7 essential steps for having difficult conversations at work (and outside of it)

russell amerasekera at stylist live google work life stage difficult conversations

Credit: Shot by Farheenxo

Stylist Network


7 essential steps for having difficult conversations at work (and outside of it)

By Lauren Geall &Ellen Scott

Updated 2 years ago

3 min read

Speaking on the Work Life with Google stage at Stylist Live 2023, executive coach Russell Amerasekera shared his top tips for navigating difficult conversations in the workplace.


“Can we have a quick chat? In private?” No matter what stage of your career you’re at, those words are enough to send a shiver down anyone’s spine. No one likes having difficult conversations – but there’s something about navigating those moments in the workplace that makes the whole thing so much more awkward.

These conversations inevitably lead to moments of progress, so it’s not like you want to skip them altogether. Instead, you want to find a way to work through the stress-induced mental freezes and strike a balance of professionalism and empathy without losing your ground. So, what’s the key to striking that balance?

At today’s Stylist Live, we learned all about how to do just that – thanks to the brilliant advice of executive coach Russell Amerasekera. An expert in personal branding, presentation skills and leadership communications, Amerasekera took to the Work Life with Google stage to share the expertise he’s gained during his career helping high-performing people to be the very best leaders they can be. And we certainly learned a lot.

First off, let’s run through where we go wrong, according to Amerasekera….      

The 10 biggest mistakes we make when having difficult conversations

  1. Avoiding the conversations 
  2. Choosing the wrong place, wrong time
  3. Failing to prepare
  4. Not being entirely clear on the issue at hand and the outcome you want 
  5. Failing to take ownership
  6. Letting too much emotion come into play
  7. Making assumptions 
  8. Thinking ‘I’m right, you’re wrong’ 
  9. Not listening 
  10. Having a lack of empathy

So that’s where we’re going wrong. How do we get it right? 

russell amerasekera at stylist live google work lifes stage

Credit: Shot by Farheenxo

7 steps for having a difficult conversation

1. Understand the context and psychology

“It’s so so important to understand the psychology at play here,” Amerasekera explained. “What’s the context of this conversation that you’re going to have? Why does this matter so much? 

“When having difficult conversations, you’ve got to care. It’s got to matter. Otherwise, why would you do it? 

“Think about what feelings are at play here – [yours] and theirs. Spend some time anticipating how the other person might be feeling.” 

2. Prepare psychologically

“If we’re anxious, it leaks,” he said. “The other person senses it.” That, Amerasekera explains, is why it’s so vital to ground yourself before heading into the chat, to pause and relax and clear your mind so you can go in fully focused on the issue at hand. 

“I see people going straight from a Zoom call or a meeting and then trying to have a difficult conversation. This is really, really hard because what happens is our mind is still buzzing. As a mark of respect to the person that you’re talking to, they deserve you going in there with a fresh mind.”

Always create hope

3. Choose the right environment

Some big no-nos, according to Amerasekera: 

  • Cold, dark environments
  • Busy environments – there’s too much distraction 
  • Sitting directly across from each other with a desk in between you (it feels confrontational)

4. Take accountability

Amerasekera said: “This is what I call owning the story. It’s crucial. I often hear ‘It’s not me; it’s them.’ That’s not taking responsibility. It’s not taking accountability, particularly as a leader.

“To take accountability, I guide you to focus on: how important is this? Does it really matter? Am I being fair? What impact is this decision going to have on that person’s life?”

russell amerasekera at stylist live google work life stage

Credit: Shot by Farheenxo

5. Understand the other person’s story

“This is probably the most crucial step of all,” he explained. “We all interpret situations differently, and it’s very easy to impose our narrative on the way that other people feel. Listen with the head and the heart.”

6. Avoid an argument

This is a conversation, not a battle. 

“Arguing blocks us from hearing each other,” Amerasekera told us. “As soon as you come into that space, you don’t hear the other person. If there’s someone who wins and someone who loses, there’s no real resolution. 

“If you feel you’re going into that space, take a pause, exit, and regroup.”

7. Co-create an outcome

View the conversation not as a win-lose situation, but a way for two people to collaborate and find a way forward. 

“Try to co-create an outcome,” Amerasekera told us. “It’s a really powerful way to resolve a difficult situation. It can result in a mutual brainstorming session; should we sit down and try to work this out together? This way the person feels really heard and understood.” 


Images: shot by Farheenxo

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