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Difficult Conversations at Work

June 19, 2024

How to Have Difficult Conversations at Work

A manager has an individual within their team who works remotely, and they are struggling to get to grips with the progress being made on projects. They feel that communication is poor and other members of the team are now saying the same. The individual is very friendly and nice, and the manager knows that they have some personal issues at home. As a result, the manager is reluctant to talk to this individual about the concerns as they don’t want to cause any upset, so they avoid doing it and this continues.

A manager has someone in their team who has had several sickness absences from work over the past 3 months for a variety of reasons including anxiety and stress. The manager wants to talk to them about this to understand what is causing the stress so they offer support, but they don’t want to stress the individual out even more by scheduling an absence meeting. The manager decides to leave it and see how it pans out.

Do either of these stories sound familiar? You can see that the manager is coming from a good place, but by avoiding these difficult conversations are they just making matters worse in the long run?

Having worked in HR for the last 30 years, I have seen, advised on and been part of many difficult and sensitive conversations at work. So, in this article I aim to impart some of my experiences and advice to help you manage what will inevitably be some difficult conversations at work that you experience during your career as a manager or in HR.

Difficult Conversations Come with the Job

Having difficult conversations at work is all part of being a good manager or working in HR. Managers, however, are often promoted to that role because they are good at the technical areas of their job rather than being experienced at people management. They don’t necessarily have the skills to have these types of difficult conversations with members of their team. Most people don’t like conflict and don’t want to upset people, especially those that they work with every day. This can make having these sorts of conversations anxiety inducing for many managers, so they avoid them at all costs.

Yet managing sensitive issues is an important part of a manager’s role to ensure good performance and attendance at work. If done well, conversations like this can be very healthy and productive but if done badly, they can cause even more issues and a bad atmosphere all round.

management difficult conversations at work

The Types of Difficult Conversations

There are many different types of difficult conversations a manager may have with a member of their team at work. These could include underperformance, disciplinary issues, that their sickness absence levels are too high, timekeeping is poor or that they are at risk of redundancy. There could also be issues within the team where two individuals are in conflict at work and there are constant clashes. It is your role as their manager to support them to work through these issues.

Good managers will address issues quickly and will be well prepared. Even if you think the issue is a one-off, it is best to discuss it now so if it does happen again in the future, you have something to build upon.

The Benefit of Having Difficult Conversations at Work

In my experience, most people don’t come to work to do a bad job and most people would prefer honest feedback about their performance. If you keep this in mind when preparing and having these conversations, then it will help you stay on track and focussed on what you want the outcome of the conversation to be. Remembering that you are there to help and not to judge will or cause any further trouble will enable you to remain focused on solving the problem at hand.

Providing honest and constructive feedback gives the individual the opportunity to change things before they escalate further. It also provides them with the opportunity to tell you about any issues that may be impacting on their performance or attendance that you weren’t aware of. This then gives you the opportunity to work through this together and put things in place to help them improve eg: working more flexible hours, having more regular check-ins and so on.

Although having these conversations may fill you with dread, avoiding them can cause you and the individual even more issues in the long term. You will have on-going underlying stress and worry if things have not been addressed. It is unfair to withhold the feedback from the employee as they may believe that their behaviour is acceptable and not realise where their performance is not to standard. Also, if you don’t speak to them directly it makes it very difficult to start any sort of disciplinary, capability or performance management process. I can’t tell you the number of times issues have not been addressed, then come to a head and a client calls us up saying ‘I want to dismiss them!’

And don’t forget that the negative implications go much wider than just you and your direct report. Quite often the issues will be negatively affecting other members of the team, as well as team and organisational performance. Others may become resentful as they can see problems are not being addressed and this may result in their performance declining or their stress levels increasing as it impacts on their workload.

How to Approach Difficult or Sensitive Conversations

The two key pieces of advice I would give on this is to prepare well and deal with it quickly. They may sound like contradictory comments but there is a balance to be struck between the two. Go in too quick without preparing and you are unlikely to get the outcome you want. Leave it too long and the issue can get worse, morale may be falling, resentment is kicking in and you will be constantly stressed about it.

So, here are my top tips for holding difficult conversations at work.

Before the meeting: (preparation and planning)

  • Where will the conversation happen?
  • How long the meeting will be (allow enough time)
  • What outcome you would like?
  • Ensure you won’t be interrupted
  • How will you approach the issue (often a good way is to ask them how they think it is going)

During the meeting: (listening and communicating)

  • Avoid being personal or judgemental
  • Remain calm and take a break if necessary
  • Silence is golden (give them and yourself space to think before speaking)
  • Listen to what they have to say
  • Give examples to support what you are saying
  • Talk about the impact the behaviour is having
  • Ask the employee what they think they can do to change (rather than telling them)
  • Offer support to help them do this

At the end of the meeting: (summarise and close positively)

  • Summarise the meeting and agree next steps
  • End on a positive note
  • The key thing is to get the conversation completed while still maintaining a productive working relationship

Every Person is Different so Every Difficult Conversation is Different

The thing with managing people is that we are all different, we all have different personality, styles and different triggers. If you think of the Fight, Flight and Freeze responses to stressful situations where you feel under threat, you will be able to understand what is happening better. For example, the employee may get angry or defensive (fight), try and change the subject or divert attention elsewhere (flight) or go very quiet (freeze).

So, when holding these meetings, no matter how much you plan and how experienced you are, you are going to have to be constantly reading the room and gauging the atmosphere. Then adapt your approach accordingly. This is where the real skill lies. You won’t always get it right but try not to beat yourself up about it afterwards. Learn from it for next time.

And if in doubt get support and advice from your manager or HR.

Claire watt

Article by Claire Watt (FCIPD)
Managing Director at DittonHR

Claire is a qualified HR and training professional who is a fellow member of the CIPD. Claire has worked in HR and Training since 1994 and is highly experienced in all areas of her field.

Claire is a Psychology graduate with a Masters in Personnel and Development, qualified in Psychometric Testing (Level A and B) and an Executive Coach. Her experience spans across a variety of sectors including the professional services, retail, not-for-profit and charitable.

Claire’s most recent roles have included Executive Director of People at Samaritans, responsible for all people aspects of the charity both employees and volunteers, and HR Director at the National Centre for Social Research. Claire has also written for the online HR resource, XpertHR.


Claire recently won the HRi Inspirational Indie Award for Inspiring and supporting other HR Indies and making a significant positive difference towards the HR Indies Community 


Claire Watt of Ditton HR Ltd won the Small Business Leader of the Year Award at the 2023 Surrey Business Awards. Her strategic vision and effective leadership have been pivotal in driving her business forward.