An Interview With Vanessa Ogle
Women’s health issues — like severe period pain or mood changes from hormonal shifts — should be openly acknowledged in workplaces. I know women whose period pain is so intense they need sick days. But instead of understanding, these issues are often trivialised with PMS jokes.
Despite strides towards equality, women remain underrepresented in leadership and management roles across various sectors. In this series, we would like to discuss the barriers to female advancement in these areas and explore actionable strategies for change. We are talking with accomplished women leaders, executives, and pioneers who have navigated these challenges successfully, to hear their experiences, tactics, and advice to inspire and guide the next generation of women toward achieving their full potential in leadership and management roles. As part of this series, we had the pleasure of interviewing Diana Robertson.
Diana Robertson is an award-winning entrepreneur, communication skills trainer, TEDx speaker, and the founder and CEO of Skillsme, an e-learning platform dedicated to empowering early-stage leaders in their leadership journeys. She also directs the Skillsme Leadership Summit, the leading event for emerging leaders, which brings together over 5,000 attendees and 20+ leadership experts, including senior leaders from major companies like Amazon and Uber.
Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?
I’m the founder and CEO of Skillsme, an e-learning company that helps early-stage leaders thrive in their leadership journeys. My journey began with my first business — a food delivery service — which I launched as a second-year university student at Bayes Business School in London.
Food delivery was a relatively new industry, and with successful apps emerging in the UK and the US, I was inspired to bring the same idea to Russia, where I’m partially from. I took a gap year from my university in the UK to pursue this idea but, while I was ambitious and motivated, I was also young and inexperienced.
It was an incredible year for learning, but also one of the most challenging times of my life, because my business did not succeed. The timing was right, the idea was solid but, unfortunately, I wasn’t the right person for the job. In hindsight, I can see why — I lacked essential skills and had limited business experience.
One of the biggest challenges I had was in communication. It was essential that I lead people and sell my idea, but I struggled with public speaking and pitching. As a result, I came across as unsure and unconvincing to my clients and partners. In other words, my lack of confidence and communication skills seriously held me back as a leader.
After closing the business, I returned to the UK to complete my studies and start actively working on my confidence and public speaking skills. I joined clubs, took training courses, and read countless books on the topic. I was determined to get better, and my determination paid off. Over time, my skills improved — so much so that, years later, I’ve even won several public speaking awards in the UK and given a TEDx talk!
At a certain point, people began approaching me for help, and this led to the creation of Skillsme as a virtual school for communication skills. Since then, we’ve expanded our focus to help early-stage leaders succeed in their careers by teaching a whole variety of essential skills. Whether it’s irony or fate, I’m not sure, but I’ve ended up offering the guidance and insights that I once needed myself.
Can you share the most interesting story that happened to you since you began your career?
When I started Skillsme, I initially planned to hold in-person training sessions. This was the traditional way to teach these skills — in a classroom, where participants could practise with each other. But then, COVID hit.
With so much uncertainty, I decided to try teaching communication skills online. At the time, this was unheard of. In fact, most training companies had shut down! However, it turned out to be one of the best decisions we made, as we gained clients not only in the UK but also in the US and beyond.
When things returned to normal, we were already established as a fully online business and have continued as one ever since. So, in many ways, it was a blessing in disguise. If not for lockdown, we would never have discovered that it’s possible for people to learn skills like public speaking online!
Can you share a pivotal moment in your career that significantly influenced your path to leadership?
Note from Diana to the editor: it would make sense to put this question after the next one (inspiring person) to make the stories chronological and better connected
In the early stages of my leadership journey, I had a lot of doubts and insecurities — I just wasn’t sure if I was doing things right. So, I decided to send out an anonymous feedback survey to my team. I did this shortly after we’d completed a major project that had gone very well on paper. But still, I was anxious to know how the team really felt about my leadership.
The feedback was overwhelmingly positive, and many team members mentioned that they genuinely enjoyed working with me! They repeatedly described me as “supportive”, “empathetic”, and “caring”.
