There are few journalists better placed to answer that question than Orianna Rosa Royle, Associate Editor at Fortune and one of the publication’s most-read writers.

In this episode of the Grayling Media Podcast, Heather Blundell, UK CEO at Grayling, sits down with Orianna to explore what she’s learned from interviewing some of the world’s most successful business leaders and why the reality of success is often very different from the headlines.

The conversation goes far beyond career advice. Orianna reflects on her own remarkable journey, from experiencing homelessness while at university to becoming one of Fortune’s leading journalists. She explains why attitude often outweighs credentials, why building relationships still opens doors, and why she’s become increasingly open about her own story.

Heather and Orianna also discuss what great leadership really looks like, from owning mistakes and communicating authentically to navigating AI, hybrid working and the future of the workplace. Along the way, they challenge some of the biggest myths around success, productivity and leadership.

Whether you’re an aspiring leader, building your career or simply interested in what makes high-performing people tick, this is an honest conversation about ambition, resilience and what it really takes to succeed.

Listen to the full episode below.

Transcript

00:00:00 Heather Blundell

Welcome to the Grayling Media Podcast.

I’m Heather Blundell, UK CEO at Grayling and today I’m joined by a very special guest, Oriana Royal, Associate Editor at Fortune.

Oriana leads Fortune’s Success vertical where she covers careers, leadership and the future of work.

An award-winning London-based journalist with over a decade of experience, she turned her own escape from poverty into a beat, unpacking how people actually get hired, build wealth, and create thriving working lives.

Since joining Fortune in 2023, she’s become one of the most read writers, known for exclusive CEO interviews and rags riches stories, and writes the weekly Fortune Success Letter.

We’ll be talking today about what it really takes to build a successful career, the lessons Oriana has taken from interviewing some of the biggest names in business, and we’ll also hear about her own story and the path that led her to becoming one of Fortune’s most read writers.

Oriana, thank you so much for joining us today.

00:00:59 Orianna Rosa Royle

Thank you for having me.

00:01:02 Heather Blundell

Orianna, you’ve had an incredible rise through journalistic ranks and you’ve interviewed some of the world’s most successful people.

After years of reporting on careers and leadership, what still surprises you?

00:01:15 Orianna Rosa Royle

The thing that still surprised me, which is kind of like a double-edged sword, it’s really good and it’s also really **** for people like me that have come from like an alternative or working class background, is just how much of an importance it is who you know, but also your personality, the amount of CEOs, you know, like even Andy Jassy from Amazon, he said literally it’s an embarrassing amount of success in your 20s, it’s all to do with your attitude and I think that’s so true.

I think who you know will open doors but your attitude once you’re there will keep them open or keep them shut, which obviously for people like me is rubbish when you don’t know anyone and you’re trying to open your own doors.

But it’s also nice to know that it’s not necessarily your credentials or your skills that employers are looking for, they’re looking at someone that’s really going to a graft and I think there’s nothing quite like a working class hard graft.

So I think it makes it tougher to enter, but then it actually makes it easier to climb the ladder.

00:02:14 Heather Blundell

You talked about your background.

How did you open those doors?

What was your journey?

00:02:19 Orianna Rosa Royle

Oh, my journey was a bit wild.

I experienced a bit of homelessness while I was at uni.

So I called my university and I was like, look, I kind of have nowhere to live.

Can you guys put me up?

And they put me up.

But it gave me like a year’s deadline of like, I need to get a job before I graduate or I’ve got nowhere to live.

I’d already been doing work experience from the age of 15 anyway, because I already knew other people are going to graduate or they’re going to finish school and then they’re going to start looking.

And I was like, I don’t know anyone.

So I need to get a head start, so that I just have some contacts, I have some experience under my belt.

I knew from a young age, I was lucky that I knew from a young age what I wanted to do.

So that gave me that goal already.

I was quite audacious.

I think that’s so important as well.

I would turn up to people’s offices with my schoolbooks and like, I’m not going to leave unless you give me two weeks’ work experience.

I did that quite a few times to people at in really senior TV roles.

I was like, let me just follow you around for a day.

