How to have difficult conversations (and why you should)


Do you relish the thought of those painful, prickly chats we all have to have at some point? Thought not. For most of us, tricky conversations are something to put off, or at least dread. Perhaps even avoid altogether.


Believe it or not, Kammeron (Kamm) Cran, founder of The Team Space, feels like this, too. Yes, even leadership experts struggle sometimes, ok?


The difference is Kamm knows why we need to have these conversations, the dangers of not having them and, best of all, how we can go about them. She’s been working with Michael Schiffner for a while now on productive conversations in the workplace and she kindly agreed to run a webinar on Managing Difficult Conversations for us recently to share some of their wisdom and now we’re sharing her practical and proven ways to do just that!

So what really happens when we avoid hard conversations? 

Nothing great, tbh. Productivity drops, stress shoots up and relationships break down. Oh, and it creates mistrust and suspicion. You see, if we’ve got little or no information about something, we’ll simply fill in the gaps with our own creative stories. 

Not exactly a leadership style we should aspire to, points out Kamm. 

‘If you don’t have these feedback conversations, you’re not actually upholding your responsibility as a leader – which is to develop other leaders,’ she says. 

Let’s talk benefits instead

At the other end of the spectrum, there are some pretty tempting perks on offer. You see, upfront, honest dialogue puts everyone on the same page, empowers people and improves relationships

‘When we grapple with hard things, it strengthens relationships; it actually builds connection,’ Kamm explains. ‘And we know that highly connected teams tend to have better performance. As leaders, when you lean into having these conversations – and you do them really well – you’re actually role modelling this growth mindset that we need.’

Want a high performing, high achieving and successful team? Kick off the (hard) conversations. 

Start with the 4 state check-in

The 4 state check-in is about understanding what’s going on for you on 4 different levels at any given moment. And it’s important because everything (even difficult conversations) are better with a healthy dose of self-awareness. 

  1. Physiological – What’s going on in your body as you gear up for a tricky chat? A racing heart, perhaps, sweaty palms or a dry mouth. All normal, all manageable.
  2. Emotional – What about how you’re feeling? Many people feel stressed, awkward or distressed by the mere thought of frank chats.
  3. Cognitive – Next up: the thoughts racing through your mind. Things like ‘I don’t want to do this’ or ‘this could go seriously pear-shaped.’ We’ve alllll been there.
  4. The narrative – Lastly, grab hold of the stories you’re telling yourself. A common one is ‘I’m not good enough’. Hence why we often prefer ducking out of these scenarios!

How all this helps

Simply taking note of how you’re feeling (and why) puts you in a better headspace to handle whatever comes your way, Kamm assures us.

‘It’s really important you get familiar with how you think you’re going to respond in those situations because they’re the sort of things that can really derail you in the moment,’ Kamm explains. ‘You want to stay clear, stay listening, stay present to really build those connections with the person you’re having the difficult conversation with.’

Learning the language

Delicate conversations call for the right words. So get yours on point with these 4 easy-to-learn talking tips from Kamm.

1. Ask permission questions

By all means, launch an attack question with a ‘I’ve got a problem with you’ kinda approach. But don’t expect good outcomes. It’s about increasing receptivity – not defensiveness

Try openers like ‘Would you mind if I asked you a question about something?’ or ‘Could I run something by you?’

Way more helpful!

2. Banish the but

How come? Because, says Kamm, ‘it’s very oppositional [and] almost negates everything you’ve said before it.’

Do yourself a favour and try ‘and at the same time’ instead. It’s a simple swap out that’s going to make you a better communicator in every part of your life.

3. Ask for advice, not opinions

People get suspicious when you ask for their opinions because they fear it could be held against them. 


But being asked for our advice? We love it. Here’s why, Kamm tells us.

You’re deferring respectfully to their expertise and experience,’ she says, ‘but it’s also inviting them in. People love being asked for advice and it’s much more collaborative.’

4. Pre-frame it

This is about warming people up to your idea before you fire it out. Something like ‘Would you be interested in an idea that will help manage workload and develop staff?’ preps people for what’s coming. And if they’re ready, they’re more likely to be receptive. 

Making difficult conversations easier

Good outcomes hinge on productive conversations. So, instead of shying away from those tough talks, focus instead on preparation, practice and listening. Because, in the end, says Kamm, taking the easy route isn’t necessarily the best path forward.

When you traverse these tricky things in another human, it does actually bring you closer together,’ she offers. ‘When you have teams that can have high rigour, robust debates that aren’t personal…that’s where you get ultimate performance.’

Want more incredible insights on navigating challenging conversations? Listen to the full recording here or check out the Strivin blog for more tips, tricks and advice!

Extras –

Kamm suggests checking out Robert Cialdini book ‘Influence’ as his work has been a big influence on her.

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How to have difficult conversations (and why you should)

Do you relish the thought of those painful, prickly chats we all have to have at some point?.