Speak up and lead – how tackling difficult conversations transforms you into an exceptional leader

Difficult conversations are the ones that leaders fear most and yet handling them well holds the key to success. People Director Shaun O’Hara explains why these chats are essential, why they’re often tricky, and how you can tackle them with confidence.

Let’s be honest, nobody likes having difficult conversations. Whether it’s talking to someone about their poor performance, addressing a behaviour that’s not working for the team, or even having a frank chat about personal issues, these situations can feel awkward, emotional, and downright uncomfortable. But the truth is that avoiding these conversations can cost your business far more than a few minutes of discomfort.

Why are some conversations so difficult?

What makes a conversation “difficult” is usually a mix of the relationship you have with the other person and the topic that you need to discuss.

Relationships

Your direct reports: These can feel personal because you work closely with them on a daily basis, and you’re invested in their professional success.
Your peers: Addressing an issue with a colleague on your level can feel political or risky.
Your boss: Telling your manager something they may not want to hear takes nerve-wracking to a whole new level.

The subject matter

Most difficult conversations fall into one of these categories.

Performance issues: telling one of your team that they are not hitting targets, missing deadlines, or delivering below standard.
Conduct problems: someone who’s behaviour disrupts the team, like bad attitude, lateness, or unprofessional conduct.
Capability concerns: When you have hired someone for a role, but they are clearly struggling despite trying hard.
Personal matters: supporting someone through a sensitive life event such as mental health issues or family struggles.

These topics tap into emotions, both yours and theirs. Which makes them easy to identify as a difficult conversation, but hard to handle.

Why you need to have difficult conversations anyway

Avoiding difficult conversations doesn’t make the problem go away; it makes it bigger. Here’s what happens when you step up and tackle these situations head-on:

Clarity and trust: Honest conversations build trust. Your team will know where they stand in your eyes, and they’ll respect your fairness and openness.
Better performance: Addressing issues early stops them from spiralling into a much bigger problem and helps people improve.
Stronger teams: Resolving conflicts or behaviours strengthens team morale and collaboration.
Company culture: Many businesses and leaders now spend a lot of time and effort defining and embedding the company values (and behaviours) that drive the future growth of the business, so it’s really important that when any employee acts in a way that contradicts these values, that a difficult conversation happens promptly, sometimes with coaching as follow up help for the employee. This is a practical way of both reinforcing and nurturing the company culture.
Your growth as a leader: These moments stretch your leadership muscles and set you apart as a decisive, empathetic leader.

How to handle difficult conversations

You don’t need magic skills to do this well. It’s all about preparation, empathy, and being direct. If you can, address issues informally first. A quick chat can often nip problems in the bud. But if it’s a serious or ongoing issue, don’t hesitate to move to a formal process. It may help to keep in mind that a difficult conversation handled well benefits everyone; you are not trying to catch anyone out, but you do want to turn a poor performer into a high performer.

Preparation is key in difficult conversations

Know the facts: Be clear on what the issue is, with specific examples (dates, behaviours, outcomes).
Understand their perspective: Put yourself in their shoes and think about what might they be feeling or struggling with?
Define your goal: What’s the outcome you want? Is it behaviour change, increased productivity, or simply awareness?

Set the right tone

Pick a private space: Choose somewhere neutral and free from distractions.
Be calm and respectful: Even if you’re frustrated, keep your tone constructive. For instance, you may have a report who is not completing their tasks on time. Instead of saying ‘You’re lazy’ consider reframing your advice in a positive manner to say ‘Its important that you to complete your tasks on time because there are a number of people who are dependent on them.’
Explain the purpose: Start with why the conversation is important—this isn’t about blame, it’s about improvement.

Stick to the issue

Be specific: Avoid vague statements like “You’re not performing.” Instead, say, “You missed X deadlines last month, and here’s how it’s affecting the team.”
Stay neutral: Focus on the behaviour or issue, not the person.

Listen as much as you talk in difficult conversations

Ask open questions: “What’s been challenging for you recently?” rather than “Have you found work challenging recently?”
Acknowledge their feelings: Show empathy, but don’t let emotions derail the conversation.

Acknowledge your own role in the situation

Recognise your own role in your report’s performance. Share your feelings of vulnerability and be open about how you could set clearer expectations going forward. No one wakes up in the morning wanting to perform badly, so it could be that you need to reflect on whether you set out clear expectations in the first place.

Agree on a way forward

Collaborate on solutions: Work together to find ways they can improve or overcome challenges.
Set clear expectations: Agree on what needs to change, by when, and how progress will be reviewed.
Follow up: Keep the momentum going with regular check-ins and support.

Holding difficult conversations isn’t just part of your job as a leader, it’s one of the most important things you can do to create a healthy, productive culture. The more you practice, the easier it becomes. And remember, these conversations are an opportunity to show your team you care enough to help them improve and grow.

So, don’t put it off. What conversations are you avoiding?