Tips for difficult conversations at work


As a boss or supervisor you will unavoidably sometimes have to deal with sensitive and difficult conversations. It could be about passing on difficult messages or bringing up sensitive questions with your employee. Lawyer Anne Lindgren-Slotte gives 8 useful tips on what is good to keep in mind when preparing for difficult conversations.

  • Give time and let it take time

Unpleasant conversations take time. This is something that is important to remember during the entire process. Don’t wait too long to bring up the subject of the conversation.The risk is that the situation develops into a far worse one and will be even more difficult to handle than if you would have dealt with it at an earlier stage.


  • Prepare yourself and structure 

Apply yourself in the subject, structure the conversation and make a plan. Think the conversation through in advance. Try to make the conversation as natural as possible in this sensitive situation. Furthermore, don’t drag the conversation out unnecessarily – this is why it is important with a thought through structure. Especially if your are about to break bad news, think about what questions that could come up during the conversation. Write down the questions and prepare yourself. It could be that they never come up, but if needed you have your answers ready.


  • Show empathy and understanding

It is important that you can put yourself in to the other person’s shoes and can understand the counterparty.You should after all know each other to some extent. In this situation it is seldom two strangers sitting across from each other. Remember that there might be a lot at stake for the person who is subject of the conversation.


  • Read up on what the law says

You should know what the law says about the subject you are about to bring up in the conversation. Which questions are crucial to bring up during the conversation?MAke sure to think this through so you can avoid having to organize multiple meeting because something was forgotten.


  • Check out the right for assistance

Make sure to read up on if the law about employee rights regarding bringing assistance to the meeting, for ex. a lawyer.  Or perhaps you are the one in need of a lawyer present? If the law so states, make sure to inform the counterparty and give them the opportunity well in advance to sort one out. It is not enough to inform one day in advance.The other party should be given the opportunity to prepare themselves.


  • Give more time 

You need to give the counterparty enough time to digest the message. You who initiated the subject for discussion , have most likely been thinking about the subject for some time before the discussion takes place. For example how and when you should bring it up and what questions might arise. However, for the counterparty it might be the first time they hear about it. Depending of the subject and the person, it might take varied time to digest and process it. Especially when there is big issues at stake, it might take a longer time to process.

  • Communication is key

As a boss you need to keep your antennas up at all times and intervene rapidly if there is a problem. Otherwise the problem might grow into a far bigger one.  Invest in preventive measures.  You should try to find natural situation where you can smalltalk with your employees and keep an eye on the situation. IT could be during coffee break, at the water machine or in the corridor. Communication should flow both ways. IT is important for the employees to feel they are also able to bring up sensitive subjects for discussion.

  • Same rules apply for everyone

This is where everything begins – the same rules apply for everyone. We are all different and have different pet peeves. Having everyone apply to the same rules prevents irritation. A discussion about basic rules is already a start.