A Guide to Difficult Workplace Conversations

difficult workplace conversations

Is there ever a good time to have difficult conversations at work, and is there anything we can do to make them easier for everyone involved? Conversations around the topic of mental health and mental wellbeing of staff can be the hardest of all. So, how do you start a conversation on mental health in the workplace? Is it best to plan a conversation on workplace wellbeing and see how employees respond? Should you use a scheduled or annual review to talk about depression, anxiety or other mental health issues and make this the only time the topic is discussed? Or is there a different, proactive approach that is worth consideration?

Our founder and Mental Health Mentor, Craig Fearn, explains how you can be part of the solution and the difference that a few words can make when you take the time to plan them.


Many of us will have experienced hard conversations at work – either on the receiving end, or starting them. Difficult conversations are an essential part of a management role, but don’t let a bad experience put you off trying to do better. And where mental wellbeing of staff is concerned, you owe it to everyone to find the right words and to keep the exchange as smooth as possible. Mental wellbeing is making the news week after week and businesses are becoming aware of the responsibilities they have to safeguard the wellbeing of their employees. But awareness about the topic is still low, some stigmas persist and sadly, people may be reluctant – or resistant to – accepting invitations to join these conversations.


So, the very best thing you can do is remove the word ‘difficult’ from the equation – and treat it positively and like any other conversation you will have this week where you expect a positive outcome. It all starts with planning: the key to successful outcomes is to learn how to handle tricky conversations in a way that is less painful for you, and less pain for the person you’re talking to.

Here at Business Mental Wellbeing we’re fans of action and goals over words and directives. We also like to stay focused so we can give the best service to the people we work with – and acronyms and visuals are a key part of this process. So, here we are: EVENT, a handy aide memoire to help you plan a workplace conversation about wellbeing and mental health.




And first up is Engage, which is is the purpose of the meeting. As with all processes it is massively important to have buy-in from the other person. If this does not happen then there is no point in the meeting and this is a key element to the mentoring approach in mental health. Remember, the meeting is not about sickness absence management or productivity. The meeting is happening because someone is going through something that is having a negative effect on their mental health and it may or may not be caused by or worsened by something happening in the workplace.


Also remember that simply being called to a conversation where wellbeing or mental health is on the agenda will increase their anxiety levels – and defences may also be put up. Active listening is a huge part of engagement, so reassuring the other person that you are genuinely interested in them and listening to what they have to say will help you establish how you can best support them during this difficult time.




Wellbeing meetings are incredibly valuable for everyone and for the overall health of the business. But to keep value in mind, difficult conversations about mental wellbeing must be about the person who is in the room with you – and no one else, and no other issues. Other topics may come up – such as performance or absenteeism – and these can be noted for future discussion. But this first meeting is not the place for these conversations. And it certainly isn’t the right place to be talking about anything from a company perspective.


The most important person in the room is the person you’re talking to: it’s their thoughts, their feelings and their fears that you are here for and nothing else. By actively listening to what is being said you are demonstrating that this person is valued, not only by the company, but by you. This will help you to build trust and, ultimately, it will enable the conversation to flow and more delicate issues may be raised.



If you think of yourself as the facilitator here not the driver, trust will continue to develop. Encouragement isn’t just verbal –you can show encouragement by expressing vocal support, with your body language or in some cases a non-judgemental but reassuring silence.

My top tip for the Encourage part of the programme is to enjoy the silence: Remember silence doesn’t always mean that people have finished talking or that they do not wish to continue. The silence may indicate that a moment for reflection is needed, that someone needs to gather their thoughts or that a difficult topic is round the corner and your colleague needs a moment to prepare for this.


Mentors, like counsellors, do not hold the magic key to all the answers. We may have suggestions or ideas based on what is talked about, but without engagement and two-way discussion, they are meaningless. Whatever outcomes of this meeting – be they future meetings, changes or objectives – these are not yours to decide. Further, determining next steps is incredibly important to the successful outcome of difficult conversations. Obviously, policies and procedures must be kept in mind and objectives are more likely to be achieved if they are realistic, but the most important thing here is to negotiate. Sometimes, the solution can be straightforward, but you will never know if the negotiation phase doesn’t take place.


It’s as important to set the appropriate timetable as it is to get the first phase right. You’ve established trust and together you have negotiated objectives. So, how does a difficult conversation become an ongoing dialogue, and is there a difference between regular conversations and mentoring? The first conversation should be just that – the start. People seek meaningful connections with other people and this is the key to mentoring for optimum mental health.


But like counselling, mentoring takes time and in the case of wellbeing mentoring that is being organised by the workplace, this needs to be timetabled and prioritised. There are many benefits to working with an external mentor, especially when workplace stress or transitioning back to work from a period of absence need to be addressed. As with any consultant that a business engages, there are credentials and qualifications to be checked and the selection process should be as rigorous as time allows.


People seek meaningful relationships with people and every business, along with its employees, is different so it is important to find the right dynamic and what will work with your business. It all starts with one conversation.

Craig is a highly regarded practitioner and mentor with more than 20 years’ experience working 1:1 with small businesses and with global organisations. Business Mental Wellbeing is a digital-first business, we’ve been confident using video technology for many years and we strive to make the businesses we work with feel instantly at ease.


Read more about why our programmes are always bespoke here.


Image credit: Christina Wocintechchat, Unsplash.


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