How To Script Difficult Conversations – Getting Hyper-Tactical With Values.

I’m insanely busy. And I still have to do my work over and above our time together. So that means you need to give me something pretty special Toby.”

I was 5 minutes into a workshop. I’d asked: “What do you want to take away from our time together?”

This immediate challenge rattled me. But I had to respond.

“Thanks for being real with me. I’ll definitely use that to sharpen up how we work through this together.”

It was the best I could do at the time. I pushed my way through the slide deck.

I was pretty relieved to get out of there. And as I did, I could feel my frustration rising.

What the hell? Why wouldn’t they come more open minded about this? What kind of attitude is that?

It chewed me up over the weekend. I couldn’t let it go.

It took a few days to get distance, to regather my perspective.

The frustration remained, but I couldn’t fault their logic. They were right. Time is precious. It is non-renewable. Theirs and mine.

Now I really felt the pressure to deliver. How could I have any kind of impact at all? Let alone ever be invited back to do any further work?

The next workshop opening felt like a crux moment.

This was a group that I might have historically put on a pedestal. I knew this was going to be a difficult conversation for me.

What I said

5 days later, I opened the second workshop with mindfulness and then individual reflections around the group. I listened to them all.

“I have a few of my own reflections.”

I jumped in.

“I know that you all have an enormous amount on your plate. We spoke about a lot of externalities last week – covid, floods, conflicting priorities, conflicting stakeholders.

I’m really grateful that you were willing to be so real with me. That’s super important and I’d like you to continue to be.

I also realise that I can’t really help you with those things. I’ve never been in your roles. But I can empathise with how that might feel – I’ve had to work with pressure too.

The one thing I can definitely do though, is help you explore a different way of working with stress. I’ve used it for myself and I’ve helped others use it to navigate and deliver in high stakes situations.

It’s also really important to me that I make a contribution here. I’ve added up the time and it’s 76 daylight, non-renewable hours that we are all committing to our work together. Including me. That’s a lot. So I’d like your help.

What is it that you truly need to take away from this program?

What are the specifics so I can tailor the work accordingly and maximise the impact?”

The intensity in the room had dialled up. I could feel the tension.

The challenger spoke up.

“I need these two things and as quickly as possible…”

We agreed amongst the group that these would be the focus. The pace quickened, the tension lifted and we were away.

The only thing missing was the slide deck. It never came back out.

Why I said it

As the stoics say, the obstacle is the way (great book titled the same by Ryan Holiday on this).

The challenge on this occasion was a gift that allowed me to get to what truly mattered to this group.

Once what matters becomes clear, I’ve seen huge shifts in energy and focus in myself and in others. It certainly worked this time.

Here’s how I arrived at the specific script above.


Having five days between the workshops gave me a chance to respond rather than react. Another stoic lesson from Seneca: The greatest remedy for anger is delay.

I’ve been given advice recently from James Charlesworth, founder and CEO of MakerOps: Know your opening line. And know your agenda. By thinking at this tactical level, it forced me to get concise with my approach.

Writing I didn’t just think it through, I wrote it down. Writing forces clarity for me. The night after the workshop, I reflected and wrote down everything – good, bad, ugly. The day prior, I wrote my script and practiced it.


I find my values most useful when I get hyper-tactical with them. The more specific the better, especially when a situation gets tough. I use them to plan my exact opening lines for challenging meetings, for key note presentations, for difficult conversations. In this instance it was the opening lines of the second workshop.

My values are: Love, Gratitude, Humility, Exploration and Contribution.

I used each of them to script a part of my reflection back to the group. Using them acted as the cues to prompt me as I spoke and as key words throughout. Here’s a deconstruction of the script by my values.


[For me, Love in a work setting means recognising and acknowledging the suffering of others.] I know that you all have an enormous amount on your plate. We spoke about a lot of externalities last week – covid, floods, conflicting priorities, conflicting stakeholders.


I’m also really grateful that you were willing to be so real with me. That’s super important and I’d like you to continue to be.


I also realise that I can’t really help you with those things. I’ve never been in your roles. But I can empathise with how that might feel – I’ve had to work with pressure too.


The one thing I can definitely do though, is help you explore a different way of working with stress. I’ve used it for myself and I’ve helped others use it to navigate and deliver in high stakes situations.


It’s also really important to me that I make a contribution here. I’ve added up the time and it’s 76 daylight, non-renewable hours that we are all committing to our work together. Including me. That’s a lot. So I’d like your help.

What is it that you truly need to take away from this program?

What are the specifics so I can tailor the work accordingly and maximise the impact?”



