Steering Through Storms: What Sailing Taught Me About Bold Leadership with Caspar Craven

What do you do when the storm hits? Do you cling to what was—or boldly redefine what could be?

Caspar Craven knows what it means to navigate the unknown.

He’s sailed around the world. Twice. Once in a gruelling yacht race as team leader. And again—just a few years later—with his wife and three young kids under 10.

But he’s not just an adventurer. He worked at KPMG, is also a serial entrepreneur, a former CFO, and a leading voice on what it really takes to achieve Big Bold Goals—not through spreadsheets and pressure, but through people, purpose, and the power of bold conversations.

Welcome to episode 105 of TIE Unearthed.

In this episode, Caspar joins me to talk about the deeply human side of leadership.

We explore how constraints—whether in the middle of the ocean or in the boardroom—unlock creativity and resilience.

Why real leadership means getting out of the comfort zone and going deep.

And how our identity, fear of failure, and unwillingness to have uncomfortable conversations are often the biggest barriers to change.

Caspar shares what happened when he led a team with a “drive hard, win fast” approach—and how it ended in burnout and dysfunction.

And he explains why it’s not enough to aim for results—you need to create a culture where people feel valued, understood, and safe to contribute.

We talk emotions. Vision. Reinvention. AI. And how the best leaders aren’t afraid to rethink the rules—and lead from a place of depth, not just direction.

So if you have ever felt stuck, overwhelmed, or unsure of how to lead when the path isn’t clear, this one is for you.

Tune in, and ask yourself:

What bold conversation are you avoiding?

And what might be possible if you had it?

So grab that favourite beverage, or throw on those running shoes, and get inspired by Caspar.

Don’t forget to share your thoughts on the episode, leave a review, and subscribe!

If you’d like to stay updated on future episodes and other inspiring stories from TIE, join our newsletter ⁠⁠[⁠here⁠⁠⁠].

If you’d like to learn more about Caspar, check out his site [here]

 

 

0:03

Welcome to the show where we expose new perspectives on our ever evolving world through the lenses
of various industries, cultures and backgrounds.

0:14

Our guests are disruptors, united by a common goal to bring their purpose to life.
Whether they’re from the commercial world or third sector, from the global North or the global S,

0:26

expect an inspirational journey that will transform your perspective on just what is possible.
My name is Philippa White, and welcome to TIE Unearthed.

0:40

What does it take to navigate unchartered waters, both in business and in life?
Casper Craven knows he sailed around the world twice, once as a team leader in a grueling global

0:55

yacht race, and again as captain and team leader of his family team with his wife and three children
under the age of 10.

1:06

But Casper isn’t just an adventurer.
He is a leading authority on the mindset needed to achieve big, bold goals through effective

1:16

leadership and teamwork.
A serial entrepreneur, he’s built and sold a tech business for a 7 figure sum, worked as a CFO and

1:25

at KPMG.
He’s also authored 5 books.

1:29

Welcome to episode 105 of TIE Unearthed.
In this episode, we dive into Casper’s unconventional journey from a high flying career in corporate

1:41

finance to stepping into a yacht race with little experience, a decision that reshaped his entire
approach to leadership.

1:51

We talk about overcoming personal and professional crises, the power of bold conversations, and why
real leadership isn’t about spreadsheets.

2:01

It’s about people, emotions, and unlocking human potential.
Casper also shares how navigating constraints, whether in the middle of the ocean or in business,

2:13

forces us to think differently, get resourceful, and push past our limits.
We explore the lessons sailing teaches us about resilience and communication and leading with

2:25

purpose.
And of course, we touch on AI identity and the leadership rules that need rewriting.

2:33

This is a conversation about courage, reinvention, and what it really means to lead.
So get ready.

2:39

This episode has stories that will make you rethink how you approach challenges both in life and in
business.

2:47

Well, let’s dive in.
Casper, thank you so much for joining me and our listeners on Tie on Earth today.

3:00

I hope you’re well.
Absolutely.

3:01

And very well.
It’s a pleasure to be here.

3:02

Thank you for the invite.
Yeah, and I’m loving your energy.

3:05

My goodness, when I called on today, you’re just, oh, it’s going to be such a good energy.
Wonderful.

3:10

Imagine my imagine my poor wife and.
Family, you know, and we’re going to get to where this energy has taken Casper in a moment because

3:20

you’re going to understand what happened.
Where are you sitting?

3:23

Because I love it.
I I speak to people all over the world.

3:25

So where are you right now?
So right now I’m in my my studio in Weybridge in Surrey, just southwest of London.

3:32

Oh, sorry.
Yeah, nice.

3:35

And we have blue skies and sunshine today as well, so I’ve skylights up there, so it’s beautiful.
So, Casper, tell us your story before you got into doing what you do now.

3:43

I think it’s really wonderful to just understand the background of somebody and just a little bit
more about them.

3:49

Your journey has been incredible.
Just bring it to life.

3:52

For us, sure.
Sure, half of life and career was more conventional.

3:57

Went to university, trained as a childhood accountants, then ended up as an investment banker with
KPMG for a number of years.

4:03

And then quite unexpectedly, quite out of the blue in early 2000, I ended up accidentally signing up
for a Got race around the world.

4:12

And as you do, as you do, there’s quite life changing moments.
And committed to that.

4:17

In the January and September I was suddenly found myself on a boat off around the world for 10
months.

4:22

There are lots of stories about that, but then it came back from that.
I reached rejoined KPMG for a year.

