A beginner’s guide to difficult conversations at work
A beginner’s guide to difficult conversations at work. Difficult conversations are a leadership challenge; this guide is here to make them easier.
You’ll find out why people avoid them, what happens when we stay silent and practical ways to deal with the most common situations. From giving quick feedback in the moment to tackling repeated performance issues and even speaking up to senior colleagues, you’ll get straightforward advice you can start using right away.
To bring this to life, we’ve drawn on the expertise of Bit Famous associate and leadership coach Heather Wright. Heather has years of experience working with organisations on culture, performance and leadership.
She knows first-hand how much confidence grows when people learn to handle these conversations well. Her insights and practical tools run through this beginner’s guide.
At Bit Famous, we design training and programmes on difficult conversations that are shaped around you – your team, your culture and the situations you find hardest to handle. If you’d like to talk through your unique challenges and explore how we can help, get in touch.
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Outline: A beginner’s guide to difficult conversations at work
Fear of conflict, lack of training and past negative experiences often stop us from speaking up.
2. The cost of avoiding difficult conversations at work
Silence erodes culture, damages trust and can even put people at risk.
Silence erodes culture, damages trust and can even put people at risk.
3. Imagination vs reality in difficult conversations
When we don’t talk, our minds exaggerate the problem and make it worse.
When we don’t talk, our minds exaggerate the problem and make it worse.
4. Difficult conversations: calling things out in the moment (stub-toe conversations)
Quick, respectful feedback helps guard your culture and stop small issues from growing.
Quick, respectful feedback helps guard your culture and stop small issues from growing.
5. Impact feedback: conversations that build awareness
A simple structure shows people the effect of their behaviour without blame.
A simple structure shows people the effect of their behaviour without blame.
6. Perfomance correction: difficult conversations that create change
Structured dialogue helps address repeated behaviours and leaves people hopeful.
Structured dialogue helps address repeated behaviours and leaves people hopeful.
7. Challenging upwards: how to speak truth to power
Speaking up with curiosity and respect improves decisions and builds trust.
Speaking up with curiosity and respect improves decisions and builds trust.
8. The one thing to remember about difficult conversations
Start with positive intent – it sets the tone for clarity, honesty and progress.
Start with positive intent – it sets the tone for clarity, honesty and progress.
Bit Famous works with businesses and organisations to help them communicate with confidence.
By Penny Haslam
MD and Founder - Bit Famous
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1. Why do people avoid difficult conversations at work?
Why do people avoid difficult conversations at work? I’m been discussing this topic with my friend and leadership coach Heather Wright to dig into one of the biggest barriers we face in the workplace – avoiding difficult conversations.
Heather has worked with countless organisations on culture and leadership, so she knows how damaging it can be when we don’t tackle issues head-on. The truth? Many of us dodge these conversations, even when we know something needs to be said.
"Nobody really teaches us how to have them," Heather explains. "So when people have had a bad experience, it sticks. They carry that fear into the next one."
Why fear gets in the way
Most of us think of conflict as something destructive – the sort of fiery bust-ups you see in films or TV dramas. No wonder we associate it with something to avoid.
But the real reasons run deeper. Heather describes four big blockers:
- Fear of conflict – We imagine the conversation will spiral into an argument.
- Lack of training – Nobody has shown us how to handle it well, so we’re flying blind.
- Past experiences – If a previous conversation ended badly, we expect the same again.
- Worry about relationships – We fear upsetting the other person or damaging trust.
"Our imaginations are often worse than reality," Heather tells me. "We start to second-guess what the other person is thinking. Before long, we’ve blown it out of proportion – and still haven’t spoken about it."
The hidden cost of silence
It might feel easier to say nothing, but silence has consequences. Issues don’t disappear – they grow. Small frustrations fester, poor behaviours get repeated, and team culture starts to suffer.
Heather points out that the impact doesn’t stop with the individuals involved. "When conversations don’t happen, teams fragment. Good people leave because they don’t feel valued or supported. That costs the business money and reputation."
Why speaking up makes things better
Here’s the surprising thing: handled well, difficult conversations actually improve relationships. They clear the air, set boundaries, and build trust.
Heather puts it simply: "If you assume positive intent, ask questions and stay curious, conversations land much better. You feel better afterwards, and so does the other person."
Building confidence as a leader
For leaders, the lesson is clear. Avoiding conversations isn’t protecting relationships – it’s undermining them. The real courage lies in leaning in, even when it feels uncomfortable.
Heather’s advice? Start small. Begin with curiosity. And remind yourself that conflict doesn’t have to be destructive – it can be the starting point for stronger, more respectful working relationships.
