None of us enjoy holding a difficult conversation in the workplace, but the reality is that they are an inevitable part of every leadership role. Whether it’s addressing poor performance or behaviours, turning down employee requests or tackling personality clashes, it can be tempting to bury your head in the sand. However, mastering the art of holding difficult conversations with employees will enable you to get the best from your team by providing them with the opportunity to grow and improve.
In this article we explore the tactics you can use to handle difficult conversations at work with confidence. We will cover:
- What makes some workplace conversations more uncomfortable than others?
- Examples of difficult workplace conversations
- Key things to avoid when having difficult workplace conversations
- Preparing for a difficult workplace conversation
- Tips for handling difficult conversations at work with confidence
- What to do after a difficult workplace conversation
What makes some workplace conversations more uncomfortable than others?
A difficult conversation in the workplace is one which involves a potentially contentious or sensitive subject, which is likely to result in an emotional reaction from the employee. Managers will often feel outside their comfort zone and worry about how to approach the conversation and how the employee will react. These difficult conversations in the workplace can be particularly hard when the manager has a close relationship with the employee and is concerned about upsetting them and the impact this may have on their working relationship.
However, as Acas states, the ‘ability to be able to talk about very sensitive and emotive issues is an integral part of effective line management and can be critical to managing performance, promoting attendance and improving team dynamic’.
Examples of difficult conversations in the workplace
There are many different examples of challenging workplace conversations, including:
- poor performance, conduct or attendance issues;
- personality clashes;
- redundancy situations;
- personal problems impacting in work;
- internal job applications;
- performance reviews;
- hygiene issues; and
- declining employee requests, for example a request for a salary increase, annual leave or flexible working.
With some of these examples a formal procedure may be more appropriate than an informal workplace conversation. Please contact our team on 0330 223 5253 or office@fitzgeraldhr.co.uk for further advice on disciplinary, capability, absence, flexible working and redundancy procedures.

Key things to avoid when having a difficult conversation in the workplace
When a difficult conversation in the workplace is handled poorly, this can have a significant impact on trust, morale and productivity.
Don’t bury your head in the sand
Most importantly, don’t avoid holding a difficult conversation in the workplace. All too often managers shy away from difficult workplace conversations in the misguided hope that the issue will blow over. As Acas states, not only does this deny the employee the opportunity to improve, it could also mislead the employee by giving them the impression that everything is fine. Furthermore, it could have a damaging impact on productivity and team morale.
Don’t wait too long
Similarly, don’t procrastinate and leave the conversation for too long. It’s much easier to have a quiet word at the first sign of trouble, than to leave things to fester or escalate.
Don’t sugarcoat
In an effort to avoid upsetting the employee, another common mistake is to sugarcoat the message. As Forbes states, sugarcoating just ‘dulls the message and robs the employee of an opportunity to grow and improve on skills and potential’.
Don’t become emotional
Finally, if the conversation doesn’t go smoothly, avoid raising your voice or becoming emotional as this will only encourage a similar response from the employee. Instead, remain objective and focus on the facts.
Preparing for a difficult conversation in the workplace
Before approaching a difficult conversation in the workplace, it’s vitally important to plan and prepare…
Build trust
Building a trusting relationship with your employees will make it easier to navigate difficult workplace conversations, as employees will feel more comfortable receiving constructive feedback and will know that your intentions are positive. They will also be more likely to speak to you proactively if they are experiencing difficulties.
Develop trust by building rapport, as well as being available, approachable and supportive to employees. In this article, we explore the organisational benefits of psychological safety and trust.
Think about the practicalities
Carefully consider the timing of the meeting. It’s important that the conversation takes place without delay. Make sure you allow sufficient time for the meeting, bearing in mind the employee might need to take a break from the conversation if they become emotional. Don’t schedule the meeting immediately before an important deadline, as the employee may need space to process the feedback.
The conversation will ideally take place in person, although this may not be possible with a home-based worker. Choose a private location where you won’t be observed or interrupted, such as a meeting room. Consider the layout of the room; sitting opposite someone can feel quite formal. Before the meeting starts, switch your phone off to ensure you give the conversation your full attention and don’t become distracted.
Don’t wing it!