4:27

Then after that, I started launching my own businesses.
And that’s taken me on a bit of an entrepreneurial journey with a whole bunch of different ventures,

4:35

some some highs, some lows, mixture different things.
And in the midst of building one of those businesses that when life was not going particularly well,

4:42

my wife and I hatched a plan to do something a little bit different with our lives.
And that culminated with us again staying around the world for two years with our three kids under

4:51

the age of 10.
So then stuff since then, but a whole bunch of different firms working in large companies, building

4:56

startups and some other board level roles as well through to a couple of circum navigations of the
planet on the blue stuff.

5:02

So whole extra things.
Oh, amazing.

5:06

And I’ve got questions.
Of course I’ve got questions about the sailing experience.

5:09

Anyone who is listening knows my my background when it comes to the sailing stuff.
But before we get there, just I’m curious, what was that catalyst that made you want to go sailing

5:21

around the world?
Where were you at in your head the 1st?

5:24

Time, yeah.
So there are two things.

5:26

The personates.
So the first thing is the context.

5:28

There was like turn of the Millennium.
There’s all that talk about Y2K change was in the air and all those sorts of things.

5:34

And I remember being the the Boat Show in London at Earl’s Court as it was back then, and coming
across this stand where they have this massive, great big plasma screen with boats crashing through

5:44

waves.
And I’d done a little bit of sailing, but I never really wanted to go and do offshore sailing.

5:49

I remember just like, it literally just captured me in the moment I’m looking at things like that
looks really cool.

5:54

And so the person came up to me on the stand and started chatting away to me.
And they said, well, would you like to sign up for the race in 2004?

6:01

So I thought, no, that’s four years away.
I can’t really plan my life that far in advance.

6:05

So they said, well, you can sign up as a reserve for this race.
So it’s like, tell me about that.

6:08

And so they explained what that involved.
And before I knew it, my hand was gliding across the piece of paper and filling in a form and

6:14

writing a check for 100 lbs.
My girlfriend at time comes over to me and says, what are you doing?

6:19

And I said, I’m trying to sell around the world, but don’t worry, it’ll probably never happen. 10
days later, I was sitting in my car on little High Street just outside where I work for KPMG and I

6:27

had a phone interview with such a Blythe.
I remember him sharing this story with me and I basically said, look Casper, there’ll come a time a

6:34

time when you’re looking down at your toes.
And he said just before you draw your final breath, you’ll ask yourself, have I done everything I

6:40

want to do in life?
And so the answer to that is no, you’re going to be pretty brassed off.

6:44

So stop messing around, work at your and go and get on with it.
So it’s like, all right, let’s go do this race.

6:50

So I did ask him.
I said, what advice have you got for me?

6:52

I said, going to take your your girlfriend now my wife out for a nice dinner.
So literally it just suddenly came from nowhere.

6:58

And I think, yeah, these things are around us the whole time, but it’s a question of whether we
seize those things or not.

7:03

So that was where that first adventure came from.
Maybe bring us to the second adventure, then the.

7:07

Life was particularly tough at that stage.
So running a small data analytics company here in London, we’re turning over about half £1,000,000,

7:14

losing money, working 16 to 18 hours a day.
And Nicola and I were on very, very rocky ground.

7:24

Should we say things were not good?
And so the business was failing and family life was failing.

7:29

We sat down and said, OK, so this is where we are in the present, let’s write a different story of
the future.

7:35

I think a lot of people look backwards and say, well, that’s what the story was, how do we get back
to where we were?

7:39

And it’s like actually I think the other way around.
I said where do we want to go in the future?

7:42

What does that narrative look like?
And they were in a month, a period of about 3 or 4 months, we literally scripted a narrative of what

7:48

we wanted our future to look like.
And it was that narrative that literally ended up pivoting our world, turned our marriage around,

7:56

turned business life around, found a life around.
And it was that power of that, what I would call bold conversation to say, let’s go and do something

8:05

differently.
And that was the seed where it all started.

8:08

So from a really, really challenged place to say, let’s do something different.
God, I mean, there are so many lessons in just that.

8:17

But let’s go to the sailing experience itself because obviously we both work in the area of
leadership development.

8:24

There’s so many people I know actually who use boats.
I mean, there’s a Brazilian Olympic sailor, Lars Grayo, kind of a famous guy.

8:32

So he’s a friend of ours.
And I mean, he does a lot of motivational speaking, but there’s a lot of training that they do on

8:37

boats, sailing because it’s everything you need from a leadership point of view.
So what did the experience teach you about leadership, teamwork, resilience?

8:46

I mean, there’s just so much in there there.
Is a lot in there.

8:49

I think, you know, one of the beautiful things about being on a boat is that literally you’re there
and there’s nothing else.

8:55

It’s just you and the people, and you can’t get off the boat and in the middle of the Atlantic with
your wife and kids and someone has a tantrum, whether it’s the kids, whether it’s you, whether it’s

9:03

your wife, and you’ve got to deal with that.
And there’s no other resources.

9:08

So it’s just literally what you’ve got.
So I love that metaphor.

9:11

And it’s not about the resources you have, it’s how resourceful you are.
And that really takes you on a journey to understanding human beings because that’s the only place

9:20

that you can go is to decoding the human animal.
And why are we doing what we’re doing?

9:25

You know, the other aspect of that as well is that you’re going out there to extremes and you know,
you don’t reach those sort of extremes of pressure, of challenge, of uncertainty in normal day life.

0:00

I don’t think most people do.

9:37

But when you go to those extremes, you have to learn very fast, especially on that first yacht race.
You know, we’re going through hurricanes and we’ve got 100 foot waves and, you know, going through

9:45

icebergs and stuff like that.
There is no alternative.