For me, that’s the heart of it: the conversations we avoid are often the ones that matter most. Step into them with the right mindset, and you’ll not only strengthen your team but your own confidence too.
What leaders can do now to overcome avoidance of difficult conversations?
Heather’s advice for leaders who want to stop dodging difficult conversations is simple:
- Expect discomfort – it’s normal and doesn’t mean you’re doing it wrong.
- Assume positive intent – start from the belief that the other person didn’t mean harm.
- Get curious – ask questions rather than making accusations.
- Don’t delay – the longer you leave it, the harder it becomes.
- Focus on impact – frame the conversation around behaviours and outcomes, not personalities.
For me, this is the takeaway: avoiding difficult conversations might feel easier in the moment, but the cost of silence is far greater. Leaning in with curiosity, care and confidence builds stronger teams, healthier relationships and better results.
2. The cost of avoiding difficult conversations at work
When we hold back from having a tough chat, it can feel like the safer choice. But in reality, silence comes with a price tag – one that’s paid by individuals, teams and entire organisations.
Culture takes the hit
Every time poor behaviour goes unchecked, it quietly sets a new standard. People start to think, “That’s just how things are done here.” Before long, values slip, trust erodes and toxic habits creep in.
It’s rarely deliberate. Most of us avoid speaking up because we fear conflict or don’t know how to start. But culture is shaped by what we tolerate, not just what we encourage.
Behaviours spread
Unchecked behaviour doesn’t stay with one person – it spreads. If lateness, rudeness or sloppy work go unchallenged, others see it as acceptable. Good people either follow suit or, more likely, get frustrated and disengage.
And here’s the sting: the very people you want to keep are often the ones who leave first.
Productivity stalls
Silence doesn’t just damage morale – it slows everything down. When conversations don’t happen, confusion builds. People aren’t sure what’s expected, quality drops, and work has to be redone. What could have been a quick correction becomes a costly cycle of errors and frustration.
Retention costs bite
Replacing a good team member isn’t cheap. Recruitment takes time, money and energy – not to mention the disruption to clients and colleagues. One avoided conversation can snowball into a resignation letter, and the knock-on effects ripple across the business.
Safety is on the line
In some cases, the stakes are even higher. Avoiding conversations about mistakes or unsafe practices can put people at real risk. It might sound dramatic, but silence can cost lives. Speaking up isn’t just about culture – it’s about protecting people.
Why the real risk is avoiding the risk
Avoidance feels comfortable in the short term, but it piles up long-term damage. Strong leaders know that the braver path is the better one. Addressing issues early protects culture, strengthens behaviours and builds a safer, more productive workplace.
For me, that’s the heart of it: difficult conversations aren’t a threat to harmony. Avoiding them is.
What leaders can do now to reduce the cost of silence
- Tackle issues early – don’t wait for small problems to snowball.
- Guard the culture – call out behaviour that clashes with values.
- Protect your best people – show them poor behaviour won’t be ignored.
- Be clear on expectations – silence creates confusion, clarity builds trust.
- Prioritise safety – never let fear of conflict override the need to keep people safe.
The takeaway: silence erodes culture, damages trust and costs more than we think. Leaders who speak up create workplaces where people feel safe, valued and motivated to do their best.
3. Imagination vs reality in difficult conversations
When we avoid a difficult conversation, our minds don’t just move on. They start to fill in the blanks. We replay looks, tones and silences, convincing ourselves that someone is annoyed, plotting or judging us.
It’s human nature – our brains are wired to look for patterns. If we think we’ve spotted something once, we’ll start seeing it everywhere, even if it doesn’t exist.
"He looked at me funny in the meeting," you tell yourself. Next time, you notice it again. Soon you’ve built a whole narrative about how this colleague doesn’t like you, isn’t listening to you, or is out to undermine you.
And yet, nothing has been said. The only thing fuelling the drama is imagination.
Why reality is usually better
The irony is that when we finally do have the conversation – even if it’s clumsy – things often get better. A simple, “When you said that, I felt X” clears the air, resets expectations and stops the mental story-building.
Heather points out that most people, when they do eventually have the conversation, come away relieved. “I’m glad we talked about it,” is the common reflection. The reality is rarely as bad as the imagined version.
Why imagination holds us back
When we stay silent, the stories in our heads grow. They sap confidence, chip away at self-esteem and damage relationships that could have been repaired with a short chat.
It’s not just uncomfortable for us – it hurts the team. Left unspoken, our assumptions can snowball into resentment or even full-blown conflict.
Facing the facts
The truth is, we can’t stop our brains from imagining. But we can stop giving those stories the final word. Speaking up – with curiosity and positive intent – brings us back to reality, where conversations can build trust instead of erode it.