For me, this was an eye-opener. I’d been worried that I lacked the “hard” leadership skills, like being more direct or authoritative, but in fact my team valued my supportive and empathetic approach. This experience showed me that leadership isn’t a one-size-fits-all, and that my style could achieve great results while fostering a positive work environment.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
Note from Diana to the editor: it would make sense to put this question before the previous one (pivotal moment) to make the stories chronological and better connected
I am incredibly grateful to my dad, though probably not for the reasons one might expect.
My father grew up in a tiny Syrian village — one so remote that it’s still not on Google Maps. With no electricity, he decided to travel by donkey to Moscow, then the capital of the Soviet Union. Against all odds and without any connections, savings, or even the language, he managed to build a successful business. Watching him overcome these obstacles throughout my childhood taught me that it’s possible to achieve anything, no matter your starting point.
But he wasn’t the most supportive father. Growing up, he often emphasised that I should run my own business rather than work for someone else, but when I finally decided to start my first business, his response shocked me. He said to me: “You’re not cut out for business. You don’t have what it takes. Why don’t you find a wealthy husband instead? It’s the best ‘business’ opportunity for a woman!”
When I asked him why I didn’t have what it took, he told me that I lacked the toughness, the charisma, and the skills to handle the challenges of business. “You’re too soft, too gentle — business will eat you alive!”
Hearing this from someone I admired so deeply was crushing. It felt like he’d already decided my limits and dismissed my potential — not to mention that he didn’t believe in his own daughter.
Oddly enough though, this lack of support pushed me even harder to succeed, and I spent the next 10 years determined to prove him wrong. Despite the self-doubt he instilled in me, his disbelief became a motivating force for me to pursue my dreams, even when it would’ve been easier to work for someone else. In a way, I’m grateful for that drive — it has led me to where I am today.
Is there a particular book that made a significant impact on you? Can you share a story or explain why it resonated with you so much?
When I was in sixth grade, we had a substitute teacher who taught us something life-changing.
He drew two intersecting lines, creating four quadrants, and explained Robert Kiyosaki’s Cashflow Quadrant from Rich Dad Poor Dad. He walked us through each quadrant: employee, self-employed, business owner, and investor, emphasising the importance of working towards the “business” or “investment” quadrants to gain financial independence.
While most kids weren’t paying attention, his words had a lasting impact on me. I went home and read Rich Dad Poor Dad, and from that young age, I knew I wanted to be a business owner. Seeing my dad’s entrepreneurial success later only strengthened my drive — but it all started with that one teacher’s brief lesson.
Do you have a favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life or your work?
A quote I live by is, “If you can dream it, you can become it”. I found the truth of this quote in my journey with public speaking — a skill that didn’t come at all naturally to me.
I used to be terrified of speaking in front of others, and often struggled even in one-on-one interactions. I couldn’t look people in the eye, and I avoided engaging with audiences. However, through consistent practise, I was eventually able to transform this fear into a strength.
From being painfully shy, I went on to receive public speaking awards, speak at TEDx, and be invited to deliver paid speeches at events. Now, I firmly believe that anyone can learn and excel at any skill if they truly want to. Natural talent helps, but dedication can make up for it, and I’m living proof of that.
How have you used your success to make the world a better place?
My decision to create an online school for communication skills stemmed from a desire to make a meaningful impact. My first business, a food delivery service, provided a practical service, but it didn’t leave a lasting impact on people’s lives. In contrast, communication skills training transforms lives, helping people unlock opportunities they might otherwise miss. I know this firsthand, having struggled with my own communication skills in the past.
One example that stands out is a student who initially had difficulty expressing himself. He was shy, spoke in short sentences, and struggled to connect with people, which held him back from forming meaningful relationships. But, through our Storytelling training, he learned to tell engaging stories, connect with others, and express himself confidently. His transformation was profound; he went from being overlooked to becoming someone people genuinely wanted to listen to.
Stories like his remind me why I chose this path: to help people not just improve a skill, but to genuinely transform their lives and unlock new personal and professional opportunities.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this report, only about 31.7% of top executive positions across industries are held by women. This reflects great historical progress, but it also shows that more work still has to be done to empower women. In your opinion and experience what is currently holding back women from leadership and management?
