Courageous conversations: Handling sensitive issues with clarity and compassion

We have a habit in Australia of leaning too hard into being easygoing. When a team member starts missing deadlines or their tone in meetings gets a bit sharp, it's easy to default to just giving them a few days.

Of course, that stems from good intentions and isn't always the wrong answer. This approach becomes problematic when it comes at the cost of actually managing a spiralling issue.
Let's look at how to move forward with both kindness and strength.

The high cost of being nice

Silence isn't always helpful. It can just as easily be a debt. As a leader, each time you look past a behaviour that isn't working, you're essentially endorsing it. This imposes a tax on the rest of your high performers.

In the work environment, your leadership is more important than your friendship. Navigating problematic behaviours through open conversations keeps the air clear for you, the person in question and the rest of your team. That's exactly where your leadership kicks in.

Why avoidance backfires

When we avoid these chats, it might feel like we're protecting the relationship. But unclear expectations are a major driver of workplace stress and underperformance. If people don't know where they stand or where they should stand, they're unlikely to make the changes needed to bridge the gap.

I've found that the best performers over time are not necessarily the ones who consistently perform at 100%. They're the ones who welcome feedback — even the prickly bits — and proactively make the effort to improve. When you hold back, you're effectively denying them an opportunity to grow. Believe me, it only gets more awkward as time goes by.

Prepare the intent, not the script

The reason these conversations feel so clunky is that we try to memorise a script. It feels robotic, and most of the time, it shatters the second the other person reacts in a way you didn't plan for. Instead, I find it's better to anchor yourself in your intent. Ask yourself: Am I here to win or am I here to help this person succeed?

Focus on observable data. If an employee has been late three times in a week, that's a fact. Inferring that they're not committed is an assumption. When you lead with facts, the defensive walls stay low. If you describe the impact (for instance, how the rest of the team had to cover the gap), it becomes a shared problem to solve together, rather than an attack on character.

Staying steady when the conversation gets tricky

You can't control how someone else reacts, but you can control the temperature of the room. If a team member gets defensive or teary, don't rush to end the chat. Stay steady and use "I" statements to own your perspective. This keeps the focus on the task, not the personality.

Explore the other person's experience to better understand. In Australia, managers' perspectives on employees wellbeing often surpass employees' perspectives, so empathy and curiosity should be a solid part of your toolkit during these discussions.

If the conversation starts circling the drain, it's okay to hit pause and come back to it later. Remember, you don't have to be perfect; you just have to stay present and honest.

Co-designing the way forward

A courageous conversation needs a way forward. Employees will generally be more responsive when they help build the way forward, so rather than prescribing them a solution, ask them what they believe can help and guide the conversation from there.

That way, you'll create buy-in. Once you've landed on a path forward, document it with a brief, friendly email summary to ensure both parties are clear on the discussed outcomes.

Retaining the human element

Holding courageous conversations around performance issues is among the toughest parts of leadership. That's because you're human, and you're also dealing with another sentient human.

The key is to keep a firm grasp on that human element, remain crystal clear in your expectations and create an auditable trail of what's discussed to pave the way towards improvement. Learn structured techniques in our Courageous Conversations workshop.