How can you better handle difficult conversations?

Nobody likes having difficult conversations.

A recent survey showed more than 80 per cent of employees procrastinate on necessary but difficult conversations.

Around 25 per cent of those who took part delayed scary talks for six months. And one in ten put them off for a year.

That’s a lot of vital conversations being avoided and delayed, and potentially never happening.

Difficult conversations might include needing to tell your boss about something happening in your personal life. Maybe it is about conduct in meetings, admitting you have made a big mistake or a performance review where the other person has not been performing.

For a comms professional, one of the more difficult conversations can be giving feedback to a senior leader about their media interview or presentation when they performed poorly.

Maybe you need to find the courage tell the CEO  the crucial comms campaign or podcast you were about to launch is delayed.

How do you stop trying to avoid and dance around these conversations? How can you keep your emotions in check?

And how can you make them that bit easier?

These are just some of the questions we explored in a recent masterclass for members of The Media Team Academy with Kirsty Waite and Dan Boniface from The BCF Group.



A vital first step is to change your mindset.

If you think about a conversation being “difficult”, you are already in a negative frame of mind.

You are convincing yourself it is going to be hard. And you are likely to be defensive and upset when it happens.

What if you call it something else?

“With these conversations, we worry about how we are going to bring the subject up and how we are going to overcome the issue,” Dan said.

“You need to get rid of those negative connotations and think about the goal – to be in a better state than you are now.

“One way to remove that negativity is to change how we think about these conversations.

“Is it a difficult question? Or is it a challenge? When we describe it as being ‘difficult’, that has negative connotations.

“If we can change the mindset to ‘challenging’, it doesn’t sound so bad. You start to think, ‘I can work through this’.

“And actually, we can build up anxiety and trepidation about these conversations and, when it’s finished, it wasn’t as bad as we thought it was going to be.”

Kirsty: “These conversations don’t need to be a big event. They don’t need to be formal sit-down situations. It could be part of everyday conversation. You don’t need to hold them back.”



Workplace culture can also be vital in removing that negativity.

Do you have a work environment where people can raise concerns and problems and where conflict is addressed?

If not, challenging conversations can feel even more intimidating.

“If you are a line manager, create a culture where they can come to you and be open and honest,” Dan said.

“If it is not happening above you, maybe that is a challenging conversation you need to have where you ask for a bit of support.

“Once you get over those barriers and build relations, having challenging conversations is not so difficult.

“Something we talk about in coaching, which is relevant here, is about removing the status. You are two humans having a conversation rather than a boss and an employee.”


How to support yourself through challenging conversations

Well, we’ve already mentioned negativity in terms of how we frame these conversations.

But another aspect of this is the way we prepare for challenging conversations.

Do you build them up in your head because you tell yourself you are not good at them?

“Remove the negative perceptions by being aware of your thoughts and recognising your negative thought patterns and beliefs,” Kirsty said.

“If you constantly tell yourself ‘I’m not good at these conversations’, you will shy away from them.

“Instead, question those thoughts and look for facts that disprove them.

“You can create the story that it is going to be horrible. Or you can create the story that it is a conversation, and you are prepared for it.”


Managing emotions and keeping a cool head

How do you feel about the challenging conversation you are about to have?

Are you calm and composed? Or are you more emotional than the situation warrants?

If it is the latter, you may need to take a minute to gather your thoughts.

“You need to become emotionally aware of how you are behaving,” Kirsty said.

“You need to check in with yourself. How are you feeling? You need to approach the conversation from a calm adult mind. Not a kneejerk reaction.

“Then you can decide whether it is the right time to have this conversation and what you need to have it in a positive way.

“Whereas, if you respond on impulse, that may not be the best way to achieve your end result.”

If someone comes to you as a comms manager with a subject that could lead to a challenging conversation, give yourself a little time.

Go and get a coffee. Have a quick walk around the block. And then come back to them when you are feeling calm.



What do you want to achieve from the challenging conversation?

Before you enter the conversation, make sure you understand the purpose.

“Another thing you can do to prepare for difficult conversations is to understand what you are trying to achieve,” Kirsty said.

“What’s the point of the conversation?

“You need to have objectives and know what success looks like. What is the desirable outcome?

“If you don’t know this going into the conversation, what’s the point?”

Kirsty says you need to consider the outcome for you and others.

“Knowing all this upfront helps you to guide the conversation,” she said.

“The whole point of these conversations is to move a situation forward. That may be asking someone to do something they don’t want to do. It could be talking to them about something they are not aware of.

“How can you move it forward so everyone is happy with what they need to do?

“If you don’t know the outcome, you could go round in circles – and that will be an uncomfortable conversation.”


Would you like access to masterclasses like this?

Speak to us today about becoming a member of The Media Team Academy.

How do we communicate with others?

You’ve reframed the conversation and removed the negativity.

You know what you want to achieve. You feel calm.

What next?

Managing challenging conversations successfully also involves thinking about how we communicate with others.

Dan believes there are a few things you need to consider.

“I’m a great believer that behaviour breeds behaviour, and if we get that right, we can guide the conversation in the way we want.

“Also, put yourself in the other person’s shoes. Lead with empathy and understand how others might feel.”

That means considering their viewpoint. If you are not sure, ask how they feel.

Having that perspective means you don’t enter the conversation with a ‘my way or no way’ mentality.

“You need to think about it as being a collaborative conversation,” Kirsty said.

“Don’t go into thinking ‘I’m right and you’re wrong’. Remove the ego.  You need to listen and understand each other. Understand where they are coming from.”

Also, consider the potential consequences of having the conversation.

Dan said: “If you don’t have this conversation, what will happen? Do I need to have this conversation? Is it necessary? Will it be beneficial? Will it address any performance or behavioural issues?


Embrace the silence

Conversations naturally have moments of silence in them.

When those conversations are challenging, we can rush to fill that silence.

But a better approach could be to embrace it.

“Ask a question and stay quiet,” Dan said.

“We can talk at about 150 to 200 words per minute, but we think at about 700 to 800 words a minute.

“So, what we first say isn’t the whole story. Let the information come out.”


During this exclusive masterclass for members of The Media Team Academy, Dan and Kirsty also explored a model that illustrates how our attitude and behaviour influences others.

They looked at how you can manage challenging conversations when the other person is in denial. And how you can end a challenging conversation effectively when you haven’t been able to reach an agreement.

If you want access to masterclasses like this and want to tap into the expertise of people like Dan and Kirsty, speak to your account manager about joining our learning and development programme.


Media First are media and communications training specialists with more than 35 years of experience. We have a team of trainers, each with decades of experience working as journalists, presenters, communications coaches and media trainers. 

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