Having Difficult Conversations: The Cost of Avoidance
People at all levels of an organisation cringe at the thought of having a "tough conversation." Most often, they delay it so long that the incident itself becomes a distant memory. They hope it "blows over" - but it does. It tends to reappear later, and usually worse than before.
Or if you do decide to confront the person, it somehow comes out all wrong. They get defensive - or worse - and you're left with an awkwardness between you, and the issue itself no better off.
Let's say Joe has been throwing his weight around lately - cocky in his communication, speaking over others in meetings, not sharing important information about status or even his whereabouts. Something that needs addressing. Nipped in the bud, there's a real chance of clarity on both sides, and an opportunity - not a guarantee, but an opportunity - for resolution. But because it feels heavy, or awkward, you leave it. You tell yourself it'll resolve on its own. And besides, that guy is a "key resource" you can't afford to lose.
That's how things get swept under the rug. Never to surface again - except they do. Sometimes at a much bigger cost than when they first appeared.
Not a great position to be in; and yet, very often, this is exactly what we do.
In this article, we're going to look at why "tough conversations" are so hard - even for someone who's made it to a leadership position, with real technical skill, good intention and a decent command of language.
We'll cover:
The journey and impact of avoided conversation
Why these conversations feel so difficult
A new way of seeing the other person's behaviour
A structure for communicating so the other person can actually hear you
Where else you can put this skill to use
From Signal to System: The Journey of Avoided Conversations
The conversation you avoid today becomes tomorrow's resentment - with interest.
It's worth knowing when it's actually time to address something. Sometimes it's a one-off mistake, or someone's having a bad day. Other times you notice a slight tension in the team, a behaviour that doesn't feel right, a missed deadline.
A rule I like to use is ...
One incident doesn't tell you much. A second gives you information - something to take note of. A third presents a pattern - and patterns require a response.
In practice:
Once, let it go.
Twice, take note.
Three times, take action.
** Though if something has a genuinely big impact, even just the once, it doesn't need to wait for a pattern. Now would be a good time to address it.
The highest cost of avoiding a conversation, though, is rarely the conversation itself. It's everything that happens after.
From your side, it's the behaviour not changing - or getting worse. From the other person's side, it can be a genuine mystery as to why things have shifted between you. Either way, it shows up as misunderstandings, assumptions about intent, and eventually corridor conversations that breathe poison into the team. Trust erodes. Conflict follows. And conflict, left long enough, becomes attrition. Suddenly HR is managing an exit interview for something that could have been resolved in a fifteen-minute conversation, a few weeks - or months - earlier.
Think back to Joe. Addressed early, it costs you five awkward minutes. Left for six months, it can cost you the whole team's trust in you - and maybe Joe himself, once it finally boils over.
I think of it as the journey of avoided conversations - one that starts small and quietly compounds.
A slight tension - low effort to address - and high influence if you do. Left unaddressed, assumptions and internal dialogue start filling the gap - "I thought they'd realise.", or "What were they thinking?".
Left longer, it becomes the grapevine - just "the way it is around here."
Finally, it ends in a performance review, an HR file, a resignation letter. High effort, low influence, damage that's now much harder to undo.
I believe somewhere between 60 and 90% of what eventually needs a big intervention started as something small enough to have been easy. That's the part that should make every leader pause.
So why do capable managers still avoid having difficult conversations? Most organisations put it down to a communication problem - poor performance, late deliveries, missed deadlines allowed to go under the radar.
What they really have is a confidence problem.
Why these conversations feel so difficult
When leaders see things going wrong, they know they should address it. Of course they do. Yet many don't.
That's intriguing in itself, because by the time someone reaches leadership, communication has surely been part of the journey - giving instructions and feedback, performance reviews, corrections. The skill is there. What determines the outcome, though, isn't whether they have it. It's how well they use it.
Now it's not because they don't care. Far from it. It's because they don't feel equipped. And that one gap, between knowing and doing, is subliminally shaping the culture of almost every team I work with.
Here's what I've noticed: the biggest resistance to having the conversation is rarely the conversation itself. It's everything that happens before it - the anticipating, the rehearsing, the imagining of how badly it could go.
I've asked a number of HR leaders and senior managers the same question: why do capable people still avoid difficult conversations? The answer is rarely because of skill. Almost always because of fear - of damaging the relationship, of making things worse, of getting it wrong, of triggering conflict.
That fear is loud enough to outweigh the willingness to speak. So we avoid it, dance around it, or finally say it badly - and badly delivered feedback creates more defensiveness, more distance, and a bigger issue than the one we started with.
Maybe that's exactly what's kept you from pulling Joe aside - not indifference, just not knowing how it'll land.
The good news: that's the part we can actually do something about.
A new way of seeing their behaviour
The meaning of the communication is the response that you get.
