After months of back and forth, an old friend and I finally found time to catch up…until he emailed, saying his weekend had been derailed by a trip to see “Richard” on “the island.” What island? Necker. Richard? Branson, of course. Apparently, that’s just a day in the life of Joshua Bayliss, CEO of Virgin Group.

Josh and I met as law students in New Zealand and worked in adjacent offices as young associates. From there, he went to a magic circle firm in London, then on to Virgin, where he rocketed from general counsel to CEO — before his 40th birthday. Thinking back, I recognized that I crossed paths with a star in the making. His talents, including a striking work ethic and natural charisma, were already apparent. But the remarkable thing about Josh was his under-the-radar ambition. He didn’t flaunt his achievements, he just did his job and did it exceedingly well — an old-school formula for success that has served him well.

When we finally got together, I learned that working for Virgin Group isn’t all rock ‘n’ roll and hot air balloons. We spoke about the challenges of transitioning from a law firm to a less structured workplace. And circumnavigating the globe at least six times a year, while raising two young children (a subject he is rarely asked about). So how does he do it? Unsurprisingly, an incredibly supportive spouse, one who was willing to give up her own career, is what holds the family together. Perhaps it comes back to a woman after ALL.

This interview has been edited and condensed.

Joshua Bayliss: I arranged to meet Richard at his house in Holland Park in London. The first words out of his mouth were, “Aren’t you far too young to be applying for this job?” That’s a good, challenging question. It was an opportunity to persuade him that age didn’t have anything to do with it, and that if I did decide that I wanted to work for Virgin, I was the right person for the job. He had been double-booked, and needed to go to a music awards ceremony at the Hackney Empire, which is on the other side of London. I had two choices: come back first thing the next morning or jump in the cab. Of course, I took the opportunity to get to know him better. We got stuck in a traffic jam on Marylebone Road for two and a half hours and had a great chance to have a conversation and figure out what makes each of us tick. I was really surprised when Richard jumped out and climbed aboard a bus next to us to take pictures with a couple of guys with long dreadlocks who recognized him.

My initial impression was that Richard didn’t have any limitations on his ability to think about how opportunity might present itself. That freedom of thought was incredibly appealing. He told me a story about sending a Virgin Atlantic aircraft into the war zone during the Gulf War to carry people to safety. His bravery — and the lack of boundaries in his ambition — are what I found critically positive.

Completely different. Incomparably different. Richard had a reputation for being a rebel. He signed the Sex Pistols when no one else would. He’s always pushing the boundaries, always challenging those around him, or, more broadly, challenging society and business. I find that enormously positive, but it gave him a reputation for being an edgy character. 
When I first met him, I wanted to find out whether he was pioneering or over the edge. It was clear to me that he was a pioneer, which has been proven over the 10 years that we’ve worked together. 
That’s a characteristic you don’t tend to find in a professional services firm.

Sir Richard Branson and Joshua Bayliss at Virgin Group’s 2014 holiday party in London.

Personality, attitude. I think he saw in me someone who was striving for excellence, looking for the best way to get things done and willing to challenge the status quo.
 But we joked and laughed — we shared a sense of humor. We talked about issues that were important in the world, and I think he saw that I was broad-minded and open. He certainly didn’t ask me about my academic background.
 That’s not the way he is — he hires people for who they are.

I was on the cusp of becoming a partner at Slaughter and May — a fantastic law firm with a stellar client list and a financially rewarding place to have a successful career. A client, who knew Richard Branson well, called to say that Virgin was recruiting for general counsel and asked if I would be interested in applying. My immediate reaction was that I would not, but I went home, thought about it for a few days and considered that this was an opportunity to do something very different with my life. I think the recent birth of my daughter, our eldest child, made me reflect on the future and what I would end up doing for the rest of my life. Still, I agonized over it, I really did. During the first two or three weeks at Virgin, I remember frequently waking up at 2 or 3 a.m., 
thinking, “Oh my God, what have I done?” Once I started to build relationships and understand the Virgin mind-set, I felt very confident that I had made the right decision, and I haven’t looked back.

