Having difficult conversations at work: a man in a blue shirt holds a smartphone whilst facing away from the camera

How to have difficult conversations at work

Difficult conversations at work can be tough, but with these tips you can transform them into opportunities for learning, growth and a stronger workplace.


Everyone knows the feeling: you know you need to have difficult conversations at work. Your stomach’s churning, and you’re considering jumping on a flight to Outer Mongolia to avoid it. 

You’re not the only one. Around 70% of employees deal with difficult conversations by – you guessed it – simply not having them. According to the same report, each of these missed conversations costs an eye-watering $7,500 and more than seven work days.

Whilst it’s entirely natural to want to avoid the few hours’ discomfort that surrounds difficult conversations at work, sweeping it all under the carpet causes serious long-term repercussions.  

Workplaces that don’t deal with friction points like poor performance, salary issues and unprofessional behavior become paranoid and unproductive. On the other hand, internal transparency has a significant effect on morale and engagement with your company’s wider goal, according to business publication Entrepreneur:

“Internal transparency is positively correlated with higher employee morale (and therefore, productivity). Transparency in this internal context also builds trust, and makes employees feel that they’re working for a company with higher ethical standards.” 

Having difficult conversations results in a transparent working environment with better outcomes for everyone. Below, we’ve laid out a guide to how to handle these potential pressure points successfully.

How to have difficult conversations at work: 4 steps to success

First step to shedding some of that anxiety? Having a clear process in place. Use this easy-to-follow four-step guide to nail the basics. 

1. Prepare ahead of time

Knowing what you want to say beforehand will help you express your point of view clearly and sympathetically. Think about how you want to phrase potentially tricky subjects. Write it out if you want, or make notes – it will help!

Content resolution coach Judy Ringer emphasizes the importance of preparing thoroughly for these conversations ahead of time. In particular, she suggests: 

  • Practicing the conversation with a friend before holding the real one.
  • Mentally practicing the conversation with yourself. Think of various pathways the conversation could take and envision the outcome you are hoping for.

2. Focus on the facts

Avoid accusations. Instead, explore the circumstances around the objective facts of the matter. “You’re underperforming” is an accusation. “Your output has dipped lately, and I want to ensure you have the support you need to thrive” starts the conversation on a more engaging and positive note. 

3. Be empathetic

Be kind. You never know what someone else is going through. Listen to their side of the conversation actively – not to pick it apart, but to start to identify solutions to the issue at hand. You might not have realized that a colleague is a single parent, for example, and that timekeeping issues are down to childcare difficulties.  

4. Seek solutions, not vindication

“How can we move forward together?” should be the ultimate question you aim to answer in difficult workplace conversations. It turns a potentially negative conversation into a productive one.

Examples of difficult conversations at work 

Having difficult conversations with employees or managers is all about knowing what to expect. Use these difficult conversations at work scenarios to plan ahead of time. 


Money is always a tricky subject, but it’s one that you’ll need to get comfortable talking about quickly in the current employment landscape. With 44% of workers considering quitting their job in 2022, and 56% of these citing a pay increase as the major driver of this decision, difficult conversations at work around salary are likely to become increasingly common.

Whether you’re requesting a raise or turning a request for one down, this is a conversation to handle with extra sensitivity. The key? Evidence. Approach it rationally, with data and examples to back up the decision. 

Inappropriate behavior

Let’s get this straight – there are some types of inappropriate behavior that should lead to immediate dismissal. Equally, there are unhelpful workplace habits that chip away at the workplace dynamic if left unaddressed. 

Common issues here include commenting on food choices or outfit choice, poor hygiene or food theft. Approach it gently – the offender might even be unaware they’re causing issues and correct behavior on request. 

Discussing poor performance

If poor performance is a recent development, try to understand the reasons behind it. If it’s a continuing issue, try to explore whether there’s any accommodations you’re missing – would training help with underdeveloped skills, for example? 

Of course, the result of continued poor performance will be demotion or dismissal. If initial conversations don’t bear fruit, it’s important to be open about this possibility so that it’s not a surprise if the time comes. 