I begged, let me. And then they’d be like, oh, she’s all right.

She could stay for a week.

And then anytime we had a university lecturer who had a professional job in the industry, I’d pounce on them the second the lecture was over and was like, give me a week’s free work experience, it will be like the best thing you’ve ever done. It’ll be free work for you.

And I think it’s a shame that now you can’t give out free work experience.

I know it’s also taking advantage of people and I know how bad it is, but it means that today people just aren’t giving out work experience.

And I did that for a year and I worked on the weekends to be able to afford to do that. I worked at Debenhams and I worked at the Rugby Ground to afford working for free. But eventually, after a few months, it wasn’t free, then people were like, she’s actually quite decent. And they paid for me.

And then I did get a full time job before graduating.

It’s your attitude, isn’t it?

And I think in the last 10 years of my job, I’ve applied for one.

That was the one at Fortune.

I think that just highlights the power of, yeah, making those connections early on, trying to knock on doors.

I think today as well, with social media, it’s like you have the door to any editor or any boss on your phone. Use it.

00:04:40 Heather Blundell

It’s such an amazing story.

I feel very challenged listening to that as in a leadership position about, we talk so much about, obviously how the impact of AI and so many positives and challenges.

One of the things we are going to be really careful about is continuing to make junior hires is continuing to encourage people into the workforce.

And it’s important, we do a range of partnerships and internships and work experience here.

We’re really passionate about it, but it is a commitment and it’s us, you know, it’s quite a lot of admin and looking after, and but it’s such responsibility in order to, give people that experience and that first taste.

00:05:17 Orianna Rosa Royle

I mean, good for you as well, because so many people are pausing hiring because of AI.

It’s such a huge mistake, because one, I think we’ve kind of overestimated just how useful AI is.

I think it’s because we’ve listened to the people that own the AI companies be like, you know, it’s going to replace all jobs.

Obviously, they’re incentivised to say that because they want all the CEOs to buy their products.

All it means is that entry level people, and especially young people that have no connections in, are missing out on those first years of experience.

I see so many people talking about how they’re unemployed despite having like maths degrees, master’s degrees, and they’re searching for months and months and months and they’ve got nothing.

00:05:56 Heather Blundell

I listened to a talk last week, which was the first time I’ve heard someone make this argument was that AI had been so amazing in their business that they had grown so rapidly that they had hired more people.

So actually it’s been turbocharged within our business.

I was like, okay, that’s a great way to say it as well.

Actually, if we use it, we can grow faster and hire more people.

00:06:18 Orianna Rosa Royle

Because you could just be more productive, just have more people push out more stuff with AI helping them be like supercharged humans.

But I don’t think it’s, I still don’t think it’s as useful as like the AI CEO are saying it is, having like played with it myself.

00:06:32 Heather Blundell

There’s been quite a lot on LinkedIn from journalists bashing PRs for AI slop pitches.

Have you seen some bad ones?

00:06:39 Orianna Rosa Royle

I think I’ve written one of these, not about like AI specific, but about, well, yeah, I guess AI specific, but ones that are just very clearly not tailored to the journalists, like sloppy, wrong. The amount of times I get pitched for Forbes, my name’s not in there, my name’s spelt wrong, or it’s about a story about like toys.

I think they’re using it to just like find press contacts easier and then you just end up on some kind of database and then you just get them bashed out with.

I think the quantity has increased, like because they can just get out so many more press releases and it’s the quantity that’s increased and the lack of relevance that’s increased.

00:07:21 Heather Blundell

Yeah, interesting.

So talking a little bit about sort of defining success, I guess success is a word that we use all the time, but it means different things to different people.

I also think it means different things at different stages of your life as well.

What’s the single biggest lesson about success you’ve learned from leaders that you’ve interviewed?

00:07:44 Orianna Rosa Royle

I think the thing that I’ve learned is that these people really do train almost like athletes, like up to the level of like an Olympic athlete.

There’s no like real secret, there’s no hack, there’s no like, if you do this, you’ll be an overnight success.

I mean, I cover a lot about their routines and their mantras and their philosophies and the things they do to be at their A-game.

