How to Prepare for a Difficult Conversation

When you know that you’re going to be having a difficult conversation with someone, it’s really easy to overthink things. This can lead to your delivery of key information and points not being as effective as it should be and ultimately, it being less likely that you’ll get to a good outcome.

It can also mean that you try to say too much because quite often, you can get nervous and when we get nervous, we tend to either say too much or skirt around important points that we need to make.

This is why you need to proactively prepare for difficult conversations. Below is a simple process for doing this and whilst it may take some time to do the first time, you’ll find that it becomes easier over time and you’ll be far more effective (and less nervous) when these conversations happen.

Gather facts and information

First and foremost, you need to gather all of the appropriate information that you’re going to need in order to have a successful conversation with someone. For example, if you’re going to speak to someone because of some worrying behaviours that you need to give them feedback on, you should have enough examples of those examples ready to use. Then you should be clear on why those behaviours are a problem, along with being able to explain the negative consequences of those behaviours. 

Sometimes, you may need to get facts and information from colleagues or peers of the person that you’re speaking with. If this is the case, ensure that you’re able to talk about the information without putting these people in a difficult situation with the person you are speaking to. For example, if a peer has given some examples of negative behaviours, avoid saying that this person has directly given you this feedback if possible. This can help preserve the working relationship of your team member and the person who has shared the feedback with you.

Get clear on the ideal outcome of the conversation

Next, think about the outcome of the conversation that you’re looking for and what next steps you’d like to take. Without this, the conversation may lose focus and direction, leading to unnecessary stress and ambiguity for the person that you’re speaking to.

For example, you may decide that an ideal outcome is to agree upon a plan for the individual to improve their behaviour over the next few weeks, providing some actionable steps for them to do this, then agreeing to meet again in two weeks to see how they’re getting on.

You may decide that getting to a solid outcome like this is going to be a step too far, so instead, perhaps a good outcome will be to have the person acknowledge and understand your feedback and have them think about how they can improve, then meeting again the next day to discuss a plan of action. 

Either way, take some time to get clear on what the ideal outcome is and have this in the front of your mind when doing the rest of your preparation.

Write an email to the person (you won’t send it!)

Now, this is a step that may be a bit of a surprise, but it’s one of the most effective steps that I’ve taught to people over the years when it comes to preparing for difficult conversations.

Essentially, you should pretend that instead of having a face to face conversation with someone, you’re emailing them instead. So write an email to them outlining the facts, information, examples, problems etc, along with the outcome and next steps.

This is likely to lead to quite a long email but don’t worry, we’ll shorten it shortly and remember, you’re not going to send it!

The key is that if you did send it, all of the key points, information and the ideal outcome would be communicated to the recipient in an effective and clear way.

The point of this step is to get everything out of your head and onto “paper”. Imagining that you’re writing the most detailed email ever to someone is a great way to do this.

Read the email and pull out the key points

This is where things really start to take shape.

Read the email that you’ve written and highlight the key points. I sometimes print the email out and use a highlighter to do this because it can make things a lot easier. The key here is to read the email enough times that you can see what the true essence of it is. You’ll have used a lot of words and said a lot of things, but what are the truly key points? 

You’ll probably find that you highlight 3-5 key points when you go through this step.

Take these key points and write them down somewhere else, either in another email, a document or in your notepad. 

Use the key points to structure your conversation

Finally, use these key points to map out the structure of your conversation. This helps ensure that you cover the most important points that you need to, whilst not overwhelming yourself with too many details or information and meaning that you miss things out. 

Essentially, the key points become your agenda and given that you’re expecting a difficult conversation, you should aim to have no more than 3-5 core points of the conversation. More than this and you’re unlikely to get through them all or at best, you’ll get through them but not go deep enough.

All of this preparation means that you can go into the conversation as prepared as possible, hopefully leading to an effective conversation, even if it is difficult.

Want to learn how to actually have that conversation? Take a look at this post for a framework that you can use.

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