Communication is never really about what you intended to say. It's about the response you get. That's the only way you'll know how your message landed.
That's because there's a whole world going on inside the other person, thinking shaped by a lifetime you weren't present for. It's that thinking that can be very different to yours, which naturally shows up as a difference of opinion, another perspective. That's the part people are actually afraid of: what if the "difference" turns into something nasty?
Have you ever noticed how two people can sit in the exact same meeting and walk away with two completely different explanations of what happened? That's because one filters what they hear through their own "stories," built from their beliefs, values, memories and blind spots. And that goes for each and every one of us. And while we're doing that, we also have a habit of deleting, distorting and generalising through our words - without ever noticing. By the time we perceive what's happening, it isn't really "what happened" anymore - it's our unique version of it.
Back to Joe: maybe from his side, he thinks he's stepping up and filling a gap nobody else will. From yours, it looks like arrogance. Neither of you set out to be wrong. You're just reading from different scripts.
The same words that land as helpful feedback for one person can feel like an attack to another. We tend to see others through the lens of our own thinking, then apply a motive to what we see. But we can never actually know what someone else is thinking - we can't - and shouldn't - attribute motive to their actions. All we can really do is notice the behaviour, name it, and ask them to address it - and it helps tremendously to get curious about what they're thinking.
Unless someone tells us how we're landing, most of us genuinely have no idea.
That single insight can change how you approach every hard conversation: it stops being about who's right, and starts being about closing the gap between two realities.
A structure for communicating
"All models are wrong, but some are useful."
Most training programmes are built around knowledge transfer - the models, the frameworks, the theory. Useful, but not the crux of the learning.
Training gives managers knowledge. Practice gives them confidence. They are not the same thing. Very few programmes create real opportunities to practise, get feedback, try again, and build the instinct until it's second nature - which is why a training room can feel energising on the day, and so little changes back at the desk.
Knowledge tells someone what good leadership looks like. Confidence is what lets them step into the moment when it matters - in real time, with a real person, when the outcome genuinely matters.
Two habits can be the game-changer - especially when they're practised until they become instinct:
Separate the fact from the story.
"Joe spoke over three people in the meeting" is a fact. "Joe thinks he's better than everyone else" is the story we've quietly attached to it. Go in with the fact. Leave the story at the door - it's usually where the defensiveness starts.
Say it in a way that can actually be heard.
A simple structure works well: here's what I want to raise, here's what I observed, here's the impact it's having, here's what I'd like to see instead. It's simple - and said in that order, calmly, it's the difference between someone hearing you and someone jumping to defend themselves. The C.O.I.N. model below spells this out beautifully - and is so easy to remember. It has become the go-to for both many of my clients and me when it comes to having those tough conversations.
Where else you can put this skill to use
You don't need to overhaul how your team communicates overnight. But before you can expect your team to have tough conversations, you'll need to demonstrate it yourself.
A few shifts that can help you do this:
Remember people are living in their own version of "the world." Communication is simply the bridge to get there. Unless someone points out our behaviour, most of us aren't even aware of it.
Ground yourself before you start. Are you in the right emotional state? Have you given it time to become clear in your own mind, rather than being reactive? What's the actual result you want - for you, for Joe? Perhaps it's leaving more space for others to speak.
Get curious about what's really driving the behaviour. Stick to the facts without the drama of your own story. Approach it with curiosity rather than judgement and you might be surprised - there's often something going on you weren't aware of.
Remember someone has to go first. It doesn't need to be a grand gesture. It just takes someone aware enough to take the lead.
As a leader you need to take 51% of the responsibility for how a conversation goes.
None of this is about changing who you are. It's about building a different kind of capability, one conversation at a time, until confident, clear communication becomes instinctive.
And it matters well beyond any one conversation. Teams that perform well aren't the ones where nothing ever goes wrong - they're the ones where it's safe to say when something has. Where a mistake becomes a lesson, not a reason to go quiet. Where feedback flows both ways, quickly, before it has time to calcify into resentment.
Anyone who's worked in an agile environment will recognise this immediately. Retrospectives, stand-ups, sprint reviews - the whole rhythm depends on people feeling safe enough to say what's actually true: what's blocked, what didn't work, what needs to change. Take away that safety, and the ceremonies become theatre. The team keeps moving, but the honesty - and the learning - stops.
The conversations we avoid at an individual level are the same ones that quietly erode a team's ability to adapt and perform at a system level. It's the same muscle. It just shows up in different rooms. By setting the tone and leading by example, you make that kind of safety - to speak up, disagree, get something wrong, and grow without fear of judgement - part of the culture, not just a value on the wall.
I work with leaders and teams to build exactly this kind of confidence - through Tough Talks Made Easy, a workshop and online course designed to turn the conversations you or your people have been avoiding into the ones that build trust, performance and genuinely healthy culture. If any of this struck a chord, I'd love to talk.
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