9:48

You learn and you figure out what what that is.
You know, I think as I’m trying to link that back to how I talk to organizations now and I think,

9:56

you know, what is it?
What are some of those key things that come out of that?

9:59

But there’s a neuroscientist, and then something escaped my mind, but he has Anthony Damasio, and he
has a lovely saying that we’re not thinking creatures who feel, we are feeling creatures who think.

10:09

And I think that is so, so powerful.
I know from having read some of your books that you will agree with this, but it’s just

10:17

understanding the human animal.
Why are we doing what we’re doing?

10:19

And it’s emotions, not thoughts, that drive so much of what we do.
And I think that those were some of the core insights that came out of both voyages, both on the

10:28

competitive race and then with the family.
My partners, you know, he’s done the Cape to Rio, he hasn’t done around the world, but I mean, I

10:34

think he’s, I don’t even know how many thousands of miles he’s he’s raced and he’s sailed in Brazil.
There’s 2 words.

10:42

One is J Tiu and there’s Gambiaja.
Now J tiu is there’s always a little way now J Tiu is considered a bad thing.

10:51

So there’s always sort of a way of cutting in front of people or getting free concert tickets or
getting free bus rides by hanging on the back.

10:59

So I mean, there’s a lot of things that are JTUS that Brazilians sort of say, oh, you don’t look
awful.

11:03

But I actually see JTU as such an amazing thing because I see the Brazilians being so unbelievably
resourceful.

11:10

And it’s because there’s a lot of people don’t have very much and you’re forced, you know, necessity
is the mother of invention.

11:16

It’s sort of you’re forced to figure out solutions to things.
And I think on a sailboat, it’s that to the extreme because you literally.

11:24

Don’t have a plumber?
So you need to figure it out.

11:26

You don’t have the pieces, so you need to figure out what on the boat to become the piece to then
find a solution to fix the toilet.

11:33

And, and it’s just, and Gambiaja is, again, it’s, it’s a type of JT, but you know, if something
breaks, you sort of get something and you get a little bit of resin and then you kind of piece it

11:44

together and then that’s the solution.
And actually it probably works quite well.

11:47

Or Gambiaja is cutting a, a coffee maker and getting a piece to then make the the solution to fix
the toilet or whatever, which did happen on one of these races.

11:57

And I just think when you see the world like that, you have to experience constraints in whatever it
is that you do to then unlock that ability that people have to realize that they know more than they

12:09

do.
They think they do.

12:11

They have access to more responses to solutions when you really have to.
And the more we can find those opportunities for people to unlock that, it’s magic.

12:21

Absolutely.
Like I think you expressed that usually I think the way I would process what you just said is that,

12:27

you know, everyday life doesn’t give us the opportunities to do that because other solutions are so
easily readily available, whether it’s going asking somebody else or you’ve got a problem with an

12:38

oil leak in your car, you drive it out the garage, you’ve got to figure out how to fix it.
And so we almost have this sort of, I think what I would call a learned helplessness in much of our

12:48

normal day life.
And actually when you sort of sit there and I remember we had some, you know, some challenges and

12:53

it’s like, OK, what we do, well, OK, just get the manuals out.
So let’s figure this out.

12:57

Let’s go back to first principles and suddenly access a whole different part of us.
But I wonder whether we have this when we’re younger, just the trophies as we get older because we

13:05

don’t need to access, access those parts of it.
But I think there’s that resourcefulness is very, very powerful.

13:10

Certainly lots of organizations, you know, challenges all over the world, right?
And I think we need to go and find some more of that challenges.

13:17

We need that fresh.
Thinking.

13:19

That fresh approach.
And it’s so empowering for people as well.

13:22

I mean, for you.
Well, and it’s connecting.

13:25

I mean, when you just think of all these things, you know, you, your wife, your children, going
through those experiences at the moment, I’m sure, you know, there’s a bit of tension.

13:32

It’s like, look after the oh, what’s happening, you know, but when you come out of it and you’ve
gone through that, you’ve actually found those solutions, it makes you so much stronger.

13:42

And it’s the same with teams, right?
And it’s, and it’s the same with as an individual, if you really don’t feel like you have much to

13:50

offer the world and then suddenly you’ve experienced a really challenging experience, whatever that
might be, and you’ve managed to overcome that and you’ve managed to thrive yourself worth and your

14:03

confidence just skyrockets.
What?

14:06

What?
You just remind me of there the I’m sure you say this, that the that Steve Jobs talk what he did at

14:11

the Stanford Commencements and he talks about I have Maple and he said, I think the phrases were he
said it was awful tasting medicine, but I think the patient needed it.

14:20

And The thing is with these challenges, they are awful tasting, right?
When it happens, it’s like you don’t know what to do and you’ve got to figure they’re uncomfortable.

0:00

But that’s I think what forces us to go to those places where we learn these different things.

14:34

So why would we go ordinarily go and find awful tasting medicine, but that’s kind of what we.
Need it is what we need.

14:41

Otherwise, you know, it’s a bit like the frog that boils himself kind of in that boiling water
that’s just kind of lukewarm and then boiling and you just kind of stay there and it’s kind of OK,

14:51

jump out of it and see what’s possible.
Absolutely right.

14:56

What?
Does being more human mean to you?

14:59

I think the being more human, to me, it just means recognizing what we are and the fact that, you
know, we have a whole bunch of different emotions and more often than not, it’s emotions that are

15:13

running the show.
We are all flawed in our own delightful ways.

