TRICKY CONVERSATIONS: The Invisible Skill We Were Never Taught

I’m going to assume that most of you reading this have learned a fair bit in life. You’ve built careers, raised families, paid mortgages, survived restructures, redundancies, break-ups, promotions, and performance reviews.

But what many of us were never taught is how to handle tricky conversations - with our partners, our kids, our parents, our colleagues, or ourselves. Especially when things get tense.

And yet they’re everywhere. At work, at home, at the dinner table, in the meeting room, on Teams calls, and in the moments in between.

Does something feel ‘off at home? Or maybe one of your senior leadership team has misbehaved and needs held to account. Perhaps you’re worried about your mate who has avoided meeting for a beer for the past couple of months. Maybe you need to have an honest chat with your son about how much he’s using social media but you don’t want to push him away in the process.

These are the tricky conversations that are inevitably going to show up in life, and rather than fumble our way through them, or put them off because they fill us with anxiety, perhaps now is the time to figure out how to navigate them.

Why Tricky Conversations Feel So Hard

What comes into your head when I say the word confrontation? What about conflict?

When people say they “don’t like confrontation”, what they usually mean is they don’t like how confrontation makes them feel.

There’s often an assumption that raising something tricky will lead to defensiveness, escalation, or things going badly wrong. And despite working with some exceptionally senior, capable leaders, I’ve seen how even the thought of these conversations can trigger avoidance.

So we put them off. We soften them. We hope they’ll resolve themselves.

But what we usually avoid isn’t the conversation, it’s the feeling we expect to have during it. Shame. Anger. Fear of being judged. Fear of getting it wrong. It’s the stories we tell ourselves about what might happen, and what that might mean about us.

So instead, resentment quietly grows. You say yes when you mean no. You become passive, sarcastic, or withdrawn. You manage people instead of actually talking to them.

At home, your temper is shorter. You get in, eat, and stare at the TV, disengaged from the person on the other sofa, longing to be seen. The same arguments surface again and again.

It’s Not Just What You Say

Most tricky conversations don’t fail because of bad wording. They fail because of state.

When we feel calm, safe, and regulated, we listen better. We speak more clearly and we’re more curious than defensive.

When we feel under pressure, criticised, rushed, or ignored, our bodies react long before our mouths do. That’s why the same sentence can land very differently depending on timing, tone, power dynamics, or stress levels.

For example:
You walk into a meeting already running late, straight off a tense call with one of the partners. The first thing that happens is someone questions a decision. Now, in a calm state, you’d probably explain your thinking, feeling rational and collected (perhaps slightly concerned). In a stressed one, it feels like a challenge. You snap. The room tightens. The conversation shifts.

The same thing happens at home.

If you’re mentally exhausted and stressed and you arrive back to your 2 kids and equally as exhausted partner in that state, the issue usually isn’t the conversation itself, it’s what you’re bringing into it. You’re not likely to communicate from a ‘safe’ and regulated and rational headspace.

Communication isn’t just an exchange of information, it’s an exchange of nervous systems.

Whether it’s with your 15-year-old daughter, your CFO, your useless brother, or the Chair of the board, tricky conversations are unavoidable. Unregulated conversations, though, these are optional.

Quick Detour: State, Safety, and the Nervous System

This is where Polyvagal Theory is useful. I find it a helpful way to make sense of why conversations go well, or quickly derail.

In simple terms, your nervous system is constantly asking one question:

“Am I safe right now?”

Not logically. Physiologically.

When it senses safety, we’re more likely to stay present, listen properly, collaborate, and repair misunderstandings.

When it senses threat, we move into protection:

• Fight: defensive, sharp, controlling

• Flight: avoidance, distraction, overworking

• Freeze: shutting down, disengaging, going quiet

These aren’t character flaws, they’re survival responses. Hardwired, ancient, and automatic.

