7 Steps to Prepare You For Having Brave Conversations

You’ve made the big decision.

You’re taking the big leap.

Now it’s time to let people know… it’s time for you to have some brave conversations, but where do you start?

In this blog (which follows on from this blog post on why we hold back on Brave Conversations) I will be walking you through seven steps that you can take to help prepare you for the brave conversations ahead.


Whether you are able to implement some, or all of these steps, I’m sure they will have a positive impact on your conversations.

Step 1: Set some intentions in advance of your conversation

Spend a few quiet moments reflecting on why this conversation is important to you.

> Why is it important that you want to take this risk, and how would you like it to go?


It's incredibly helpful to even visualize yourself in the conversation and consider how you want to show up.

👉 Think about where you'll be.

👉 Think about your posture.

👉 Think about what you're going to wear.


You can also listen for your tone of voice in this visualization.

➡ How would you like your voice to sound?

➡ How would you like to come across?

➡ How would you like to feel?

And what would you like to celebrate coming out of this conversation? Choose a measure of success for you. This prior reflection can have a big impact on you, and how you enter and carry yourself through the conversation. (I also recommend writing it down, which can make it clearer and more concrete.)


Step 2: Consider the Risks and Possible Payoffs

Our minds have an incredible capacity for imagining what can go wrong 🤯

It's okay to spend a little time with what you consider are the risks and your fears. Become aware of them, but don't linger or ruminate too long on them because that is not helpful.

It IS helpful to know what those thoughts are, and sometimes it can be helpful to think through what you will do, even if the worst of your fears come true. This helps you be prepared in advance for how you will handle it.

Remember also to imagine all the positives that could come from this conversation. This is something that our minds are not great at doing. Our brain has a negativity bias, as Dr. Rick Hanson writes in his book, Hardwiring Happiness.

Our brains are like Velcro for negative experiences and Teflon for positive ones.

Hanson shares a practice called ‘Taking in the Good’ to help you rewire your brain to take in more positives. It's an intentional practice to really help these good experiences stick. I'd recommend doing something like this when you consider risks.

Take a little time to consider what all the potential upsides of having this tough conversation might be.

👉 Maybe you end up being closer to this person as a result of this conversation.

👉 Maybe you'll gain more confidence speaking up for yourself in the future.

👉 Maybe if you're going in to negotiate a raise, you’ll actually get it. (This happened for one of my clients recently and I love celebrating this)


Step 3: Create your Super Simple Top-line Message

Back in my communications roles, whenever I began a communications strategy or campaign, I would make sure that we started with a top-line message; the top key messages that we wanted to communicate.

I now use this with my clients. Whenever they need to deliver some news to someone or to a group of people, we come up with their super simple and safe top-line message.

Let me give you an example: When I was preparing to take my year sabbatical, I dreaded telling my boss, and I did in fact experience the worst-case experience of getting yelled at by a boss when I gave her my two weeks’ notice. Now, more than ten years had passed since someone yelled at me when I quit my job, and this boss was nothing like that one. But I still worried when I imagined telling my boss I was leaving to take a year off. These were the kinds of thoughts that were happening in my head:

💭 Would he get mad?

💭 Would he be disappointed?

💭Would he tell me?

💭Was I making a big mistake?

Also, my boss happened to also be the CEO of my organization. So this is a conversation with someone in a very high-up leadership position. So the stakes definitely felt very high, and this conversation was so final. Once I gave notice, it was a point of no return on my decision.

Then one day as I was at my desk doing my work, drafting talking points for my boss to use at an upcoming conference, I suddenly realized the obvious. I was a communications professional. If I felt so nervous, I could write up my own damn talking points for myself. I could be in control of my own story. So here's what I did to prepare for our conversation. I made my top-line message very simple. I made it easy to remember. I remembered that I didn't need to include every messy detail in my story. And yes, there were many. I didn't have to include all my doubts and misgivings, my fits and starts and all my vulnerabilities and fears. I knew it was safer to save all of those details for a few trusted friends. For my boss. I wanted a simple and positive story. I was sharing my dream in this conversation, and it was also important to protect it. So I wrote out this and then I practised saying it.

I said, “I've decided to take a year off to travel. It's been a long-time dream of mine and something I'd always thought I'd do in my twenties. I realized that if I don't do this now, I'm never going to do it.”

It worked. I remembered it easily, even with the nerves of that moment. And when I shared my decision with him in a simple, positive way, it was easy for him to support me, albeit somewhat grudgingly. Eventually, he said, “You know, if you want to take this time off to travel now, I'd say Do it”

Looking back, that's the advice I'd give you. I walked out of his office. I had given my resignation. It had gone well. I was elated. I had handled it just as I wanted.


Step 4: Write Some Talking Points

Talking points are helpful for the moments after you share your simple top-line message.