15:18

And it’s just understanding.
I think it’s human beings.

15:21

We give ourselves such a hard time.
You know, we compare ourselves to other people and you know, we should be more of this, should be

15:28

more of this.
And I think it’s just understanding that both for ourselves and for other people.

15:35

And, you know, there’s so many different places I could take that.
I mean, think about in teams, you know, people, any of them do things for their reasons, not for

15:41

your reasons.
And so therefore, if you want to ignite a team that’s speaking to each person, what is the thing

15:46

that really matters to them?
How do I ignite that person?

15:49

It’s about igniting human potential.
So for me, it all comes down to these conversations to understand people, for listening to what’s

15:56

going on and, yeah, to listen to yourself, to listen to others.
And for me, that’s what sits at the heart of humanity.

16:03

And, you know, we are sort of, you know, habitual creatures as well.
We have a pattern here.

16:07

We tend to follow that pattern every other place in our life.
And we have a stop to go and think about that.

16:12

Or what?
What is that actually telling us?

16:15

I’m writing my next book at the moment, and it’s all about the bold conversations.
And, you know, what are the bold conversations that we have where you’d step outside our comfort

16:22

zone?
What’s that thing that we’re avoiding?

16:24

What’s that thing that we’re not seeing?
Because we’ve all got those blind spots.

16:28

We’ve all got those different things that are going on as humans.
And so I just think, you know, human beings are endlessly fascinating in terms of why we do things.

16:36

They’re like sort of curious.
You still puzzle what’s going on there.

16:39

What’s happening with this person?
Why is this happening?

16:42

And so I think it’s.
Yeah, spending the time listening to that, tapping into that and using that as the sort of the the

16:49

source material.
So how are we going to do anything together?

16:52

It’s so interesting just listening to you say that.
I saw something on LinkedIn the other day and it did actually make me think because there’s a woman

17:00

and she was on a plane and she took a picture of her space in the plane and the guy next to her was
taking up basically sort of 1/2 of her space like his legs I saw.

17:11

The same post Bubbling did.
You did you.

17:14

Yeah.
And she and she said I didn’t say anything.

17:18

And I’m kicking myself that I didn’t.
But I hate, you know, I hate the fact that I didn’t say anything.

17:22

Would you have said anything?
And I find it fascinating because there’s obviously different cultures who have chimed in.

17:27

Now she’s British and she didn’t say anything.
And I would have one.

17:32

I’m also really tall.
I’m 6 foot 1, so I need my space.

17:35

So.
But again, I don’t believe that these conversations need to be aggressive.

17:40

I mean, it’s just you would sort of tap them on the show.
Sorry, I got really long legs.

17:45

Like I need my space.
I’m really sorry.

17:46

Just would you mind?
And again, I don’t know the sort of premise of what you’re talking about with bold conversations,

17:51

but I think it’s having that confidence and that assertiveness to be able to bring up the things
that bother you.

17:56

But again, I think those boundaries are so important.
They’re an important part of being human actually, and human leadership.

18:04

It’s it doesn’t mean always being nice and a pushover.
Well, the boundaries clearly really important that there is a chapter on boundaries in the book.

18:12

Yeah, the whole sense of it.
There’s a wonderful Richard Dawkins book, The Blind Watchmaker.

18:17

There’s a wonderful analogy he draws at the beginning of that book where he says there’s 2 levels of
understanding.

18:22

The level of understanding, when we hear the words, we kind of get them, and the level of
understanding where we feel it in the marrow of our bones.

18:29

And for me, conversations are like that.
I think we live in an increasingly shallow world that’s dominated by the sound bites, and I think it

18:37

requires us to get to depth on these different things.
When I look back and I look at the pattern across all the big shifts that I’ve done in my journey,

18:45

the big shifts that I see happening in leadership teams where they’re doing something different,
they really sit with those different things and they drive that depth into it.

18:53

Ray Dalio, who read the amazing book Principles, he talks about the concept of struggling well, and
for me, it’s that whole thing.

19:00

How do we get into the depth on this?
Because that I think really is where the magic happens.

19:05

When you get, when you get to that depth.
That for me is what the bold conversations about.

19:09

What are those conversations you’re avoiding, whether it’s an internal dialogue or whether it’s
something with the team and the people around you.

19:15

Yeah.
Because at.

19:16

The end of that, there’s something really interesting.
A. 100% So just for our listeners, Casper has written a number of books.

19:22

What number is this now?
Sorry, bold conversations.

19:26

But 5.
Five OK 5 SI mean that’s pretty impressive.

19:30

So in your book be more Human, which was one of your books, you challenge traditional views on high
performance teams.

19:38

And so I just wonder what are some of the outdated leadership kind of rules that need rethinking And
perhaps, I don’t know, it’s possible that we can reflect on current situations that are happening

19:51

maybe in the world, I don’t know.
But anyway you take this where you want to go but.

19:56

So yeah, no, it’s it’s really interesting is I was I was flicking through that book earlier in
advance this and I was looking at that and think, yeah, there’s a resurgence of this stuff that’s

20:03

going on.
Let me.

20:04

Study right now of what is not going to.
Work.

20:07

So let me let me tell you a story.
The first yacht race that we did, we followed what was the, the mentality of the day, which was

20:16

well, I might almost describe as the Gordon Gekko approach.
It’s all about the results, it’s about the numbers.

20:21

Drive hard, just push for the results and you know, forget about people, just do your job and just
get on with it.

20:27

And that was the whole approach prevalence in the business world for quite a long time.
Certainly when I came into the working world in the early 90s, that was what it was all about.

