The way you think shapes the way you lead

At the 59club Global Awards, high-performance coach Lora Caven hosted a round-table conversation about leadership mindset – with clear takeaways for all those with senior roles in business

I work with senior and aspiring leaders who are already successful but want to push further, with clarity, courage and conviction.

On the stage at the inaugural 59club Global Awards, held at The Belfry, I was joined by three outstanding leaders who know first-hand what it means to take big bets and back themselves.

Peter George, Chairman of Enigma Holdings and a serial entrepreneur, has taken many companies public.

James Black, Chairman of Mirriad, has become a serial investor who now puts his own capital into the leaders he believes in.

Simon Wordsworth, founder of 59club, once gambled his own house to bring his vision to life.

Together, we explored two themes that sit at the heart of leadership: how to approach risk, and how to build real confidence.

Lora Caven

High Performance Coach

About Lora

Lora Caven is a high performance coach with a career background in golf and hospitality. As a longstanding partner of 59club, she works alongside some of the most respected names in business and sport to help unlock clarity, confidence and courageous leadership.

Lora’s Coaching Tips

RISK

Taking risks will never feel comfortable, and that is the point. The goal is not to avoid risk, but to take the right ones. When you feel the pull, check yourself and ask: Is this aligned with my bigger vision? Can I handle the downside? Do I trust myself either way? If you can answer yes, then that decision is not reckless, it is progress! That is how leaders grow – not by avoiding risk, but by stepping into it with clarity and conviction.

CONFIDENCE

Confidence is not built in a single leap. It is built in the everyday moments where you choose courage instead

of comfort: Speaking up when it would be easier to stay quiet, taking the decision when it feels safer to wait. Each act of courage is evidence that you can handle more than you think. Stack those moments, and before you know it, you are leading with a confidence that others can see and feel. The secret is simple: stop waiting for confidence to arrive. Choose courage and let confidence follow.

RISK

Reckless, or right move?

Risk often gets painted as reckless. From the outside, bold moves can look crazy or dangerous to others. But when you are the one taking the risk, it rarely feels like that. It feels like the next obvious move in your growth, your vision or your business.

Risk is uncomfortable, yes, and can be scary too, but it is also clarifying. It forces you to decide what you really believe in and whether you are willing to back yourself when the outcome is uncertain.

The best leaders are not thrill-seekers. They are not reckless. They are willing to bet on conviction, and they trust themselves to handle whatever comes next.

Taking companies public is high stakes. What gave you the personal conviction to make that leap, knowing what was on the line?

Peter George: If you believe in your story, if you believe in its potential, if you believe in your team’s ability to succeed and if you can translate that belief and conviction to investors, then raising money on the public markets is possible.

If you then deliver on the story, investors will back you again and again.

When you back a business, how much of that decision is about the plan, and how much is about the person? What convinces you to put your own money on the line?

James Black: The first answer is you don’t need to back any business – there are more opportunities than you have time and money! The first gating item is whether the individual has a good track record, deep knowledge in business, a high level of integrity. Are they fun to work with and have a good sense of humour. Is the business going to make investors money with a focus on the following: Size of market opportunity; simple business plan and model; margins; investment required to get to critical mass. If I get positives on all the above I will only invest alongside the entrepreneur on the same terms.

Simon, you once gambled your house on a golf club membership. From the outside that looks extreme. From the inside, what made it feel like the right move, and how did you hold your nerve?

Simon Wordsworth: I knew how Loch Lomond made me feel – warm, comfortable, happy and relaxed. If prospects of mine felt like that then I had 100 per cent confidence and belief that I could sell something of mine in that mode.

CONFIDENCE

Built, not born

Confidence gets talked about like it’s something you either have or you don’t. That’s not true.

From the outside, leaders can look bulletproof, but most will tell you they felt nerves, doubt and hesitation before they stepped up – and often still do! Nobody starts out confident.

Confidence never comes first. Courage does. Every time you act before you feel ready, you prove to yourself that you can handle it.

That proof stacks up, and over time that stack becomes confidence.

Real leadership confidence is not about bravado or pretending. It is about choosing courage often enough, so that one day, without noticing, you realise you have built the confidence everyone else can see.

Peter, do you believe courage builds confidence, or confidence builds courage? How have you seen that play out in your own leadership?

Peter: I had the courage to tell my story, believe in it and drive the organization to deliver. This built confidence as the results started to come.

Not everything worked, but maintaining that courageous approach delivered more results than failures. Success builds confidence but you have to have the courage to stop things that aren’t delivering to expectation. Your staff will feed off the energy this brings.

James, what qualities in a leader give you the confidence to invest in them, beyond the numbers?

James: I have already given the initial screening but confidence should be continually assessed.

What might lead to a change in view? Deviation from the business plan without full explanation; radio silence; high staff turnover; not treating customers, staff and investors fairly; poor attitude to questions from both you and others.

Simon, when you were building 59club, it took real confidence to see that vision through, especially when the risks were so personal. Where did that belief come from, and how did you keep it alive through uncertainty?

Simon: Rejections are hard, they really test your resilience. I absolutely believed in 59club. Therefore, when someone said no, I took it as a not yet, and dealt with it that way. They will come later, it’s just not their time at the moment with us.