When to Have a Difficult Conversation

//When to Have a Difficult Conversation

When to Have a Difficult Conversation

pdf_buttonThe majority of the 2,000 plus leaders we have assisted in our work over the past 10 years struggle with having difficult conversations. This is only natural, as we tend to get anxious around having to confront another person about inappropriate or performance blocking behaviours.

Leaders ask themselves: ‘What if I get it wrong?’ or ‘What if the person gets defensive/emotional/ angry?’ or ‘Will they still like me after I have this conversation?’. All of these are valid questions that are part of what is called the Identity Conversation. This is the self-talk we engage in prior to having a difficult conversation. But mainly we use this self-talk to convince ourselves not to have the conversation at all.

The result is quite predictable; the issue does not go away and the people affected get angrier as time goes by and no action is taken. The reason is that most people are not conscious of their behaviour. If nobody tells me that they have a problem with me talking too loud on the phone, I will never know that it’s an issue. Why? Because to me talking loudly is natural. The longer I don’t get confronted, the more convinced I am that it is OK. If nobody complains, everything must be fine.

In too many cases action is only taken once anger trumps anxiety. But with anger bursting to the surface it is easy to see how waiting that long can be counterproductive – the conversation might deteriorate into an accusation excuse spiral or even into a shouting match.

So when is the right time to have a difficult conversation? The easiest way to picture this is to draw a scale of relative anger (see below).


The further you are to the right in regards to your feelings towards the person, the less likely the conversation is going to be effective. The trick is to heed the signs along the way as an issue slowly creeps from mildly annoying to making you furious.

This means you have to pay attention to your self-talk in relation to this person. In the first instance it might be along the lines of ‘I wish he would quiet down a bit’. Over time that self-talk mutates into ‘God, he is at it again. How can anybody work with him shouting into the phone?’ and eventually into ‘That’s it! I’ve had it! One more time and I am going to throw his phone out of the window!’

That’s great for next time you will say, but what do I do now when I am already angry? Well, you literally have to drain your anger. Since you can’t vent to the person, what most people do is vent at home to their spouse or vent to colleagues and friends. In short, we go to people who can’t do anything about the issue. That’s not fair on them and it is not fair on you.

The best way of draining your anger short of seeing a coach or counsellor is to get it off your chest by writing it down. Create a work journal specifically for these situations: ‘John is a bloody % @$&@!!! and he is really #%&*$@ me off’ is a good way to start. The key is to write uncensored, to write how you really feel about the person.

The second iteration is to move past the person and constrain your anger to the behaviour. If there are several, write down how you feel about each of the behaviours. Then choose the one that annoys you the most and stick with it for the remainder. You can only address one behaviour at a time.

The third step is to write down all the evidence you have accumulated. The first iteration of your evidence is likely to be full of generalisations like ‘always’ and ‘never’. Absolutes are easy to counter and the feedback will not stick. John doesn’t always (meaning every single time he makes a phone call) shout on the phone. You need to refrain from anything that isn’t a specific, observable behaviour. Ideally, you only use first-hand observations (that’s not always possible).

Finally, you need to detail the impact on yourself, other people and on the business. Once you have written all of this down and ran it past someone you trust and respect, your emotional state should have moved considerably to the left on the anger chart (see below). If that is not the case, you will have to seek help from a coach or counsellor.


The final step before you have the conversation is what we call the ‘self-deception test’. Because we all have our own emotional baggage and we operate with very different models of the world, it is easy to confuse a behaviour that is quite acceptable in the business context for something you personally find offensive or inappropriate. In a situation like this you are literally chasing your own tail – projecting your issues onto someone else. We all do it and it’s easy not to notice when you do it.

For example, you may consider it inappropriate that the person next to you interrupts you with trivial requests or questions several times a day. It disrupts your flow of work and your concentration, so you tend to get angry when it happens. Whether this really is inappropriate behaviour would depend on a number of factors starting with how closely you are working together(e.g. on the same deliverables). It might be worthwhile to ask yourself why you react this way and why the other person feels the need to ask in the first place. Again, seek input from someone you trust and respect and who ideally is not a friend (your friends likely have a similar model of the world to yours).

Then, and only then, organise a meeting with the person in a private space and confront them about the behaviour using the evidence you collected and the impact it has on you, others and the business. In most instances you will be surprised how positively the person responds.

The examples we have chosen in this article are deliberately trivial. In our experience individuals who routinely avoid difficult conversations should start on the small issues to gain confidence and practice before addressing more serious behaviour or performance issues. The process remains exactly the same as described, just the amount of preparation increases.

By |2019-01-13T16:50:13+00:00August 14th, 2009|Blog|Comments Off on When to Have a Difficult Conversation