How to handle difficult conversations at work — 7 tips to make it easier

29 July 2022
 minute read

Table of contents

Preparing for a difficult conversation with an employee? Here are some psychologically informed tips on how to make it a lot less painful and awkward.

Few of us like dealing with conflict, breaking bad news or seeing another person upset or angry. And it can be especially hard to have to navigate these things in a professional setting.


In part one of our series on handling difficult conversations at work, we looked at the deeper psychological reasons for why we dread these interactions so much. Now let’s look at smart strategies that managers and HR professionals can take to make tricky chats a lot less tricky…


7 steps for managing difficult conversations at work


A core part of being a manager is knowing how to steer awkward or painful interactions tactfully. Here are a few key steps:


1. Decide on the purpose of the conversation

Are you trying to better understand an employee’s behaviour? Help them to improve their performance? Issue them with a warning? Be clear about your goal as this will affect the direction that the conversation takes.

For instance, if you are raising the possibility of redundancy then you may want to keep small talk at a minimum at the beginning of the chat.

2. Plan it in advance

Refer to notes if it helps you communicate clearly and specifically but don’t script it. It’s good to have an idea of what you want to say but you also want to avoid seeming practised or robotic. 


Also, think about how you want to be in the conversation and what values or qualities you want to embody. For example, if one of your core values is fairness, think about how you can bring that to the interaction.


3. Be willing to manage your own emotional state

You can’t control how the other person will react but you can aim to steer your own reactions. Set an intention to stay as calm, compassionate and assertive as possible.

Also, have you noticed in the past that these kinds of conversations trigger a younger part of you or a particular protective strategy (fight, flight, freeze or fawn)? If so, remind yourself of past successes and try to connect to the capable adult side of yourself.


4. Be understanding without taking responsibility

Allow the other person to feel how they feel without taking responsibility for their feelings or feeling you have to make everything comfortable. As we explored in part one, people can react in all sorts of ways to difficult conversations. Remember to show empathy and set appropriate boundaries where needed. 


Bear in mind that even if they react negatively, there’s a good chance it’s not personal. Instead, they are probably responding to the situation or what your role represents to them.

5. Aim to reach an amicable solution

Of course, this isn’t always possible, especially with issues like rejecting pay raise requests. But even in situations where it isn’t, try to make sure the employee feels seen and heard, even if you couldn’t give them what they wanted.

6. Make sure everything has been understood

Where appropriate, try to have a recap at the end of the meeting. For instance if the issue is with performance, then create an agreed-upon progress timeline.

7. Reflect and learn

How do you think you handled the meeting? What are your growth areas? How do you think you can do better next time? 


Remember not to be too hard on yourself if everything didn’t go perfectly. Difficult conversations can bring up painful emotions in both you and others, so it’s natural for there to be awkwardness or tension.

7 tips for creating a better interaction


With all of the above in mind, here are some ways that you can successfully navigate a challenging conversation in the moment:


1. Try not to get personal

If you’re experiencing strong emotions, you’ll likely achieve a better outcome if you manage your own feelings first before meeting the other person’s. Also, avoid sweeping generalisations or assumptions about the employee’s personality or character, as this could feel like an attack. Stick to the facts and to communicating both compassionately and assertively. Avoid shaming or blaming.

For instance, it’s more productive to highlight specific incidents where someone has forgotten to complete tasks than to say ‘You seem to be very forgetful’. Aim to focus on the pattern of behaviour rather than the person.


2. Listen carefully and deeply

Try to understand their perspective on things. Let go of your assumptions. Remember that opening up can be difficult for some people and they can be fearful of the consequences. Try to reassure them of confidentiality, where possible. Ask deeper questions if it feels okay to do so (but don’t push too hard).


Ask yourself: what do you think the problem is? What does the other person think the problem is? Is there a difference? If so, how can you reconcile this? Because your idea of what the issue is might be totally different from theirs. For instance, for you the problem could be their repeated lateness. For them, it could be that the company’s policy against flexi-time  — and the fact that they have to get their children to school across town — makes punctuality difficult.


3. Show empathy

Repeat what they have told you to show that you have understood. Make sure to acknowledge their feelings. But remember that your role is not to be their therapist. If the person discloses mental health issues then ask if there are any accommodations that would help. You could also offer guidance on additional support that they could access, for instance, your workplace wellness programme.


4. Aim to stay calm and within your window of tolerance

If you come in all armoured up because you think the conversation will be difficult, you’re likely to receive a defensive response back. If you find that things are getting tense or escalating, then slow down the pace of the conversation. You could even suggest time out for a break if needed. 


One way to deal with your own feelings of distress or anger is to observe those reactions in a mindful way. Ask yourself: ‘How am I feeling in my body right now?’ ‘What emotions are coming up for me?’ ‘What is this interaction reminding me of?’ Then aim to breathe deeply and press your feet firmly against the floor to ground yourself. Give yourself time to think before you respond. Speak slowly when you do.


5. Try to balance negatives with positives

If you’re giving someone a poor performance review then also try to highlight their strengths and things that they have done well. Starting with this is more likely to enable people to hear more challenging feedback constructively. Aim to end the conversation on a constructive note, focusing on how they can improve and how you can best support them.

6. Be illustrative and specific

If you need to see an improvement in performance, give concrete examples. For instance, what does ‘good’ look like to you? Are you helping your employee to create goals that are S.M.A.R.T.  — Specific, Measurable, Achievable, Relevant and Time-Bound? 


7. Try out the T.A.L.K. technique

This approach was created by the Chartered Management Institute as a way to manage difficult workplace conversations. It stands for the following:

T – Think about framing the conversation differently. If you view it as ‘difficult’ then it’s more likely to be difficult. If you frame it as a positive, constructive opportunity for growth then it could feel more positive for you both. 


A – Always use clear, simple and neutral language. Try to be specific with your examples rather than making sweeping statements. 


L – Listen to what the other person is saying and try to understand their point of view. 


K – Keep the focus on the issue, not the person. For instance, focus the discussion on performance and behaviour, rather than assumptions about the person’s overall character.


The truth is that no matter how professional we aim to be at work, none of us can fully leave our past experiences at the door. That is why difficult conversations can be so painful at times, because for many of us they bring up old patterns, dramas and wounds. 


And often, people aren’t even aware that this is happening — all they know is they are suddenly feeling deeply ashamed, angry or afraid. However, a good manager will learn how to hold space for the human side of every interaction, although it does take time and practice.


And by preparing for difficult conversations in advance, learning to be aware of your own reactions and taking the time to really listen, these interactions can feel less difficult. At their best, they can even be an opportunity for greater growth and self-awareness for everyone involved. 


Want to take employee wellness to the next level? Ask us about our on-demand, expert therapy packages for businesses. 

How to handle difficult conversations at work — 7 tips to make it easier
Clinical Director
Lumo Health team
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