20:35

So we applied that on our yacht race.
On the 1st yacht race, we sailed from the UK to Boston.

20:41

We came in in first place.
And you know, that’s the thing about this approach, right?

20:45

It does work, it gets results.
However, it’s not a sustainable approach because by the time we got halfway around the world, we

20:53

ended up getting burnt out of the team because people didn’t feel understood, respected, didn’t feel
valued and the the cracks were starting to show.

21:04

We had, you know, some fights on board and it came to a head when we became a dysfunctional team.
We literally crashed our boats.

21:11

We drove our 45 ton boat into the side of another boat thing.
No, and we put.

21:16

Ourselves out of the race.
So I have seen first hand what that leads to over an extended period of time.

21:25

And a yacht race like that, it’s quite a powerful metaphor, right?
And business is not, it’s not a Sprint, it’s a marathon.

21:32

And you can apply that sort of drive hard thing and it’ll get you short term results coming back to
the current situation.

21:40

You do that and then you end up being the sort of person who has litigation following you around
everywhere and lots of different issues which will follow you around.

21:47

And lots of disgruntled people and things will come out of the woodwork later on.
If you follow certain sort of world leaders, that’s exactly how they’ve lived their life.

21:58

So I’m sticking to my guns.
So I’ve seen first hand how that how that goes wrong.

22:03

And so therefore I very much advocate not what I would call like, you know, just sort of a softer,
well, let’s be lovely to everyone, all sorts of stuff.

22:11

It’s just understanding what’s driving each person, having those in depth conversations, helping
each person to become, you know, just unleash all of their talents still, you know, drive hard,

22:23

still go off those big bold goals, but do it in a way where you’re actually taking care of people
when you’re unlocking those things.

22:30

So for me, that’s the outdated approach, which is just numbers and results above all else.
And all my standard sayings is, you know, when you put people first, the results will follow.

22:41

And I think we have, we’re right now in the world, we’re essentially seeing an inversion of that or
well, let’s just put numbers first and then people will follow.

22:48

If it wasn’t so unbelievably tragic, it would literally just be a comedy sketch.
Literally playbook of everything not to do to just see the complete implosion of organization.

23:02

Or in this case it’s.
I mean, it’s so complex and nuanced and I think, you know, there’s clearly sort of a lot of, let’s

23:08

say, heat and energy in the world at the moment with lots of different things going on.
I still very much advocate and I believe in going back to first principles, you know, exactly what

23:16

we have to do on the boat when things go wrong.
Well, OK, actually what are the fundamentals here?

23:19

What’s actually going on and looking at those?
But I think the way that we do these things really important and the conversations that fit fit

23:26

around this.
So I mean, that’s one of the things I’m very mindful of is, you know, the the world, yeah, ends up

23:31

being in these sort of, we see it on social media, the very simplistic sound bites without actually
getting into that, that struggling well and the depth behind these different things.

23:39

And I wonder actually, you know, how much, you know, people would actually agree from all different
things actually, if we did spend that time to get into that depth and really get into the sort of

23:47

the things that are going on.
But I think that’s just lost through the way that we communicate these days, which I think is a real

23:53

shape.
It’s true.

23:54

And you know, technology is great, but you know, real conversations in depth, spending that extra
time, you know, everyone’s so busy.

24:01

But it it does make a difference, doesn’t it?
One of the other human things I was thinking about, you know, people only hear what they understand.

0:00

I remember this when I was sort of building my businesses and I would be saying these different

24:11

things to people because I had a really trying to drive my team quite hard to the point my team sort
of that all basically threatened to walk out on me because I hadn’t understood this point.

24:19

And that was the point where I had to get and sort of, OK, what do I need to go and do differently?
And I’d absorb all these different things and I would say it to my team, assuming they understood

24:26

it, but of course they didn’t.
And where people are coming from, everyone’s developed their own narrative, where they’re coming

24:32

from.
They know exactly what they mean by that, but they’ve got no understanding what other narratives

24:36

mean.
And so that’s where that nuance and that complexity list, I think have to come out.

24:40

So so.
How do you?

24:41

Balance then, and that sort of brings us to where we are now, the big bold goals.
So, you know, win the race, get around the world, conquer, but while also still fostering that

24:54

culture of psychological safety and human connection.
So, you know, we’ve touched on it just now, but I just wonder, do you want to go a little bit

25:01

deeper?
What does that look like?

25:03

What what works for you and what form the?
Thing that, you know, picked up on there is my obsession is with those things that everyone else

25:09

says.
That’s impossible and you can’t go and do that.

25:11

And the traditional way of doing going after that is, you know, the the windmill cost approach to
that, the approach that I favour in terms of going after that.

25:18

And I see lots of different organizations employing this very well, is this whole notion of
experimentation.

25:24

We don’t know what the future looks like because we’re going after a big ball goal.
There is not a set route to go and get there.

25:31

And so therefore how do we iterate?
How do we experiment our way forwards to go and get there?

25:37

And the only way we can have lots of different experiments is having lots of people contributing
different ideas and then finding ways of testing those different ideas and moving this along.

25:47

So one of my, one of the people interviewed, the last book that I wrote, The Big Bold Mindset, he
bought a small insurance company for £10 million, turned it around, scaled it, sold it for just

25:58

under half a billion.
And he said he basically put culture values, it’s a very clear mission at the heart of it, but also

26:04

built in this culture of experimentation such that they ran on average 66 zero different experiments
every single week and nobody knew the right answers.