And you know, there are loads of high performance habits, but the reality is they’re putting in 12 hour days, bare minimum 10 hour days.

And it’s that secret, it’s not secret, sorry, it’s that simple equation that if you put in more hours, there’s more opportunity to be successful.

Like if you’re simply outworking everyone, you’re meeting more people, you’re getting more done, then there’s more chance that you’ll be successful.

It really is that simple.

And I wish, and I hate saying that because I know everyone’s already so stressed and everyone worked so hard already.

But the reality is that the people who are successful are just outworking their peers, like the majority of the time.

And especially in, I’m doing a lot of rags to riches.

So obviously the people that I’m interviewing especially, that’s the case, is that they just worked really hard and they outworked everyone that was in the room with them.

00:08:55 Heather Blundell

It’s so interesting.

If anyone ever asked me like, how have you, I’ve just, I’ve just always worked really, really hard, but you can sometimes feel a bit shameful now, especially as we talk so much about balance.

And I think to a generation coming up in the workforce, it’s much more important than it ever was.

When I was coming through the ranks, I remember just being absolutely delighted that we had a bar in the office.

I mean, like that would be pointless to do now.

It’s a completely different generation.

I’m not saying it’s wrong, but that kind of 12 hour day work ethic isn’t something, but you can still see it at that high performance leadership.

00:09:35 Orianna Rosa Royle

I’ve had leaders tell me, oh, this is how many hours I do, but don’t put it in print because they don’t want to be seen.

But I think that’s dishonest.

Like I think we need to be super like transparent, young generation of if you want to be in this job, then this is the toll it takes.

And it’s okay if you don’t want to sacrifice that, but that just means you don’t get there either.

You know, it is a sacrifice.

And so many CEOs, I was literally at the Formula One the other day talking to Orwin CEO and he was like, you can have it all, but not at once.

00:10:11 Heather Blundell

Okay, so talking a little bit about sort of behind closed doors with CEOs, of all the CEOs and business leaders you’ve interviewed, of which there’ve been many, which conversation has really impacted you the most and why?

00:10:22 Orianna Rosa Royle

I really had to think about this because I interview a CEO or like a millionaire every single week and I’ve been doing that for God,

Yeah, nearly a decade.

00:10:34 Heather Blundell

A weekly millionaire, how fun.

00:10:36 Orianna Rosa Royle

I know, it’s so fun.

A CEO, millionaire, founder, someone that’s made it.

The one that made the biggest impact on me was the CEO of Buddy Media, Sam Budd.

And the reason for that is he, we went for like lunch together before I did the interview as just a,

I don’t do pre-interviews, but the PR was like, I know he’s not someone you usually interview because the revenue of the company is really small.

He wasn’t a unicorn yet.

He didn’t have the, like, quite the business metrics that you would need to be a Fortune interview necessarily.

But he had a background that was just, I want to say even potentially worse than me, like in terms of adversity, what he’d gone through, like his dad was a heroin addict.

And his, he had periods where he lived on the streets too.

I’d never heard a CEO, and I’ve done rags to riches for years, and I’ve never heard a CEO talk that brutally honest.

You know, I’ve had people say like, oh, I had financial hardships or imply it by I started out working in the shop floor of McDonald’s.

That implies that, you know, you came from a working-class background.

But I’d never had someone be so just brutally honest and own their, own their like upbringing.

And after that, he was the first person I actually ever talked to about my own background and my upbringing and how similar it was.

I was like, we’ve got to cover your story because there’ll be so many people that just don’t know you can be a CEO and have that background.

Because I’ve been doing this all these years and I didn’t know that they’re these CEOs that had like the background I’ve had, even though I’ve been doing this as long as I have.

And it was the first CEO that got me to A, talk about my story, but also talk about it in a public sense, talk about it to peers like no one at work.

They knew I came from working-class background, but not quite the things that I’d been through.

And then I started talking about my social media and things like that and the reach that that’s had and the like my LinkedIn went from having like a couple of 1000 followers to now I’ve got over 11,000.

And that’s just by being, I guess, more authentic.