Everyone is late sometimes. That’s life. Avoid pulling anyone up on occasional slipups – they’ve likely stayed on past their shift more times than they can count, or put in countless extra hours whilst working remotely. 

According to a recent BBC study, workers post an average of 9.2 hours unpaid overtime each week. Overwork figures have risen globally in the wake of Covid 19, with free hours worked in North America more than doubling. 

Whilst many frontline teams really need punctuality to function, it’s therefore important in any conversation on the topic to identify whether your colleagues are putting in extra hours elsewhere, and consider whether this could be an early sign of burnout.

Is your colleague feeling tired and overworked? Do they have a difficult child care situation or are they simply stopping at Starbucks for a double ice mocha? Listen empathetically and assure them that their work elsewhere is appreciated as you try to understand the root cause of habitual lateness. 

Conflict between employees

“They-said they-said” conflicts are a nightmare if you weren’t there for the original disagreement, or don’t have the bandwidth to monitor how both parties interact with each other over the course of the day. 

Try to understand the root cause of the conflict, understand why each person feels aggrieved and work towards a common solution. Lengthier disputes should be escalated to HR – it’s what they’re there for and you’ll likely get a better outcome that way. 

How to have difficult conversations with managers

Difficult conversations with your boss can seem like an uphill struggle because of the power dynamic between you. The right approach can help ease the pressure and turn a difficult conversation into a productive one. 

This doesn’t have to be around a raise, a promotion or anything that concrete. Your boss’s behavior has an enormous impact on your ability to work productively, so it’s important to be able to address major pain points here. 

‘Micromanagement’ for example, was cited by 23% of workers as their boss’s worst trait – and it all too frequently feels impossible to bring up how restricting you find it. The key, according to a recent Forbes article by Heidi Lynne Kurter, is starting with a direct but respectful conversation:  

“This starts by having an open and respectful conversation with their manager. Using an ‘I feel’ statement with specific examples, such as ‘I feel like you don’t trust me when you X’, is a great starting point.”

Further tips for having difficult conversations at work with your manager include: 

  • Be prepared: setting an agenda helps you stay on point.
  • Know what you want: work towards a specific outcome, and suggest clear steps to get there.
  • Be open to suggestions: ask for input from your manager and consider other points of view. 
  • Practice: seriously – practice in the mirror, to your cat or however you feel comfortable. Expressing yourself out loud will give you more confidence when the time comes. 

How to have difficult conversations with employees 

Having difficult conversations with employees is all about connecting on a one-to-one level and not wielding the company hierarchy like a blunt weapon. If you do, responses won’t be ideal. 

Remember to: 

  • Keep communication ongoing: schedule a meeting and let your employee know what to expect in advance. This reduces anxiety and increases the chance of a good outcome. 
  • Engage: listen empathetically to your employee’s thoughts and suggestions, rather than communicating top down. 
  • Be truthful, direct and transparent: if a poor outcome is on the cards (such as dismissal or redundancy) be clear about this – avoid ambiguity. 
  • Keep it confidential: discuss the outcome of the conversation on a need-to-know basis.
  • Follow up: check in on your employees’ progress in the weeks after the conversation. Hold them to any goals and offer congratulations if they are meeting them. 

Difficult conversations at work are hard, but…

Having difficult conversations at work is very much a ‘stitch in time saves nine’ strategy. That makes us sound like Grandma, but it’s the truth. 

Identifying reasons for poor performance helps you make reasonable accommodations and allows employees to improve. 

Pulling up someone on continued lateness prevents bad feelings building up among team members. 

Nipping problematic behavior in the bud builds workplace cohesion, employee engagement and job satisfaction. 

To do this well, all it takes is a little preparation and a willingness to empathize with whoever you’re dealing with. Reigning in negative emotions, actively listening and articulating your needs clearly help reframe tough conversations from ‘difficult’ to ‘helpful’ or ‘productive’. 

It’s not easy out there, but with the right approach, you got this. We believe in you!