And the workplace is full of invisible triggers:

• Authority

• Feedback

• Deadlines

• Unclear expectations

• Feeling overlooked or undermined

This helps to reframe tricky conversations. They’re not just communication challenges, they’re regulation challenges first.

If you’re disregulated, no framework is going to save the conversation. Instead of asking, “Why am I like this?”, a more useful question is:

“What’s my nervous system trying to protect me from right now?”

Before the Conversation: Regulate Yourself

Self-regulation doesn’t mean “calm down” or “be professional”. It just means noticing what’s happening in your body and supporting yourself before you respond.

1. Notice

Before you snap, shut down, or fire off an email, tune into your body:

• Tight chest?

• Shallow breathing?

• Jaw clenched?

• Racing thoughts?

That’s your cue.

2. Regulate: Slow the Body First

Regulation is personal, but one of the most accessible tools we all have is breathing.

What helps:

• Longer exhales than inhales (in for 4, out for 6–8)

• Feet flat on the floor to feel grounded

• Letting your shoulders drop

Thirty seconds can change a lot.

Most people already know what helps them regulate — they just don’t use it intentionally.

For example, if I’ve had a long, tough day and I’m stressed, overwhelmed, and irritable, I know my partner and children won’t get the best of me. I’ll be responding from fight or flight — emotional, short, and grumpy.

So I intervene.

A run if I can. Or, if there’s no time, music in the car before I collect the kids — a deliberate transition from work-me to off-duty-me.

Other strategies clients use:

• A quick Peloton session

• Calling a trusted friend

• Calm app

• A shower

• Five minutes of stretching

• A walk

• Cooking

3. Buy Yourself Time

If you’re not regulated, don’t respond yet.

Try:

• “Can I come back to this later today?”

• “Let me think about that and get back to you.”

• “I want to respond properly, not quickly.”

That’s not avoidance, it’s regulation, and it’s often what separates leaders who create psychological safety, from those who unintentionally create waves of unsafety around them.

How to ACTUALLY Have THE Tricky Conversation

Once you’re regulated, structure matters.

I often point clients towards psychologist and mediator Marshall B. Rosenberg’s Nonviolent Communication model because it keeps conversations clear, grounded, and less reactive.

In simple terms:

• What you observe (without judgement): “I see”

• How you feel: “I feel”

• What you need: “i need”

For example, instead of, “I deserve a promotion. I’m doing way more than my role”

Try: “Over the last year I’ve taken on two additional projects, I’m regularly covering beyond my remit, and I’ve delivered X and Y outcomes. When my pay hasn’t shifted alongside that, I’ve started to feel undervalued and frustrated. I want this to be a place I stay and grow, so I’d like to talk about how my contribution can be reflected in my salary.”

Same message. Very different energy.

It’s grounded in facts, it names the emotional impact without blame, and it’s clear about what’s being asked for.

Another example at home. Instead of:
“You always dump the kids on me as soon as i’m through the front door and hardly even acknowledge me”

Try:
“When I get home from work and take over with the kids, I sometimes feel hurt that you hardly speak to me or acknowledge me. I need to feel like we are part of the same team and take care of one another as well as the kids. Can we sit and talk about this?”

What this does is shift the conversation from blame to clarity. Less “you did THIS”, more “this is what’s happening for me, and this is what I’m asking for”.

Final Word

Whether you manage people or not, relationships are the work.

They affect psychological safety, performance, retention, mental health, and culture.

We see this clearly with children. My friend’s nine-year-old currently has a visibly stressed, ‘shouty’ and authoritarian teacher. The class is rushed, and constantly corrected.

The result?
Her son dreads school. He’s anxious in the mornings, avoids speaking up when he’s stuck, and has become withdrawn at home.

Adults are no different.

The environment you create, how you show up in conversations, your internal state, has a ripple effect on everyone around you.

Learning to regulate yourself, communicate clearly, and have braver conversations isn’t about becoming softer.

It’s about becoming steadier.