Turning Conflict into Connection: Why Leaders Struggle with Challenging Conversations (and How to Get Better)
- Shiv Martin
- 1 day ago
- 5 min read
When I walk into a workplace conflict as a mediator, I can almost guarantee that the conversation everyone is avoiding is the one that started it all. By the time I’m called in, what could have been a quick, respectful chat has usually grown into something bigger, involving complaints, team breakdowns, or even resignations.
So why do good leaders hesitate? And what can you do to get better at having the conversations that matter most?
Why Leaders Put Off Challenging Conversations
It’s not because leaders don’t care. Quite the opposite. I often see managers care so deeply about their staff that they delay speaking up because they don’t want to hurt feelings or make things worse. The trouble is, silence usually does more harm than the words we’re scared to say.
Psychologists tell us that people are wired to seek belonging, which means anything that feels like rejection can trigger discomfort or even fear. In a workplace, this looks like leaders tiptoeing around performance problems or avoiding tension between staff. But the issues don’t disappear. They build.
I see it all the time:
Grievances lodged months after a “small” issue was brushed aside.
Good staff quietly leaving because they feel the problem will never be addressed.
Teams losing trust in their manager because they see avoidance as weakness.
In other words, avoidance feels safe in the moment, but it often guarantees bigger problems later.
The Mistakes I See Over and Over
When I coach managers, a few patterns keep popping up:
Going in unprepared and hoping the right words will appear.
Cramming every frustration into one heavy conversation.
Pointing the finger at blame rather than aiming for outcomes.
Handing things to HR too quickly, which leaves staff feeling unsupported by their direct manager.
The good news is that these are learned habits, which means they can be unlearned.
Strategies That Actually Work
Here are the approaches I teach in training and use myself in mediations.
1. Contain Before You Clarify
When emotions are high, the first priority is to acknowledge what’s happening. A simple, calm statement helps contain the moment.
“I can see this has been frustrating for you.”
Containment isn’t about fixing. It’s about creating enough safety that the other person feels they can talk openly.
2. Give the Conversation Structure
Unstructured conversations turn into blame sessions. A simple structure keeps things clear:
Start with purpose: “I’d like to talk about how we’re working together and how we can make this better.”
Name the issue factually: “I’ve noticed deadlines slipping, and I’d like to understand what’s getting in the way.”
Invite their perspective: “How do you see it?”
Move towards shared action: “What can we both commit to from here?”
3. Watch Your Words
Neuroscience shows that certain words make people defensive while others encourage problem-solving. For example, asking someone to be “honest” can feel like you’re questioning their truthfulness. Asking them to be “open” feels more like an invitation. Small choices like this matter more than we think.
4. Focus on Impact, Not Intent
I often hear people stuck on whether behaviour was “meant” to cause harm. The truth is, intent matters less than impact.
“Regardless of what you intended, this is how your behaviour has affected the team.”
Focusing on impact keeps the conversation constructive.
5. End With Clarity
Don’t leave the room without clear next steps. Summarise:
What did we agree?
What actions are we taking?
When will we check in again?
Without clarity, the conversation risks becoming another loop in the conflict.
What I See in the Mediation Room
When staff finally open up in mediation, they often say things like:
“I didn’t want to rock the boat.”
“I hoped it would just blow over.”
“I didn’t know how to raise it without causing more drama.”
These are the exact fears leaders feel too. When I coach managers, I see the surprise on their face when they role-play a difficult conversation and realise how quickly tension diffuses when it’s said out loud with calmness and care.
Early conversations, even if they feel uncomfortable, prevent months of silent frustration.
Practice Tips You Can Try Straight Away
Practise your first sentence out loud. If it sounds harsh to you, it will sound harsh to them.
Schedule the talk rather than springing it on someone. A short heads-up shows respect.
Balance facts and feelings. Both matter. “The deadline was missed” and “The team is frustrated.”
Let silence do the work. Listening without rushing creates space for the other person to reflect.
Ask questions about the future. “What would a better way forward look like?” is more useful than dissecting the past endlessly.
Why This Skill Matters More Than Ever
Research tells us unresolved conflict costs Australian organisations billions each year in lost productivity and turnover. But the bigger cost is trust.
Leaders who can sit with discomfort, structure a difficult conversation, and focus on outcomes build psychological safety. This isn’t about avoiding conflict. It’s about modelling courage and clarity.
Questions I’m Often Asked
Isn’t this HR’s job?
HR plays a vital role, but staff look to their manager first. If you avoid the tough conversations, your credibility takes a hit.
What if they get angry?
That’s normal. Acknowledge it. Pause if needed. Anger is a signal, not a deal-breaker.
How do I know I’ve handled it well? Check in: “Did this feel useful to you?” If they can say yes, you’re on the right track.
Final Thoughts
The disputes that take up the most time and energy are rarely about huge issues. They’re about everyday conversations that never happened.
The skill of managing challenging conversations is not just about avoiding complaints or legal risk. It’s about building trust, respect, and stronger working relationships.
👉 If you want to build confidence in this space, take a look at my conflict resolution and leadership training programs. Or book a one-on-one coaching session with me to practise your next conversation before it happens: Book a free discovery call to find out more
Free Resource: DIY Facilitated Conversations
If you’d like to see how facilitated conversations could help your workplace, I’ve created a free resource: DIY Facilitated Conversations.
This guide outlines the key steps of running a structured conversation, with prompts and tips you can use straight away.
Shiv Martin is a nationally accredited mediator, practicing solicitor, conciliator, decision-maker, and certified vocational trainer. With extensive experience in complex dispute resolution, stakeholder engagement, and team building across business, community, and governmental sectors, Shiv brings over a decade of unique and diverse expertise in Law, Management, Vocational Education, and Mediation.
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