For those who want some hand-holding
The mere thought of a difficult conversation is enough to stop me from having it.
By delaying the short-term difficulty, I’m causing long-term pain as I work around unsaid things, making my own life and others’ lives harder.
To help build my confidence, I’ve reframed them as courageous conversations, and I’ve created this structured step-by-step guide to remind me to be more curious and provide prompts for when I get stuck.
Ok, it’s clunky, but I think there are others out there who might benefit from a bit of hand-holding to build their confidence. Perhaps:
- You need to have a feedback conversation with a colleague.
- You want to understand someone’s perspective on an issue you feel ‘triggered’ about.
- You can use the guide to role-play and practice for a courageous conversation.
Before you begin…
We often think about giving feedback, or having a difficult conversation, when we dislike someone’s behaviour and we want it to change. But before you go any further, it’s helpful to ask yourself:
“Is this issue ‘in the way’ for them, doing what they want to do?”
“Is this issue ‘in the way’ of us, doing what we want to do together?“
‘In the way’ can mean:
- preventing them from reaching their potential, or
- affecting your relationship, making it harder to work together and achieve your goals.
This helps us to shift from thinking about ‘me’ towards ‘them’ and ‘us’, so the feedback comes from a place of wanting to help the other person be even better.
If it’s about me, and only me, then stop here.
Get the mandate
Next, ask permission and be willing to accept ‘no’ for an answer. Here are some suggestions:
- “Would you be okay to talk about <thing I’ve noticed> with me?”
- “I noticed / heard / saw <something> could you tell me more about it?”
- “I want to get better at tricky conversations, would you be up for practising with me?”
Using the guide
The guide is colour-coded to represent the person who is talking. Each step has some suggested words or prompts you could try. Feel free to rephrase things so they feel more natural to you.
Real conversations aren’t linear like this guide; they are more of a dance. However, this guide is designed to help you slow down and support you through each element of the conversation. Once you get more confident, you’ll jump around and it’ll become more natural.
If you notice things getting a bit awkward, you can refer to the guide and say, “Hang on, the guide says we should be talking about this at this point, would that be helpful now?”.
Tips
- You may want to start by being honest that you find this kind of conversation difficult. This can help you both relax and realise you are both human.
- If you realise you need to rephrase something, try: “That’s not how I meant that to come out; let me try again.”
- Take a pause. If it’s feeling tricky (maybe your emotions are taking over, making it difficult to think clearly), take time out, either for a brief moment or a longer period of time. “I’m finding this difficult, can we take a break?”
- Check they’ve been heard. Sometimes, we jump too quickly to strategies and solutions. Slow down and go back if needed, summarise what you’ve understood so far, check that you both feel heard, then it’ll be easier to move on.
- Stay ‘people positive’. Look for the good in others and assume positive intent. Underneath it all, we have similar needs.
- Understand your own needs before you have the conversation. If you’re unsure what you want, understanding your own ‘needs’ in the situation can help. Check out this ‘needs’ list and see what resonates with you. If you want to learn more about Non-Violent Communication and ‘needs’, this book is a great place to start: Needs Understanding by Alice Sheldon. You might discover that this conversation isn’t the best way to meet your needs after all.
- Be aware of your own biases. Our evaluations of others are inherently biased and more likely to be a reflection of our own understanding and previous experience.
A call to action
The best thing to do is practise; start with small conversations with people you trust and build your confidence.
An easier place to start is to try the guide with positive feedback. Describe what you experienced in a moment when someone excelled. This helps others see more clearly what they are good at – the best gift of all.
If you’d like some help in your team or organisation, either through mentoring and support, or if you need someone to do the work, please get in touch.