I’m not at all surprised by this statistic. Recently, while searching for senior leaders to speak at the Skillsme Leadership Summit, I found that 90% of the CEOs of the companies I looked at were men. That was staggering to me.
At one point, I realised I had predominantly sent out invitations to white men — not intentionally — so I actively sought out female founders to balance the agenda. To my disappointment, many of these companies were ones I’d never heard of, and most were in the beauty or fashion industries. It’s not that there’s anything wrong with these sectors, but it’s disheartening that female leadership is concentrated in just a handful of fields.
So, what is holding women back? I believe there is a mix of factors at play, including historical, cultural, and social expectations, as well as uncooperative behaviours and a lack of awareness among some men. Systems set up both by governments and workplaces also play a role, as do the effects all these factors can have on women’s confidence and self-esteem.
This might be intuitive to you but I think it will be helpful to spell this out. Can you share a few reasons why more women should become leaders and managers?
Simply put, women can be exceptional leaders. I’ve found that they often bring a collaborative approach that fosters success in team dynamics.
It’s also incredibly powerful for girls to see women in leadership positions and think, “My mum is a CEO”, or “My friend’s mum runs a business”, and to see it as just as normal as a dad running a business. This visibility can build confidence and ambition from an early age. Without these role models, where would young girls get the inspiration to dream big?
Can you please share “5 Things We Need To Increase Women’s Engagement in Leadership and Management?” If you can, please share an example or story for each.
Certainly!
- Accessible and Flexible Childcare
Everything starts with the system, and systems begin with government policies. Let me share an example that’s rarely discussed in the West — likely because it challenges common assumptions.
Did you know that in Russia, nurseries are free and open long hours — until 7pm? When I was a child, my mother could leave me at nursery from 8 a.m. to 7 p.m. every weekday at no cost. In the USSR, parents even had the option to leave children overnight if needed! My grandmother, who held a prominent leadership position and travelled a lot for work, would sometimes leave my mother overnight when her work demanded it. This kind of support enabled generations of women to thrive in leadership and management fields.
By contrast, in the UK and the US, expensive and inflexible childcare remains one of the main reasons many women feel forced to choose between advancing their careers and having children. In the UK, even with some government assistance, childcare options are still limited. For example, I initially received only a 20% tax return on childcare costs, which barely made a dent in expenses.
While the situation is improving, we are still far from having flexible, affordable childcare options that meet the demands of today’s working world — especially for busy senior leaders. It’s simply not right; women shouldn’t have to choose between affording childcare and building their careers.
2. Reducing the Burden of Unpaid Labour on Women
One major barrier women face to pursuing high-responsibility leadership roles is the unequal distribution of unpaid labour, which drains time and energy that could otherwise be spent advancing their careers.
Tasks like managing the household, caring for children, and looking after elderly relatives still largely fall to women. Studies (1, 2) have shown that when women start living with a partner, they often end up doing significantly more house work — sometimes several extra hours every week — compared to when they were single.
These additional responsibilities create a “second shift” that leaves less room for professional growth and higher-level leadership roles.
Personal Story:
Although my partner has always tried his best to be supportive, he didn’t fully realise the weight of the burden he and our child added to my responsibilities. About a year after giving birth, I had a severe case of burnout because I couldn’t admit — to myself or to others — that I was struggling to combine being a mum and a business owner.
The situation was finally resolved through therapy for me and couples coaching for both of us. This helped my husband to understand the unpaid hours I was putting in — and how far from equal our task distribution really was.
Solution:
Equal parental leave is one way we can start shifting these norms. When both parents are given equal parental leave, it signals that caregiving is a shared responsibility — not a default expectation placed on women. By setting the stage for a more balanced division of labour, we can empower more women to dedicate time and energy to career advancement, without being disproportionately weighed down by unpaid labour at home.
3. Raising Awareness About Inequality Among Men
Many men have no idea about the subtle and not-so-subtle biases women face daily — not out of a desire to be uncooperative, but simply because they don’t tend to notice them.
