How to approach difficult conversations as a leader

Lydia Smith
·Writer, Yahoo Finance UK
·4 min read
Close up of two business people having a meeting outside the office
Some managers don’t receive adequate support in order to deal with these situations. Photo: Getty

All leaders have to have difficult conversations at some point. Whether it’s telling someone they aren’t getting a promotion, informing an employee they are going to be made redundant or letting someone go, it is never easy.

“Many people find it challenging to address issues that may cause concern for the other people, it’s no different for leaders,” says Gemma Leigh Roberts, an organisational psychologist and founder of The Resilience Edge.

“It can be a very uncomfortable feeling knowing you need to address a challenging issue, there can be apprehension when you don’t know how someone will react, or dread if you know the information won’t be taken well.”

People who are extremely empathetic may also feel the pain the conversation may cause the other party, particularly if they know the individual personally. If you’re informing someone that they are losing their job, for example, you may be aware that they have a family to support.

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Some managers don’t receive adequate support in order to deal with these situations, too. “Leaders that don’t feel equipped either practically or emotionally to deal with the situation, or don’t have support from the organisation may also find challenging conversations particularly difficult,” Roberts says.

However, putting off these conversations can make things much worse, as you’ll have more time to dwell on how it will go, prolonging the anxiety. It can also be unfair on the employee too, who may know that bad news is coming and want the conversation over and done with. So what is the best way to approach these conversations with a worker?


Leaders often doubt their skills in dealing with the fallout of a challenging conversation and this can lead to rushing through a conversation, almost as if they’re trying to get it out of the way. However, this isn’t an effective way of dealing with the situation, Roberts says.

Instead, it’s important to gather together all the information you need ready for the conversation.

“You might need to gather some advice or feedback, or you may need to check policies or procedures,” she says. “Make sure when you have the challenging conversation you have the facts and data you need ready, so plan when you’ll gather this information before the conversation - and don’t leave it to the last minute. Also prepare to signpost the person you are talking to towards supporting resources, groups or people.”

Show empathy

Showing empathy is about understanding the other person’s perspective and situation and considering what the process may feel like for them. Put yourself in their shoes and consider how they might feel.

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“It’s important to remember however, you can deliver bad news and feel for the person on the receiving end whilst still doing what needs to be done – balancing a professional and personal approach,” explains Roberts.

“For example, telling a team member they’re at risk of redundancy is an unpleasant situation to be in. You can deliver the facts clearly and follow the correct process, whilst also making it obvious you feel for the person at risk, and you’ll do all you can to help.”


If you’re delivering bad news, or having a difficult conversation, it is important to listen when the other person reacts. They may be angry and want to vent, or feel sad and cry. They may react differently to how you might expect because we are all different.

“You don’t know how someone else will react, and this unpredictability and uncertainty can make leaders put off difficult conversations,” Roberts says. “Make it clear to the person you are talking to that you will listen to their response - even if you don’t agree — and you will take what they’re telling you on board. This is a respectful and supportive approach.”

Make sure the person is treated fairly

No matter what your relationship with the individual is like day to day, they need to be treated fairly and respectfully. Ultimately, we never know what people are dealing with in their personal lives and how this might be impacting them at work. Even if you are disciplining someone for bad behaviour, make sure you listen to what they have to say and try to understand the situation to the best of your abilities.

“Check procedures or processes you need to follow, gather feedback from others who may be able to give you some advice on how to approach the situation, and look at the situation from the other person’s perspective,” says Roberts.

“Ask yourself, if you or a family member were in this situation would you feel that although the news being delivered isn’t ideal, the way it’s being handled is fair and transparent. If you can’t say yes to this, change your approach.”

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