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September 1, 2026Navigating difficult conversations in ever-changing workplaces
Over the last few months in working with clients, I have noticed that the question of how to manage difficult conversations is resurfacing more and more frequently.
For leaders, this particular challenge has never really disappeared but in recent years, the specific complexities of the workplace have shifted for a multitude of reasons – industrial relations law changes, remote/hybrid work expectations, the right to disconnect, the entry of a new generation into the workforce, and the introduction of AI … and that’s only the tip of the iceberg.
For teams all over the world, work looks very different than it did just five or six years ago.
As a result, there can be friction within teams as some forge forward, while others are reluctant to jump into the new way of working, and leaders can struggle to know how to communicate their expectations in the face of it all.
There are so many conversations on the table and, often, the difficult or uncomfortable topics need to be tackled head on in order to get on the same page.
Preparation is key for difficult conversations
Difficult conversations can be delicate spaces to navigate. Take time to consider your key points, understand the facts and steer clear of assumptions, and consider the other person’s point of view. In doing this, you may come to a better understanding of the situation which can help to create a more constructive conversation with your team members.
Things to consider in preparation:
- Central issue
- Impact – on individual and team
- Facts
- Avoiding assumptions
- Ideal outcomes
Understanding communication styles
In any conversation there are two parties with their own communication styles. First, leaders need to consider their own communication style. In my workshops I unpack four different styles leaders often have: The Peacekeeper, The Avoider, The Bulldozer, and The Professional Communicator.
Often, leaders are quick to identify themselves as Professional Communicators, but the reality is that we all skew to some unproductive habits that are characteristic of the other three styles. Take time to understand the things you might do subconsciously – do you make assumptions? Jump to conclusions? Want to keep everyone happy? Put honesty above kindness?
The next step is to consider who you are speaking to. High performing teams are diverse, which means that each team member will have their own style. Who are you talking to? What do they respond well to?
While you may have your own style, leaders cannot have a one-size-fits-all approach. It is the leader’s obligation to adjust their style in order to bring the best out of each individual team member.
Focus on solutions for your team
Every difficult conversation needs to take place so that a different outcome can be achieved. Keep that in focus as you talk to your team. Don’t play the blame game, keep things constructive and focus on what the next steps are, so that everyone leaves the conversation knowing what is expected of them.
There is no cheat sheet that will tell you exactly how to navigate difficult conversations – the complexities of today’s workplace are being experienced by all, but every conversation will have its own unique combination of considerations and the challenge is to understand your team in a way that allows these conversations to happen and for change to take place without bitterness or frustration.
Effective leaders know that a difficult conversation always has the potential to end in a win-win-win situation – for the leader, the team, and the individual.
Need support in navigating difficult conversations? People Make the Difference can help. To find out more, visit www.pmtd.com.au or call us on 0412 333 415.