And it was something that I was, I don’t know why, ashamed of, ashamed of that background.

I think because you’re always in a room talking about success and CEOs and LinkedIn can be quite cringe and you don’t want to be adding to that either.

So I think I was just too in my head about it.

But yeah, so that definitely had like the biggest impact on me personally being able to accept my background and accept that there are other people that have also been through that and they’re talking about it.

00:13:03 Heather Blundell

And I thank you for sharing.

It’s so powerful.

And it’s, you know, from whether it’s your background or whether it’s through a period of real hardship in your life, which so, you know, most people go through to varying degrees, but to be able to turn that into fire and to turn that into purpose, I think is one of the most powerful things you can do.

And I can see that in people sometimes, where they’re like, I’m going to let this define me and break me or I’m going to use it to be this absolute force.

It’s so true, I’ve always said this, I have so many people that I grew up with, obviously, I think you grew up in a deprived area, a lot of the people you surround yourself with and boyfriends you date, are from us in the background, and so many of them end up jobless or saying like, well, I deserve this because like I deserve to be funded by the state because this was my background.

And I’ve always come from a position of I’ve seen what absolute like eating out of bins is like and having to take clothes out of bins.

Like I’ve seen the level of poverty that you can reach and I’m never going there.

I’m like never going to be in a position where I don’t have money.

And it’s so funny because I could have been a victim of it just like many of my friends, partners that I grew up with ended up doing.

And yeah, I used it, as you say, like fire, to do the opposite.

00:14:21 Heather Blundell

It’s absolutely amazing.

And then speaking still about sort of CEOs and leadership, what’s the biggest communication mistake you see senior leaders consistently make?

And don’t say media training.

00:14:36 Orianna Rosa Royle

I feel like this is going to get so much hate.

It’s actually, it’s talking about RTO, return to office, framing it in a way that’s beneficial to staff.

And I think we all know that’s ********.

We have all seen the study that engagement, productivity, all of it goes up with hybrid, you know, some working from home, some going in the office.

So CEOs are like, I’m doing it five days a week for your benefit, it’s better for your mental health, it’s better for your productivity.

And I think obviously, you’re not hiring children, you’re hiring adults who know where they’re most productive, they know what works best for their mental health.

If you give them that kind of offer of you could do from home and from the office, then you’re trusting them to do what’s best for them.

But you telling them, I know what’s best for you.

00:15:26 Heather Blundell

It’s almost like a controlling religious cult, isn’t it?

00:15:29 Orianna Rosa Royle

Yeah.

Exactly.

It’s also like, it’s the thing that’s so obvious is, well, if you ask them to go five days a week, it’s because, you know, A, you don’t trust them to work from home, as you say, but also you clearly have like an office lease that you want to max out.

You don’t want to waste money.

And it’s so obvious.

And if that’s the case, just say it.

Just say, look, we’re paying for the office.

It’s a nice office.

You get coffee for free, you get breakfast for free.

We want to make the most of it.

Say that.

And I think employers would respect that much more than being like, this is for your good, like they’re, you know, school children.

00:15:58 Heather Blundell

Yeah, I couldn’t agree with you more.

We know that the best leaders aren’t judged when everything is going well.

What have you learned about great leaders and how they respond when things have gone wrong?

00:16:13 Orianna Rosa Royle

I mean, I think it comes to that classic saying, isn’t it?

It’s like, if you’re a CEO or even just a manager, like, your wins are my wins, but your losses are my losses.

And I think so many managers and CEOs, I see them shouting about the wins when like their staff are doing great, like, oh, it’s like my strategy, it’s my vision, like doing so well, but then things go bad and it’s not their fault, it’s the teams.

In reality, the buck ends with you.

If things have gone wrong, even if it’s not your fault, you need to be like, you know what, I’m owning this.

And I think on the flip side, when things are going well, you should be thanking your team and being like, my team are awesome, they’re amazing.

I think it’s much better to lead in a place of like, I want all my stuff to want my praise than to fear me.

00:16:52 Heather Blundell

Yeah, totally.