I once watched a TEDx talk by Paula Stone Williams, a transgender woman. She shared how she noticed an immediate change in how people treated her once she’d transitioned. For instance, a man once took her seat on a plane and refused to move his stuff from it. When she’d been living as a man, these sorts of microaggressions never happened.
This experience opened her eyes to the challenges women face — ones she’d been oblivious to before. So, it’s crucial that we create awareness among men about these disparities so that they can be allies, rather than bystanders or perpetrators.
4. Raising Awareness About Inequality Among Women and Teaching Them to Tackle It
Another key step is ensuring women are fully aware of the inequalities they face. By not talking openly about biases and systemic barriers, we allow these issues to be normalised.
It’s like the “awakening” in the Barbie movie, where the characters suddenly realise that, just because something has always been the status quo, doesn’t mean that it’s right or unchangeable. This awareness should extend to any form of unfair treatment due to gender, including harassment.
Personal Story:
In the early days of my career, I attended networking events in London to interview entrepreneurs for my university dissertation. I was clear with everyone I met: I was a student gathering data for my study.
Although I remained professional throughout, six out of the eight men I interviewed made unwanted advances, with some choosing intimate settings or touching me inappropriately. Most of these men were older than me, and I had no idea how to make them stop or what to say. I wish I’d been taught that this behaviour was harassment and how to tackle it effectively. At the time, I felt I had to tolerate it just to complete the interviews.
In an odd way, I’m almost grateful this experience happened early in my career because it shattered my “pink glasses” — the illusion that men and women are treated equally. It showed me the true challenges women face to being seen as professionals, even in business environments.
This is why I believe so strongly in raising these topics more often, and ensuring that women learn to identify harassment and other forms of unequal treatment, as well as to set boundaries confidently.
5. Normalising Women-Specific Health Issues
Women’s health issues — like severe period pain or mood changes from hormonal shifts — should be openly acknowledged in workplaces. I know women whose period pain is so intense they need sick days. But instead of understanding, these issues are often trivialised with PMS jokes.
No one chooses these symptoms, and I truly believe that more openness around them would relieve a lot of the unnecessary pressure many women leaders face.
As an example, I know a woman who once faced criticism when her breast leaked during a high-stakes meeting because she was still breastfeeding. But this shouldn’t be a source of shame. Addressing these realities with respect and openness would boost women’s confidence in the workplace.
In your opinion, what systemic changes are needed to facilitate more equitable access for women to leadership roles?
I believe that the issues women face when it comes to securing leadership roles are rooted in fundamental questions of gender equality.
Societal expectations for different genders start diverging from a very early age, often unconsciously. It’s something I noticed with my own son. I remember that, when he was born, I wanted to buy him bright-coloured clothes, like a yellow T-shirt. But I quickly discovered that most yellow shirts were designed for girls, and would often feature unicorns and other “girly” symbols. In contrast, clothes for newborn boys tended to be in muted colours like grey or blue. While this may seem trivial, it illustrates how gender expectations are ingrained from the very beginning, shaping what’s “appropriate” for each gender before they’ve even developed their personalities.
If we’re creating such distinctions from birth, it’s no wonder that as adults, women are underrepresented in leadership. To see more women in leadership, we must examine and address these ingrained biases across society. When we start treating genders more equally in all areas of life, leadership roles for women will naturally become more common.
What strategies have you found most effective in mentoring and supporting other women to pursue leadership positions?
A while ago, I was mentoring a team member who struggled with her confidence and doubted her own ability to lead. So, although she was talented, she resisted leading, and strongly believed that she wasn’t cut out for it.
To help her, I increasingly started to assign her more leadership-oriented tasks — ones that required her to make decisions rather than just follow instructions. My approach was twofold: to give her leadership opportunities slightly outside her comfort zone, and consistently reinforce her strengths to build her self-belief.
At first, she was uncomfortable, and even asked me to stop giving her leadership tasks. But, over time, I saw her confidence grow as she handled each challenge. Eventually, she moved on to a managerial role in another company, where multiple teams reported to her. And, later, she called to thank me for believing in her.