I also knew I’d be nervous before this conversation. I had to practice acceptance and expect the nerves, the sweaty palms to show up. They did. I had to accept that all of this was the price of entry to this conversation and me making a contribution with this group.


I open nearly every workshop with a very simple mindfulness activity. It’s a 4-7-8 breath: breath in for a 4 count, hold for a 7 count and out for an 8 count. Do that three times and come back to the room in your own time. (You could try it now if you like. It only takes a minute.) This was an easy one to include in the flow of this situation.

I’ve come to learn that I don’t need to lose my eyes and breathe though. Some people wriggle their toes in meetings and notice the sensations. Others mindfully take a sip of water. Another time, when my father was dying, a Zen Master Mary Jaksch told me that I would know I was present in conversations with him if I could tune into the sounds around me.

I see mindfulness as the scalpel between my reaction (which I can’t control) and my response (which I can choose).

In the end, this script and process worked for me. I recovered the situation and found consensus on the exact items that would make this time most valuable. I feel immensely grateful to the challenger. As uncomfortable as it was, we were all substantially better off.



I was taught early the value of difficult conversations. Growing up, my mum insisted on us having them. Often prefaced with “This might be an uncomfortable one, but I have to ask you…”, she continues to be one of the people who challenges me most directly.

The nuance I’ve added from this situation is that I now have a repeatable process to practice. By getting extremely specific with the application of my values, I know more precisely how I can step into difficult conversations. And with practice, hopefully it won’t take me 5 days to respond.

I’ll still inevitably “fail” in these conversations at times. For sure. But I also feel now that I’ll walk away from them at the very least having tried to be the person I want to be in the process.

And that matters to me.

What Now? Filling The Olympic Void – 18 Years Later.

I was asked a question recently: “What did it feel like coming home from the Olympics?”


This was from a guy who’d spent 37 days in a boat with 3 mates rowing across the Atlantic Ocean unassisted. 


He was grappling with his own observation: “I still have to take out the rubbish.”


I gave an initial response on the call, then sent an email the next morning with more detail. I want to expand on it here.


The Void

After playing water polo for Australia in Athens in 2004, I had about 3 weeks of contentment. 


A week on Santorini Island in Greece. The welcome home parades back in Australia. A week on South Stradbroke Island. Then I started to get restless.


The Olympics was the culmination of an 11 year journey. It left a huge void in my time, focus, energy, commitment, passion, drive. So I filled it. Fast. Seemed simple enough: job interviews or start my first business? 


I chose the latter and jumped in.


Missed Opportunity

But I think I missed a key opportunity to integrate the Olympic experience. It took me years to come to appreciate, talk about and actually feel some sense of satisfaction from the work that went into getting there, the experience itself and the lessons I learned. 


It seems mad looking back, but I virtually dismissed the Olympics when I returned. 


I found it hard, if not impossible, to communicate to others what had happened over there. How on earth do you explain the entirety of an Olympic Games to someone who wasn’t there?


  • The insane, near out-of-body high of the opening ceremony after 11 years of chasing my dream. Of seeing my family in the stadium as I marched around. Of jumping up on a speaker next to the running track to raise my arms to them, to connect across the crowd, to attempt, if only for a few seconds, to share that moment with them.

  • The adrenaline of lining up to play against Greece in front of 6,000 Greeks going berserk. Then the heart break of missing a shot in that same game that might have given us an edge to stay in the hunt for medals.

  • The mundanity and tedium of sitting around waiting for the next training session.

  • The disappointment of playing in front of small crowds for most of the tournament.

  • The embarrassment of having diarrhoea from the day I arrived. I thought it was a tummy bug but it was nearly certainly a physiological response to the situation. It completely stopped the day I left the Olympic village.

  • The shame and fear of a media mistake that nearly had me sent home mid way through the Games. 

Coming back

When I returned, I felt a huge pressure, real or imagined, to share only my highlight reel. I was terrified of people thinking I was big-noting myself or being ungrateful or simply feeling sorry for myself. Often that meant superficial conversations or quickly changing the topic.


I think, in some strange way, I left parts of the 23 yr old Olympian in Greece. It has taken me years to bring him all home. Years to own the ups and the downs. Years to understand the lessons that might be applied in my life, and even more importantly, that might help others. 


In hindsight, I’ve seen this void play out for me numbers of times, most obviously after intense experiences like the Olympics, the death of my father or the decision to leave my business


The uncertainty can feel brutal. 


I’ve also spoken to many others about it over the years.


From retiring Olympians and pro athletes to parents moving into the next “stage” of parenting, from execs closing multi-year, multi-billion dollar deals to people leaving jobs, from special forces veterans returning to civilian life after 10 years of service to founders stepping away from their own companies…


The circumstances differ but the theme of transition is the same. 


