Breaking Barriers in Business: Charlie Whyman’s Lessons on Leadership and Diversity

Charlie Whyman is a seasoned business leader and keynote speaker whose career has spanned aviation, engineering, healthcare, technology and even olive oil production. Now Managing Director of TGIS Aviation Ltd, Charlie draws on a rich mix of hands-on experience to deliver talks on leadership, change and growth. 

She is also a speaker with The Female Motivational Speakers Agency and a passionate advocate for diversity and inclusion, encouraging businesses to embrace different voices, perspectives and lived experiences. With a background in engineering and an accidental route into sales and marketing, she has spent nearly 20 years helping teams and organisations rethink how they work and step into their full potential.

Having broken barriers as one of the youngest female MDs in aviation and built businesses from the ground up, Charlie speaks openly about the reality of leadership – including its pressures, fears and rewards. 

Her mission is simple: to show others that success doesn’t come from waiting to feel ready, but from choosing to move forward, even when it’s uncomfortable. Through her speaking, mentoring and past roles with the Professional Speaking Association, she helps others find clarity, courage and momentum.

In this interview, Charlie shares why courage matters more than confidence, how inclusive leadership really works, and what it takes to support others – and yourself – at the top.

Q: You often share your career story – how do you use it to challenge traditional views of leadership?

Charlie Whyman: “It’s a really good question because I find speaking still quite terrifying. A lot of people always ask me why I speak, why I post content on LinkedIn, why I share my story. I think there are so many people I speak to who are afraid of putting themselves forward for opportunities because either they don’t have the right qualifications, they don’t feel confident enough yet, or they’re waiting for some form of permission or external signal to say, actually, I can go for it.

Some of the best opportunities in my life have come from someone asking me if I’d be willing to do something or if I could do something, and I’ve just said yes with the view that I’ll figure it out later. I want to share my story to inspire people to go: ‘You know what, just because that job description isn’t for me from a qualification point of view, if I know I can do that, then I’ll go for it anyway’.

I speak to so many people held back by all of these external factors. They don’t need to be held back – they can just go for it.”

Q: Why should businesses prioritise courage over confidence right now?

Charlie Whyman: “Courage is an interesting word for me – as is confidence. I feel like they’re mixed up a little. So many people within organisations are waiting to feel confident enough before doing the thing they need to do. Whereas if you flip it around and reframe it – focus on courage – courage to do the thing with a view that it might not be perfect, but you’ll try anyway, and then learn from that experience, then go do it again but do it better.

For me, courage is really important because it encourages people to do what they need to do with the aim of learning from it, rather than acting from a place of confidence, where there’s no expectation to learn. Courage is contagious: if you see someone doing something they don’t know how to do, or something that’s a bit scary, and they’re being courageous – they’re being brave – it inspires people to think, ‘Maybe I could do the same thing’.

Whereas if you see someone doing something from a position of confidence, the narratives are usually around, ‘Oh well, I can’t do that’, or ‘I don’t have the skills’, or ‘I don’t have enough experience’. If organisations promote courage, I believe they can get a lot more from their teams. I’ve witnessed this first-hand from the teams I’ve worked with and the people I’ve spoken to.”

Q: How do you support women in business to find their voice and build self-belief?

Charlie Whyman: “It’s an interesting topic – supporting other women in their careers, leadership roles, and in business. I kind of wish people would stop focusing on the ‘women’ element and instead look at what we need to do to make things more inclusive and create more opportunities for people. That said, I’ve worked across many male-dominated industries. A lot of the women I speak to, especially in junior roles, are afraid of putting themselves forward or asking questions in case they’re wrong. They fear consequences, and those consequences can vary widely.

For me, it’s about helping lift people up and giving them opportunities to have what I’d call compassionate conversations, so they can address challenges – challenges we all experience, with compassion and empathy. I don’t believe most of the everyday sexism we experience comes from a negative place – I believe it comes from ignorance. If we address it with compassion and empathy, we can solve the real problem.

I’m keen to start having the deeper conversations I believe we need to have. There are a lot of surface-level discussions that don’t get to the heart of things. One example: how do we support women not just as they rise through the ranks, but when they’re at the top? Leadership and business can be lonely places, with emotional pressures both at home and at work. If we don’t have the right support network, that pressure can affect our behaviour toward others.

There’s fear around addressing this, but again, if we come from a place of compassion and empathy, asking: ‘How can I support you?’ rather than tearing people down. That’s more productive. I see it all the time: women at the top being judged and belittled. For me, it’s not just about helping women rise up, it’s about helping those at the top support other women to rise as well. Be supportive instead of thinking others must go through what you went through.

Also, how can they recognise their own behaviours? I’ve got an incredibly supportive network. When things get overwhelming, or the emotional burden of leadership and business gets too much, they force me to rest and address what’s going on – instead of that pressure spilling over onto others.

People often focus on, ‘Women aren’t getting the opportunities’, but women also aren’t putting themselves forward. I’m where I am because I’ve put myself forward – I’ve not waited for someone to say: ‘Here you go, Charlie’.

And something I’m passionate about: throughout my career, it’s always been men who’ve supported me – given me tools, training, and time. The most traumatic experiences, which have even sent me to therapy, have come from women trying to take me down – usually from jealousy or their own unresolved issues.

For many years, I believed women were the enemy. I didn’t have many female friendships. I’ve worked hard to change that, and now I have some incredible ones. But we need more support at the top – not judgment.”

Q: How have male-dominated industries shaped your perspective on leadership?

Charlie Whyman: “For me, it’s not about focusing specifically on men and women, but on which leadership qualities I want to adopt in my role and in what I do.

What I’ve realised, and I was ignorant to this, is that if someone asks me to recommend a speaker, author, or podcast, more often than not, I recommend male-driven ones. That’s not intentional exclusion; it’s just been my world. But I’ve been making a specific effort to seek out and acknowledge female authors.

I was asked for leadership book recommendations recently, and three of my top picks were written by women. I want to move away from having to think, ‘Right, I need a female-led expert’ or ‘a male-led expert’. I don’t like that we have to talk about this – but we do, because if you’ve grown up in a male-dominated world, taking the time to seek out content from women is important.

It’s not about men vs. women – it’s about diverse perspectives. A male voice, a female voice, a Gen Z voice, a millennial voice, a baby boomer voice, a neurodiverse voice – all perspectives matter. You can’t rely on one train of thought just because it’s your normal.

I want us to just talk about people. But we also have to acknowledge that women haven’t had a voice for very long. We’re expecting centuries of progress to happen in a couple of decades. If we step back and say, ‘Actually, we have come far, but what do we focus on now?’ – then self-awareness becomes key.

We need to check ourselves: am I only recommending men? Am I recommending people of a certain age? That was something else I realised – many of the authors I recommend are in their 50s and 60s. Where are the fresh perspectives?”

This exclusive interview with Charlie Whyman was conducted by Roxanna Farthing, Operations Director at The Female Motivational Speakers Agency.