difficult conversations

One of the most regular training requests I get asked for is advice on handling difficult conversations. Whether it’s managing a tough client negotiation, dealing with a grievance, or even asking for a pay rise… there are certain conversational topics which we seem to come pre-programmed to want to avoid.

The irony is, by branding these conversations as ‘difficult’, we subconsciously get ourselves onto the back foot before we’ve even started. Psychologically, the mindset we go into these discussions with can have an enormous impact on how successful (or otherwise!) the outcome is.

The trick therefore is to get ourselves out of that negative mindset, and in order to do so, we need to have a strategy which we can implement in order to be confident of a successful outcome. Planning and preparation are key for almost all significant undertakings, and a so called ‘difficult’ conversation should be treated as exactly that.

While there is no magic formula to successfully navigating your way through discussions, there are certain things which, by employing, give you the best possible chance of doing so. These are those:


The old adage of ‘fail to plan, plan to fail’ is never more apt than when it comes to difficult conversations. While it can be the case that a conversation takes an unexpected turn and you suddenly find yourself thrown headfirst into conflict, this is very much the exception rather than the rule. With most difficult conversations – breaking bad news, asking for more money – you will have plenty of advance notice that such a discussion is coming up, and should therefore plan accordingly.

Define your desired outcome

A core part of this planning process should be about understanding and defining what success looks like. Too often, we focus on the act of having the conversation itself, rather than working towards our desired outcome. If we know we are going to have to break bad news to a client, we get hung up on how they are going to react – which we have very little control over – as opposed to thinking about where, post the sharing of the information, we want to ensure we get the relationship back to. Think about how you want the conversation to end. Then start to plan out the steps you will need to take and the things you believe you will need to say in order to get to that point.

Know what you want to say, but be prepared to flex

As part of your planning process you will inevitably start to sketch out in your head what you want to say in order to get your point across. This is an important part of your preparation, but don’t fall into the trap of writing the whole conversation as if it were a script and assuming it will run that way! The nature of a two-way conversation means that the other person is an unpredictable commodity, and therefore you need to ensure you are able to flex your planned wording in response to their questions and dialogue, yet still achieved your desired outcome.

See things from the other person’s perspective

We are all at the centre of our own lives, and consequently, unless we plan to do otherwise, we are in perpetual danger of seeing events only from our own perspective. Let’s imagine you’ve been asked to go and have a conversation with someone who you’ve had a dispute with, in order to resolve things. If you go into that meeting thinking of things only from your own point of view, your conversation is likely to be emotive and combative, and your chances of a successful resolution are minimal. What if, though, before you went into the meeting, as part of the planning process, you took time to see things from the other person’s perspective. Why are they frustrated with you? What might help alleviate that frustration? Remembering that your desired outcome is to achieve a way of moving forward together, if you can plan the conversation to acknowledge and respond to their frustrations, your chances of success are that much greater.

Lose the emotion

It is human nature to emotionally invest in these difficult conversations. The stakes are higher, so the emotion surrounding them is likely to be proportionately higher. However, what we can’t afford to do is to bring that emotion into the meeting room with us. The risk if we do so is that it acts as a barrier to our desired outcome, and prevents us from getting our points across cleanly and clearly.

When you plan your conversation, stick to the facts. Know how to present them concisely, and in a manner that your audience will be receptive to. For example, if you’re meeting with your line manager to ask for a pay rise, ensure your focus is on the facts – the level of pay increase that you’re asking for, the reasons that you feel it is justified, etc – as opposed to how unfair you think it is that you haven’t had a pay rise when you really think you deserve one. The former approach equips your manager with the information they need to go away and make a decision; the latter is likely to simply frustrate them.

Know how to move on

Ultimately, by their nature, not all ‘difficult’ conversations will have an outcome which goes in your favour. Part of handling them successfully is learning to move past them when, despite your planning and preparation, you haven’t ended up where you thought you would. Perhaps the client has left the meeting room unhappy with the news that you’ve shared with them. Perhaps that pay increase you’d hoped for isn’t going to happen this year. In any such scenario, it’s important that we are equipped to move past this point. Your focus and planning then needs to switch to what you do next. How do you now rebuild that client relationship? How do you ensure that you don’t get hung up on your lack of pay increase, and instead focus all your abilities on delivering outstanding results so that it will end up being your manager approaching you and proffering a raise? Difficult conversations are a part of life, and the real skill lies not only in handling them successfully, but also then knowing how to move on.