What leaders can do now to close the gap between imagination and reality
- Notice your stories – catch yourself when you’re filling in the blanks.
- Test your assumptions – ask, don’t assume. Curiosity clears up confusion.
- Start small – a short, honest chat often defuses imagined conflict.
- Value clarity over comfort – avoiding the moment might feel easier, but it leaves space for imagination to take over.
- Expect relief – most conversations end with, “I’m glad we talked,” not the disaster you feared.
Our imaginations will always run ahead, but brave conversations pull us back to reality – and that’s where trust, clarity and confidence live.
4. Difficult conversations: calling things out in the moment (stub-toe conversations)
Sometimes, the most effective difficult conversations are the shortest. A stub-toe conversation is exactly that – quick, immediate feedback when something isn’t right.
Think about what happens when you stub your toe. Instant pain. Instant feedback. The same principle applies at work: if someone says or does something that clashes with your organisation’s values, it needs to be addressed straight away.
Guarding the culture
Stub-toe conversations aren’t about nit-picking. They’re about protecting the culture you want to build. Left unchecked, a throwaway comment or casual remark can undermine trust, fuel division and normalise poor behaviour.
This isn’t about tackling extreme issues like gross misconduct – those need formal action. It’s about the everyday slips: the off-colour joke, the casual exclusion, the sarcastic remark. These are the moments that shape whether your workplace feels safe and respectful.
How to keep it constructive
Not everyone enjoys conflict. In fact, most of us feel our stomachs knot when we think about calling someone out. The key is to assume positive intent. Instead of labelling someone as rude, sexist or a bully, you might say:
- “I don’t think that landed the way you meant it – would you like to rethink that?”
- “Can you tell me what you meant by that? It didn’t sound quite right to me.”
Simple phrases like these invite reflection without escalation. They call out the behaviour while giving the other person the benefit of the doubt.
Why stub-toe conversations work
Handled well, these moments don’t drive people apart – they bring them closer. They show that you care about standards, that you’re committed to a safe culture, and that everyone has a role in protecting it.
And the beauty is in the timing: quick, respectful feedback stops issues from growing into something bigger and harder to tackle.
What leaders can do now to use stub-toe conversations well
- Act quickly – feedback works best in the moment.
- Assume positive intent – give people the chance to rethink, not retreat.
- Keep it simple – short, clear phrases work better than lectures.
- Guard the culture – remember you’re protecting values, not scoring points.
- Normalise calling things out – make it part of everyday respect, not a rare event.
That’s the power of stub-toe conversations: they’re small, quick interventions that keep your culture healthy, your values visible and your people safe.
5. Impact feedback: conversations that build awareness
Not every workplace slip needs instant feedback in the moment. Sometimes, it’s better to step back, choose your time and place, and have a short but thoughtful conversation about the impact of someone’s behaviour. That’s where impact feedback comes in.
Why it matters
Often, people simply don’t realise the effect they’re having. Maybe they dominate meetings without meaning to, use a sharp tone, or unintentionally exclude someone. Without feedback, they’ll keep repeating the behaviour – and the frustration will keep growing.
Impact feedback is about shining a light, not pointing a finger. It’s a way of saying: when this happens, here’s how it affects me (or the team), and here’s what could work better.
A simple structure
The beauty of impact feedback is its simplicity. It follows a clear, three-step flow:
- When you do X…
- The impact is Y…
- Could we try Z instead?
It’s short, factual and focused on behaviours, not personalities. You’re not blaming, you’re educating. And you’re inviting the other person to reflect and respond.
Real-life example
In one case, a colleague thought she was being glared at by another team member in meetings. For years, she assumed this was hostility. Eventually, she found the courage to give impact feedback.
The truth? The colleague wore hearing aids and was lip-reading to concentrate. What looked like scowling was actually focus. A conversation that had been avoided for years cleared the air in minutes – and completely transformed their relationship.
Why impact feedback works
It’s respectful, it’s constructive and it’s brief. Done well, it helps people understand the effects of their behaviour without making them defensive. And it gives them a chance to change for the better.
What leaders can do now to use impact feedback
- Choose your moment – don’t rush it; pick a private, calm setting.
- Keep it short – a few clear sentences are enough.
- Focus on behaviour, not character – “When this happens…” not “You always…”
- Share the impact – explain how it affects you or the team.
- Offer a way forward – suggest an alternative or invite ideas.
This is the value of impact feedback: it turns awkward assumptions into open dialogue, and small frustrations into stronger working relationships.