Undoubtedly, the high quality of the people. Very early on, one of the partners said to [the summer associates], “Some of you are incredibly smart; you’ve all done very well to be here, and that’s terrific. But from now on, every single piece of work you produce on the firm letterhead has to be at an A+ standard.” That really stuck with me — that it was never enough to rest on your laurels; you had to apply yourself and bring all of the law firm’s resources to bear to get the best possible result for the client. The strange thing about a law firm is something that I discovered after I left. When I started at Virgin as general counsel, no one was focused on me. All of a sudden, I recognized that the whole infrastructure of the law firm had been built to enable me to be the best lawyer I could be. Out in the real world, it was entirely up to me. No one — except for me — cared whether I sank or swam. If I failed, I would go do something else; if I succeeded, it would be because I’d driven myself to do it. That was an enormous shift in the way that I thought about my career and motivated myself. For me, it was a really positive change.

It clearly works very well for a number of firms. My own view is that, over time, there has to be a transition. The next generation doesn’t have the same mind-set regarding material rewards, which, of course, is the carrot of partnership (as much as the name itself). And, of course, the increased focus on costs and leverage in the model means partners now work harder for longer. That, to me, is an unsustainable model, and having a great number of people chasing very few rewards isn’t necessarily in the clients’ best interests. When I hire lawyers, I would much rather have a wide variety of views from very smart people who are not sleep-deprived and exhausted three quarters of the time.

At Auckland Law School, I saw that the lecturers who were in love with their careers flourished and brought a sense of wonderment to the subjects they were teaching. As a judge’s clerk for the New Zealand Court of Appeal, I learned that very intelligent, reasonable people can have wildly different views. And that it’s important to respect, listen to and take into consideration those points of view, rather than being dogmatic about your own position. I saw the judges do that with each other, and it’s something that I’ve carried with me throughout my career. By the time I joined a law firm [after clerking], I was in a position to work with more junior lawyers and help them develop their own careers. To this day, I find it enormously rewarding to help people get the most out of themselves.

How I remember him: Joshua Bayliss at the start of his career. Photo: Bell Gully

As an analytically minded person coming into a very informal environment, the first challenge was to try to understand how things worked so I could assess how we could be more effective, more efficient and manage risks appropriately. After that, the challenge was to persuade everybody to transition from where we were to where I envisioned we should be in a way that was consistent with the business’ objectives and the brand, without causing friction. It went to the heart of the group’s processes and plans for the future, which was a fantastic thing to be involved in so early.

I didn’t realize the importance of patience. I overestimated people’s desire for change. I probably went too fast in some respects.

I was a litigation attorney, but the firm that I practiced at in London is very much a corporate-led firm. We described ourselves as like the Dutch football team of the 1970s — total footballers, we could play any position. What that meant was that I got involved in all aspects of transactions, from anti-trust to corporate law to takeovers. My foundation was as a litigator, but as my practice developed, I developed my own clientele based on broader legal relationships, not just litigation. Nevertheless, there were changes in my role when I became general counsel, which was almost exclusively transactional. I can remember having been at Virgin just a couple of weeks and being thrown a 240-page U.S. bank credit agreement for refinancing of one of our U.S. businesses, and I, honestly, had never dealt with anything like that before. Getting involved in that process, and managing it, was a real challenge.

You’ve got to think business first. You are a senior executive on the commercial side of a business. You need to be achieving commercial objectives. If you don’t understand the business thoroughly, or don’t understand the commercial drivers in the markets that you operate in, you can’t be a good general counsel. It’s not enough to know the law. It’s about using the tools that the law provides to achieve business objectives.

People who take the time to understand the business. When you work with high-caliber law firms, you almost always receive perfect legal advice, but that is not enough. A lawyer who can think in the context of your business and give you options, give you flexibility in your commercial positions, so you can do the right thing for your business, is the best sort of lawyer.

Virgin is a very meritocratic place to work. There were opportunities to get involved in anything and everything, provided that you could add value. Over time, I got much more involved on the corporate finance side of the business, making decisions as an investment committee member and looking at things through a financial and business lens. I was also asked to become involved with the Virgin brand-licensing company, Virgin Enterprises. I found that I was drawn to both the commercial and marketing aspects of Virgin Enterprises’ business. I was able to become involved in the look and feel of the brand, how it could be developed and deployed for marketing campaigns, examined the industries and markets we should be in. I was never afraid of making mistakes and was always prepared to offer a view, and I found that people listened to what I had to say, including the CEO and Chairman.

