Friday, 10 March 2023 10:02

Holding Difficult Conversations

Difficult conversations are difficult because we don’t want to hold them; and in particular, initiate them. There’s also the fact that we believe the person with whom we’re going to hold the conversation probably doesn’t want to hear what we’re going to say either, which is often the case. But hold them we must, and as employers, it is incumbent on us to do so professionally, and whilst maintaining everyone’s dignity.

Support with holding difficult conversations continues to dominate as a reason why our clients contact us, and as an area in which we are asked to provide guidance. It’s clearly not just us that finds this. Numerous books have been published on the subject and we often see training courses like our own, to tackle it.

It’s pretty easy to come up with a list of the types of conversation or subject matter that make for a potentially difficult conversation. For example, to tell someone they are underperforming, that they can’t have the holiday they asked for, that they need to do a job no one wants to do, that they’re going to be made redundant, that they smell.

But it’s not the subject matter that makes a conversation difficult; it’s the potential emotions in ourselves that it might induce, namely:

  • Fear (of conflict): We’re afraid that the person or people we must speak with won’t like or agree with what we are going to tell them and so conflict will arise. Most people will go to some effort to avoid conflict so it’s understandable that we don’t want to put ourselves in a position where conflict is a potential outcome.

    As a people manager in an organisation however, we sometimes, have to do or say what is in the best interest of the business rather than what is going to keep our own personal relationships or popularity intact. Have indisputable facts prepared and behaving assertively without being confrontational will prevent the other party from finding a conflicting standpoint.

  • Embarrassment: Ill-preparedness is the main cause of embarrassment. If we don’t have all the facts or feel that we may not have all the answers, especially if a conversation is at risk of taking a direction we’re unsure of, we worry that we’re going to look foolish and become embarrassed.

    A topic of conversation might be of a delicate or personal nature, but if we are prepared in what we plan to say and how to approach it, there is no need for the conversation to be embarrassing and therefore difficult. Remain factual and offer support. Not discussing an issue it won’t solve the problem.

    Embarrassment can become self-fulfilling when it comes to making conversations difficult. If poor behaviour or performance remains unchecked for a period of time, possibly because we fear conflict, then it’s likely to be embarrassing to justify why the behaviour has suddenly become an issue and is no longer acceptable .

In our experience, the discomfort that might be felt in having to hold a difficult conversation is rarely as bad as has having to deal with the results of failing to hold the conversation  We have come across some quite convoluted and costly courses of action that individuals have taken in order to avoid having to hold a difficult conversation. In reality, they’re just kicking the problem down the road and creating a much bigger issue that is going to have to be dealt with eventually.

If you feel that a difficult conversation is looming, here are some tips that can help:

  • Be prepared. Make sure you have as much information as you think you’ll need and have a clear idea of the outcome that you are after. Think of a mental flow-chart so you can keep the conversation on track.
  • Get on with it. Preparation is good but don’t use it as an excuse for procrastination.
  • Make an appointment. Don’t just call an ad-hoc meeting. Pre-arrange a time and date in a suitable, private environment to add formality to the meeting and gravity to your message.
  • Be direct but use open questions. Don’t beat around the bush. Get to the point of your discussion but use open questions to draw out the subject’s views. Eg. “We’re meeting today to discuss your sales figures. How do you think you are doing?”.
  • Keep emotions in check. Be aware that the subject of your conversation may cause emotions to run high. Keep your composure at all times and don’t get personal – show empathy.
  • Find a solution together. Where possible, ensure that the outcome is agreed between you and that both parties “buy-into it”. Create a written next-steps plan if needed which will aid your position if the issue arises again.

Holding difficult conversations is a perpetual issue and we run full and half-day workshops on the topic, as well as including it as a module in our ILM programmes. If required, we can come on-site and hold difficult conversations alongside you or on your behalf. The best option however is to learn to hold them for yourself.

Talk to us about some training or coaching for you and your team. Contact us on 01452 331331 or e-mail This email address is being protected from spambots. You need JavaScript enabled to view it.


Read 969 times Last modified on Friday, 09 February 2024 15:16


HR Champions provide first class HR and Employment Law support and advice to UK businesses; operationally and strategically. If you're an employer you'll potentially need some, if not all, of the services we offer.

We deliver excellent management and soft skills training suitable for all organisational levels. We are ILM and City & Guild accredited and Ken Blanchard approved.  





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We have clients all over the UK but predominantly within about an hour's drive time of our offices; in Gloucestershire, South Gloucestershire, Worcestershire, Bristol and Swindon & Wiltshire.