Rugby Icon Will Greenwood on Resilience, High Performance and Leading with Heart

Widely recognised as one of the UK’s most insightful rugby speakers, Will Greenwood has built a career on teamwork, tenacity and high performance.

A central figure in England‘s 2003 Rugby World Cup-winning team, he earned 55 caps for his country and became known for his sharp rugby intellect and fearless playing style.

Beyond the pitch, Will transitioned seamlessly into broadcasting, writing over a million words for The Telegraph and spending 15 years as a Sky Sports pundit.

Today, he brings his sporting insight to the corporate world—drawing on experiences from elite sports, media, and business to help organisations perform under pressure and embrace leadership with purpose.

In this exclusive interview with The Champions Speakers Agency, Will reflects on the defining decisions of his career, the lessons he brings to business, and how winning teams—on and off the field—are built through clarity, culture and connection.

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Q: Reflecting on your early life and professional journey, were there any defining moments or decisions that significantly influenced your path—both in rugby and beyond?

Will Greenwood: “A 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-seen moments. Loads of moments. I mean, 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—would’ve felt I’d had enough of education.

“Yeah, these moments—I’ve been very privileged to have some wonderful offers down the years, and with it, 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?

“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-axis 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—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 or physically a real test, then I tend to find myself signing up.”

Q: How have the experiences and pressures of elite rugby shaped the way you now motivate and connect with audiences in the business world?

Will Greenwood: “Fascinating. So I wrote a book in lockdown with my great friend Ben Fennell called World Class, and it sort of—celebrates difference, forges togetherness, and accelerates growth. So the reality is that 21 years after winning a World Cup, there are lots of lessons I took from that.

“But actually, the amount of time I’ve been able to spend with world-class leaders—whether it be Amanda Blanc of Aviva, Dana Strong (ex of Comcast, now CEO of Sky), or Philip Jansen at BT—the list goes on.

“I’m tremendously honoured to be able to get time with some of these great people and do some work with their organisations. It’s meant that I’ve been able to take some of the lessons of ’03 and understand if they translate into business—but also vice versa, to listen to some of the great businesses and see if they can translate back into the world of sport.

“So I think it’s often talked about in the business world—what can we learn from sport? The reality is sport is often stealing and borrowing the IP and going the other way.”

Q: Drawing on your time at the highest levels of sport, what core leadership and teamwork principles have stayed with you, and how do you embed them in your current work?

Will Greenwood: “What did I learn from rugby? I mean, rugby gave me everything. I’m a big believer in empowering those around you, and we were very fortunate to have a leader—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—so we had many leaders underneath our outstanding captain, Martin Johnson.

“Huge belief either in teams—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—needs real work in articulating, and often documenting, to understand that those that join the organisation can have an input, can help iterate, but understand the type of organisation and the behaviours and 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. 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.”

Q: Culture is often cited as the cornerstone of high-performing teams. As a former World Cup winner, how did you help cultivate an environment of trust, excellence and resilience within your squad?

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.

“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, and 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 be: 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 where you very rarely fix problems yourself, but you create environments where people are empowered to fix the problems around you.

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

“I think you’ve got to know when to stand up for your beliefs and your convictions. I got a great piece of advice from an outstanding leader called Jeremy Darroch. 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 for?

“And if you 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 Chris Tompkins of The Motivational Speakers Agency.