An introduction to difficult conversations at work

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An introduction to difficult conversations at work. I’m joined by my friend and leadership coach Heather Wright to talk about why so many of us avoid difficult conversations at work – and what we can do to get better at them.

Heather has spent years working with organisations on culture, performance and leadership and she knows the impact these conversations have, not just on relationships, but on results.

"People leave jobs because of relationships," Heather tells me. "And if leaders don’t tackle issues head-on, the cost of re-recruitment can be huge – not just financially, but culturally too."

So why do we dodge these conversations? Fear. Fear of saying the wrong thing, fear of being seen as a bully, fear of conflict. But as Heather points out, conflict doesn’t have to be destructive.

Why do we get difficult conversations wrong

Most of us see conflict only through the lens of heated arguments in films and TV dramas, where it’s written to escalate. No wonder we associate it with something negative.

But in reality, handled well, conflict is essential for high-performing teams.

"On TV, we rarely see a conflicting conversation go well," Heather says. "That’s why we need to learn how to do it – and how to prepare before issues even arise."

Difficult conversations at work - culture is everything

Great teams don’t just wait for conflict to happen. They set expectations upfront.

Heather encourages leaders to have "conversations about conversations" – agreeing as a team how they’ll handle disagreements when they inevitably occur.

"When leaders set the culture, people feel safe," she says. "They know a challenge isn’t a personal attack, it’s about helping each other work better."

The cost of avoiding difficult conversations in the workplace

Failing to address poor behaviour or underperformance sends the wrong message. It silently endorses bad habits, chips away at trust and damages productivity.

And the numbers are stark: replacing an employee costs on average £30,000 – much more at executive level.

"Teams that trust each other and speak honestly get better results," Heather explains. "They’re more creative, more innovative and more resilient."

Building braver leaders to encourage open, honest dialogue

For Heather, it comes down to self-awareness, trust and emotional intelligence. Leaders who encourage open, honest dialogue don’t just solve problems – they unlock motivation.

"There are two things people want at work," she says. "To be seen and to be understood. If leaders can give their teams that, they’ll get engagement, creativity and loyalty in return."

What leaders can do now to build confidence around difficult conversations

Heather’s advice for leaders who want to build confidence around difficult conversations is clear:

Expect conflict – it’s normal and healthy.

Set the culture early – agree how your team will disagree.

Frame feedback well – it’s not personal, it’s about working better together.

Don’t avoid it – silence is more damaging than the conversation you fear.

For me, this is the heart of it: getting more comfortable with difficult conversations means embedding better culture, better behaviours and better results.

Listen now to hear why avoiding these conversations costs far more than having them – and how you can build the confidence to lean in.

Read the transcript: Cont:

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Transcript: An introduction to difficult conversations at work

PH (00:03)
Hello, Penny here, this time we're discussing an introduction to difficult conversations at work. And joining me is leadership coach, speaker and trainer and a dear friend of mine, Heather Wright. Welcome, Heather.

Heather (00:22)
Thank you Penny, it's good to be here.

PH (00:24)
Now, I love being your friend. I also love knowing that you're an expert on all things difficult to discuss at work. And there's often been a time where I've come to you for a bit of kindly advice about how to proceed with something. Now, we've ⁓ recently delivered some training together on this topic and it struck me that people just really want to know... ⁓

how to have a conversation at work that's difficult, yes, and we do that in our training. But let's take it back a step, you know, why are people getting it wrong? Why aren't they doing it? Let's ease into the topic. And as a general sort of introduction to it, because people are really worried about having them, getting them right, being the best at them, winning at them. So let's ease in with that.

I've got a stack of questions for you. Are you happy to be answering? It's like mastermind, isn't it?

Heather (01:20)
It is! da da da da da! Yep! I am happy.

PH (01:24)
Okay, let's go.

I'll be Clive Myrie. I won't. ⁓ From a leader's point of view, let's take it back to that. From a leader's point of view, let's set the scene with some examples of what might be a difficult conversation. What are people coming up against?

