Quick Win: The AI experiment that made a CEO obsolete

What if the smartest thing a leader could do is try to make themselves obsolete? 
That’s exactly what Georgie Holt, co-founder of Flight Story, set out to test. Her 60-day AI experiment wasn’t about replacing herself - it was about freeing herself from the operational noise that stops leaders from thinking, leading, and creating. 

 In this Quick Win, Georgie shares how she built Scout - a custom AI assistant that automated the admin side of hiring and saved her 20 to 25 hours every week. By “killing off” the operational part of her role, Georgie found more time for what truly matters: people and purpose. 

Georgie and I discuss: 

• The question that sparked Georgie’s 60-day AI experiment 

• How she built Scout in a few conversations with GPT - no coding required 

• Why mapping out her pain points was the real unlock 

• The mindset shift from efficiency to presence 

• How she now uses that freed-up time to focus on people and long-term vision 

Follow Georgie on LinkedIn: https://www.linkedin.com/in/georgie-holt/ 

Listen/watch Diary of a CEO: https://www.youtube.com/@TheDiaryOfACEO  

Listen to the full conversation with Georgie here. 

 

My new book The Health Habit is out now. You can order a copy here: 

https://www.amantha.com/the-health-habit/ 

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Get in touch: [e-mail] 

 

Credits 

Host: Amantha Imber 

Episode Producer: Sam Blacker, The Podcast Butler 

See omnystudio.com/listener for privacy information.

Episode Transcript

Speaker 1 (00:01):
I'm trying to kill myself in sixty days. That's how
Georgie Holt describes her latest experiment with AI, not literally,
of course, but her mission was to see if she
could hand over the operational side of her CEO role
to AI and free herself up completely. Georgie is the

(00:22):
co founder of flight Story alongside Stephen Bartlett, who you
might know from Diary of a CEO, and by the
end of this quick Win episode you will hear how
Georgie built a tool that slashed twenty to twenty five
hours from her week and changed the way she shows
up as a leader. Welcome to How I Work, a

(00:49):
show about habits, rituals, and strategies for optimizing your date.
I'm your host, doctor Amantha Imber. I love that example.
I want to digg into how you built that, Like
is this something that anyone can build, you know, with
the tool like report, which is a vibe coding tool

(01:10):
for mere mortals who are not programmers. Or is this
something where you built a GPT and chat jpt so
or did you have a programmer help you? What did
that look like?

Speaker 2 (01:20):
I built it in a GPT, I sat down and
mapped out the process end to end. I worked with
GPT a lot, so it has a standing of who
I am, how I work, or you know, the kind
of leader and sort of character I am, and so
it sort of understands some of my watch points when
I'm interviewing with somebody. And then I sat down with
our data scientists. I said, look, I think I've got

(01:42):
something here, and I would like to spend some time
just qualifying whether you think I have to, and we
asked the GPT to build it. So we challenged it
to build it for us, and I gave it everything
that I wanted to achieve. I spoke to it a lot,
so it wasn't just entire I kind of had a
conversation with it, explained my pain points, explain what I
want to create, what I think I wanted it to,

(02:02):
show what it needed to do for me, and we
went back and forth like a team, and we brainstormed
with the GPT, and eventually it built itself.

Speaker 1 (02:10):
That is amazing. I would love to hear a couple
of other examples of where AI has completely changed your workflows.

Speaker 2 (02:18):
Absolutely, I have this deep feeling around AI that is
one of our greatest tools. But my fear is that
it will sometimes take away the most important thing that
we have, which is our ability to summarize intellectually really
important problems and challenges. Because I think one of the
biggest skills that a leader can learn over time is

(02:39):
the ability to assimilate and summarize information and then take
that information you distribute it into an organization, distribute it
into a team, understanding how the sales team might want
to receive it, understanding how a data science team wants
to receive it. Because your job as a leader is
to take a team on a journey with you. So

(03:00):
we took inspiration from the great writing machines of the world,
and I think, and I looked to Hollywood, if I
looked to Hollywood Studios, and I looked at the great
narrative creators in the world, and I thought, well, what
do they have. They have a writer's room. So quite
often they will have building out narrative or building out scripting.
They will have multiple writers attacking a challenge or a

(03:25):
storyline from all different perspectives, and they'll all come together
to debate and discuss those different points of view. And
I thought, well, what an interesting thing to try and build.
Because I don't want chat GPT to write for me,
but I want it to challenge what I'm writing. So
I asked it whether I thought it could build out
a writer's room for me, and we would have different
personas as each writer to anyone from the sort of

(03:48):
the format and the function expert, to the disruptor, to
the emotional story arc to the person who maybe wrote
for sort of more Jeopardy. And so I basically constructed
a writer. I said, look, what are the eight archetypes
of a writer's room that you might find in Hollywood?
What are the great script writers? Do you think we
could build out a writer's room or all of those

(04:10):
personas exist? And if I write something and I can
call on you, I can literally say, please bring the
writer's room to this piece of communication and challenge it.
So I now have a writer's room. So everything that
I create, which I think I have got to a
good enough place, I will then put it into the
writer's room and they'll challenge it and say the emotional

(04:30):
art isn't strong enough, or this could be format about that.
Actually the disrupture will come in. And so you could
create such a more compelling narrative if you put in
a little bit of jeopardy, So they don't write for
me because I am extremely conscious and I think it's
one of our greatest challenges that we are going to
lose some of the things that make humans extremely special,

(04:55):
and that is storytelling, and that is the ability to
summarize and distill information to the world in a way
that is well understood. And I think about Google Maps.
It's like, when was the last time you really remember
the direction to somewhere unless it was somewhere within sort
of twenty miles of your home. So I am concerned
that we're going to lose our way, and we're going

(05:16):
to lose how to remember how to do things and
do things well in the same way we just rely
on Google Maps, we leave the house and we hand
over the direction of our journey to somebody else. I
would hate to think we were handing over our creativity
and our consciousness to something.

Speaker 1 (05:30):
What stayed with me from Georgie's story is how AI
gave her the most valuable resource back time, not to
cram in more tasks, but to be fully present with people.
So the next time you're heading into an interview or
a high stakes meeting, think how could you strip away
the admin so that you can show up with curiosity

(05:51):
instead of distraction. And of course, if you want to
go and listen to my full chat with Georgie, there
is a link in the show notes. If you like
today's show, make sure you hit follow on your podcast
app to be alerted when new episodes drop. How I
Work was recorded on the traditional land of the Warrangery people,
part of the Kulan nation.