How to have tough conversations at work

Tough conversations aren’t easy anywhere, let alone at work where you have to face the same people every day. It’s important to handle difficult discussions with great tact and care. Here are our top tips.

Plan the conversation

Planning what you want to say will help keep you on track and make sure you touch on all the points you want to. But thinking ahead is vital to not only prepare what you want to say carefully but also how you might have to respond. It is helpful to anticipate several reactions from the person you are speaking to from highly emotional to completely understanding. If you can mentally prepare yourself for each reaction and have a brief idea of how you will handle it, this will help to keep the conversation from getting out of hand.

Choose the right setting

Make sure you choose a private setting such as a meeting room that isn’t entirely made of window walls. Or go for a walking meeting away from the office and sit at a park. It’s important to have some privacy away from other people so that the message being delivered is only to that one person and not others around them which may make them feel further embarrassment or shame.

Be direct and specific

Make sure not to distract too much from the purpose of your conversation. The other member of this discussion will likely know you want to talk about something important (hopefully you prepared them for this), so get to the point! Whilst getting there, it’s also good to be specific. If you are too broad, you may seem to be personally attacking the other person. Use specific examples of situations or performance that require improvement or deserve warning.

Act with compassion

When speaking, put yourself into the receivers shoes and hear your words from their perspective. This will help you to adjust the words you use and how you deliver the message, but it will also help you to try and understand why their behaviour or performance has been different. You can ask them questions such as ‘Is everything ok? Has something happened recently where you may need more support?’ Or ‘Is there something else that’s going on that I could help with?’. When you ask these types of questions you show genuine concern and care for the other person. They will be more likely to open up if they know that you understand that life situations can cause changes at work.

Realise the persons values

You can do this before or after you deliver your message, or you can do it at both times. But it’s helpful to let the person know of their strengths and what they bring to the table, not just what they’re doing wrong. If we remind them of their good qualities, we are able to motivate them and let them know we see their potential. It can also soften the blow of any feedback and help them to not attach to isolated negative comments.

Watch your words

Like acting with compassion, it really pays to watch your words. Avoid attacking phrases like ‘Everyone says that…’ or ‘You always…’ and lean towards ‘I’ phrases. For example, ‘I feel that…’ or ‘I have observed…’. Don’t get too emotional yourself, even if the matter feels personal. It’s vital that you remain objective and keep your cool. The goal with your words is to calm down any escalation that occurs, not to light the fire!


You can’t be the only one talking. It’s so important that you listen to the other person. Not only to listen to their side of things but also to clarify anything that may have been miscommunicated. When we listen to where others are coming from, we can gain a better understanding of how their minds work and what solutions would best suit ourselves as well as them.

Think of a resolution/add value

It’s no good to just go into the conversation with the intention of telling someone off. You have to think of and offer a resolution. First you talk and set the tone for the conversation, then you listen and hear the other person. After this, you can calculate out of your pre-planned options (with a mixture of ad-hoc thinking if necessary) what the best course of action is. Never leave the conversation without offering some potential solutions. This in fact should be the whole intent – you want to help someone improve and become better.

Come to an agreement

Make sure you shake hands, or nod heads, or come to any type of professional agreement so that you can measure the success of the conversation. An agreement will also add a level of accountability on both parts so that both you and the other person in the conversation will take action after sharing words. 

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