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Q&A with Diana Robertson

Updated: Jul 20, 2023

Exclusive Trusted Magazine Q&A with Diana Robertson, CEO @Skillsme



How could you describe your career path in few words?

I chose the path of entrepreneurship and so far it’s been the most emotionally rewarding career path I’ve ever been on. It hasn’t always been like that though. At the beginning, it was absolutely terrifying. I had no client base, no brand recognition and no financial support. My journey was full of ups and downs: my team and I would get excited about launching a product or trying out a new marketing strategy and put an enormous amount of time and effort into it. But when launch day came in 9/10 cases we’d get no results, or results that were so insignificant they didn’t compensate for the amount of work and money we put in. That was devastating. I felt like I was being sent through a maze with my eyes closed. The majority of the time, I didn't know what to do and kept taking the wrong turns. I can't recall the number of times I thought of giving up and getting a “normal” job because in that moment, all the "normal" job challenges seemed trivial. I thought, "it would be so EASY to have a job that pays my bills instead of making me risk losing all my savings". But I kept going. After a year, certain patterns started to emerge. My team and I started to notice things that brought results. These results were still small, but they were repeated again and again. This gave me hope and courage to continue. One step at a time we built brand recognition, a customer base and a stable revenue stream. Two years in I couldn’t think of a better way I could have spent my last two years. I’m doing what I love and what I believe in, I don’t have a boss telling me what to do, I’m not forced to blindly follow other people’s vision and I got the flexibility I needed for maintaining a healthy work-life balance (all the things I couldn't do in past employment and the reasons why I escaped in the first place). In other words, although I took a very risky and challenging path, at the end of the day it turned out to be the most emotionally rewarding path I could ever take because it gave me all the things that I care about the most. What was your most challenging experience and it has changed your mindset?

I never saw myself as a leader type of person. Leadership skills simply didn’t seem to be a part of my personality. I wasn’t good at leading projects or people and hated even the slightest idea of doing it. One day, I was put in charge of a relatively small non-profit project that was falling apart. I didn’t want that role but if I didn’t take it the project would have collapsed after years of effort put into it by my colleagues and myself. I had no choice but to accept the role. This turned out to be one of the most challenging experiences I have ever encountered. I was full of self-doubt and had no idea how to motivate and manage my team. For several months nothing went smoothly and the project kept falling apart. However, I got so obsessed with the project that very soon it became my life mission to make it a success. I had to do whatever it took to save it. Once I started thinking this way I realised that I no longer had time for self-doubt and second guessing myself. There was a goal, and I had to achieve it. As simple as that. After one year the project became so successful that nobody could believe it. It performed better than in any of the last 5 years. I was so happy and relieved. But the true success was that I came out of this experience with confidence that I could be a pretty successful leader after all. And it’s okay that I wasn’t born with those skills, because now I know that if I truly want to reach a certain goal I can develop any necessary skills along the way.

When you get surprised by unusual or uncertain context, what do you think?

I try to be open to new ideas and possibilities even though I might feel natural resentment at first. I keep an open mind, get people’s opinions and do my own research. After I get a deeper understanding of the matter I form my opinion about it. For example, recently I came across a company specialising in AI that created a product that could become a potential threat to the service that my company offers (communication skills training). From reading about the service I got the impression that AI technology could substitute trainers and coaches, so my first reaction was a serious concern about a drop in demand for our services in the future. However, I kept an open mind about it and talked to the founders of the company to see how they viewed it. Talking to them made me realise that their service could become an excellent complementary product to what we offer rather than our competitor. This totally changed my outlook on AI’s role in communication training and made me seriously consider bringing it to our company.

Based on your experience, what’s the key success factor for a female leader / manager?


I think the key to happiness and success at the workplace for female leaders is about working in an environment where they could succeed by being their true selves. Places where they don’t need to pretend or be expected to adhere too much to other people’s values and norms. Although I truly believe that females can succeed in any male-dominated environment, having worked in such an environment myself I no longer feel that it’s worth the aggro, not when we live in a world with unlimited alternative options. Also, if a female leader chooses to have children I think there’s nothing worse than being in an environment that isn’t supportive or accommodating of such life choices. To summarise, I believe that whatever a female leader’s work and life goals are, to be truly happy and successful, it’s crucial to be in an environment that allows for thriving by being one’s true self.

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