6. Performance correction: difficult conversations that create change
Some issues at work aren’t one-offs. They’re habits or behaviours that repeat and start to cause real problems. That’s when a performance correction conversation is needed.
Why it matters
Performance correction isn’t about catching people out. It’s about helping them get back on track. Left alone, repeated behaviours drag down quality, frustrate colleagues and damage trust. Addressing them shows you care about standards, culture and the person’s success.
The CLU approach
Performance correction works best with structure. One simple framework is CLU:
- Context – set the scene by inviting the person to a conversation. Make clear your positive intent, name any elephants in the room, and explain how the conversation will run.
- Listen – give them space to share their perspective.
- Understand – acknowledge their side and check assumptions.
- Empower – agree next steps and leave them feeling hopeful about the future.
Too often, leaders jump straight into “what went wrong.” CLU slows things down and turns the conversation into a collaboration.
Why tone matters
The most important part is how you start. If the opening feels like a lecture or an ambush, the other person will switch off or push back. But when the intent is clear – this is about helping you succeed – people are more open to change.
And the end matters too. The conversation should close with encouragement and a clear plan for what happens next. The goal is progress, not punishment.
Building trust through correction
Handled well, these conversations build trust rather than break it. They show that leaders are willing to be honest, but also supportive. And they give people confidence that issues will be addressed fairly and constructively.
What leaders can do now to use performance correction well
- Set context clearly – explain why the conversation matters and what it’s for.
- Name the elephants – acknowledge what everyone is already thinking.
- Make it a dialogue – invite their voice, don’t dominate.
- Leave with hope – agree positive next steps and follow up.
- See it as support, not discipline – correction is about growth, not blame.
Performance correction conversations aren’t about calling someone out – they’re about calling them forward.
7. Challenging upwards: how to speak truth to power
Not all difficult conversations are with peers or direct reports. Sometimes, they’re with the people above us – managers, directors, even the CEO. And that can feel especially daunting.
Pushing back on an idea, questioning a decision or offering an alternative view takes courage. But done well, it shows leadership, not disloyalty.
Why it feels risky
Most of us worry about looking negative, awkward or even insubordinate when we challenge upwards. The fear of damaging relationships with senior colleagues often keeps us quiet. But staying silent doesn’t help anyone. Leaders need diverse views to make the best decisions.
The STATE approach
One way to make challenging upwards easier is to follow STATE:
- Share – explain your perspective.
- Tell – outline your concerns or observations.
- Ask – invite their view to keep it collaborative.
- Tentative – use language that shows openness, not certainty.
- Encourage – build on their thinking with constructive ideas.
The magic is in the tentativeness. Instead of saying, “You’re wrong,” try: “I’m wondering about…” or “Could we look at this another way?” It frames your input as contribution, not confrontation.
Why it matters
Leaders at every level benefit from challenge. It tests assumptions, improves decisions and builds a culture of openness. If no one feels safe to speak up, blind spots stay hidden and poor ideas go unchallenged.
When you push back thoughtfully, you’re not undermining authority – you’re strengthening it by helping the team avoid missteps and find better solutions.
What leaders can do now to get better at challenging upwards
- Drop absolutes – avoid “you’re wrong.” Use tentative, curious language.
- Frame it as contribution – position your view as adding, not opposing.
- Stay calm and respectful – tone matters as much as content.
- Invite dialogue – ask questions to keep it collaborative.
- Remember the goal – it’s about better outcomes, not point-scoring.
That’s the essence of challenging upwards: it’s not about making noise, it’s about making things better. Done well, it shows courage, builds respect and makes stronger decisions possible.
8. The one thing to remember about difficult conversations
If you take away just one thing about difficult conversations, let it be this: don’t be afraid of them.
So much of the stress comes from what we imagine might happen – the row, the fallout, the awkward silence. But as Heather Wright says, most of that fear evaporates when you start well.
Start with intent
Assume positive intent. Go in with curiosity. Ask questions instead of making accusations. When you approach someone with openness, the conversation is far more likely to land well.
It doesn’t mean the issue disappears, but it does mean you’ve created space for honesty, clarity and progress.
Why it matters
The start sets the tone. If it’s defensive or aggressive, things go downhill fast. If it’s calm and curious, you can work together to find a way forward.
What leaders can do now to make conversations easier
- Assume positive intent – begin with the belief that the other person means well.
- Lead with curiosity – ask questions before making judgements.
- Keep the focus forward – it’s about solutions, not blame.
- Practise small steps – start with everyday conversations to build confidence.
- Remind yourself – most conversations end with relief, not regret.
For me, this is the heart of it: confidence in difficult conversations isn’t about being fearless – it’s about starting in the right way.
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