My go-to script for handling a super tough conversation I know I need to have

If I can have a tough conversation without bottling it or dying on the spot, so can you.

Earlier this year, I had a REAL toughie. A deep-breath, boundary-setting, speak-truth-to-power conversation.

We have these tough conversations because either:

1. Something is hurting us long term and breaking a relationship that matters 
OR

2. There is a problem and it’s our job to fix it

I was in category 1. Let me be clear - I did not enjoy it one bit. I loathed it before, during and after and it still makes me feel a bit sick just thinking about it.

The reason why initiating these conversations is SO hard is the unpredictable consequences: the threat to our valuable relationship, our income, our shared connections and tribe.

As I’ve talked about many times before, work is highly tribal. A threat to a relationship is a threat to our status and we are wired to perceive this as a threat to our safety.

Tribal thinking goes like this:

🦎 Someone’s wrong/bad and it’s either me or them.

🦎🦎 What if they are so angry and the relationship breaks down completely??

🦎🦎🦎 What if they tell other people and everyone decides it’s not themthat’s wrong/bad but me that’s wrong/bad??!

You get the idea.

Tribal thinking can keep us silent for years. Too risky, don't go there.

But these days, if it's in everyone's interests, I go there and here's how.

Here's where I start.

Am I sure this is the right route?

I start by checking with myself - do I really need to have THIS conversation?

By THIS conversation, I mean a boundary-setting conversation where the stakes are high?

I ask myself:

What’s my boundary here and is it a reasonable one? Can I live with the problem? Can I get round it? Am I making things worse by not having it? Am I getting in the other person’s else’s lane? What’s the right thing to do here? What’s most fair to everyone?

If there is no boundary to enforce, it’s a coaching conversation - totally different.

What’s my responsibility and what’s theirs?

I remind myself that I’m only in control of what I say and do. So I unhook from trying to ‘get them’ to do something differently and hitch up to gaining more insight and setting a boundary 👉 two excellent outcomes with my circle of power.

Put another way, I’m not trying to persuade them to agree with my point of view - but to complete my picture with their point of view and hear my boundary.

Let's have this conversation

What is right and what is effective - two totally different things.

If I go down the ‘what’s right/wrong’ or, worse, ‘who’s right/wrong’, we spiral quickly and get nowhere. I am drawing the other person to take the opposing side.

Even if I'm right, our brains cannot accept we are wrong/bad in this kind of conversation - our pride simply will not allow it.

And even more important - a positive outcome from the conversation is dependent on my powers of persuasion. I'm not trying to convince anyone that I'm right - I'm trying to be effective at setting a boundary.

So here’s my structure for a conversation that keeps both people in dialogue, no matter how tough the subject.

✅ First, I get straight to the point.

I don’t try and warm things up if I know I have something specific I need to talk about.

👉 “How are things? What shall we talk about? Actually, here’s something I’d quite like to discuss.”

No. This is misleading.

Take responsibility for the specific conversation you have already decided to have.

✅ Then I share my 'story' in 60 seconds

The most helpful thing I can do is get my thing out as cleanly and clearly as I possibly can. My format is some variation of the following. I've used a fairly benign example so we don't get hung up on the content.

👉 First I honour the strength that underpins the behaviour I don't want: “I always value your incisiveness and energy”

👉 I describe my observation of their behaviour with an example but without labelling them as the behaviour with “you are”. So I don’t say: “You are disrespectful to people…”
Instead I say: "Sometimes I see you talk over other people or dismiss their ideas quickly in team meetings. One time I’m thinking of is …”
(The word sometimes is crucial)

👉 I might acknowledge any contribution I have made to this: “My contribution is making those meetings shorter which has put us under more pressure” or “My contribution is not bringing this up sooner.”

👉 I show them the story I’m telling myself, stacking my observation with an indirect inference: “When I see this, it's easy to think that you don’t respect the people in the room.”

👉 Finally I explain the impact as an observation: “I’m noticing that people are reluctant to say what they really think in meetings with you and it feels like important opinions are getting missed.”

60 seconds. I’m done. Now them.

✅ Next it’s a “fact find / feel find”

It’s time for their story. Mouth shut, let go of my agenda, open up. Just listen.

I ask them to tell me about the specific example I shared - this is a safe entry point and allows us to dissect something real, not just trade opposing opinions.

I try to remember that I prepared for this conversation but they didn’t. So I give it lots of time and lower my expectations.

👉 “Can you tell me more about what was going on for you in that meeting?”

This is a good time for things like paraphrasing back.

👉 “It sounds like you were feeling frustrated about the speed of our product launch, is that right?”

And asking probing questions.

👉 “If you think back to that moment, what was contributing to you feeling that way?”

✅ I’m looking for a story match.

Their story plus my story help to fill out a more complete picture.

I’m looking for overlaps in our stories. Where do we have the same account? Where are our goals and motivations aligned?

And I’m going to play back that common ground. Doesn’t matter what it is - I’m going to find a way to keep us on the same side of the table.

👉 “It sounds like we are both trying to reduce customer churn any way we can.

👉 "We can absolutely agree that as a team, we're under a lot of pressure and that the meeting was intense!”

✅ NOW I can set the boundary

I’ve now positioned boundary firmly in the specific behaviour space - and it’s rooted on one real instance so it’s much easier for the other person to consider the concept.

One of the reasons these conversations are so difficult is that situations are never black and white. Here's a common thought process. “I know they can be difficult in meetings, but we’re all under so much pressure and I know they want the best for this project.”

The fact find / feel find allows me to account for this and set a clean boundary.

👉 “Even thought we’re all under pressure, we always value each other’s contribution in this team - it’s how we are effective. That means letting others speak in full and giving their ideas and opinions consideration. We need your critique of ideas but it’s not ok to make the person feel they shouldn’t have raised it.”

✅ I might need to give my boundaries words AND action

Just telling someone what is and isn’t ok isn’t always enough. Here’s how I might add some action to this if I felt I needed to. The third person ('if anyone is') softens this. The second person ('if you are') hardens it.

👉 “I get that these meetings are intense, so if anyone is finding it difficult to let others speak up or feeling too frustrated, I will encourage them to skip a meeting or two until they feel able to do this - or to come out of a meeting early.”

✅ Then I get back into accepting mode

I can’t control how they react to this conversation.

I can’t control what they do with my boundary.

I may have to use actions as well as words to reinforce that boundary.

But I don’t have to just accept a behaviour that causes long term damage (or is my job to address).

I’ve made my greatest effort to resolve it clearly and supportively.

And for now, I will let that stand and accept whatever comes next.

✅ And of course, I will never get it perfectly right

Inevitably I will get the timing, the tone, the delivery… some part of it wrong. There is no perfect moment or a perfect way to have a tough conversation.

Trying to get it perfect is driven by the desire to control the outcome. So I'll let go of that and accept that the outcome will always be somewhat unpredictable