26:14

But As for how do we find that way that everyone brings these ideas forward, Everyone is safe to say
these things.

26:20

And it might be a crazy idea, it might be a big idea, it might be a small idea.
But it’s only when we run lots of those different things and we embrace the fact that loads of those

26:28

are going to fail.
But when you’re captured in that sense of experimentation, you’re not putting your personality, your

26:34

identity on the line for any of those different things.
You’re part of the culture, which is saying, well, let’s just find out what that answer is together.

0:00

I think that provides a level of safety where you’re not saying this is the idea that’s going to win

26:46

because you just don’t know.
And I think there’s more important of that.

26:49

So that’s one of the things that I think is really crucial to going after big bull goals is that
sense of experimentation.

26:55

That’s that if it provides that safety.
Beautiful.

26:59

Also, I mean, obviously phenomenal for being able to get that innovation and get those ideas from
literally everywhere, but to create that environment within an organization that’s just, yeah,

27:11

fantastic, I mean.
It’s not easy for every organization to do that and.

27:14

No, of course, yeah.
But it’s it’s leaning towards that where that is the more of the default experiment, try, fail,

27:23

learn, all those sorts of things, right.
So.

27:24

Yeah, and, and, and again, the reason why people wouldn’t be offering up well, one, they might not
be given the opportunity.

27:32

So again, you, you have a lot of, you know, teams where you’ve got the team leader and if they have
all the ideas and it’s sort of they don’t even ask for the ideas from other people and they don’t

27:42

have that confidence to say, I don’t know, I don’t know.
So I, I want other, you know, you might be a really junior person in the company, but you probably

27:50

have some great ideas and just having that maturity to be able to open it up like that.
That’s, that’s genius, genius.

27:57

So from your experience, I’m, I’m curious because we know that a lot of people have potential.
We know a lot of any age.

28:06

I mean, my 10 year old, she blows my mind many times when I ask the right kind of questions and she
sort of comes up with such amazing ideas.

28:12

I think, Oh my God, did I think like that when I was 10?
I don’t think I did, but what are the biggest barriers that you think that prevent teams or leaders

28:20

from unlocking their full potential?
What do you see a lot of?

28:25

Yeah, hubris.
And this brings to mind as you say that, but you know, I’ve got all the different.

28:28

I’ve got all the right answers, fixed mindsets, I’ve got to look good.
What brings to mind actually is with the family of sailing adventure and you know, something broke

28:37

with our electronics and I’m getting increasingly I’m not very good with instructions and I’m
getting increasingly agitated with this trying to figure it out going through the manuals and

28:46

Columbus, my son, he’s 8 years old comes over to me and he says something and I’m like a snap of him
a few minutes past and actually come back here and it’s like he’s an 8 year old kid.

28:55

He’s like, let’s try dad just do this.
It’s like of course.

28:58

So I think it’s just sort of recognizing those answers can can come from anywhere.
I think it’s giving people space to be able to do that.

29:08

So why don’t we to do that?
I think, you know, so much this is tied to the identity that we have, the story that we have.

29:14

Well, I’ve got to be the person who has the answers and I’ve got to be doing this and I’ve got to be
doing this.

29:18

And I think there’s a lot of identity protection that as well.
What will it mean to me if I don’t have the answers to this?

29:24

So I think there’s levels of fear and I think more people feel settled inside themselves, more
secure and who they are.

29:31

Then I think they’re much more open to those different ideas.
And there’s no doubt they’re having a diversity of ideas from a whole range of different places.

29:39

And you put those together, you crass also those that is you’re of course you’re going to get a far
better answer because not no one person has all the answers.

29:45

God I couldn’t agree more and it just again, it just makes me thank my 10 year old.
The other day I was needing to shred documents and I don’t have a shredder.

29:54

And I just always sort of sit there just like shredding.
But it was so busy.

29:59

And she’s always looking for ways to make money.
And I was like, do you want to make some money?

30:02

You can shred my documents.
And so then I had to go out and take my daughter to a dentist appointment or something.

30:07

My other daughter and I get a phone call from my 10 year old, from the woman who helps us in the
house.

30:11

And, and I was like, yes, Maya.
And she said, look, I just want to know, can I wet them?

30:16

Can I just get a bucket and wet them?
And I was like, yeah, yeah.

30:20

She goes, yeah, because I know what you want to do.
And so I don’t have to just shred.

30:23

And I said, yeah, you can.
So basically she just took all of them in water, let them, and then she created mulch.

30:29

Genius.
Amazing, amazing.

30:30

Why does that not all like and then you can create paper again if you wanted to.
But anyway, it’s just so funny because you’re just saying God for years, literally years, I’ve been

30:39

shredding and it’s just, you know, no paper cuts genius as.
Humans, we operate in habit, right?

30:44

And we have, there are good reasons for those heuristics and doing those different things because,
you know, they provide us predictable ways to navigate through the world.

30:51

But actually, when we stop saying, hang on a second, is there a better way?
And actually, I was with a friend of mine last weekend and she talked about the whole concept of

30:58

principled rebels, people who are going around good principles and good intent and challenging,
well, why are we doing it this way?

31:04

And so that’s actually, you know, why the whole must thing, it’s like, you know, there is some
validity in this because the way we’ve got to, it’s like, well, actually things should be challenged

31:12

regularly.
Why are we doing this?

31:14

Again, get back to different, there’s different ways to go about it.
It’s like all ideas should be should be open for discussion and challenge.

31:22

I love the idea about the paper and wetting it I mean.
It’s like genius, right?