I didn’t really see it as a stark division anymore, given the nature of the role I was fulfilling as general counsel. But I did want to be much more closely involved in driving the strategy of the businesses.

I listen to people. I’m very democratic and I like to build consensus, but I’m decisive when I need to be. I try not to start from a point of telling people. It is important to me to ensure that people bring their whole selves to what they do — and you get that by involving them in the decision-making process. Offering people clear guidance on the business’ strategy, objectives and, above all, its purpose — then showing them how they can help to achieve those is of the utmost importance to me. That is how you build accountability and self-awareness.

I look for personality. What someone can bring to the business, other than subject-matter expertise.

When I’m at work, I give it everything I’ve got. When I’m at home, I give that everything I’ve got. When my family waits all week for me to get home, they want the whole of me to be there and they deserve that, not some tired shell. So I try to throw myself into family life in that way.

I circumnavigate the globe six to eight times a year. Something like, 150 to 200,000 miles per year. I have five gold cards.

My lifestyle is better now, I think. I can remember a time when I was pushing hard for partnership at Slaughter and May. I would get home six nights a week at about four in the morning. On three of those mornings, my wife would be getting up to go to the Covent Garden flower market in London to buy flowers for her floristry business, so we would chat for 10 minutes, maybe over a cup of tea, then I would go to bed for two or three hours before going back to the office. I wouldn’t see her again for a couple of days. In law firms, it’s like a roller coaster, and that lack of control over your own life is very challenging. In the commercial world, the business never stops, so you don’t have those same ebbs and flows, but you don’t have those extremes either. When I am not on the road, I always see my kids before they go to bed and I can take them to school in the morning. With 68,000 employees across 34 countries, I am on the road a lot, which is a challenge. But of course, as a CEO, you have a high-quality team that you hand-select to support you. And I am able to delegate to some very strong people.

Yes, of course. But it’s a team effort. I couldn’t do any of the things I do without my wife and her support. She’s always been incredibly supportive and tolerant in the past with my ridiculously long hours and, these days, with my extensive travel schedule. She has always fueled my ability to be successful. I also make it a rule, unless it’s an absolute necessity to be away, to be home on my kids’ birthdays. I always try to get back home for the weekend.

My experience has always been that women have a much greater ability to see the whole picture and the importance of home and family life, whereas a number of men I work with work hard, but then want to put their feet up when they get home, or go out and play golf.

Not very often. I think it’s almost taken for granted that it’s probably not going to be ideal.

Absolutely. I think there’s been a shift in our expectations as parents, members of society and executives. There’s an enormous amount of pressure to do and be good at everything. And in that context, you don’t want there to be an aspect of your life that’s lacking. I personally think it’s much harder for a woman to achieve that same balance, and I’m in awe of the women I work with who do it.

In my experience, when a child falls and scrapes a knee, they want their mother. It’s hard to balance being a working mom with children who need you when they need you and keep perspective on where you’re going professionally.

I’m not sure I entirely understand the rationale. But if it is to attract more women to want to work in the tech industry, I’m not sure I see it working. Women should be free to have children when they want to. Basing that decision on your career progression seems to me to skew priorities in a very unnatural way. I’m not sure how that’s appropriate in an employment relationship. I would prefer it if tech companies did more to support young women in making education choices that give them access to a tech career.

Everyone has to make their own decision about what works for them. When anyone makes a decision and spends more time with their family as a result, I think that’s a pretty high-quality decision.

When the children were born, she decided to sell her floristry business so that she could spend more time at home. So, she’s been at home with the kids looking out for all of us. As I said, it’s very much a partnership.

I think it’s different strokes for different folks. Some people are really happy to live a family life that revolves around both parents working difficult and demanding jobs. We made the decision that family life was going to be crucial to us, in part, because we have always lived far away from our respective families. It was really important for us, as a couple, to create time and space to focus on our kids and their development. To do that, only one of us could work the sort of career that I have now, but I do think my wife works harder than I do because it’s a 24/7 job that she’s got.

