Let’s be honest nobody enjoys having a difficult conversation at work. Whether it’s about poor performance, a conflict between colleagues, or a sensitive personal issue, these conversations can feel uncomfortable and sometimes overwhelming.
But here’s the truth: avoiding them doesn’t make the problem go away. In fact, it often makes things worse. As people managers, business owners, or team leaders, how we approach these moments can make a huge difference to individual wellbeing, team morale, and overall business performance.
At My HR Hub, we work with leaders every day who face these exact challenges. And while every situation is different, there are some practical steps you can take to manage challenging conversations with confidence and compassion.
Spot the Signs Early
Most problems don’t appear overnight. Often, there are warning signs — a dip in performance, changes in mood, lateness, or tension within the team. Addressing issues early with a quiet, supportive chat can prevent them from escalating. Think of it as nipping the problem in the bud rather than letting it grow into a bigger issue.
Prepare, Don’t Panic
Going into a conversation unprepared can leave you feeling defensive or overwhelmed. Instead:
Get the facts straight – have clear examples and evidence.
Check policies – make sure you know your organisation’s approach (such as performance, absence, or grievance procedures).
Plan your structure – decide how you’ll open the conversation, what points to cover, and the outcome you’re aiming for.
Remember: preparation builds confidence.
Communication is Key
The way you communicate will shape the entire discussion. Here are some tips we share with clients:
Ask open questions to encourage the other person to talk.
Listen actively – pay attention not just to words, but tone and body language.
Stay calm and professional – even if emotions run high.
Focus on the behaviour, not the person – this keeps things objective.
Stay in Control, But Be Human
It’s natural to feel nervous before a difficult conversation. But staying in control doesn’t mean being cold or unapproachable. It means setting boundaries, staying on track, and ensuring the discussion remains respectful.
At the same time, empathy matters. Sometimes, a performance issue may have an underlying cause such as health, stress, or personal challenges. Giving space for this, while also setting clear expectations, shows you value your employee as a person as well as a team member.
Agree the Way Forward
The most effective conversations end with clarity. Together, agree on:
What needs to change
What support will be provided
What happens if things don’t improve
When you’ll review progress
Documenting this helps avoid misunderstandings later on.
Final Thoughts
Challenging conversations may never feel “easy” but they can be constructive. Handled well, they can rebuild trust, improve performance, and strengthen relationships at work.
At My HR Hub, we regularly support clients in preparing for and navigating these conversations. Through training, coaching, and hands-on HR advice, we help leaders approach them with confidence and care.
If you’d like support with managing challenging conversations in your business, get in touch we’d love to help.