31:25

Like I just.
Yeah, Anyway, yeah, it was quite incredible.

31:29

I offered her whatever the money was.
I can’t even remember.

31:32

And I didn’t have change when I paid her.
And I was like, you know what?

31:36

You get more because you used your brain and you actually thought out of the.
So just keep doing that.

31:41

Keep doing that.
It was faster.

31:42

I mean, that was the other thing.
She’s going to be there for ages and she did it super fast as well.

31:46

Like, I love it.
I love it.

31:47

I love it super.
Smart, Yeah.

31:49

So you’ve written about big, bold ideas as well.
And so how do you encourage people to think beyond limitations and aim higher?

31:59

Lots of different ways to do this, but my favorite way actually is doing what I call a reality
disconnect because we have all these different strict rules about what reality looks like.

32:09

You know, when I think about when Nitra and I came up with our story to go and sell around around
the world, we didn’t have the money because my business was losing money hand over fist.

32:18

The idea of doing it was ridiculous.
Nicola couldn’t sail.

32:21

She’d been on the boat twice, she’d been sea sick both times and we didn’t have a boat either.
And most rational people would look at that.

32:27

So there’s no way you should go and do that.
We looked at that so well, actually, let’s not start there.

32:31

Let’s start out there with that picture.
Let’s detach ourselves from reality from today.

32:36

Let’s just imagine a story that’s five years out there.
You know, I studied at Cambridge University a couple of years ago on on disruption and the professor

32:43

Kamal Munir, he said exactly the same thing, basically says look, every organization should be doing
this.

32:48

Go out five years, look at the patterns, look at the trends, look at the changes, look at the
ecosystem.

32:51

What will it look like in five years time?
Orientate your story around that and then work backwards.

32:57

The challenge that we have is we start from today and say, well, OK, well how do we make those steps
up to there?

33:03

It’s completely the wrong way around.
So therefore I think we have to liberate ourselves from the construct of today.

33:10

Imagine what tomorrow is and then get really, really clear.
So we spent, you know, three or four months as a family team talking about what that picture is

33:18

there once it was so crystal clear, we literally encapsulated in something we call the Winner’s
Bible.

33:22

We had a vision thing put on the wall.
We had a big map of the world.

33:25

And it’s like so, so clear.
That is what’s going to happen.

33:29

OK.
Now and only now will we start to figure out how do we close that gap.

33:34

If we’d started to do that earlier, we would have been overwhelmed.
It would have killed the process.

33:39

We would never have got out of the starting blocks.
O it’s that reality disconnect lookout there.

33:46

What is that picture anchor on that and then work backwards.
OI think it’s providing teams and people the space to explore that and you know you’re going to do

33:57

these typical civil, you know, sort of like off sites and people having a couple of hours to do
that.

34:01

So that’s not enough.
You need to have more.

34:03

You have to have that sense of fun, that sense of play, sense of exploration and you know, it’s a
big investment.

34:08

Again, do that right.
But I think that’s fundamentally important.

34:12

One of my mentors always used to say to me, if you plan to be in the business that you’re in today,
in five years time, you won’t be in business.

34:16

And I think that’s more true than it’s ever been today because of the speed at which we’re going.
And I seriously believe there’s so many organizations, they’re going to be in a very, very

34:24

challenged place because they’re not investing the time to look at what that picture looks like and
to work backwards from there.

34:30

Say, OK, what do we need to do to move forward from that?
I just love that so much.

34:36

And it’s funny because when I started my business in 2006, I did have my, you know, manifestation.
So I had a very clear idea as to for me what what is success.

34:47

But you know, I was 20, I don’t know, four or something like that.
I was sort of 24 years old, didn’t have any kids, you know, starting this business for me, success

34:56

was very different to five years ago, but I hadn’t redone that.
And it was so crazy because I also spoke to one of my mentors and I just love the, I just love how

35:07

powerful a vision board, how powerful manifestation is and just having it all there because then all
your conversations change, everything you do changes because you’re working towards that.

35:18

And then it does happen and we can, we can do that as leaders.
We can do that in our personal lives.

35:24

We can do that with our businesses, our teams.
And it is so powerful.

35:28

And I love that you’ve said that because that is such a beautiful example.
Well.

35:32

What’s interesting as well about that?
So in the book, basically I create this index, basically it’s it’s a depth index to how deep your

35:37

conversations and goes from one through to level 5.
And I think the challenge is most people don’t get deep enough.

35:44

They’ll like, you know, say level 1 is you don’t have a conversation at all.
Level 2’s, you have a conversation a couple of times, whether it’s move to action and so on.

35:52

And I think most people might stop at level 2, Level 3 certainly in sort of corporate world when
we’re talking about different things.

35:56

How much have you really driven that depth?
And I see this with lots of, you know, vision boards as well.

36:00

It’s like, well, OK, well, I’ve done that, but no, you haven’t done that.
You need to drive that right into that depth.

36:06

I have speaker and friend in the UK and he also talked about the thing about that five year vision.
What will you see?

36:11

What will you hear?
What will you feel?

36:12

And just to be so invested in that world that you can see that so so clearly.
So it’s driving the depth into that.

36:19

That’s where I think that that really happens.
And this book is the big bold ideas one, right?

36:24

So.
This is going to be the, well, actually the working title for it.

36:27

It actually comes up then I should announce it just yet, but sorry I don’t.
Know can you?

36:31

Yeah, that’s so.
The first book is called Where the Magic Happens, which of course is where you step outside of your

36:37

comfort zone.
This is all about where the magic begins, and it all begins with that bold conversation.

