How We Talk Ourselves Out of Difficult Conversations
You know that person at work who’s driving you mad? The one whose mistakes you keep fixing, who you’re constantly chasing, and who somehow never seems to get the message? You’ve vented to colleagues. You’ve dropped hints. You’ve tried to be patient. And you’re pretty sure they know exactly how frustrated you are.
But what if they have no idea? What if everyone at work knows there’s a problem except the one person who actually needs to hear it?
The stories that let us off the hook
In Crucial Conversations, Kerry Patterson and his colleagues describe three types of stories we tell ourselves when emotions run high.
“They’re completely unreliable. I can’t trust them to do anything properly.” That’s the villain story. We turn someone’s behaviour into a character flaw, assuming the worst about their motives. They’re lazy or simply don’t care. There’s little room to consider what else might explain their behaviour.
“I’m the one who keeps staying late, apologising to colleagues and sorting out their mistakes.” That’s the victim story. We focus on everything we’ve had to put up with, casting ourselves as the innocent party. Our frustration may be entirely justified, but the story leaves out anything we might have done, or failed to do, that contributed to the situation.
“I’ve tried everything. There’s no point talking to them again.” That’s the helpless story. We convince ourselves there’s nothing more we can do. By treating the situation as beyond our control, we overlook the options we still have, including conversations we may have been avoiding.
All three stories have something in common: they turn a complicated situation into a simple one. They’re the problem, we’ve done everything we can, and nothing is going to change.
The trouble isn’t necessarily that these stories are untrue. It’s that they’re incomplete. And once we’ve convinced ourselves we know the whole story, we stop looking for other explanations, questioning our own behaviour or considering what we could do differently.
The conversation that never happened
It’s Friday afternoon, and a manager is once again finishing work their direct report should have completed on Wednesday. They’re furious. They’ve spent the week chasing updates, picking up the slack and wondering how many reminders it takes to get someone to do their job. On the way home, they rehearse exactly what they’d like to say.
But by Monday morning, they’ve talked themselves out of it. They’ve always promised themselves they wouldn’t be that kind of boss: the one who makes people anxious, jumps on every mistake or treats grown adults like children. They want to be understanding and approachable. Besides, they’ve already raised the issue several times. Surely the employee knows how serious it is by now? So they send another polite email. In the manager’s mind, the warnings couldn’t be clearer. In the employee’s inbox, they’re still polite reminders.
In Radical Candor, Kim Scott calls this ruinous empathy: caring about someone while avoiding the direct feedback they need. The manager is trying to be kind, but by avoiding an uncomfortable conversation, they may be denying the employee the chance to understand the problem, explain what’s happening and put things right.
Perhaps the employee is new to working life and hasn’t learnt the unwritten rules about managing deadlines. Perhaps they find prioritising particularly difficult due to neurodivergence, or something at home is affecting their work. Or perhaps they really haven’t been taking deadlines seriously. The point isn’t to assume the best or the worst. It’s to stop treating an assumption as a fact. The deadlines were missed. Why they were missed is something the manager still needs to understand.
Instead, the manager keeps picking up the slack, growing more convinced that the employee simply doesn’t care. When they finally raise the issue, months of frustration and resentment may come pouring out, making the conversation far harsher than it needs to be. The manager feels they’ve reached the end of their patience, while their direct report may feel the situation has escalated without warning.
Of course, sometimes expectations have been perfectly clear and the other person still hasn’t met them. But even when we’re right about someone’s behaviour, we can be wrong about their motives. And when we decide someone is hopeless or deliberately difficult, that judgement starts to influence how we treat them. We become less patient, less willing to listen and quicker to interpret every mistake as further proof that we’re right. The other person may become defensive or disengaged, reinforcing the very story we’ve told ourselves about them.
As Crucial Conversations, puts it: “If you don’t talk it out, you’ll act it out.”
Three questions before your next difficult conversation
The villain, victim and helpless stories each have a useful antidote.
If they’re ‘the villain’: Why might a reasonable person behave this way? What could I be missing? You don’t need to excuse their actions to consider another explanation.
If you’re ‘the victim’: What am I leaving out about my own behaviour? Have I been clear about expectations? Avoided a conversation? Allowed resentment to build without addressing the issue?
If you’re ‘helpless’: What can I do now, whether or not they change? You can’t control their choices, but you can give direct feedback, clarify expectations, set boundaries or take appropriate action.
For example, instead of saying “You clearly don’t care about deadlines,” the manager might say: “Three deadlines have been missed this month. It’s putting pressure on the rest of the team, and we need to agree how that changes. What’s been getting in the way?”
The performance issue hasn’t been softened. The manager has simply addressed what they know while remaining open to what they might not yet understand.
Perhaps your colleague really has let you down. Perhaps you’ve been more patient than anyone could reasonably expect. But until you’ve had an honest conversation, you may be responding to a story you’ve told yourself rather than the full picture. And sometimes, the conversation we’ve spent weeks avoiding is the one that could finally move things forward.
Helping managers have the conversations that matter
Difficult conversations require us to be clear about what’s happening while remaining open to what they may not yet understand.
UNLRN’s Difficult Conversations & Performance Feedback programme helps people prepare for challenging discussions, separate facts from assumptions, give constructive feedback, listen effectively and agree meaningful next steps.
To find out more about the programme or discuss training for your team, send an enquiry using the button below, or contact us at info@unlrn.co.uk.
FAQs
What is difficult conversations training?
It’s about learning to tackle the conversations you’d rather avoid, from poor performance and missed deadlines to difficult behaviour and workplace tensions. UNLRN’s training helps managers speak openly, handle uncomfortable reactions and move towards solutions.
Who is the training for?
Anyone who manages people or needs to give honest feedback. It’s especially useful for managers who put off tricky conversations, worry about upsetting people or struggle to balance empathy with accountability.
What will I learn?
How to prepare for challenging conversations, challenge your own assumptions, give feedback that actually gets through and handle defensiveness without making things worse. Above all, how to be clear and direct without being confrontational.
What if the other person gets upset or defensive?
You can’t control how someone reacts, but you can influence what happens next. Our training helps managers stay calm, listen properly and keep the conversation constructive, even when emotions run high.
Can training really make difficult conversations easier?
It won’t make every conversation comfortable. But it can help you stop avoiding them, feel more confident about what to say and handle problems before frustration turns into resentment.
Want to help your managers tackle the conversations that matter? Get in touch at info@unlrn.co.uk to find out more about UNLRN’s Difficult Conversations & Performance Feedback programme.