And the question that remains is hard: 


What now?



What now?

I was fortunate. Post Olympics, I transitioned relatively easy. My parents had (thankfully) insisted I study all the way through my water polo career. I didn’t think much, just launched myself into work.


When Dad died though, it was a completely different story. I’d lived my life setting goals and suddenly I couldn’t find a single goal I cared about.


When I resigned from my businesses, I worked hard to deliver the best possible handover. On both occasions I didn’t know what was next. And both times, when I looked at my calendar on that first Monday of the new chapter, it was empty. I felt alone.

What worked?

We all face the void sooner or later. I have – many times over. It just happened that on this occasion my Olympics were public, visible, branded. There have been plenty of mine that weren’t.


Below are tactics I’ve accumulated that have helped me navigate these kinds of situations. Sometimes all I need is one of them to help me just get clear on the next step. If they’re useful, please take what suits and make it your own.


  1. Reflecting and writing up private notes about specific elements of these experiences as and when I felt the urge. Sometimes I’ve written down a single statement in my phone. I’ve written articles like this one or whole letters to people. Some I sent, some I didn’t. Other times, to remove the intimidation of a blank page, I’ve followed reflection frameworks to provide more structure and drill into the details to extract lessons.

  2. Story telling publicly – in speeches, written, on podcasts – and over time getting more and more real with what it was like: the good, the bad and the ugly. Now I try to drop the filter altogether and focus on highlighting lessons and actionable insights.

  3. Discussing experiences privately with others from similar situations but different contexts – business, sport, life, military, relationships, etc. I’ve found comfort in sharing some of the intensity of each other’s experiences, even if I can’t ever fully comprehend the details.

  4. Philosophy – Stoicism, Taoism, Zen, The Bible, The Quran and others. Without a doubt, this process of change and transition is universal and has been going as long as humans have been able to write about it. For me, it’s about reading these books and content from the standpoint of seeking wisdom.

  5. Connecting to my values. Two questions I often reflect on have been particularly useful when navigating uncertainty: What are my values? [Answer: Love, Gratitude, Humility, Exploration, Contribution.] How can I bring them to life today? [Answer: a specific action related to a conversation, an interaction at home, a business decision, my health, nearly anything. Specificity is critical here.]

  6. Clarifying importance. Three questions I like to reflect on for this: Who is important in this situation? What is important in this situation? How can I make a decision or take action that moves me towards these?


  7. Mindfulness. It doesn’t require a lotus position on a mountain top. Eyes open or closed, at my desk or on a bus, I breathe in for a 4 count, hold that breath for a 7 count, then breathe out for an 8 count. I most often do this 3 times but even once will make a material difference.

  8. Acceptance. I now find myself talking about the uncertainty of a void (and the associated anxiety, loneliness etc) as “the price of entry” to the change I’m working through.

  9. Doubling down on my energy. Two more questions I find useful here: What energises me? [I plan and action ways to do more of these.] What drains me? [I plan and action ways to do less of these.]

What next?

Whether it was from a deep sense of loss or the high of accomplishment, from all of the conversations I’ve had with people over the years and my own experience, the resounding theme is to look inwards. 


Suffering is a shared condition of humanity regardless of anyone’s “success” or otherwise. There is an immense beauty in how it connects us all. 


I’ve known for a long time the privilege of becoming an Olympian, of being able to fulfil my dream, of being supported by so many along that path who didn’t get the accolade but without whom I would never have made it. 


With privilege comes responsibility. And that responsibility, as I see it, is to own and share the lessons from all of my stories – good and bad – not just the highlight reel. 


I’ve seen enough highlight reels.

The mirror is the hardest place to look.

2022 didn’t start as planned. For weeks, I was waking up before 3am.


One morning I woke absolutely wired. There was no chance of getting back to sleep. I needed a whiteboard to think through some work challenges, so I crept out of the house to not disturb my wife and 3 girls. I swiped into WeWork at 2:30am.


Another morning I woke with my whole body tingling. It felt like a fountain of electricity was pouring out of my chest. I could only lie there to wait for it to gradually subside.


Another morning I woke crying. My heart rate was 74 bpm.


What the hell was going on?


Sure, there was a bit on my plate:

  • a new local COVID wave with isolation over the holidays,
  • plans to raise money to build a tech product,
  • an ongoing hamstring injury that had stopped me training for 8 months,
  • a metallic taste in my mouth triggered by anti-inflammatory medication that just wouldn’t go away…

But it still all seemed disproportionate to the circumstances. I also knew literally billions of people had it far worse than me. So I kept working at it – the business plan, the iso activities, the rehab program, the diet, the meditation, everything I thought I could do. Regardless of what I did, the sense of pressure in me just kept rising.