Heather (01:40)
There are all sorts of things that people are coming up against, especially in a world where we've got a lot of DEI and people are frightened of getting phrasing wrong. They're frightened that they're going to be accused of being bullying. They're frightened that they're going to say the wrong thing. They're frightened of picking people up on stuff. if somebody is casually racist or casually sexist or they say something, they've heard something in the news. People just don't know what to do. They don't know.

PH (02:02)
Casually.

Heather (02:08)
First of all, they're not quite sure what the rules are anymore because the rules change every day about some of those things. But then there's the other stuff, which has been there for a very, very long time. A colleague who has an issue with body odour, somebody who's underperforming, those kind of things, or just something you want to say to somebody, but they're a little bit prickly. If we work in teams, any team is going to have the people you can say absolutely anything to and they won't take it personally, and you're going to have those people who are sensitive.

And so those are the kind of things and it's like, we need to work on being able to have those, you know? But when our brain goes, I'd love to say that, if you just ask yourself at any moment, what would you love to say to somebody that you've never said? Yeah, even if, other than the rude stuff you'd like to say, I think you've got, know, think one eyebrow is higher than the other or I think your nose is too big. It's the other stuff. It's the stuff about performance or I wish you wouldn't keep doing this or that gets in my way.

PH (03:08)
I had a colleague at work who used to blow her nose and then leave the tissue on her desk. But I couldn't bring myself to say anything because I didn't know how to say anything other than, could you please stop doing that? It's horrible. And so I avoided what I thought was conflict on that tiny aspect. So, yeah.

Heather (03:21)
Yeah.

And that's

a good point, Penny, because we see things as being conflict when they don't have to be. And when we see things as being conflict when they don't have to be, the challenge is our only experience of conflict has been negative. So we see a lot because now we watch lots of TV and lots of entertaining programmes. The only time we see conflict is when it's written to make the plot good. If Shakespeare had written his plays,

in a lovely way and everyone had handled conflict well and people hadn't fought and they'd said, hey, right at the beginning of Romeo and Juliet, Mercutio says, let's have a conversation about this. Then funnily enough, the plot is ruined. If you watch anything, I mean, I constantly watch TV programmes going, ⁓ that conversation went wrong, they should have done this. And then I have to remember, if I'd have done that, the TV programme would have ended after five minutes and it wouldn't have been as entertaining. We very rarely, we don't.

PH (04:18)
So we don't have good role models, do we, around us? Role modelling.

Heather (04:21)
We

don't, and we very rarely witness a conversation, a conflicting conversation that goes well. I was in Belfast Airport the other day waiting for somebody to come off another plane that was arriving in 20 minutes or so. to, it's because I'm an international speaker and Belfast Airport, mean, you know, it's just one of many airports I hang around in.

PH (04:35)
Is that because you're an international speaker? Yes, darling. Yes, yes. Jet setting.

Heather (04:43)
That's right, but two people got off a plane and one of them must have upset the other on the journey. And these two women were having a shouting match. And their body language was leaning in and jabbing their fingers at each other. And, it's the way you speak to me, it's the way you talk to me. And it's like, wow. And there's a woman trying to get in between them. And this is in the middle of an airport screaming, everyone's of looking over their shoulder. And it's like, wow.

We're not taught how to have those conversations. So when we do have them, we have them when we're in an emotional state and we say things that at the time feels good to say them, but actually just makes things worse. And I'm curious now, a week on, are those people still friends? Probably not.

PH (05:26)
No, it's interesting, isn't it? It kind of spills into the idea of like managing your emotions, being in touch with how you are feeling and what other people prompt in you that triggers all sorts of difficult behaviors, perhaps. yeah, self-awareness, I would say, is a really good ⁓ element of this. But actually what people are searching for, what people really want answers for is how to have these difficult conversations, ⁓ not...

Heather (05:35)
Yeah.

PH (05:55)
How do I become more self-aware and in control of my emotions? What, you know, if we were to put ourselves in the position of a leader, there's always going to be situations where you're thinking, I don't want to have that chat. What would you say to that? What would you say to those people who are trying to avoid difficult conversations?

