Search & Replace S03E01: Diana Robertson

Diana Robertson struggled with shyness and social anxiety that affected her career, particularly during interviews and networking. To overcome these obstacles, Robertson sought help online, bought public speaking books, joined public speaking courses, and started speaking publicly. Eventually, she discovered a passion for helping others overcome their communication challenges and launched an online virtual school to develop communication skills. Discover how developing new skills, regardless of age and background, is possible on Search and Replace.

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[00:00:00] Announcer: Support for the following podcast is provided by the user experience specialist at Johns and Taylor. More information follows this episode. 

[00:00:11] Joe Taylor Jr.: What if your biggest fear gets in the way of your chosen career path? I’m Joe Taylor, Jr. This is Search and Replace.

Diana Robertson didn’t think of herself as who’d ever enjoy public speaking. In fact, she says she found it challenging to get through many daily conversations. 

[00:00:37] Diana Robertson: Shyness was an obstacle for me many times in my life and really, just pick and choose which part of my life to look at. If we look at the very young age where I was a schoolgirl and I was absolutely afraid of raising my hand and answering any question just because I was so shy.

Or is it a bit later, in high school, when I started to change schools a lot, that meant new people and I had no idea how to approach them and resulted in some schools without any friends. Or no friends until the point when somebody would come to me and say, ‘hi do you wanna be my friend?’ Or when we look a bit later, maybe, at my university time when I was applying for internships, and I was one of the top students in the class. So I would go through the CV stage or the test stage, I’d get to that final stage, but then every time I would come to that room, everything would go wrong. 

[00:01:34] Joe Taylor Jr.: Even though Diana spent her academic career focusing on developing skills that wouldn’t go wrong, she still sensed a creeping deadline. 

[00:01:43] Diana Robertson: I was always this type of studious person who was good at studying and I put a lot of hard work into it. But then later realizing that all of that I’ve been doing, actually doesn’t matter if I can’t pass the interview stage. Made me realize that, oh my God, I do have a problem and it’s a big one because, well, I simply cannot find a good job. 

I’ve always wanted to become an entrepreneur but, you know, entrepreneur means also being able to make the sale. It also means being able to network with people, people you’ve met for the first time. And all of these things I just could not do. It was absolutely super terrifying, super hard, and I was bad at it on top of that. I need to do something about it. 

And that was, I would say, one of the biggest turning points, and that’s when I started to look for solutions to my problems.

[00:02:35] Joe Taylor Jr.: Formal education programs don’t always include support for public speaking or communication skills. Some classes might require you to work on group projects or present your findings to a large class, but it’s not always obvious where to get help for this kind of social anxiety. That’s why Diana started searching for help online.

[00:02:55] Diana Robertson: So the easiest thing for me was to read some articles about becoming more confident. One of the things that popped up was public speaking. I also bought a book in public speaking and I joined a course in public speaking. The hardest part is actually doing, since this is the only way to learn, you’re like, this means I can’t just sit at home and learn some stuff online or something, or read a book about it. It means that I have to go out there and actually present in front of those 20, 30, 50, 100 people. It’s like bitter medicine. I mean, yeah, it’s terrible when you taste it, but eventually it’s good for you. 

[00:03:32] Joe Taylor Jr.: Diana sought out opportunities to get herself in front of crowds, whether that meant speaking at an informal networking event or even taking an improv comedy course. And after developing her confidence on stage, she discovered her real strength was in her ability to look more closely at her audience. 

[00:03:51] Diana Robertson: I realized that I actually really enjoy seeing the difference in people and seeing how I can help people, not by saying something to them, but actually seeing the difference in maybe who they are, or maybe I resolved the problem, something like that. It’s a deeply satisfying feeling. 

Then I just started to map down, so things I’m good at, things that I enjoyed, like things I could do and all together gave me the answer of why not launch a virtual school for developing communication skills. 

I know that I made the correct decision because once I started working with people, sometimes people connect with me and say, oh, I did this thing. Or sometimes after some workshop they’re like, oh, there is this one thing that you said that changed everything. And I’m looking at this one thing. It wasn’t even an important thing but for them it was life changing. 

[00:04:44] Joe Taylor Jr.: Today, Diana runs a business teaching public speaking and personal confidence skills online. Making it even easier for her clients to skip all the trial and error she endured on her own journey. 

And there’s something important Diana likes to share with everyone who enrolls in one of her courses or coaching programs. 

[00:05:02] Diana Robertson: Skills are called skills for a reason, because they can be developed. You don’t have to be born with them.

And literally, no matter at which stage of life you are; how old you are, what’s your background, what’s your financial situation, all of these things don’t matter because if you want to learn some skills, I guarantee you can. But the point is that you still have to do it yourself, and slowly but surely, you will start observing the difference in yourself.

And most importantly, you start seeing the incredible results in your life, in your personal and in your professional life. I guarantee it. 

[00:05:40] Joe Taylor Jr.: That’s Diana Robertson, founder of the Skillsme soft skills Academy. We’ve got links to Diana’s work in our show notes and over on our website at

Also in our show notes, Harvard University’s Division of Professional Development has a list of eight critical things you can do to improve your communication skills. 

From, Executive Coach Melody Wilding works with professionals she calls highly sensitive high achievers. And she notes that Diana are much more common in the business world than you might think. For business people wrestling with shyness or anxiety, melody says that it’s better to stop pretending to be someone you’re not and to build a set of systems that make communication with colleagues easier, authentic and effective.

And the folks that Thrive Global, they work on tools to help prevent personal burnout. They’ve posted an article about the roadmap in your brain that can show how much your self-esteem affects your communication. The good news, according to the researchers, you can rewrite that roadmap through self-care and other consistent practices over time.

All those stories and more are on our website, 

Search and Replace was produced by Nicole Hubbard with support from Christine Benson, Connie Evans, Amelia Lohmann, April Smith and executive producer, Lori Taylor. 

Our theme music was composed by Alex or Rufire.

I’m Joe Taylor, Jr. 

[00:07:05] Announcer: This has been a Podcast Taxi radio production. 

Support for Search and Replace is provided by Johns and Taylor, user experience specialists serving media and technology companies that want their websites to work.

Learn more about how top performing businesses eliminate barriers between customers and their goals at

Joe Taylor Jr. has produced stories about media, technology, entertainment, and personal finance for over 25 years. His work has been featured on NPR, CNBC, Financial Times Television, and ABC News. After launching one of public radio's first successful digital platforms, Joe helped dozens of client companies launch or migrate their online content libraries. Today, Joe serves as a user experience consultant for a variety of Fortune 500 and Inc. 5000 businesses. Twitter | Facebook | Instagram

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