Tough Conversations: The Leadership Test Most Avoid
“Radical Candor is humble, it’s helpful, it’s immediate, and it’s in person.” – Kim Scott
You know exactly which conversation you’ve been avoiding.
That underperformer.
That culture-killer.
That one person whose attitude sucks the energy out of the room.
Or the restructure you’ve been putting off because, well… it’s going to get messy….
You’re not alone. Most MDs (especially the new ones) dodge these moments... not because they’re clueless, but because they’re human.
Fear of confrontation.
Fear of hurting feelings.
Fear of being the “bad guy”.
But…
What you avoid, you permit.
What you tolerate, you endorse.
You get the staff you deserve!
Silence doesn’t solve problems. It feeds them.
Why These Conversations Matter
This isn’t about being bossy. It’s about protecting your culture.
Most difficult conversations fall into one of four camps:
Performance that’s slid below par
Behaviour that doesn’t fit your values
Attitudes that poison the team
Changes that feel personal... restructures, redundancies, role shifts.
When you let these fester, you build up culture debt: an invisible backlog of unresolved stuff that quietly erodes trust, clarity, and morale.
And sooner or later… it explodes.
What's Really Going On?
It’s not ignorance. It’s fear.
“What if they cry?”
“What if they leave?”
“What if I totally mess it up?”
These fears are normal. But they’re not an excuse.
Clarity is kindness.
As Brené Brown puts it, “Clear is kind. Unclear is unkind.”
When you sugar-coat, delay, or sidestep, you’re not protecting them.
You’re denying them the chance to fix it, grow, or step up.
The Simple Framework That Works
Let’s strip this back.
Use the SBI model. It’s not rocket science:
Situation – What was the context?
Behaviour – What specifically did they do or say?
Impact – What effect did it have on the team, client, or business?
Pair this with Radical Candor: Care personally, challenge directly.
That’s the leadership sweet spot.
10 Questions To Ask Yourself
Before your next awkward chat, grab a pen. Seriously.
Ask yourself:
What conversation am I avoiding right now... and why?
What’s my biggest fear about having it?
When did I last give honest feedback? How did it go?
Am I more worried about being liked or respected?
What damage is my silence doing to the team?
What’s the toughest type of conversation for me: performance, behaviour, attitude, or clarity?
Who on my team models honest, clear conversations well?
What frameworks (if any) do I use to prepare for tough talks?
Which conversation, if I had it this week, would improve our performance or culture?
On a scale of 1–10, how confident am I leading hard conversations? What would make me +1 more confident?
Building The Muscle
This is a skill.
Like presenting. Or pricing. Or riding a bike.
It improves with preparation, repetition, and reflection.
Try this checklist before your next big conversation:
Get clear on your intention. What do you want to happen next?
Be specific. Clarity > perfection.
Talk about what you’ve seen... not what you assume.
Ask for their view. Make it two-way.
Follow up. Don’t let the conversation die in the meeting room.
Final Thought
Leadership is about doing what needs to be done, not what’s easy.
Difficult conversations are not a side job. They are the job.
Done well, they build trust, drive clarity, and raise the bar.
So, here’s your challenge:
What’s the one conversation you’ve been avoiding… that would shift the dial if you had it today?
Now go have it.
Further Reading
Radical Candor – Kim Scott
Crucial Conversations – Patterson et al.
Dare to Lead – Brené Brown
The Five Dysfunctions of a Team – Patrick Lencioni
A Framework
Before the Conversation
The goal here is preparation, mindset, and clarity of purpose.
Clarity & Intent:
What outcome do you want from this conversation?
What is the real issue you want to address (not just the symptom)?
How will you know this conversation was successful?
What are you afraid might happen? What's the worst-case scenario?
Empathy & Perspective-Taking:
What might the other person be feeling or thinking about this issue?
What might be going on for them that you’re not seeing?
What assumptions are you making about their intentions or behaviour?
Self-awareness:
How are you feeling going into this conversation?
What part of this is triggering or emotionally loaded for you?
What stories are you telling yourself about the person or the situation?
During the Conversation
The aim is curiosity, clarity, and a balance of challenge and care.
Opening & Framing:
Can I share something that’s been on my mind? I’d love to hear your thoughts on it, too.
This might be a tough conversation, but I care about getting this right together.
Exploration:
How do you see the situation?
What’s been your experience with this project/team/client?
What do you need from the team or me to be successful?
Challenge with Support:
Can I share how your actions are impacting the team/client/agency?
How do you think this aligns with our values or goals?
What needs to change for us to move forward positively?
After the Conversation
Reflection and action to build learning and accountability.
Debrief & Reflection:
What went well in the conversation?
What could you have done differently?
What did you learn about yourself or the other person?
Commitment & Accountability:
What specific actions were agreed upon?
How will you follow up?
What support do you or they need to make the change?