Eventually, I felt it was centred around work so my business partner and I had two good conversations and planned a third.



When I woke up on the morning before the third call, I found myself contemplating a concept from the Tao Te Ching, about how a bowl’s usefulness is created by the emptiness it defines. It’s similar to a martial art concept of meeting force not with force, but with emptiness. It made me also think of Michael Singer’s book, The Surrender Experiment.


So how could I be empty? How could I stop fighting this building sense of pressure? How could I surrender?


As I was drawing up an agenda before the call, it hit me.


Surrender was resigning from the business and going out on my own.


How on earth was that going to work? What would that mean?


That would mean I’d have to tell my business partner about the decision when our call started in 30 mins.


That would mean telling Luce when I got off the call and figuring out what it meant for us and our three girls.


That would mean going back to the people and clients who’d invested time, networks, money, support; to share my decision, to say thank you, to make sure they were looked after.


That would mean resigning as founder and director, after going all in for 3 years.


That would mean resigning, for a second time, from a company I’d founded.


Maybe the purists would say that two resignation data points don’t make a trend, but the pattern seemed obvious.





I cried telling my business partner. I had learned an enormous amount over the 3 years from him, from our clients and from the company building process.


When I finished the call, I went upstairs to Luce. She was reading on the bed, so I lay down next to her and shared it with her. I felt exhausted.


Then I walked back downstairs to my home office to start thinking through what was going to happen now.



2 weeks later, I sat down to reflect on the process of arriving at that decision. I love the quote from American philosopher, psychologist, and educational reformer, John Dewey:


“We don’t learn from experience, we learn from reflection on experience.”


I used two frameworks to guide me. (You can download my reflection template.)


After Action Review

  1. What was supposed to happen?
  2. What happened?
  3. Why was there a difference?


  1. What worked? Why?
  2. What didn’t work? Why?
  3. What would I do differently? What did I learn?

I was surprised to find 13 pages of typed notes fall out of me. My notes explored decades of patterns and crystallised some critical insights that crossed over into multiple domains – business, health, relationships and more.



  1. Over the last 3 years of this business I reconnected to my ability to go all in. I cannot overstate how valuable it is for me to feel that I bring all of myself to an endeavour. I’ll now need to stay connected to that moving forward.

  2. There is a kindness and excitement to recognise that I have changed over the three years and become more of myself.

  3. I understand in a new, very real way the importance of sequencing in the company building process – start with the idea (problem/solution), market, product, competition, team, traction, funding etc.

  4. I’m hugely grateful to have met and learned from all the awesome people who’ve contributed along the way.

  5. To trust my gut and if necessary seek additional data, second opinions, and alternatives. Then own the decision and keep moving.

  6. That the feeling of excitement or feeling “pumped” that I see a lot of people chasing, is a key hook of mine. It means I tend to jump all in without slowing down to pause and understand the strategic landscape and how decisions might play out. When I look back, I see this pattern clearly – particularly in water polo and business.

  7. I have learned to decouple “me”. That means I can choose, everyday, who I want to be at my core. I then have the chance to express that as a husband, father, colleague, entrepreneur, coach, friend. I get to express it in my health, in every conversation I have, in what I choose to explore and where I invest time, effort, energy, money and focus. It offers the choice and the responsibility to bring the best version of myself to as many moments as possible in a day. It also frees me up see “me” as an ongoing process of daily reinvention rather than something that is fixed and static.

  8. Finally, the power of surrender. I’ve learnt how to meaningfully and repeatedly practice it – through mindful awareness of my thoughts, emotions and physiology, through reconnecting to what matters to me, and through constant reminders to myself that stress and pressure are the price of entry to doing anything that is important to me and an absolutely natural part of life and growth.

The ongoing process

The reflection process was hard and uncomfortable – especially as it dawned on me just how much ownership I needed to take for my circumstances. It helped me to truly understand and has changed my behaviour.


It has also helped me to surrender to the clarity of the decision. Not just once, but again and again and again. The emotional impact of this decision isn’t something that gets dealt with once, it’s a process too.


Until two weeks ago, it had never occurred to me that the process of reflection holds up a figurative mirror to my actions and decisions to attempt to truly see them – warts and all.


It’s why questions are little mirrors, because they force me to pause and actually see my actions and decisions for what they really are.


And it’s why, perhaps unsurprisingly and especially in situations of pressure or stress, the mirror is the hardest place to look.