How to Have Difficult Conversations – 10 Steps

by | 24 Nov 2021

Do you put off having difficult conversations – at work and at home? If you do, read on as there is a lot more to mastering difficult conversations than you think. It’s not good enough to have a ‘chat’ and think you have dealt with ‘it’. You need to get your head around what to do before, during and after the conversation. I recently listened to Rachael Robertson as she shared some leadership tips and tools from her time managing a team to the Antarctic. I was taken by her authentic and practical style. But what really clinched the deal for me was how much she cared for her people, her team, her colleagues, and ultimately on a year long expedition to Antarctica, her friends. Check her out at For now, I want to share her 10 steps to having successful difficult conversations. Give them a go and see how much of a difference they make…..

BEFORE: Plan what to say and when to say it

Timing and timeliness – Choose the right time and place. Don’t hold the conversation when the other person is upset or angry. Respect the other person’s privacy by minimising the chance that you may be overheard. Whenever possible, have these conversations face to face. As soon as you realise you need to have a conversation, do it! Don’t dwell on it, leaving it too long only makes it more difficult. Never use email.

Anticipate that you may not be on the same page – Different perceptions of intent, interpretations of the facts, and judgements about what is right or best are usually at the root of all difficult conversations. When you begin with this in mind, you will not be surprised when these root issues arise. Try to understand the point of view as well as the emotional state of the other person. Understanding the other party’s position helps you make better decisions about how to address the situation. When you show genuine interest in understanding the person’s side of the story, you are more effective in resolving the matter.

Rehearse – If time permits, it helps to put the details of the situation in writing. Include what you wish both parties to achieve. Doing so gives you an opportunity to consider all views and nuances of the situation. Taking the time to prepare properly for any important conversation yields better results. Rehearsing in your mind and trying to anticipate how the conversation will go is often helpful.

DURING: Keep the conversation on track

What and Why? Ask questions – Ask questions.  Use specific examples, What is at stake?  Why does this matter? Ask questions to establish what is going on in their view. We demonstrate respect for the other person when we acknowledge that we may not understand the full complexity of their situation. For example, ‘I’d really like to understand what is important to you in this situation and what has occurred before.’

Identify your role in the situation – How have you contributed to the situation? Show some vulnerability, but be selective. For example; ‘My part in creating a growing rift between you and the others is that I didn’t bring this to your attention earlier.’

Maintain eye contact and stay in control – As in any constructive face to face communication, maintaining eye contact helps you gauge the receptiveness of the other person throughout the conversation and demonstrates your honesty and desire to listen to the other person. If yo express anger, it is natural for the other person to respond accordingly to match your emotional state. Do whatever it takes to remind calm.

Clarify – Confirm you understand what is being communicated and paraphrase it to acknowledge their point. This behaviour helps them to see that you are listening and also clarifies your understanding of the situation. For example; ‘Okay, so what I am hearing is that you are disappointed with X because of Y. Is that a fair description of the situation?’ Clarify your expectations and work together to identify options to meet those expectations.

Don’t interrupt – When the other person is speaking, never interrupt. Show the other person the respect you want to be shown when you are talking. In addition, don’t appear to as though you are anxious to respond. People who can’t wait to speak generally aren’t listening, because they are so focussed on what they want to say.

LADAR – Turn on your LADAR (language radar) and listen for ‘ping’ words such as always, never, everyone, no one, can’t and won’t. Avoid saying things like, ‘Everyone in the department feels the same way’ or ‘I have heard about this from countless people’. Often when we hear these kinds of statements, we immediately discount what is being said because in most cases they are exaggerations. If the issue is so serious that you need to being others into the discussion, make sure they are present. Listen to both yourself and the other person. If you exaggerate, quickly clarify.  If they do, ask for specifics. Use facts.

AFTER: Consolidate and move forward 

Follow up Try to speak to the person again within a day or two, even on an entirely unrelated matter. It keeps the conversation in perspective and shows you ‘said what you had to say’ and are now prepared to move on.

As leaders you will be faced with difficult conversations.

Please reach out via our leadership laser hour one on one program if you’d like support Click here for more information

I hope to see you soon.

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About the Author

Jo Eady

Jo Eady

I’m a leadership specialist, a human centred facilitator and a modern day storyteller. I live in Victoria, Australia. For the past two decades I’ve developed and facilitated a range of leadership initiatives, strategies and programs and have coached many across Australia’s agricultural and rural sectors. I love being a change agent and my key motto right now is courage over comfort. I support others to develop their own leadership essence and shine from the inside out.