Sitting across the table from a teacher, ready to give difficult feedback, is never an easy moment. I’ve done it enough to remember that sinking feeling it always gives. But it is a necessary part of our growth as a team.

While supporting my middle leaders through their own “difficult conversations” journeys, I’ve been able to reflect on how we handle these moments and the importance of finding that balance between support and accountability.

Difficult conversations aren’t enjoyable, but when handled sensitively, and with due care and consideration, they can lead to growth for both the individual and the team. Here are six ways to make difficult conversations with staff a little easier based on my experiences.

1. Prepare thoroughly

We’ve all been there: going into a conversation unprepared, only to realise halfway through that we’re missing key details. As such give yourself time to gather all relevant facts, whether it’s about classroom performance, deadlines or behaviour.

Linked to this - what you want to achieve: are you correcting an issue? Clarifying expectations? Offering support? Knowing your goal keeps the conversation on track.

Preparation also helps in anticipating reactions - whether it’s defensiveness, frustration or even tears - and thinking ahead about how you’ll handle those emotions.

2. Be direct, not harsh

One of the biggest challenges is not wanting to hurt feelings; we work closely with our colleagues and we don’t want to damage relationships. Skirting around the issue, however, doesn’t help anyone so be clear and direct.

A colleague once told me, “If you take too long to get to the point, you’ve already lost them.” I’ve kept that in mind ever since.

As such, being upfront - while remaining polite, sensitive and clear - saves time, avoids further misunderstandings, and removes the pain of a protracted discussion.

3. Think about time and place

The setting can make or break the conversation. A rushed chat in the corridor doesn’t show the respect the issue - or your fellow professional - deserves. Find a private space where both you and the staff member feel comfortable.

Timing matters, too. If you know someone’s had a particularly stressful day, perhaps it’s worth holding off until they can give their full attention. These small efforts can ensure the discussion is focused and effective.

4. Acknowledge emotions, but stay grounded

We’re human, and emotions will naturally play a part in these conversations. Whether it’s frustration, defensiveness, or sadness, it’s crucial to acknowledge this. Let the person express how they feel without derailing the conversation.

I’ve learned that staying calm and grounded, even when emotions run high, helps keep the discussion productive. A simple, “I understand this is difficult,” goes a long way in showing empathy without losing focus.

As we know from working in education, raising our voice or becoming emotional ourselves usually makes the situation worse, so remain calm and composed.

5. Encourage ownership and focus on solutions

It’s tempting to say, “Don’t worry about it” when things go wrong, but this can stop someone from truly reflecting on their actions and you may “steal” a learning moment from somebody who wants to reflect on their practice.

Encourage ownership of the issue and help your colleague to think through what went wrong and, more importantly, how to fix it. Focus on solutions, not just problems.

I’ve found that framing the conversation around future steps rather than past mistakes creates a more positive, productive outcome.

6. Follow up and reflect

The conversation doesn’t end when the meeting is over.

A quick check-in shows that you care about their progress and are invested in seeing positive change. It also holds everyone accountable.

After a particularly tough conversation, I once made the mistake of assuming the issue was resolved, only for it to resurface later.

Finally, take time to reflect on how the conversation went - what worked, what didn’t and what you could do differently next time. Reflection helps us improve and makes the next tough conversation easier.

A chance to grow

Difficult conversations are never pleasant, but they’re part of leadership. When handled with empathy, honesty, and preparation, they become opportunities for growth - not just for the individual but for the entire team.

Remember, you don’t have to do it all alone; lean on your colleagues for support, and reflect on your own wellbeing, too. As leaders, the conversations we dread most often lead to the greatest improvements.

Ian Watts is assistant head of secondary (student wellbeing and community) at The International School @ ParkCity, Kuala Lumpur