These are to help you handle people's responses, because people will have responses, and often they have questions or even challenges. So talking points are prepared answers that people have to tough questions. They're designed generally to help a speaker stay on track in a presentation when meeting with the press or in a meeting.

If you've ever watched a press conference where the president or CEO of some big company (especially the ones embroiled in scandal) is answering reporters’ questions, you can bet they're working off talking points prepared for them by their communications team.

They keep you on track under pressure - here’s how to write them:

Write down every single question that someone could ask you about your leap or whatever you're communicating to them about. (Especially write down the questions you hope they do not ask - for me, this was based around getting a job after my sabbatical)

➡ Once you have these dreaded questions down, draft an answer for each one. Keep your answers simple and easy to remember. Your answers should be true and authentic and at the same time don't include so much detail that puts you in a place where you feel unempowered or unsafe. You can always choose to share more of your story later when you're ready to do so. So for my own dreaded question ‘What about your job?’ Here's what I drafted in response to that question:

“I've definitely thought about that, too. And so what I did was I met with a few mentors of mine who know my work and the market well, and they reassured me that I'll have no problem finding work again and that I can even use this experience professionally if I want to.”

Don't get nervous and stray from your messages. You know that line, that's my story and I'm sticking with it. It's actually really good advice for those moments when people start to pepper you with uncomfortable questions that you're not prepared to answer. Don't let them rattle you.


Step 5: Practice

Sometimes tough conversations can rattle us. That's why they're tough. The thing that can help counterbalance you getting rattled is having done this prep work, including practicing what you'll say.

👉 You can practice by yourself, grab your simple top-line message and talking points and read them aloud

👉 You can practice by doing a role-play with a friend or a coach. (I'm one of those people who used to avoid role plays at any cost, but now I welcome the chance to do them and to have my clients do them because they're so helpful)

👉 You can also practice by recording yourself and playing it back to yourself. (This can be painful for those of us who don't like seeing or hearing ourselves on camera. But again, it is so worth it. Think of it as collecting information. You're going to learn so much)

Here are a few other tips:

  • Don't practice too much - you don’t want to sound rehearsed and stiff. (And if an inner perfectionist or anxiety is driving you, it will make you exhausted). Practice for just a few minutes.

  • I also find it's best for me to write down a script about the day before, and then I practice about an hour before the meeting or event for just 5 to 10 minutes. So for example, in advance of a presentation or interview, I will grab my script and walk and talk to myself under an olive tree outside of my office door. It feels nice to be outside and it's just more pleasurable. When I come inside, I also record myself using Zoom and watch it back until I feel like I've got it. (Credit for this idea goes to my speaking coach Jackie Harper, a former BBC presenter for this Zoom Self recording tip!)


Step 6: Prepare Yourself Energetically Before You Have an Important Conversation

Do what you can to get yourself in your best energetic place.

💃 This can be having a quick dance party.

💤 This can be getting a good night's sleep.

🚶‍♀️ It can be taking a short walk right before

😌 It can be taking a deep breath or anything else you need to do in the moment to calm down your nervous system

🍀 It can be choosing a comfortable place to have the meeting / making the phone call wearing your power suit / having your lucky stone in your pocket - Do whatever rituals give you a boost because all of these things make a difference.

It's also important to remember that just because you have a nervous reaction, it doesn't mean that what you're doing is wrong or that you're making the wrong decision. It simply means that your nervous system has recorded something about this from the past and that you'll need to do some self-calming to bring yourself back to this present moment.

Whenever I have to quit something, I have to be aware of my own nervous system reaction because I had that traumatizing quitting experience when I was in my early twenties. So if you have a nervous reaction, first check in with yourself. Are you safe? Are you okay? It's incredibly important that you are safe, so always prioritize that. If you don't feel safe, get yourself out of there. Abort mission. If you are safe. Okay. Take a deep breath. See if you can soothe yourself. Find a friendly face or a thought to focus on. Even turn up the corners of your mouth. We can work through these moments.


Step 7: Celebrate

Whatever happens, take a few quiet moments after to reflect on how it went and always take time to celebrate and acknowledge yourself for what you did.

🎉 What are you proud of yourself for doing here?

🎉 What progress did you make in getting better at having tough conversations?

🎉 What did you learn about yourself?

🎉 In what ways did it go better than expected.

🎉 What do you want to remember for the next time you're about to have a challenging conversation?

As I mentioned before, when you pause to take in the positives, you are rewiring your brain and this can help you so much to feel more empowered and positive and capable in the future.

And that is all of the seven steps to better prepare you for tough conversations!

Try out even one of these ideas and you are going to see a big difference.

Modify them so they work for you. And so you can be brave and have those tough conversations that are fundamental to you, living a life that expresses you and your values.

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Brave Conversations Open Up a Happier Life