How to have critical conversations

The inability to initiate and follow through on critical conversations is a common presenting issue for my coaching clients. It is also at the heart of many of the challenges facing the students I have worked with at the School for Social Entrepreneurs and in group programs over the years. My clients and students often present with statements like:

“I don’t know how to…”
“I don’t understand why… “
“How can I get what I want from…”

Often they are holding critical conversations in the manner depicted in this comic.


Critical, challenging, crucial, difficult… Whatever language you use, I consider critical conversations to be the ones where you need to make significant progress on an issue or else you will pay a significant price. This may be by stopping a path of action, or by initiating a new way forward. It may be about you and your behaviour or it may be about the other person hearing what you have to say. Ultimately critical conversations are about shifting the status quo. So that means change.

Often my clients are asking themselves, “When will I be ready enough?”.

In reality, you will probably never feel 100% comfortable. But don’t let that stop you. Whenever you challenge the status quo you are asking yourself and others to step out of the comforting reassurance of the known. This always prompts an emotional response. Most often it is our base instinct to flight or fight or freeze.
I suggest to clients they will be ready enough when they have a plan and an intention in place.

Over the years I have distilled my approach into the PEADOF method. These are my principles for having critical, status-quo busting conversations.

If it is really that important you will make the time to plan. If you don’t plan for the conversation, you plan to fail. By planning, I mean taking a moment to consider and write down the key messages you need to get across during this conversation, thinking about the best time and place to have this conversation, and completing a cost benefit analysis of holding the conversation.

If you are feeling uncomfortable, so will the other person. Can you anticipate what their response may be? How can you plan for that response and not let it get in the way for either of you. Empathy does not mean you don’t have the conversation or abort it early.

During the conversation you should acknowledge the other person’s perspective and experience of the issue. This is different from being right or wrong.
“I hear your experience has been X, and we still need to change this situation”. The crucial part here is “and”.
As soon as you challenge or doubt the other person’s experience, you turn the conversation into a right-wrong, win-lose game, where both parties are trying to come out on top. Nobody likes to lose so use “and” to avoid that.

You may or may not be okay with being forthright, it doesn’t mean that the other person will feel the same as you. If you or the other person is feeling or looking to be in discomfort, it doesn’t mean that something is wrong. It just means that the status quo is being challenged. Stick with it.

All crucial conversations (and meetings!) should have outcomes that are documented and understood. These outcomes may be different than what you thought they’d be, or they may seem like non-actions. A good example is when “we agree to disagree” and to meet again. No matter what, have next steps documented and agreed to.

A conversation is nothing without action. Whatever outcomes are decided, you should follow up on them as agreed. Follow up means more than just ticking off the action items. It also means reflecting on the conversation and thinking about what you learnt about yourself, the other person and the system you work in.

I think it was Susan Scott that wrote “we succeed or fail one conversation at a time”. While I agree with this sentiment, I think it is also useful to remember that most change processes are a long game. So give each critical conversation your best shot, but know you’ll have to do it time and again to get any change to stick.

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