To prepare for a difficult conversation in the workplace you need to have established the relevant facts. If the purpose of the meeting is to discuss a performance, conduct or absence issue, make sure you have specific examples that you can share with the employee and don’t forget to check the relevant employment policies.
Think carefully about how you will approach the conversation. An article in the Harvard Business Review recommends asking yourself ‘what’s the best way for this person to hear the message?’. It can help to jot down notes and key points ahead of the meeting, but don’t make the mistake of scripting the meeting as things rarely go to plan and it’s difficult to anticipate how the employee will respond.
Example
Bob was late for work on two occasions last week, and didn’t contact Tina, his manager, to let her know that he was running late.
Tina has a close working relationship with Bob and has noticed that he hasn’t seemed his normal self recently. In preparation for the conversation, Tina makes sure she has written down the dates that Bob was late, and the times that he arrived. Tina also prints off the Absence Policy, which states that employees are required to contact their line manager before their normal start time if they are running late.
Tina considers how best to approach the conversation with Bob.
Tina decides to start the conversation by referring to Bob’s recent lateness and asking if everything is ok given that this is out of character for Bob.
Tips for holding effective workplace conversations with confidence
If you approach difficult workplace conversations from a position of empathy, compassion and honesty, and you are willing to listen to the employee’s perspective, it is more likely that the conversation will be effective. Here are some tactics for holding challenging workplace conversations:
Be clear, specific and honest
It’s important to be clear and specific to prevent miscommunication and to ensure the employee understands the issue and can change their behaviour where appropriate.
Speak honestly with the employee, and don’t give false hope. This will just make things worse in the long run and will damage the trust in the relationship.
Actively listen
Give the employee space to explain the situation from their perspective. Listen to what they have to say without preconceived notions or judgment. Active listening techniques include:
- Remaining present, i.e. maintaining your focus on the employee rather than becoming distracted or preparing your next response.
- Asking clarifying questions and paraphrasing.
- Using non-verbal cues to show that you are listening, i.e. eye contact, open body language, nodding in acknowledgement.
- Observing their non-verbal cues.
This will show the employee that you value their perspective and is likely to mean that they will be more receptive to the conversation.
Put yourself in their shoes
Always be mindful of the emotional impact of the conversation and treat the employee as you would want to be treated in that situation. Even a conversation to dismiss an employee can be done respectfully and with empathy and compassion. As the Harvard Business Review states: ‘It might not necessarily be pleasant, but you can manage to deliver difficult news in a courageous, honest, fair way’.
Respond appropriately to emotional reactions
Difficult workplace conversations can provoke a wide range of emotional responses from employees. Some employees will be really open and receptive to feedback, while other employees may become upset or angry. Make sure that you remain calm and professional in this situation. The conversation won’t be effective if the employee is too upset or angry to listen, so consider taking a break or adjourning until another day. The individual may need some space and time to process the feedback before continuing with the conversation.
Take a collaborative approach
Act collaboratively by encouraging the employee to brainstorm ideas together, rather than dictating the solution. Use questions such as ‘how could we do this differently in future?’ or ‘do you have any suggestions for how this could be improved?’. Collaboration will encourage accountability and will improve the likelihood of a positive change.
Agree clear expectations
To avoid ambiguity and a lack of clarity, close the meeting by summarising the expectations for the future.

What to do after a difficult workplace conversation
After the difficult workplace conversation takes place, it’s important to check in with the employee to see how they are. Once they’ve had time to process the conversation, they may want to discuss the feedback further or ask questions. This ‘check in’ is a way of reconnecting and ensuring the relationship is maintained.
Keep an eye on their progress and celebrate successes to keep them motivated. If progress falters, then quickly address this with them and brainstorm how to get back on track.
To avoid a breakdown in trust, make sure you treat all team members fairly and consistently by holding them to the same performance and behaviour standards. It’s also really important that you maintain confidentiality, as failure to do so can damage the relationship and contribute to a toxic working environment.
How we can help
If you would like advice on how to hold a difficult conversation in the workplace, please contact our team on 0330 223 5253 or office@fitzgeraldhr.co.uk. We would be delighted to help you.
Further reading
We hope you found this guide useful. You may find the following articles on our Knowledge Hub an interesting read:


