Challenging Conversations:
3 Key Factors

18 April 2022

CC: 3 Key Factors

Most conversations become challenging due to three key factors. This video offers explanations of what they are, and how to manage them effectively

One way of looking at Challenging Conversations is to look at the three factors that are most likely to make it challenging. And they can be represented as a Venn Diagram: context, them, and you. Looking at each in turn:


There are really two types of context difficulty. Firstly, whete the context, or situation is inherently difficult; and secondly, where the situation is not itself difficult, but poor organisation and management has made it so. Inherent difficulty is largely to do with giving or receiving ‘bad news’ – such as changes at work or difficult relationships, or health or financial issues. If you are about to have a conversation with anyone which they are likely to see as being ‘bad news’, you can expect the conversation to be emotionally difficult for them and perhaps for you. And so it is the issue itself that is difficult, rather than either party. It is the nature of the context that is challenging, and leads to emotional and challenging behaviours. For example, suppose a member of your team has persistent and unpleasant body odour, and it is adversely affecting the team. You feel you need to raise the issue with that team member. Such a situation, such a conversation, will be inherently difficult – the difficulty is in the situation, rather than in the individuals involved. So a tip: always remember that it is often the situation that is difficult, not the person. Without the difficult context, the behaviour of both parties would be absolutely fine. So separate the issue from the individual. However, some situations are not difficult because they are inherently so; nor are they to do with the individuals concerned. They are difficult because the set up and organisation of the conversation, the meeting, has been mismanaged. For example, if you have called a meeting, consider: is it a suitable location for both of you? would somewhere more relaxed and neutral be preferable? Is it a suitable time for both of you? And have you given the other person sufficient notice, in terms of both time and information. In terms of time, it might be worth giving them a choice: if the issue is difficult for them, they might want to discuss it straight away, otherwise they will fret; on the other hand, someone might prefer some time to reflect, and think about their response. So give them the information to help them make such a choice. And in terms of seating, make sure you have no strong light source (such as a window) behind you – they won’t be able to see your face clearly, which will put them at a disadvantage; and consider seating which is round a low circular table, rather than a formal ‘across the desk’ arrangement, which will feel adversarial.


The next key factor is Them – that is, the other person’s behaviour (I know you might have a conversation which is difficult and involves more than one person). So it could be the other person is behaving in a difficult manner, so here are some ways you might be able to minimise, prevent or deal effectively with such behaviour.

Equity: there are a number of ways you can work to create equity, before and during any conversation For example:

give them proper information and time to reflect: otherwise it will feel unequal, You might have been thinking about this for days, anticipating their and your responses, and planning for all eventualities – and yet they may not have been given the same opportunity. It won’t seem – or be – fair

make sure that the relationship has two-way equivalence: what you claim for yourself you should give to them; and what you might object to in them, you should not condone in yourself. For example, if you want them to listen to you – then make sure you listen to them; if you don’t want them to make claims without evidence, make sure that applies to you, too. People hate double standards

acknowledge the validity of their views and feelings – even if you don’t agree with them; treat them as you would like to be treated

Explore: Look for reasons why they are behaving as they are; if possible, accept how they are behaving for now, whilst trying to get past this, and find out what is behind such behaviour. So don’t criticise – ask. Seek to find out, rather than condemn

Empathise: acknowledge their behaviour as genuine, and driven by some degree of genuine discomfort. Give them the opportunity to offload, let of steam, if it is in a safe and private place. Being allowed to discharge may reduce their distress. Where possible, focus on the issue, rather than the individual

Explain: it should be clear at the start of any conversation what the purpose of the meeting is, and any desired outcomes. But during the conversation, it may be necessary for you to explain what’s acceptable and what isn’t; what’s negotiable and what isn’t. Something else you may want to raise, and explain, is their blind spot behaviour – again, more on that later.


Of course the third crucial factor in this diagram is you. And there are two significant ways in which you can affect the process and outcome of the conversation: through your external behaviours, and through your internal state Your external behaviours: it’s possible that you may aggravate or exacerbate the situation from how you are behaving. Your body language, the words and tone you use. So it’s a good idea – now – before any such conversations happen – to work out what you will guarantee to do and not do, when any conversation gets difficult or challenging. This is covered later in this block. And of course you might also have one or more unhelpful blind spots;;;; Your internal state: essentially this relates to your emotions and feelings before and during the conversation. In fact, this is perhaps the single biggest influence on how well the conversation will go So if you have negative thoughts about the upcoming conversation, that it is bound to be difficult, and that you will be ‘found out’ and won’t be able to cope; then in the meeting, start to struggle, and feel your own thoughts and emotions telling you how bad it is, and how bad you are – then is will be no surprise to find the conversation is going badly. Your mindset is predicting the worst, and so becomes a self-fulfilling prophesy: what we believe we give ourselves permission to achieve. So if we say to ourselves (or others) ‘I’m going to have a difficult conversation this afternoon” – guess what….a difficult conversation is more likely because it has been predicted. All of this can be radically changed, if you can substitute a positive mindset for the negative one. Develop some useful techniques; decide what you can control in the meeting, and focus on that; be your own best supporter, rather than your own worst enemy.

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