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Managing a difficult conversation at work

Managing a difficult conversation at work
Richard Hiron Mar 23,2021
blog post

In the ordinary course of their daily duties, business owners and managers will need to manage conversations with members of staff that can frequently be challenging or uneasy.

The key to managing these sorts of discussions is to be prepared.

What that means is that you need to have a structure in your own mind about what you want to discuss and how you would ideally wish the discussion to go, but you will also need to flexible both in your approach and your expectations. After all, if you set yourself a goal and then find yourself being confronted by something unexpected, you are likely to be disappointed if things do not go entirely to plan. Furthermore, if you persevere with your goal without considering the impact of what the employee is saying, you could risk causing irreparable damage.

You also need to be prepared for the possibility that a single conversation may not solve the issue at hand and that its resolution may need to be handled across numerous conversations or across a process such as a performance management, grievance or disciplinary procedure. Whilst this may seem disheartening, it is actually a positive step to follow the right course.

You should therefore seek to:-


  • Map out what you want to discuss;
  • Have an idea of what you want to achieve from the conversation, but be prepared for the outcome to be affected by what you discuss. The same outcome may still be achievable, but the actual content of the discussion may also change the goal posts or even the outcome itself;
  • Consider how close you are to the issue at hand. It is likely that the closer you are to the issue, the more difficult you will find it to distance yourself from it. Therefore, you might wish to appoint a colleague with managerial responsibilities who is distanced from the issue to either take the lead in the conversation or to handle it in its entirety;
  • Listen. Bear in mind that, whilst you will have had the time to prepare what you want to discuss, members of staff will often be caught on the spur of the moment by what is being said, so may need time to formulate an answer or may not have the opportunity to refine their answer to you;
  • Be professional. Alongside being at a sufficient arm’s length from the issues for them not to become a personal involvement for you, it is essential that you are professional in your approach. Remember that you will be representing the business in holding the conversation and, whilst you cannot predict or control how the employee will react at the meeting, if you behave unprofessionally, you will risk undermining the mutual trust and confidence that both the business and the employee owe to each other.


This article is intended for information purposes only and not as a substitute for legal advice. TP Legal does not accept any responsibility for any decisions that you may make as a result of reading this article. If you require employment law advice, please do not hesitate to contact us on 01483 751878 or at