Experimental with Amale Ghalbouni & Jodi Cartwright on Turning Conviction Into Action

Amale Ghalbouni & Jodi Cartwright in conversation. Excerpt taken from the conversation featured in Experimental

There’s a particular moment when a strategy stops being a document and becomes real.

For Jodi Cartwright, it happened when a customer she didn’t know bought the first policy from Coveley, the insurance start-up she’d helped build from scratch.

The team gathered around a laptop in their small office and watched the sale appear. It was the first proof that someone outside their immediate circle believed in what they’d created.

That moment came after months of research, proposition development and uncertainty. It also came after another defining moment, when an investor finally said: “Let’s do it.”

In our conversation, Jodi and I explore what happens between those two events. How do you build enough conviction to pursue an idea, take a measured risk and turn it into something another person values?

These insights feature in my book Experimental.

Conviction needs evidence

Jodi believed insurance could be a force for good.

It can keep a small business alive after a flood, help an organisation recover from disaster and allow people to take risks they couldn’t afford to carry alone.

Yet the experience of buying insurance can feel like the opposite. It’s often complicated, full of jargon and designed around the provider rather than the customer.

Jodi felt confident Coveley was solving the right problem.

“I was 100 per cent confident we were solving the right problem,” she said.

That confidence wasn’t blind.

The team interviewed customers, explored their assumptions and adjusted the proposition as they learnt more.

This is the balance leaders need when pursuing uncertain opportunities.

Conviction without evidence can become stubbornness. Evidence without conviction can create endless analysis.

You need enough belief to move and enough curiosity to find out whether your belief survives contact with reality.

What measured risk actually means

Jodi has taken several significant career risks.

After 17 years with Aviva, she moved between different organisations, start-ups and roles. Some decisions worked as expected. Others didn’t.

Her long-term test is the rocking chair question:

“When I’m old and sitting in my rocking chair, I don’t want to think, ‘I wish I’d done that.’”

The question pulls her attention beyond the immediate fear.

What regret might she carry if she stayed where she was? Would she continue wondering what could have happened?

Her shorter-term test is more practical:

What’s the worst that could happen?

That doesn’t mean dismissing the real consequences of a decision.

Jodi is open about having a financial and family context that made some risks more possible. Courage shouldn’t be presented as though everyone has the same safety net.

Measured risk means understanding what you could lose, what protection you have and what smaller step might reduce the danger before you commit fully.

The useful questions aren’t simply “Am I brave enough?” They’re:

What am I really risking?

What would I do if it didn’t work?

What support do I have?

Could I test part of the idea first?

Which choice is more likely to create lasting regret?

The environment shapes your appetite for risk

Jodi describes restlessness as a combination of nature and nurture.

Some people are naturally curious and ambitious. But the environment around them determines whether those qualities grow or disappear.

Earlier in her career, stability carried significant weight. Later, she found herself surrounded by people in the insurance technology world who were building companies, testing propositions and rethinking the industry.

Their energy was contagious.

“You’re the average of the five people you surround yourself with,” she said.

One risk made the next feel more possible. Seeing other people step beyond their comfort zones helped her distinguish between danger and the normal discomfort of learning something new.

Leaders can shape this environment inside established organisations.

Teams need to see experiments happening. They need honest stories about what succeeded, what failed and what the organisation learnt.

They also need chances to own contained pieces of work rather than being told to become more innovative while every decision remains controlled from above.

You can’t ask people to act entrepreneurially inside a culture that punishes every imperfect outcome.

Small experiments create movement

Innovation inside a large organisation looks different from building a start-up.

The business already has customers, systems, responsibilities and limited resources. There may be dozens of good ideas competing for attention.

Jodi’s focus is on choosing the next move likely to create the most value.

That might be a marginal improvement to the customer journey rather than a complete reinvention. It might be a small AI test, a change in process or a new way of reaching customers.

The scale of the bet changes. The discipline remains the same.

Start with a real problem. Be clear about the value. Test the assumption before investing further. Bring the right people into the vision.

This is the approach I call experimental change.

You don’t need to bet the organisation on one unproven idea. You need a change that matters, enough support to get moving and a first action small enough to teach you something.

Pushback doesn’t always mean no

Conviction isn’t refusing to listen.

When Jodi encounters pushback, she tries to understand what sits behind it. Has the person spotted a weakness? Are they protecting a genuine business need? Could the idea be adjusted without losing its value?

Sometimes the problem is timing.

“Sometimes it’s the best idea, but it’s not the right timing.”

An organisation may lack the capacity, leadership attention or confidence required to back the full proposal.

The answer might be building a smaller test, finding a different sponsor or returning when another priority has moved.

That’s very different from abandoning the idea at the first sign of resistance.

It also helps you recognise the difference between an objection you can work through and an environment that will never support the work.

Restlessness needs unpacking

Jodi’s advice to restless leaders isn’t to resign and start a company.

Start-up life can be thrilling, but it can also move from a major win to a disaster within the same day.

Instead, get specific about what your restlessness is trying to tell you.

Are you frustrated by one idea you can’t progress? Do you need more autonomy? Are you curious about another industry? Or is the dissatisfaction wider than work?

Turn the feeling into something you can investigate.

Research the idea. Speak to the customer. Build a rough proposal. Size the opportunity. Find the decision maker. Explore a side project or small internal test.

A vague feeling becomes more useful when it produces evidence.

Protect the energy to keep going

Restless leadership requires fuel.

Jodi treats sleep and recovery as part of her performance, not something separate from it.

“You have to have the tank full to have the energy to go after what you want.”

A leader running on empty is more likely to misread resistance, make poor decisions or turn conviction into inflexibility.

Rest isn’t the reward after the risk. It’s one of the conditions that makes measured risk possible.

That theme sits throughout Experimental, my bestselling business book on leadership, culture and transformation. The goal isn’t reckless action. It’s building an environment where people can take smart risks without burning themselves or the organisation down.

It’s also central to my work as a leadership keynote speaker: helping ambitious leaders turn restlessness into useful action rather than frustration or exhaustion.

Start by asking:

What am I restless for, and what’s the smallest useful step that would help me understand it better?

To unlock this conversation and all the other conversations featured in the book,

Grab your copy of Experimental now →

And if you’d like to bring these themes to your audience, get in touch or connect with me on Linkedin.