Skip to main content

The Power of Listening and 4 other tips for Having a Difficult Conversation with an Employee

06 December 2021

If you are a parent, chances are you have experienced having one or two difficult conversations.

If you are in a long-term relationship, you have probably been involved in a difficult conversation. Naturally, you were not the one at fault!

If you have ever had the privilege of managing people, it’s very likely that you have had to have a difficult conversation with one of your team.

In fact, the chances that you have never had to have a difficult conversation are extremely slim.

Yet interestingly, one of the areas of coaching our team at Donovan Associates are often asked for when we coach is advice on how to have ‘that chat’ with… you know… ‘that difficult person’. This is because in truth, many have never previously been coached to lead a difficult conversation.

So let’s start by breaking a myth. There is no such thing as a ‘difficult person’. OK, so there may be the odd exception to that particular rule but in all seriousness, the likelihood of this individual waking up one morning and making a conscious decision to be difficult, just to make your life tricky just doesn’t stack up, at least once the emotions have dispersed.

What does make sense however is that people experience difficulties from time to time; be that in their private life, professional life or sometimes both.

Let’s start thinking about certain individuals as people with difficulties, and not "difficult people", especially if we don’t yet truly understand what these difficulties are.

So how do you go about having a difficult conversation without the need for a tin hat, full body armour and a bucket load of courage?

There are many aspects to this, but to start, here are our five key pieces of advice that will make your life considerably easier when having a difficult conversation in the workplace.,


It is easy to concentrate on delivering the right message, making sure that what you say is compliant and does not breach any employment legislation. And you won’t hear any arguments from us about how important this is.

It is equally important however to begin the thought process by thinking about the outcome and behaviours you are looking for, immediately after the conversation and in the weeks that unfold afterwards. Focusing on your desired outcome will reduce your stress levels and help you to maintain your composure as the conversation unfolds.


When faced with having a difficult conversation, it is logical that you would want it to get off to the best possible start, and therefore the opening line is all important. It is also very easy to get off to the worst possible start. Let’s look at some examples:

Please don’t be offended by what I am about to say… By virtue of the fact you have told them not to be offended… they will be

IPlease don’t shoot the messenger, but… You have now undermined yourself as well as the individual who has tasked you with breaking this news

If it was down to me… Ditto

It has been brought to my attention… Really? Who by? Now that really will be a difficult conversation…

Our advice is to be upfront and honest. The reason we are having this conversation is because…

Oh, and if it really was brought to your attention, there is no need to mention the name of any individuals involved. Just be sure there is some evidence and start by saying that ‘I have noticed…’ If you don’t have the evidence and the conversation is based on hearsay, are you really ready to have the conversation?


A conversation is by definition a two-way process that involves input from all parties. Those all-important questioning and listening skills can easily go out of the window however when a difficult message needs to be delivered.

Linking back to our second point, think about the outcome that you are looking to achieve and which questions you can ask to help you understand their view of the world and how you can progress. The tried and tested TED technique can be very effective here:

Tell me about…

Explain to me….


And make sure you listen. Really listen to what they say. Silence can be awkward but by holding back, giving space and time for your team member to think and speak means they’re more likely to open up, tell you what they really think, what’s really going on.

As William Ury, an experienced diplomatic negotiator says in his Ted Talk, the most successful negotiators listen more than they talk.

And as Zeno of Citium, a Greek philosopher said: “We have two ears and one mouth, so we should listen more than we say. For people like being listened to.” 


Let’s be honest, few of us enjoy being told off or what to do so our internal defence mechanism will kick in whenever we receive a challenging message, especially one that is personal.

Experience has taught us that if we treat people like children, they will oblige and play the role of the child… throwing big ted out of the pram for good measure. This can be avoided by taking care of the language that is used.

Compare for example, “your report had several errors” with “the report had several spelling mistakes and the graph on page 33 was three months out of date

Both statements may be true but the second is based on fact rather than opinion and by focusing the feedback on the report as opposed to the person, there is room to discuss this in the remainder of the conversation.

The use of the word ‘perception’ can also be helpful, especially where the conversation is behaviour based. For example…

Rightly or wrongly, the lack of input and constant checking of emails during the project meeting this morning gave the perception that you appear not to care.

Again, the individual may protest that this was not their intention, but regardless of whether this is true, the perception remains and needs to be resolved.


Plucking up courage to have a difficult conversation can be difficult enough, but there is no point doing so if the outcome of the conversation is vague.

Phrases such as ‘well I hope that has given you something to think about’ are well meant but ultimately mean little.

One way of avoiding an open ending is to send a follow up email clarifying the key points of the conversation and next steps if indeed any have been agreed. Having something in writing that is dated and has proof of receipt can give you something tangible to fall back on.

In some instances, it may be appropriate to invite the other person to drop you an email instead, highlighting their understanding of the conversation and how they will respond. The tone of the email and how long it takes for you to receive it are often strong indicators of how well the other person has received the message and how they intend to proceed.

If you have any questions about having difficult conversations or want to find out more about our other services, please call us on 01295 675506 for a friendly no obligation chat.

To find out more or to book a free consultation: