The conversationyou keep not having.
Most advice on difficult conversations starts with what to say. That is already too late. This starts earlier, with understanding what you are actually walking into.
There is a conversation sitting in the back of your head right now.
You have rehearsed it in the shower. You have drafted the message and not sent it. You have told yourself you will do it next week, and you have been telling yourself that for a while.
- Feedback you have been putting off giving someone.
- A behaviour that keeps happening and keeps not getting named.
- Performance you have been working around instead of addressing.
- A relationship that got damaged and has stayed that way.
- A boundary you needed to set months ago.
- Something that has been quietly bothering you since spring.
- A conversation you are avoiding because you think they will get angry, or go quiet, or cry.
The longer it waits, the heavier it gets, and the harder it becomes to have well.
Everyone wants to hand you a script.
Say this. Then say that. Use the phrase. Follow the formula. It sounds helpful, and it fails for an obvious reason: the script was not written for the human sitting opposite you, and it was not written for what you are actually trying to achieve.
A conversation to repair a relationship and a conversation to hold someone accountable are not the same conversation. Treating them the same is why so many of these go wrong.
There isn’t one right way to have a difficult conversation. The right path depends on the humans involved and the purpose of the conversation.
Four things to understand before you open your mouth.
Know Self
What am I bringing into this conversation?
You do not just bring words. You bring your emotional state, your expectations, your assumptions, every previous version of this conversation and however many months of accumulated frustration. All of it shows up in your tone, your face and what you hear them say.
Know People
Who is the human I am actually talking to, and what might I not understand yet?
Not who you have decided they are. The actual person, including the parts of their situation you cannot see from where you are standing.
Know Purpose
What am I actually trying to accomplish?
To understand. To coach. To give feedback. To correct. To repair. To set a boundary. To hold someone accountable. To deliver a decision. Different purpose, different path, and most people never stop to pick one.
Know Path
Given these humans and this purpose, how should I navigate it?
Where, when, who goes first, how direct to be, how much silence to leave. The room is part of the conversation whether you designed it or not.
Most of the damage is done before anyone speaks.
Facts, interpretation and the story you built
These are three different things, and by the time a conversation feels difficult they have usually fused into one.
Know which parts you know, and which parts you filled in.
It might not be about you
Something happening to you does not automatically mean it is happening because of you. You can be the target of a behaviour without being the reason for it. Impact and motive are different questions, and confusing them turns a solvable problem into a personal one.
This does not excuse the behaviour. It changes what the conversation is for.
Your part in it getting this hard
Ask honestly whether this became difficult because an easier conversation got avoided earlier. Feedback delayed. Expectations never made explicit. Frustration accumulating on your side while the other person had no idea anything was wrong.
You have had six months of this. They may be hearing about it for the first time.
The trouble with their shoes
Imagining how you would feel in their situation is not understanding their experience. It is simulated empathy run through your own lens, and it produces confident conclusions about people that are frequently wrong.
Don’t put yourself in their shoes. Get curious about the person wearing them.
When their behaviour makes no sense
Add one word and the whole conversation changes. Their behaviour doesn’t make sense to me yet. Then ask the question that actually opens something up: what would have to be true for this to make sense to them?
Understanding behaviour is not the same as accepting it.
Curiosity is not a delay tactic
Empathy and curiosity can quietly become another way of not saying the thing. At some point you have to name the behaviour, its impact, and what needs to be different.
Empathy without clarity can still leave someone completely confused.
You bring the real one. Not a case study.
At the start you choose one actual conversation you need to have. You work on that same conversation the whole way through, and you finish with it prepared rather than theorised.
- Choose your conversationThe real one. The one you have been carrying.
- Work through Self, People, Purpose and PathShort videos, guided reflection and practical tools, applied to your situation rather than a generic example.
- Build your Difficult Conversation MapIt fills in as you go. By the end it is a preparation document for your specific conversation, not a worksheet you abandon.
- Go and have itWith a plan for what you want, how you will open, and what to do if it goes somewhere you did not expect.
Not phrases. Judgement.
- A specific conversation you are actually prepared to have
- The ability to separate what happened from the story you built about it
- A way to work out what is driving behaviour that makes no sense to you
- Clarity on what you are trying to achieve before you start
- A method for choosing an approach that fits this person and this purpose
- Language for naming a behaviour and its impact without softening it into nothing
- Something to do when they get defensive, angry, tearful or silent
- Something to do when you are the one who gets triggered
- A way to tell resolution apart from relief that it is over
- A repeatable process for the next one, and there is always a next one
Difficult Conversations
- The full self-paced course. Six modules: Start Here, Know Self, Know People, Know Purpose, Know Path, Go Have the Conversation.
- Short teaching videos from Kip throughout.
- The Difficult Conversation Map. Built progressively around your real conversation.
- When It Goes Sideways. A reference guide for defensiveness, anger, silence, tears, blame and the unexpected.
- Written reference material and practical preparation tools.
- Guided reflection applied to your situation, not a generic scenario.
- Lifetime access. Come back for the next one.
Work through it. If it does not help you with the conversation you are carrying, email me within thirty days and I will refund you. You do not have to explain yourself.
Who this is for, and who it isn’t.
- You are responsible for other people and some of those relationships are hard
- You have a conversation you have been avoiding and you know it
- You keep having the same conversation with no change
- You are good at the work and less sure about the human parts of it
- You want to understand the situation rather than perform a technique
- It is not a work conversation at all, and you still need to have it
- You want a script to read out
- You want a guaranteed way to make someone react the way you want
- You are looking for permission to avoid the conversation
- You want theory and research rather than something to use this week
- You are in a situation involving harassment, abuse or safety, which needs proper support rather than a course
Kip Jon
Applied behavioural scientist, executive coach and speaker. For more than two decades he has worked with leaders, teams and organizations on what is actually driving behaviour, rather than what it looks like on the surface.
This course is built from that work. Not from a communication model, and not from a list of phrases that tested well.
Understand the human before designing the solution.
Before you decide
When does it open?
Late October 2026. The waitlist gets first access and the opening price, and you will hear from me directly before it goes live rather than through a sequence of marketing emails.
Is this only for managers?
No. It is built for anyone responsible for other people, which includes managers and executives, and also includes people with no direct reports who still have to navigate colleagues, clients, peers and family. The framework does not care what your job title is.
What if my conversation is personal rather than professional?
It works. The examples lean professional because that is where most people encounter these first, but Self, People, Purpose and Path apply to a conversation with a partner, a parent or a friend in exactly the same way. Plenty of people take this for a work conversation and end up using it somewhere else entirely.
Does the course give me scripts?
No, and that is deliberate. A script written for someone else’s situation is the reason these conversations go wrong. You get structures, questions and tools for working out your own approach, including clear language for naming a behaviour and its impact when that is what is needed.
What if the other person gets defensive or emotional?
There is a whole reference guide for exactly that. Defensiveness, anger, silence, tears, blame, denial, and information you were not expecting. It also covers what to do when you are the one who gets triggered, or when you realise partway through that you were wrong.
The aim is not to control the conversation. It is to stay capable of navigating it.
How long do I have access?
Lifetime access. This is not a course you do once. Most people come back to the Map the next time something difficult lands on them.
How long does it take?
It is self-paced, so it moves at whatever speed you do. You can work through it over a weekend or spread it across a few weeks while you prepare for a specific conversation.
What if I am not sure it is worth $297?
Think about what the conversation you are avoiding is currently costing. A team member who stays disengaged. A relationship that keeps degrading. Six more months of carrying something that could have been handled in twenty minutes if it had been handled well.
And if you buy it and it does not help, you have thirty days to ask for your money back. No forms, no explaining yourself. Email me.
Have theconversation.
Self-paced · Lifetime access · $297 USD · Opens late October 2026