Joshua celebrating with his wife, Sophie, after the 68-mile Cape Town Cycle Tour — a short trip for a man who travels more than 150,000 miles each year.

I think each generation learns from the one before it and seeks to develop based on that learning. Our ambition as parents has been to give our children as much opportunity as possible, whether that’s cultural, social, languages, sports, etc.

I was adventurous. I was curious about the world and self-sufficient. Both of my parents worked, because they had to work just to put food on the table, so I’d spend a lot of time on my own and then, as I grew up, with my younger brother. It was a fantastic childhood really, very liberating, and we had parents who always encouraged us to set our own individual objectives. I was very sporty. I played every sport that I possibly could. I worked hard from a young age; I was diligent when it came to getting my homework done and things like that. I was a pretty well-behaved kid, really. Maybe because our background was rather limited financially — and we saw our parents working very hard just to keep their heads above water — my brother and I have worked incredibly hard to generate a bigger future for our own families.

When I was about six years old, I wanted to be a scientist, so that I could emulate Spider-Man and The Incredible Hulk. Clearly, that changed over time. I was attracted to discursive subjects, so when I started looking for a career, I knew I wanted it to be something that involved using language and words.

On the board, which consists of six directors, we have one woman. 
On our executive committee, we have one woman. We are actively working to change that mix right now, and I expect that to come in the next couple of months. Creating greater opportunity for the very high-quality women that we have at the company is a real focus for us. That will happen, partly, as a matter of time, because some of my senior colleagues will move on or retire. But it also has to be an active decision that we take as a business. And I have made that decision. We have a program to encourage diversity and inclusion, not just in hiring, but in career development. And that revolves around providing flexibility in the workplace. We have all sorts of flexible working policies, including unlimited leave — people can take as much holiday leave as they like. We have introduced these polices, in part, to create an environment in which women can prosper. And diversity and inclusion aren’t just about gender. We are also working hard on programs to embrace the differences of our colleagues from minority cultures, sexual orientation, religions, etc.

Historically, businesses have been regimented places, which haven’t always thought about the challenges that are involved in being a working woman. We are trying to change that by introducing policies with flexibility to encourage women to stick around to break through that ceiling after their families expand.

We’ve never been the kind of organization to reward people based on their working hours. We are incredibly flexible. People can work from wherever they need to. They turn up in the office when they need to, but they can work from home or from the beach. That’s always been a part of Virgin’s culture. And I think by making a public statement by introducing unlimited leave reinforces to people that it is something that we are looking to change — not just at Virgin, but beyond. I would hope that all businesses start to think about clever ways that they can encourage women to develop careers beyond that point when their children are growing.

Richard is a great practical joker. Some of my special moments with him have been when he’s rung me and said things like, “Isn’t it great news that we’re selling Virgin Atlantic?” and I’ve felt my palms go sweaty and my throat tighten up, and I wonder what the heck he’s done. He is probably the greatest British entrepreneur of his generation. He has achieved that by dedication, bravery, good instincts — and trusting them — and choosing good people to rely on.

Virgin has given me the most incredible platform and opportunity to work with a brand that stands for change and stands for shaking things up. It’s a purpose-driven business, a business that has built a community where people are essential to the decision-making, rather than just profit. Taking the business in that direction is an enormous challenge and a fascinating one. So, when I think about the future, I think that’s what I’m very excited about doing.

I would love to go to space. I’m on the board of Virgin Galactic and I’ve watched the program develop. Clearly, we have suffered a setback recently, but we are more determined than ever to make advances for humanity and build a successful spaceline. I would love the opportunity to go to space. My wife, on the other hand, absolutely hates flying and has a pretty strong view that I shouldn’t be going to space. As I said, we work as a team. So, I’ll have to confirm that she’s okay with it before I make any final commitments.

Don’t be afraid to make mistakes, and never give up trying. If it doesn’t work out the first time, just go again. Too many people take one or two small setbacks as a signal that they should change course. My advice is just to go with your gut instinct and believe in yourself.