World Cup winner Will Greenwood reveals why hard work means nothing without purpose

Will Greenwood is a World Cup-winning former England rugby player, broadcaster, author and sports speaker whose career has moved between elite sport, finance, media and technology.

Best known as part of England’s 2003 Rugby World Cup-winning side, he has since worked with major businesses on leadership, teamwork, performance and culture.

Before rugby became his profession, Will worked as a foreign exchange trader at HSBC.

After retiring from the game, he spent 15 years with Sky Sports, wrote extensively for The Daily Telegraph, co-authored World Class with Ben Fennell, and moved into the commercial world through senior roles in AI and business.

In this exclusive interview with the SpeakOut Speakers Agency, Will discusses the decisions that shaped his career, the leadership lessons he took from England’s World Cup-winning team, why high performance depends on meaning as much as hard work, and how businesses can build teams that are tough on issues but genuinely human with people.

Q1. Was there a pivotal moment in your childhood or early career that significantly shaped your journey in rugby and beyond?

Will Greenwood: “I think it was Malcolm Gladwell who said hard work is only a prison sentence if it doesn't have any meaning, and we had meaning in trying to win a World Cup.

“So, the graft and the effort we put in, away from the bright lights, the big stadiums and all the sponsors, was where trophies and business wins are truly won. And you have to find a way to give it real purpose and meaning.

“I was a foreign exchange trader for HSBC back in the early ’90s, and then I took up professional rugby in 1996.

“I was part of a magnificent England team. I was a small cog that won the World Cup in 2003. Since then, I've worked for Sky for 15 years and written for the Daily Telegraph, over a million of my own words on the game of rugby, by and large. And then seven or eight years ago, I moved into the commercial world, working in AI.

“Pivotal moment, it's probably plural pivotal moments. Every three or four years, I seem to come to inflexion points, forks in the road, damn scene moments, loads of moments.

“I nearly stayed in the city, but I went for professional rugby. I turned down Cambridge when they came for me as a postgrad because I had 21 and felt I'd had enough of education.

“These moments have been very privileged to have some wonderful offers down the years, and with them I've had to make some big decisions.

“But I keep coming back to what challenges me, what connection is there between reward and effort, how complex is it, and how much control or how much input will I be allowed to have into organisations.

“And if there are ticks where I feel like I can co-support, co-drive, co-lead, if it is testing physically and mentally, and there is a real XY AIS linear connection between how much graft I can put in and what I can get out of it, then I tend to go for it.

“I often wonder where the other me might be if I hadn't stayed in the city working for HSBC rather than going into professional rugby, if I'd taken a job in teaching when I finished as opposed to going into journalism.

“So, I think the reality is most of my pivotal moments have been based around the pursuit of better. And just trying to finish each day, if I break it down into the real micro, just finish each day a little bit better than I started.

“I have what is called by my friends a relentless enthusiasm, often described as Donkey from Shrek. And if there's a fascinating project that's both cerebrally challenging and physically a real test, then I tend to find myself signing up.”

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Q2. What lessons in leadership and teamwork have you learned throughout your rugby career, and how do you apply them in your current endeavours?

Will Greenwood: “What did I learn from rugby? I mean, rugby gave me everything.

“I'm a big believer in empowering those around you, which we were very fortunate to have a leader in Clive Woodward, who gave us autonomy over the different facets of the game because the game of rugby can be broken up into, we broke it up into seven areas, and so we had many leaders underneath our outstanding captain, Martin Johnson.

“Huge belief in team ship, you can call that culture. High-performance teams create an extraordinary togetherness, which is often taken for granted in high-performing organisations and teams but actually needs real work.

“It needs real work and articulating and often documenting to understand that those who join the organisation understand that they can have an input, can help iterate, but understand the type of organisation and the behaviours and the values that are cherished and valued.

“We were relentless in our pursuit of marginal gains in pursuit of our 1% improvements on a day-to-day level, and we never shied away from hard work.

“And I think it was Malcolm Gladwell who said hard work is only a prison sentence if it doesn't have any meaning, and we had meaning in trying to win a World Cup.

“So, the graft and the effort we put in, away from the bright lights, the big stadiums and all the sponsors, was where trophies and business wins are truly won. And you have to find a way to give it real purpose and meaning.”

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Q3. As a former rugby captain and World Cup winner, how did you create a culture of teamwork and excellence within a team environment?

Will Greenwood: “There are many different ways of leading. I think as a leader, you often have to be pretty ruthless, pretty relentless, but in the same breath, understand the humans. The athletes, they're not objects, they're not tools. Your employees are not just delivering KPIs, they're real people.

“And so, if you can connect, if your words can connect with the head and the heart, then I genuinely think you can beat anyone, win anything, be the best in whatever mode of employment you're in.

“Captains and leaders often do thankless jobs. You have to be relatable. You have to roll your sleeves up. You have to do as I do, not do as I say.

“Often the easiest way to lead is to serve. That's an interesting way of looking at it.

“You have to create environments whereby you very rarely fix problems yourself, but you create environments where people are empowered to fix the problems around you.

“Communication is key. A big believer in little and often with the communication, the key messages, what it is you're trying to drive home. And often just at the point you might be getting bored with your own voice, that's the point where the messages are starting to stick.

“I think you've got to know when to stand up for your beliefs, your convictions. Got a great piece of advice from an outstanding leader called Jeremy Derk, and he said you've got to know what you're prepared to get sacked over.

“What is it that you're going to draw a line in the sand? And if you are to understand some of these key questions, it sets you up for success.

“I think what's also key is the great leaders, and it took me some time, my wife will say I'm still not there yet, at the very top, you've got to be in control of your emotions.

“If you have huge highs and huge lows, I think you can have a massive impact, but it'll be short and sweet. I think if you can chop off the tops of the mountains and flatten the troughs and keep that heart rate between 70 and 90, you've got half a chance. Otherwise, up at 36,000 feet, it'll drive you to an early grave.”

This exclusive interview with Will Greenwood was conducted by Tabish Ali of the Motivational Speakers Agency.

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