Difficult Convos

How to Have Difficult Conversations at Work

5 min read
Lynsey May Sutherland
Lynsey Sutherland

No one enjoys having difficult conversations. 

The very thought of it can be anxiety-inducing, especially when you’re worried about hurting someone’s feelings or provoking a negative reaction. But if you want a happy and healthy workplace with a high-performing team, you must step up and have those tricky conversations. 

Recently, a poll by VitalSmarts found that more than 80% of workers were avoiding a conversation they knew they needed to have – and that 11% of those would leave their job rather than talk about the problem! 

The only way to ensure that issues are addressed promptly is to create a culture where difficult conversations don’t have to be scary – and here’s our complete guide to getting started.

What are difficult conversations? 

What is considered a difficult conversation can vary widely and depend on the person you’re having the difficult conversation with. 

A conversation about underperformance or wellbeing can be straightforward with someone balanced and calm. On the other hand, it can be daunting if you’re planning a similar discussion with someone who’s feeling scared or angry. 

However, putting a conversation off very rarely results in the problem going away. In fact, without intervention, it’s far more likely to escalate. 

Examples of difficult conversations 

Some very common tricky conversations at work include:

  • Investigating reports of bullying in the workplace
  • Discussing employee underperformance
  • Turning down employee requests or ideas
  • Carrying out a disciplinary meeting
  • Notifying employees of potential redundancies

What you need to know about having difficult conversations 

The biggest thing to remember about difficult conversations at work is that they don’t have to be. They can be a hugely valuable opportunity for change and a great way to build trust, as open and honest communication can help foster a good workplace culture. 

There’s also evidence that your conversation may not be as emotional as you think. A study found that 82% of employees feel comfortable engaging in honest conversations about work topics with their managers.

How to handle difficult conversations: 

We wanted to give you some handy advice for getting to the heart of the matter and keeping cool. 

But some official training can also be helpful for your organisation, as around 61% of people said they would like to learn how to manage workplace conversations more confidently. 

Training can go a long way – especially for middle managers and anyone hoping to become successful disruptive leaders

Preparing for the conversation 

Here’s our step-by-step guide to ensure you’re well-prepared and ready to handle your next difficult conversation.

1. Check in on how open and honest your culture is

Ideally, you will have built an open and honest workplace culture that allows you to communicate well with your employees. 

If you’re not sure how successful your attempts have been, or you’re worried that you’re not seen as an empathetic leader, you may need to put extra focus on ensuring that your employee feels reassured and respected in that moment. 

If you have a supportive culture with a strong background in employee recognition, you might find you will balance out your difficult conversation with positive reinforcement. 

2. Give plenty of warning and share the key points beforehand

No one likes to feel blindsided. Sharing the topics you’d like to cover allows employees to think about their responses and mentally prepare themselves ahead of the meeting. It can also keep people grounded and avoids undue feelings of stress or paranoia. 

For example, it’s much better to say, ‘I’d like us to discuss your KPIs around time management, whether there’s anything specific that’s affecting your performance and what we can do to help’ than to say ‘we need to talk about your performance’. 

The first one clearly shows that you are searching for a solution, and the second suggests there’s a telling-off on the cards. 

3. Stay on topic and try to stick to facts

It is almost inevitable that emotions will run high when it comes to complicated conversational topics.

This counts for your employee and also for you. However, it is your job to try and keep things calm and constructive. 

One good way to do this is to stick to the facts. Come prepared with specific problems or incidents to discuss, and make sure you don’t get drawn off down paths that aren’t relevant to the conversation. 

4. Remember that this is about teamwork and understanding

For most difficult conversations, the real aim is to find out what is at the heart of the problem that prompted the need for discussion. It’s about empathy and understanding more so than agreement. 

It could be that you are unable to come to a consensus about the particular issue, but what you can do is work on a solution or way to alleviate some of the stress or negative outcomes that might be associated with it. 

Treat a difficult conversation as an opportunity to work together, and your employee is far more likely to be motivated to help.

What to do after having a difficult conversation 

Immediately after the conversation, schedule some time for you and your employee to cool off. 

Tell them to go out and get a coffee, take a brief walk, and do the same for yourself. This will give you time to cool off and process residual emotions. 

It’s also very important to book a future catch-up, where you can look at the topic raised and see if there have been improvements or whether it still needs attention.

This will help you both stay accountable and demonstrate that you want things to change for the better. 

Transform your culture with Mo

Recruitment Collaboration
Book a free demo to learn how Mo can help you:
  • Improve employee engagement scores
  • Reduce employee churn
  • Build a collaborative culture
Book your free demo

Mo is an employee recognition and engagement platform that can help leaders improve collaboration and morale, reduce employee churn and drive change. 

Our platform creates a vibrant culture by developing team habits, encouraging people to celebrate success, recognise results and appreciate colleagues.

Your complete toolkit for connecting and motivating teams in the new world of work. Book a demo with our team today!

Join our Community

Sign up to our monthly newsletter for industry insights, employee recognition tips, and news from the world of workplace digital transformation ⚡️