The art of having difficult conversations – part 1

You probably looked at this title and thought “The ART??” Yes, you’re reading it correctly. Welcome to a three-part series on the art of having difficult conversations. Any leader will tell you that being able to hold such conversations is an essential skill of a leader.

Having difficult conversations – be it with your Team members or anyone in your organisation – takes practice. There is definitely an art to it – how you approach them, how you carry them out, and what steps you take afterwards.

So, this is what the three parts are going to walk you through: the prep, the conversation itself, and the aftermath. It’s a complex topic indeed. It’s also a skill that is very much possible to be mastered. Let’s do it.

The benefits of holding difficult conversations

“Ugh, I so don’t want to talk to [a person’s name]. It will be unpleasant and stressful, and I can’t predict their reaction”. If a similar thought crossed your mind, I promise you you’re not alone.

Why would you want to put yourself through this kind of a stress? Or anyone else for that matter?

The short answer is because otherwise a problem at hand is likely to keep growing until it becomes impossible to harness. In fact, there are many other benefits of carrying out a difficult conversation:

• you show your integrity
• you address a situation that others are also noticing and are wondering what is going to happen with it
• you show that you don’t shy away from tackling problems; and this makes you a respected leader who exhibits consistency
• if handled right (we’ll get to that), you build trust with the person(s) you spoke with, and other people around you
• and this trust leads to your team members – and other people – being more open and keen to work with you

While having difficult conversations is far from pleasant, it is an inevitable part of being a leader. And the best way forward is to learn and practice how to hold them.

Let’s prepare for a difficult conversation

Before we dive into the prep actions, a word about what difficult conversations may be about.

We quite often think that such a conversation is about a person’s work performance or their inappropriate behaviour. Let’s not forget that there are many other areas that you may need to have a conversation about. For example, a person’s personal hygiene, someone’s bereavement or divorce, or something as odd as someone helping themselves to another person’s lunches from the communcal fridge.

While the topics are multiple, steps to prep are quite universal.

Step 1 – Decide why a conversation is needed

Establishing why a conversation is required is important because this will drive what you want to achieve with it. Being clear why there is a need for holding space for it will help with crafting the content of your meeting.

It also helps with wording your opening line of the conversation. For example:

• I have asked for your time because I noted you’ve been consistently coming in 30mins late to the office, and I’m keen to understand as to why
• I’d like to go through the meeting that took place 2 days ago because I’m keen to hear your take on it
• I know there is a lot going on in your life right now and I’d like to position myself to be of as much support as possible.

Without a clear reason why a conversation is required, the person you’re speaking with will be confused and is likely to be defensive. And this will scupper the potential work on the solution.

Step 2 – Gather the facts

You cannot go into the meeting with statements such as ‘Someone told me’. Make it a rule that you don’t use this phrase.

A difficult conversation becomes more meaningful if you can present facts that support it. Sometimes the facts will be quite obvious – such as the instance of you both being in a meeting that didn’t go very well.

Other times, you will need to do some work to gather the facts that cannot be disputed by the person you’re speaking with. In the example where someone comes in consistently late to the office, you may need to obtain some data from your IT department on their login times. You may also need to keep a note of the person’s ‘appearance’ times.

In essence, the more solid information you have, the less room there is for challenging your statements. And this leads to greater likelihood of achieving your aim of the conversation.

Photo by Vitaly Gariev on Unsplash

Step 3 – Establish your aim for the conversation

This step is super important. And there is a right and wrong way of approaching it. Let’s look at the wrong ways and aims:

• “I want the team member to confess to their wrongdoing”
• “I need the person to agree with me”
• “The person has to apologise at the end of our chat”
• “I need to put them back in their box”

If you set off with similar aims, I can guarantee that you are likely to fail. Why? Because you don’t allow for a CONVERSATION to happen, and you will force the exchange to go only one way. And that is not how to hold difficult conversations (we’ll explore this in Part 2).

So what are the right aims of a conversation? Let’s have a look:

• “I want to better understand the situation that occured”
• “I’m keen to see their perspective to work out our next steps”
• “I’d like to help and to do that I need to learn more from the person on a particular matter”

Notice the words that are used in these statements – ‘understand’, ‘see someone’s perspective’, ‘learn more’.

By establishing your aim around such phrases, you allow for the conversation to indeed be a conversation. You don’t set the aim in stone and potentially lead to a disappointment. And fundementally, you show the other person that you are there to work together on the situation and solution.

Step 4 – Book the time and location

Some situations will require a pretty immediate action. If you witnessed someone being rude or unprofessional in any way, you need to address this as soon as possible. Otherwise, the conversation becomes less relevant.

Other conversations will require time becasue for example you need to gather the facts or data.

In either case, leaving too much time between a situation – a trigger for the conversation – and the conversation itself is not good. Don’t do it.

A classic example is for a manager waiting till the annual review to tell their report they did something wrong months ago. Not only does it leave to confusion – “Why didn’t you tell me this earlier” – it also diminishes the importance of the observation. And suggests you as the leader weren’t ready or brave enough to tackle the problem when it occurred.

The location of your conversation is equally important. Make sure you book a space that allows for a confidential and uninterrupted conversation. Do not hold such exchanges in the office coffee shops or open plan spaces. Show the person you’re speaking with that their inputs will be treated with confidentiality and respect, and they don’t need to worry about anyone eavesdropping.

I hope it is a bit clearer why I referred to the art of having difficult conversations. If you get the preparation right, you’re on the right track.

In the next part, we’ll have a look at the ins and outs of having the actual conversation, such as the skill of listening. In the meantime, I invite you to explore the methods and tools of a good conversation shared by Jefferson Fisher. He is an attorney that has been teaching thousands of people across the globe how to communicate.

What advice would give to a budding leader about having a difficult conversation?

Feature image by Korney Violin on Unsplash