And which actually leads nicely onto the next question around like authentic leadership.

We hear that a lot, what do you think, and we were talking about this a little bit before we started recording, but what do you think like authentic leadership actually looks like?

00:17:08 Orianna Rosa Royle

I think that’s a misconception of authentic leadership, meaning soft leadership.

And I don’t, like we were talking about a CEO who’s like quite brazen, quite bold, and that will empower the people within his teams to also, if they’re like that, be like that and feel like it’s okay to bring my full personality to the office, no matter how loud and brilliant that is.

I think we have this misconception that it means like a soft and a kind and empathetic leadership, which is important too.

If that’s your style, then you should totally bring that to the office.

But some examples of authenticity was like Netflix’s co-founder being like, I leave the office every day, every Tuesday, sorry, no matter what there is, come rain or shine because I need to stay sane.

And that’s like my one day where I see my friend a week or Emma Greed saying, sometimes in the evening I’m on the laptop again, but every day I leave the office at 5pm.

It’s just that being honest about your actions, being like, I have childcare or Mark Randolph didn’t have children, but he saw his friend and it’s being honest of like, this is why I’m doing this, it is who I am. I do what I do.

And I think that enables your staff to do the same.

00:18:15 Heather Blundell

Totally, and to be able to view you as a real person.

I think I spent years of my sort of career trying to cover up slightly, especially post-children, slightly sort of messier side of my life, or not even like messy, just be like pick-ups or drop-offs or a tennis lesson, and just pretending that I was elsewhere or whatever, but actually now I just block it out of my diary and I’m like picking boys up or taking them here, like, and people can see, and I had to bring one of my kids in, it was a while ago now, but I had to bring him in because he had a strop and didn’t want to go to his summer camp.

And I was like, well, you’re going to have to come to work with mummy.

And he was just like, okay.

And he did, I got so many emails about it because he just sort of followed me around all day.

And I had to sit there doing his colouring in and actually by the end of the day he was like standing on a table doing paper airplanes and like described it as the best of his life and that mummy’s work is like a party.

But I think it was like the fact that I was walking and being like, nightmare was helpful because other people were like, well, I can do that.

00:19:14 Orianna Rosa Royle

And I think otherwise, if you had it all blocked off, people would have seen your diary blocked off and just assumed, oh, wow, like she’s got children and she’s managing to do all these extracurricular meetings and things and felt like, why can’t I do all that, you know?

00:19:28 Heather Blundell

Yeah, absolutely.

We’ve talked a little bit about this in terms of the workplace.

Your beat also encompasses the future of the workplace.

What are the best leaders thinking about in terms of the workplace that others aren’t?

00:19:43 Orianna Rosa Royle

I think one thing that really stands out to me is equity and also giving time back.

Mark Cuban talks a lot about this.

It’s like the fact that these businesses, like, and you said, like, people are like supercharging their productivity of AI.

If you’re making like loads of profits, invest that backing your stuff.

Bring them on board on these changes.

And instead of being scared of AI, they’re going like, this is great.

I’m more productive, getting more work done.

And also, like, if you have output goals, and you’re finishing your work, say 30 minutes, an hour earlier because of AI, because you’re so much more productive and you’re still doing way more work than you were previously, like give that time back.

Mark Cuban was really honest about like, you’ll probably see an hour freed up in the day from most workers because of what AI can do.

What you do with that hour, you force them to do more work or you’re giving them that back, especially as you say in a world where work-life balance is so important stuff.

That’s like a really easy way of engaging them.

I’ve been like, you know what, you get your work done an hour earlier, just leave an hour earlier.

00:20:42 Heather Blundell

That’s a good idea.

Do you think workplace trends are receiving too much attention or overhype or are there any leaders that are still underestimating it today?

00:20:53 Orianna Rosa Royle

I mean, as I said, I think AI was overhyped and I think the damage to that to young staff has been like unforgivable, really, the amount of people that just, and it’s like, I feel like it’s akin to, like a property that’s for sale for like six months a year, then it’s just harder to sell that property.

