Leadership: it’s all about the conversations


Most of us are pretty decent conversationalists. We’ve had plenty of great (and not so great 🥱) chats in our time, so we generally know how it all works

As a new leader, though, conversations take on more meaning. They have more riding on them, a wider circle hears you and your speaking skills (or lack thereof) really start to matter. 

It’s the currency you’re dealing with – and it’s worth a lot. 

(Btw, talking the hind legs off a donkey isn’t what we’re getting at here. Even if you do have some insightful anecdotes, Karen).


Thankfully, leadership whizz, Jon Osborne, knows what a good yarn sounds like and why leadership is actually a conversational activity

In our 4th podcast chat with Jon, he gave us the lowdown on conversation as a currency, how to trade in it and why practicing (and mastering) it will make you a better leader

Listen up, new leadership league: it’s time to talk…talk tactics

What conversations does a leader have?

Sure, there are a million ways to lead. But if we think about the most memorable orators in recent history (we’re looking at you, Churchill and Mandela), they had conversations that changed things.

So what conversations actually effect change? How do you master those conversation skills? And does listening really matter that much?

It boils down to 3 primary conversations around:

  • 👥 Relationships
  • 🫤 Emotions
  • 🔗 Interactions

⚠️ No, no, keep reading⚠️

We’re not taking you on a hippy love-in excursion – these conversations are completely relevant to the workplace, says Jon. 

“The context in which everything happens is relational; it has an emotional flavour to it,” he explains. “The interaction is absolutely crucial – the quality and the types of interactions we have. And if anything goes wrong? One or more of those three things will be missing.”

Point taken, Jon. 

Relationships (and why you need to invest in them)

Workplaces where relationships matter just feel…better. 

And it’s conversations (you’d be surprised to hear 😉)  that set the scene for close working relationships

Investing in team talking means you’ll get really good at tuning into the accurate atmosphere of the room (the ‘vibe’, if you will). Because it’s those subtle, unspoken clues that give you real insights into emotions and behaviours – and help you support your employees through the ups and downs of office life. 

Sure, you might need some practice, but ignoring the ‘background music of the conversation’ doesn’t help anyone.

“This emotional context is a blind spot for many people,” he tells us. “So part of this conversational skill is learning to read not only the content, but also the context – and working within that.

“[People] new to leadership would do well to match, to feel what’s going on,” Jon recommends. “[Because] if we can’t accept where we are, it’s very hard to move into the future.”

And that, new leaders, is exactly where you’re meant to be taking people. 

Emotions: all the feels

Literally no one can escape emotions. Yes, some of us have got rather crafty at burying those uncomfortable feelings, but they’re still there. So you may as well accept they’re going to rear their dramatic little heads in the workplace, too. 

“We don’t need to be emotional about emotions,” Jon assures us. “They are facts of our being…and a key part of our survival.”

Relieving 😅

Take Jon’s advice:

  • Get your head around what an emotion actually is (the usual culprits: frustration, elation, sadness etc.)
  • Understand an emotion’s purpose (that is, they tell us what’s going on inside a person’s mind)
  • Know how to work with emotions (accepting, validating and working through them).

When you allow emotions to be a part of your conversations, people know they’re accepted – warts and all. And that means they’re far more likely to want to join you on your leadership journey. 

Interactions and your approach

Just like relationships and emotions, you first need to acknowledge they are happening all around you, in many different ways. You won’t see them all – and you don’t have to.

Your job is to know how these interactions are playing out, whether they’re affecting the mood and when it’s time to step in

Trust, respect and openness play a huge role. And when a workplace brings those into the everyday, effective interactions take care of themselves

Practicing and mastering conversations

Again, it comes down to awareness. Because when you’ve got that licked, you can choose to change. Not that you can rest on your laurels then (as if!)

“After that, of course, there’s practice,” Jon points out. “And practice is what takes you from knowing about something to being able to do something – which is where basic competence starts to emerge.”

Ok. What about mastery? 

Not gonna lie: it takes a while (sorry).

“Mastery doesn’t happen until you’ve done that many times, in many different contexts,” says Jon.

Obviously, it’d be nice to morph straight into mastery – but we’re simply not wired for that (sorry again). In fact, by seeing yourself as a beginner, you’ll actually master more, says Jon encouragingly.

“The irony of mastery is that you can only get there if you remain a beginner,” he explains. “It’s the regular conversation with someone [who’s giving you] a combination of feedback and practice [that progresses you].”