Heather (05:59)
That's right.

Okay, so leaders have to have conversations. That's really, really important. And as we said, there's a big piece about being self-aware and emotional intelligence. But before the leader even starts with, no, I'm in a position where there's a thing I need to deal with with that person, we have to assume as soon as we become a leader, as soon as we enter any team, that at some point,

It's a bit like when you get married. At some point you're going to have a row about something, you know. ⁓ surely not. We're in the honeymoon period. I love Boo Boo. I'm never ever going to have a row with Boo Boo. No, that's not true.

PH (06:53)
I don't trust

people who say, we don't ever have a crossword. It's like, really? That's weird.

Heather (06:57)
No, really, really, that

means you're sweeping a lot of stuff under the carpet and one day, one day that's gonna come to the surface, you know. And so, that might be the last day of one of your lives. But so what we have to do is we have to set up a team culture. We have to have, weirdly, we have to have conversations about having conversations.

So we actually prepare for it before it ever happens because it's easy to prepare for it when there isn't one in that, you know, there isn't one on the horizon. So we set the culture in such a place that says right at the beginning, we're a team at some point, we're going to fall out. How are we going to do that? And plus the other point is conflict is good. It is essential for all high performing teams, but it has to be done well. So yes, it's essential, but not

in a bad way. Bad conflict isn't essential. Good conflict is essential. So we have to have conversations about that. So we have to build trust that when we have conflict, what we're not saying is, can't stand you and I can't work with you. What we're actually saying is, I really like working with you. There's this thing that will help us work better. And I think we might disagree on it. So let's have a conversation. So it's all about that. It's all the phrasing.

PH (08:12)
So just zooming out then to motivate,

sorry, I spoke over you. ⁓ We could have a difficult conversation about my interrupting levels, couldn't we? ⁓

Heather (08:18)
That's okay.

That's okay.

PH (08:26)
⁓ Interestingly, there is a bigger picture, isn't there, about, and this might motivate people to lean into the idea of being braver around these sort of things. ⁓ And that is the cost. You talk about it builds trust and people feel safer when they have or able to have conversations like this or conversations about having conversations, right? But what's the cost if they don't? Let's just bring the list out.

Heather (08:52)
There's, I mean, there's quantitative costs and there's qualitative costs. The quantitative cost is the cost of re-recruitment, which on average costs around about £30,000 per person you have to re-recruit. So that means when...

PH (09:03)
Much more if you're executive

level. Huge amounts. Yeah.

Heather (09:06)
Absolutely. I'm sort of averaging it out there. So

you're right. It's more of his executive level. People leave because of relationships a lot of the time, a lot of the time. The relationship, the toxic culture, ⁓ what appears to be bullying behaviour or people feeling bullied, ⁓ things just not being said. So there's actually a financial cost, which is huge. But other than that...

There's also the cost which says if we know there is huge amounts of research, teams that work well together, that trust each other and have honest conversations have better results. They sell more, they're more creative, they have more, massively more innovation. ⁓ The quality of what they do is greater because they're able to challenge each other and say, actually, we could do this even better. ⁓ I was chatting to someone,

only the other day where they said, have a culture where nobody speaks up, nobody dares speak up. The leader comes in and says, right, this is the way we're doing it and just cuts everybody off. We also have people who are what I would call the, ⁓ not the invisible leader, but the one who's not good on their business card.

but behind the scenes is also a leader. And I met someone a little while ago in a business and they were sort of middle management. And I was chatting to them and said, why don't we say this? He went, no, we don't do that. And as soon as he started saying that in front of other people, they instantly clammed up. He's looking after our interests in front of the bosses. So he would have a pre-meeting before all other meetings to tell people what they could and couldn't say in the meeting in front of the boss. ⁓

PH (10:44)
but his recruitment rate was a bit high. Recruitment.