36:42

What’s the conversation you’re avoiding?
Step into that The world.

36:44

Economic Forum recently launched the job report, Which for anyone that’s working in in soft skills
development, probably was not surprised, but also happy to see that what we’re doing is actually

36:57

making sense.
And it says that the human competencies basically of what we’re talking about, empathy, flexibility,

37:02

resilience, curiosity, cultural intelligence, etcetera, are vitally important in the next 5 years.
So I’m just curious from your point of view.

37:11

I’ve got lots of thoughts on this, but I’m really curious to know what you think.
So reflecting on the rise of AI and machines.

37:15

And of course, if you look at the skills that are needed, you know, AI and technological skills are,
are right up there.

37:21

But literally right below it is the softer skills.
Why do you think human competencies are now and in the future going to be so key so.

37:31

For me, it’s still humans are going to be communicating with humans who are going to make making
decisions.

37:34

And the funny thought I had about that, by the way, I saw something earlier on LinkedIn which was
2A2 AI’s talking to each other, which I thought was hilarious.

37:42

And then they moved to basically sort of like a sort of a ZX spectrum sort of type language
communicating together.

37:47

Like then there’s like it’s still human beings who are going to be driving the world making
decisions, but I think they’re going to be supported by AI.

37:54

I mean, I use AI unlocks in terms of what I’m doing.
I use it as my sounding boards.

37:59

I literally use the voice activated version of it.
And I just find it so incredibly powerful to bounce ideas around the soul and the thought of that.

38:09

I’m using it as a challenging thing.
You know, the role of human beings, it’s exactly as we’re doing now.

38:14

It’s personality, it’s engagement, it’s understanding those emotional things.
You know that whole thing about Anthony Damasio, we’re not thinking creatures who feel, we’re

38:21

feeling creatures who think that’s what human beings are.
That’s how we experience the world as human beings.

38:27

Well, that’s not going anywhere.
I think for us, I think it’s just, you know, the next cycle of the world, I think it’s going to be

38:33

tremendously exciting when we use these things and sort of say, actually, I think potentially has
the ability to showcase even more what, you know, amazing humanity looks like because we’re not

38:43

spending time doing a whole bunch of other stuff.
So we spend time connecting with people more and, you know, unleashing human potential.

38:51

Yeah.
And it’s interesting, the analogy that I’m using at the moment that I quite is you can have a robot

38:56

dog and the robot dog can go and get your paper and can go and I don’t know, do something else.
I don’t even know what a robot dog could do.

39:04

But you wouldn’t hug a robot dog.
I.

39:07

Wouldn’t pet a robot dog.
I wouldn’t sniff his head.

39:11

I just so I mean, there’s it can do the sort of tasks, but the connection that you sort of feel just
is is not there, is it so?

39:22

Absolutely, right.
I think, you know, sort of just understanding more of what it means to be human.

39:27

I think it’s just sort of it just places a higher importance on that and therefore into the whole
world of emotions.

39:34

Well, why?
Why do we do what we do?

39:35

I think it’s a really interesting place to go.
Interesting.

39:37

Yeah.
Do you have a quote that you’d like to share with our listeners that you actually mentioned a few at

39:42

the beginning so that they might be your quotes?
I mean, I think you know, the the core of the the be more human essence, I think, you know that

39:49

that’s all about putting people 1st and results will follow from that, which I think is a useful
reminder of all things that are going on in the world today.

39:55

But I think very much given in the lens that I’m going with the next book, it’s, you know, what’s
the conversation you’re avoiding?

40:02

And step into that bold conversation.
I think where it’s uncomfortable, you’re uncertain.

40:06

Have a crack at that.
There’s some really interesting things in there.

40:08

That wasn’t quite that was quite a long, but it was.
It was a we got the, we got the sentiment.

40:13

That’s great.
Is there anything that I haven’t asked you that you’d like to share with her this?

40:18

That’s a very generous question.
Thank you.

40:20

I think if I was going to pull everything back, actually it’s funny the the story I shared about
shade life at the top of this is one that suddenly bubbles back up in the top of my mind is the

40:29

essence of humans.
And so I’m just going to just quote back his words, which I’ve already shared, which is now you’re

40:34

looking down at your toes and just where you draw your final breath.
You know, have I done everything that I want to go and do?

40:39

Encourage everyone to go out up there and sees the things that are really important.
So go and do that.

40:44

Oh my God, how inspirational.
Thank you so much.

40:48

This is just flown by.
I truly appreciate your time and your brain and your enthusiasm.

40:53

Thank you my.
Pleasure.

40:55

Lovely to chat to you, Philip.
Thank you for the generous questions and for your story as well, which I’ve really enjoyed hearing

40:59

as well.
I’ve got a vision fucking a robot my mind now.

41:06

Amazing.
Until next time, Casper.

41:08

Take care, Take care.
Hey everyone, this is Philippa again.

41:14

I hope you enjoyed listening.
Now this is your chance to get involved with Ty.

41:19

If you’re looking to create better leaders, better companies, and a better world, that’s just what
we do by helping leaders tap into their greatest asset, their humanity.

41:30

We have a number of corporate programs that impact a range of people, from individuals at a company
to 500 people around a business.

41:37

Or check out my book, Return on Humanity Leadership Lessons from All Corners of the World.
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41:50

forefront of competition.
You can find all the information you need on all of this at tieleadership.com.

41:57

Get in touch and I can explain more.
A huge thanks to Ben Naviera for Co producing this with me and for creating the music.

42:06

I hope we’ll meet up again soon.

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