Practice won’t make perfect – but it’ll get you pretty close. 

Are you really listening?

No, really. Are you? 


We know, we know – we’ve talked a LOT about this in other blogs. And for good reason. 

You can have all the conversations you want, but if you’re not actually listening, it’s pointless

Cringing at some of the…less than ideal chats you’ve had?

Don’t worry, says Jon, listening is a filter. It’s recognising it that matters.

“Of course, there are blind spots in our listening because we’re human and we’re finite,” Jon says wisely. “But it really pays to start learning what those blind spots are, so we see how that affects the way we listen to people.”

Top 2 mistakes we make:

  • Listening for compliance (listening to see whether someone is right or wrong)
  • Listening to respond (conjuring up a clever response before the person talking has actually finished)

Leadership, says Jon, is about listening for commitment. In other words, will the person you’re talking to actually do something?

“If you’re interested in leadership, you’ll be listening for where there is likely to be action, where things are likely to happen as a result of what you’ve said – or what someone else has said,” he explains. “If you can’t see the path and what you’re listening for, how do you help people find a journey forward?”

Good question. 

The art of good conversation

Conversations happen everywhere, every day. Done right, they’ll create cohesive teams of motivated employees who are reaching their potential

And it’s all about consciousness, practice (so much practice) and modelling.

“The art of leadership as conversation is a performance art,” Jon says. “We’re not trying to learn our lines; we’re trying to learn how our body needs to respond when the heat is on, when there is conflict or frustration, or someone gets triggered.

“And that happens through practice, embodiment and awareness of ourselves.”

Conversations bring people together. The best ones herald change. Want to start acting, feeling and behaving like a leader? You can listen to our entire New Leader podcast series here!

Latest articles, podcasts & resources

The Power of Self-Reflection – How to get ready for 2024

Well, wasn’t that another wild ride! As 2023 comes to a close and we turn our attention to.

Developing Effective Performance Reviews for a Hybrid Workforce – Key Event Takeaways

Strivin and HiBob have joined forces once again to bring you a series of insightful events to help.

Strivin & Thrivin EP1. Samantha George & Lee Shorter – How To Build An Award-Winning Recruitment Team

In the latest episode of the Strivin & Thrivin podcast we got to do things a little differently..

Networking: What you’re missing out on by not getting out there.

We’ve all been there, in a crowded room of other professionals, probably feeling self-conscious, nervous or just bored..

Coaching 101 – What is coaching and why do we need it?

What do you think of when you hear the word coaching?  It might conjure visions of those persistent.

Strivin & Thrivin EP63. Brooke Tierney – Dad Knows Best

In the latest episode of the Strivin & Thrivin podcast we catch up with Brooke Tierney, Founder and.

Strivin & Thrivin EP64. Alex Lennon – Head of Talent

Strivin and Thrivin is the career development podcast inspiring you to make some bold changes. Each week, we.

The Art of Feedback – How to make the conversation a two-way street

What’s the best thing you can give your team?  They would probably say more money and more holidays,.

Strivin & Thrivin EP61. Chloe Spillane – Talent Acquisition Leader & Career Coach

This week on the Strivin and Thrivin podcast, we chat with Chloe Spillane, Founder of Chloe Spillane Consulting,.

Strivin & Thrivin EP62. Genevieve Gorin – People & Culture

For the latest episode of the Strivin & Thrivin podcast we had a chat with Genevieve Gorin, People.

Eat, Sleep, Check on Your Mental Health

While there certainly weren’t many positives to come out of Covid, one thing we did see was an.

Strivin & Thrivin EP60. Jessica Gibson-Jones – Head of Talent Acquisition & Sourcing

In the latest episode of the Strivin & Thrivin podcast, we sat down for a chat with Jessica.

Strivin & Thrivin EP.59. Samuel Williamson – Master of MySpace & Marketing

Strivin and Thrivin is the career development podcast inspiring you to make some bold changes. Each week, we.

Strivin & Thrivin EP58. Samantha George – Advertising to Recruitment

In our latest episode of the Strivin & Thrivin podcast we talked with Samantha George, Principal Recruitment Consultant.

Strivin & Thrivin EP57. Sam Garven – A non conventional path to people & culture

In our latest episode of the Strivin & Thrivin podcast we got the chance to sit down and.