Heather (10:49)
The reason I was

in was because of a massive turnover rate which has now, I'd like to say, hugely improved. Thank you. I feel personally responsible.

PH (10:53)
Right.

Great, good work. Excellent. Yeah, there's a real jeopardy with it

at that level, isn't there? And then there's also, like you say, that qualitative aspect of like behaviors. If you don't call out someone's poor behavior, then essentially you're endorsing it, aren't you? your behaviors, culture, values, they all get interwoven and you end up with a real sort of hodgepodge mismatch of how people do things and how people approach things, which causes, I think, you know, a poor productivity environment.

Heather (11:07)
Hmm

Absolutely.

PH (11:26)
⁓ And that's the golden, that's the dream, isn't it? Increasing productivity, ⁓ if nothing else.

Heather (11:31)
Imagine

if you weren't able to speak up and you were flying a plane.

And in actual fact, this happened. If anybody's ever read the book Black Box Thinking, which is a superb book about how airline industries looked at how they handle mistakes. But one of the pieces was making sure the culture meant that people could talk to each other. And if you were there, there was a huge hierarchical society in aviation in other countries where if the pilot made a mistake, the copilot wasn't able to speak up and it was causing issues. Imagine it in the medical world.

where somebody can't say, excuse me, I think maybe we've missed a point here. So the cost is huge. And obviously in all businesses that applies.

PH (12:16)
Mm-hmm,

yeah, and so you're embedding better culture, better behaviors, better values, better ways of working when you're able to have all sorts of different conversations that are difficult. And I know that you've categorized them into three or four different types of conversation. We don't have time to go into them today, but we will do in the future. So it's so handy to understand the nuances or differences between them and then how to have them.

What is the value ⁓ of a leader or a person who looks after people in their team and encouraging others to have difficult conversations or get some training on it? What value do you see, what transformation do you see happening in organisations when you've been in to support around this issue?

Heather (13:00)
But if you think about people's motivation for being in the workplace, other than, you know, they have to go to work because have a mortgage to pay, most people like something that challenges them. Most people like their brain to be active and your brain can't be active if all you do is follow orders. Somebody says something and you do it, you carry it out. doesn't inspire people. So if a leader encourages people to challenge, encourages people to have conversations, and by the way, what we call difficult conversations aren't just about somebody's done

something wrong and we're challenging them. It's literally just saying, actually, I hear what you're saying about that particular idea. I've got a different idea. Can we talk about it? People even find those kind of things challenging. Or for instance, I work with multidisciplinary heads of departments where everybody's there from a different department. And if we're not careful, people are kind of, well, my department's doing this. well, I'm not going to challenge you on your department because you're a, but my department, wait a minute, we've all got to work together. We're all in different departments, but our aim

is the same. So when a leader encourages people to have proper, crucial conversations and creative conversations and really honest feedback, then actually departments work together better. People are more inspired and motivated because they can be heard. There two things people want in life, just generally in life. One is to be seen and the other is to be understood. Now those are our basic needs and you may have heard them with different words, but those are basic psychological need. If you have an idea and

you don't feel you're seen because you're just being given orders and you can't do anything and you're definitely not heard, you're definitely not going to be understood, then you're not going be putting ideas forward, you're not going be able to play with those ideas and have great input and go away going, yeah, that was a, you know, you and I have these conversations, don't we Penny? You go, that was a great conversation. We started over there and then we played with these ideas and then we moved on, you know, and we just come away with more ideas. So for any leader,

getting away from this idea of I tell people what to do and they follow or if I'm not in charge somebody else has to be in charge of that and this hierarchical thing. It's going to squash people's creativity. Fear is a huge creativity crusher.

PH (15:15)
So if we can get away from the fear of having difficult conversations, we'll be more creative, more collaborative, more innovative and happier at work, which is always a bonus, absolute bonus. Okay, well, that's all we've got time for today, Heather. And if difficult conversations is an issue you're facing in your organisation, drop us a line, hello at bitfamous.co.uk. And thanks for listening.

Heather (15:20)
Yeah.

Definitely.