or real needs won't last anyway so it's worth putting in the sweat equity to find the right solution and not just the first one you come up with.

This could be a very simple process, or you might need to both go away and give the issue some more thought. Either way, agree a time to meet again to either check on how things are going (whether the solution is working out) or what the next steps might be. I've had some difficult conversations that have been resolved in one five minute meeting and others that have involved multiple meetings over a number of weeks. It all depends on the complexity of the issue and how readily each person is willing to move towards a mutually agreeable outcome. By agreeing to meet again, it keeps the issue alive and the negotiation open. Try not to walk away from a meeting without having made at least some progress.

Sometimes the outcome of meetings will involve one person writing up notes as a record of what has been said or agreed, and these can be shared with all those involved. Most of the time this is the responsibility of the adult(s) but it can be a good idea for you to jot down a few thoughts, even if it is a more informal issue that you've dealt with. The good thing about writing down key points from the meeting is that it can help you refine your negotiation skills for the future. By reflecting on what went well, where you found sticking points and what could have worked better, you'll accelerate your ability to manage conflict.

Don't be afraid of the big bad wolf

The final thing I'd invite you to consider is that conflict is not always the big bad wolf that it might appear to be. There will always be points of tension and disagreement when we are engaged in complex relationships with other people. I like to think about conflict as being like an invitation for growth. If we manage conflict, rather than fear it or run away from it, it can lead to stronger bonds between people, greater understanding and mutual respect. Just as physical exertion and effort can make us physically stronger, challenging conversations can strengthen us socially and emotionally. I'm not suggesting that we should go looking for arguments, but perhaps we shouldn't be so quick to shy away from them either.

So, the next time you face a challenging discussion, why not try some of the steps outlined here and see if they can help you navigate a way forwards. If you'd like a handy infographic that summarises the process, you can download a copy here.

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Andy Fisher is the creator of Tests of Life - an educational project designed to help students, parents and teachers navigate the 'hidden curriculum'. He is an English teacher and PSHE co-ordinator, based on the east coast of the UK and uses his blog, podcast and digital products to spread the word that schools should be preparing young people for the tests of life, and not just for a life of tests!