So, to sum up, I’d say that you need to provide your female team members with leadership opportunities, even before they ask. And, when you do, to consistently reinforce their achievements with positive feedback.
How would you advise a woman leader about how to navigate the challenges of being a woman in a leadership role within a male-dominated industry?
One challenge in male-dominated industries is not being taken seriously. Thankfully, my current field — education — is fairly balanced, possibly with a slight skew toward women leaders.
However, this is a topic that I recently discussed with my friend Jina Park, a successful entrepreneur from the UAE who built a chain of supermarkets. Unfortunately, she faced significant challenges when working with suppliers and landlords — in the UAE, these industries are heavily male-dominated. As a result, she felt that she had to adjust her approach when entering into meetings with men.
She told me that she stopped wearing makeup and high heels, and opted for a plain, professional look to avoid any potential misunderstandings. Her demeanour in these meetings was also much more serious, and she smiled less than usual to establish the tone as professional right from the start. Then, if she sensed a lack of respect, Jina would either redirect the conversation back to business, or ask tactical questions that highlighted her knowledge and experience.
This is why I believe that staying focused and assertive is essential in environments where being perceived as “soft” or “feminine” can undermine your credibility. It’s an approach that has worked well for my friend, and it’s something that’s helped me in a few situations too!
How do you balance the demand for authoritative leadership with the stereotypical expectations of female behavior in professional settings?
I don’t think women need to adopt an authoritative style in every situation. It depends on the industry and the specific environment.
In more gender-balanced industries, empathetic and collaborative leadership can be highly effective. However, in certain, more male-dominated settings, acting with authority can help to ensure you’re treated with respect. When I sense that I’m not being taken seriously because of my gender, I tend to adopt a more assertive approach.
Otherwise, I believe that empathy, understanding, and collaboration can be powerful strengths in leadership.
You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.
I would advocate for true gender equality, starting from the home and extending through education, university, and the workplace. From how household responsibilities are divided to who takes care of elderly parents or children, gender equality should be present at every level of life. This kind of systemic change would have a lasting impact on future generations and help to break down deeply embedded gender stereotypes.
How can our readers further follow your work online?
You can visit the Skillsme website to learn more about our trainings, or explore the Skillsme Leadership Summit.
This summit will bring together over 5,000 attendees and 20+ leadership experts, including senior leaders from major companies like Amazon and Uber, as well as world-class trainers. It’s a fantastic opportunity for early-stage leaders to develop their skills and advance in their leadership journeys. We’ll also have a special session led by Jina Park, whom I mentioned earlier, on navigating male-dominated industries. Following the session, there will be open discussions on this topic. I’ll be personally present, and I’d love to hear your perspectives.
Thank you for these fantastic insights. We greatly appreciate the time you spent on this.
About The Interviewer: Vanessa Ogle is a mom, entrepreneur, inventor, writer, and singer/songwriter. Vanessa’s talent in building world-class leadership teams focused on diversity, a culture of service, and innovation through inclusion allowed her to be one of the most acclaimed Latina CEO’s in the last 30 years. She collaborated with the world’s leading technology and content companies such as Netflix, Amazon, HBO, and Broadcom to bring innovative solutions to travelers and hotels around the world. Vanessa is the lead inventor on 120+ U.S. Patents. Accolades include: FAST 100, Entrepreneur 360 Best Companies, Inc. 500 and then another six times on the Inc. 5000. Vanessa was personally honored with Inc. 100 Female Founder’s Award, Ernst and Young’s Entrepreneur of the Year Award, and Enterprising Women of the Year among others. Vanessa now spends her time sharing stories to inspire and give hope through articles, speaking engagements and music. In her spare time she writes and plays music in the Amazon best selling new band HigherHill, teaches surfing clinics, trains dogs, and cheers on her children.
Please connect with Vanessa here on linkedin and subscribe to her newsletter Unplugged as well as follow her on Substack, Instagram, Facebook, and X and of course on her website VanessaOgle.
Diana Robertson Of Skillsme On How We Can Increase Women’s Engagement in Leadership and Management was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.