These poor young, you know, Gen Z, 21 year olds, they’re coming out of uni and they just can’t land work because some CEO thinks in five years’ time, maybe,

AI will be able to do that job.

And then instead of hiring, because they’re like, the economy bad, inflation is bad, whatever, instead of hiring someone, we’ll just wait and see what AI is like in a few years.

it means that these young people could be for years in kind of limbo and they’re never going to get the talent to be that, medium, that mid-tier hire that in five years time once AI might be useful.

So it’s like just give them the entry level work now.

AI is not there yet.

00:21:49 Heather Blundell

Yeah, totally.

But it’s also like an absolutely, I think, a bit of a.

I might be making a sweeping generalisation based on one conversation that I’ve had, but I feel like the education system and the workplace aren’t that connected in terms of this as well, because we are still making, lots of junior highers and

I’ve just hired someone who had been like, had reached out to me quite a few times in order to meet up with me.

And in the end, we went for breakfast and halfway through the meeting, she pulled out her laptop, genuine story, and she’d redesigned our website.

And it looked absolutely stunning.

It blew me away.

I was like, finish your omelette.

And I took her back to the office.

I was pulling people out of meetings.

I said, look what she’s done.

Two days of AI.

And we had, I won’t disclose how much, but like, you know, we had picked someone a fortune to design that website.

It looked absolutely stunning.

We’ve created a role for her.

But I feel like there’s still, within the education system, quite resistance to AI.

And actually, probably what do I want from my junior clothes?

I want them to be amazing at it.

I want you to be, I want to be learning, you know, all your AI tricks and to turbocharge this business.

So I think it needs to be encouraged a bit more within the education system so that they can fly into the workplace rather than being like, well, actually, I’m not allowed to speed with it.

00:23:04 Orianna Rosa Royle

I think regulation, education, all of those things are always quite slow to catch up.

Do you know what I mean?

I remember when I graduated,

I was getting asked, oh, do you want to be a TV journalist or print journalist?

And at the time, actually, digital media was like coming up and no one was talking about it.

So I kind of made my career of being like a film and I can do articles that’s perfect for digital.

But that’s something that like the education system just wasn’t prepared for.

And you know, AI has come quite quickly, right?

It’s so in order to change an entire curriculum around it, I understand it’s like a huge hassle.

Like the young example you highlighted, it’s a case of, okay, well the school’s not teaching me, I’m going to teach myself.

I remember YouTube tutorialing how to like, do you know what, like do things, like use WordPress and things like that.

Yeah, it’s free to do that to, your school’s not teaching you and it’s annoying if you’ve paid, like I was the year that they changed the fee.

So I know how annoying it is if you’re spending like 30 to 50 grand on a degree and you’re coming out of it actually with not the right skills for the workforce today.

Like I understand how frustrating that is, but no one’s going to champion your career as much as you are.

00:24:11 Heather Blundell

Then there’s responsibility.

00:24:13 Orianna Rosa Royle

Exactly.

It’s up to you to do what she did and message that CEO, show them that new website design use, like teach yourself to use AI and do that.

00:24:20 Heather Blundell

Yeah, she absolutely blew me away.

I know she’s been an amazing hire.

Okay, final question.

If you could interview any business leader tomorrow, who’d it be and why?

00:24:29 Orianna Rosa Royle

Oh my God.

So I get this one.

I have a whole list.

I don’t think it happened.

Of people that I want to do.

But I thought Martha Stewart has to be #1 because she like, she became a self-made, but she became America’s first self-made billionaire, female billionaire.

30 years ago.

And yet today in her 80s, like last year, she launched 2 new products.

And she’s still getting up at 4am every day, working on her farm, working in the city, like commuting to New York.

And I just want to know how she gets that kind of motivation, but also how she’s not burnt out, because that’s a very long career to have at that level.

So I was like, early, I said, there’s no secrets to success, but maybe Martha has it.

00:25:12 Heather Blundell

Maybe she’s got it.

We need to find her.

Orianna, thank you so much for joining us.

I’ve absolutely loved speaking with you and thank you so much for coming in.

00:25:20 Orianna Rosa Royle

Thanks for having me.

 

 

 

 

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