No one enjoys having tough conversations at work.
Whether it’s addressing an employee’s underperformance, calling out inappropriate behaviour, or setting boundaries with a colleague, the stakes always feel high.
But avoiding these conversations is not the answer. It will only make things worse.
The good news? With a few simple strategies, you can tackle even the most awkward discussions with confidence – and achieve the results you need. Read on for our no-nonsense tips for navigating those uncomfortable but crucial talks.
1. Don’t wait for things to spiral
We get it: It’s tempting to put off difficult conversations.
Maybe you hope things will magically fix themselves, or you dread the confrontation. But waiting too long often makes things worse. Problems fester. Misunderstandings grow. And by the time you address the issue, emotions are running high.
As soon as you notice an issue, plan to address it. Quickly.
For example, if you see someone consistently missing deadlines, it’s easier to have a conversation early on, rather than waiting until they’re completely overwhelmed. Timeliness shows that you’re engaged – but it also helps prevent the conversation from feeling like an attack.
2. Be direct, but kind
It’s all about balance. Being too vague can lead to misunderstandings, while being overly harsh can put people on the defensive.
You need to hit the sweet spot: Clear and direct – but respectful.
So how do you go about it?
Start with the facts. Then move on to how the issue is impacting your team or workplace. For example, instead of saying ‘You’re not pulling your weight’, try ‘I’ve noticed that your recent reports have been late, which is impacting our ability to meet deadlines as a team’.
By focusing on behaviour rather than character, the other person is less likely to feel attacked.
3. Create a safe space for dialogue
Difficult conversations shouldn’t feel like an interrogation. The goal is to create a space where both parties can discuss the issue openly.
This means actively listening. Asking for input. And being open to feedback.
For example, ask open-ended questions like ‘How do you feel about your recent workload?’ or ‘Is there something preventing you from meeting deadlines?’. This gives the other person the chance to share their side of the story and can uncover underlying issues you might not be aware of. Plus, it shows you value their perspective, which helps build trust.
4. Keep emotions in check (yes, yours too)
When it comes to tough conversations, emotions can run high – especially if the subject matter is sensitive or personal. While you can’t always control how the other person will react, you can control your own emotions.
So always do your best to stay calm and professional.
If things get heated, you may benefit from pausing and taking a breather. You could say, ‘I can see this is a difficult conversation. Let’s take a moment to think about what’s been said.’
This helps defuse tension – and gives you both time to gather your thoughts before moving forward.
5. End with a clear path forward
The conversation isn’t over when the talking stops.
Wherever possible, close it out with clear next steps so both parties know what’s expected moving forward. This helps avoid any ambiguity and keeps everyone accountable.
Summarise what’s been discussed and agree on a plan of action.
For example, ‘Let’s agree that from now on, you’ll check in with me every Wednesday on the status of your reports, and I’ll offer any support if needed. Does that sound good?’
Clarity is key here. Make sure both sides know exactly what’s next.
A final thought: Practice makes perfect
No one is born with an innate talent at having difficult conversations. But it’s a skill you can absolutely build.
The more you practise these techniques, the more confident and effective you’ll become.
And remember, it’s not about dodging conflict. It’s about handling it like a pro – with empathy, clarity and confidence.
Want to arm your team with the skills to manage difficult conversations with professionalism and tact? Our inhouse course for teams, Navigating Difficult Conversation will teach your people proven strategies to manage challenging talks, stay calm – and turn conflict into progress.