A Daughter Defies Expectations

In this Toastmasters Podcast episode, Diana Robertson shares how she went from being a shy introvert to participating in Toastmasters speech contests, taking on leadership roles, and owning her own business.

Growing up, Diana Robertson knew she wanted to run her own business. Why? Because her father did.

But that didn’t happen when she became an adult—at least not at first. Her father didn’t think she had the right stuff, and Robertson believed him. Toastmasters helped her overcome her self-doubts. Her experience as an officer and leader in the organization, says Robertson, helped propel her to success in business.

She is now an educational entrepreneur with her own business and a better perspective on what real-world leadership is. As she learned in Toastmasters, soft skills are a strength.

“I realized there are some other qualities in leaders that are way more important than, I don’t know, being tough,” says Robertson.

Early Influence

Her father, a hard-nosed, extroverted man, ran an importing business between China and Russia. “Ever since I was a kid, he always told me that you should never work for other people—never in your life,” says Robertson, who grew up in Russia and now lives in London. “He said, ‘You should always own your own business.’”

So imagine the daughter’s excitement when, as a young woman, she told her dad—her role model—that she planned to start her own business.

His response?

“‘Darling, just forget it. Look, this is just not for everyone,’” Robertson recalls him saying. “I asked him, ‘Why, what’s the problem?’ And he said, ‘Well, I mean, come on—it’s your personality type. You’re not the type
of person who should be having a business.’”

She was crushed by his words. Sensitive and idealistic, she didn’t have the toughness to thrive—according to her father. One thing Robertson did know is she wanted to improve her self-confidence, and her communication skills.

Remembering one venture where she pitched a food-delivery service, she says that just calling people to set up meetings was “terrifying.” “I had a schedule where I needed to make 20 calls, and I think I spent most of the day procrastinating, basically thinking, This is too hard. What am I going to do? What am I going to say? And in the end, maybe I would make two calls.”

In 2016, she joined the WorldSurfers Toastmasters in Moscow, Russia. She felt her confidence grow as a communicator. But she says what really surprised her were the leadership opportunities Toastmasters provided. In February 2018, she became WorldSurfers’ Vice President Membership and about six months later, President of the club, whose membership numbers were rapidly dwindling. These steps were a pivotal turning point, says Robertson. Serving as an officer, she no longer felt daunted by the idea of reaching out to people.

“I actually started to enjoy it. I learned how to do it … I really enjoyed meeting new members. I actually even really enjoyed persuading members to join the club.”

Then her next big leadership step: becoming director of the District 91 (South United Kingdom) Conference in 2020. That year, she had moved with her now-husband to England and joined her current club: Riverside Communicators in London. Directing the District conference in the months after COVID-19 emerged was a unique challenge. Conference organizers were forced to cancel plans for an in-person event at a fashionable London hotel and presented a virtual conference instead.

Helping steer the conference to success amid such obstacles was huge for Robertson.

“All of that played a major role in developing my confidence in my leadership abilities and gave me the courage to start my current venture,” she says.

Career Skills

Defying her dad’s expectations, Robertson has become a successful business owner. In 2021, she started the online Skillsme Academy, which helps people hone communication, storytelling, and other soft skills. Robertson describes it as training that supplements what Toastmasters teaches. In fact, her coaches are all Toastmasters. And key to her success is her experience in Toastmasters, she says, where she has served as an officer, organized big events, and gained positive feedback about her strengths.

“For example, things like showing empathy are some­thing people told me many times that they actually really valued in me.”

Robertson gave a speech at a TEDxYouth event in London in late 2022. In “How to Learn Communication Skills,” she talked about her Toastmasters journey, how important it is to develop communication skills early, and how they contribute to career success. Afterward, she says, one of the parents told her, “Every teenager must hear your speech at least once in their life.”

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