Give Space to Grow: Interview with Robb Wilson, Founder of OneReach.ai

I recently went one on one with with Robb Wilson. Robb is the founder of OneReach.ai and the author of the new book Age of Invisible Machines.

Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks or challenges have been most instrumental to your growth?

Robb: I helped establish one of the world’s first UX agencies (Effective UI) almost 20 years ago, and I always viewed conversational experiences as some of the worst interactions people were having with technology. Most IVR systems and other attempts at automating voice interactions are laborious and frustrating—often for both customers and the businesses attempting to implement them. This presents an interesting paradox because there’s nothing that can make interactions with machines easier than using our most natural forms of communication: conversation. Conversation is an interface that requires zero training, which gives anyone the ability to leverage powerful problem-solving machines.

Speech and text are methods for sharing information that nearly everyone on the planet can employ without special training, but bridging this gap between humans and technology was a massive undertaking. Over the years, I’ve been a part of more than 2,000,000 hours of testing with over 30,000,000 people participating across 10,000 conversational applications. Through thousands of use cases and tens of thousands of user stories, we learned a lot about what we could be doing better, usually the hard way. Even realizations that seem obvious in hindsight—more syllables aid speech recognition; designs with fewer interactions fare better; storing contextual data from an interaction can improve future interactions—took a lot of time and effort to reach. What’s been most instrumental to our growth is accepting that success with technology this powerful and expansive is a matter of failing fast and often. The most important thing is to get started as soon as possible and commit to a development process that’s more agile than Agile. 

Adam: What do you hope readers take away from your new book? 

Robb: Age of Invisible Machines is the distillation of the decades of experience I’ve gained working in both technology and design. The book provides a high-level view of the AI marketplace along with a blueprint for crafting a strategy that can put conversational AI and hyperautomation to work in meaningful ways. “Hyperautomation” is a term that Gartner coined that refers to intelligently sequencing technology within an ecosystem that connects people, systems, and things. By their estimation, hyperautomation is “an inevitable market state.” What business leaders need to realize right away is that they’re already in a race toward the adoption of hyperautomation, whether they realize it or not. 

Adam: What are the most important trends in technology that leaders should be aware of and understand? What should they understand about them? 

Robb: Conversational AI is going to completely change the way people interact with businesses both as employees and customers. When organizations have an intelligent mesh working behind the scenes to connect all of the people, systems, and things inside their organization—as well as a conversational interface serving as a portal into that ecosystem—they are capable of doing far more with far less. Hyperautomation is an astounding force multiplier, but it’s also a holistic undertaking that requires involvement across an entire company as well as significant restructuring efforts. It’s a massive undertaking, but a necessary one, as hyperautomation will quickly become a base requirement for existing as a business.

Adam: What do you believe are the defining qualities of an effective leader?

Robb: Vision, empathy, and flexibility.

Adam: How can leaders and aspiring leaders take their leadership skills to the next level? 

Robb: I’ve seen leaders level up by being empathetic and flexible in difficult moments without losing sight of their guiding vision … that makes it sound so much easier than it really is.

Adam: What is your best advice on building, leading and managing teams? 

Robb: In my company, people work in small teams and we follow a process for co-creation that allows time for individual work and close collaboration. Our organization is flat, and anyone who needs my input can get time with me. Even though we have team members all over the globe, our interactions feel familial. That’s not necessarily by design, but I think it arose naturally with a culture geared toward transparency and creative co-working. We’re also very deliberate in hiring people who are problem solvers at heart. We can always teach someone the technical aspects of completing certain jobs, but you can’t really teach people how to be creative. 

Adam: What are your three best tips applicable to entrepreneurs, executives and civic leaders? 

Robb: 

  1. Technology is available now that can allow anyone to create intelligent automations without having to write code. This essentially means it will become increasingly easier for organizations to create their own software solutions that use AI to automate tedious tasks in novel ways 

  2. Get involved with this technology as soon as possible. You’re already in a race toward adoption, whether you realize it or not.

  3. As you’re putting new products into the world, ask yourself if what you’re doing is genuinely helping people.

Adam: What is the single best piece of advice you have ever received?

Robb: I don’t have a specific adage, but growing up, my family was part of a tight-knit community of engaged neighbors in Toronto that included renowned philosopher Marshall McLuhan. He more-or-less predicted the Internet 30 years before it emerged, so you can imagine the kinds of ideas I was exposed to growing up. But really, the best thing he, my mother, and the other adults in my life did for me was to give me space to grow. They didn’t bug me about following the rules set forth for children in society. As I made my way in the adult world, I would consistently notice how my greatest asset was usually the fact that I hadn’t been institutionalized. It was natural for me to think differently. You don’t need to do things the way everyone else does them. That was clear to me early on.


Adam Mendler is the CEO of The Veloz Group, where he co-founded and oversees ventures across a wide variety of industries. Adam is also the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal winning athletes, political and military leaders - for intimate half-hour conversations each week. Adam has written extensively on leadership, management, entrepreneurship, marketing and sales, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities and non-profit organizations.

Follow Adam on Instagram and Twitter at @adammendler and listen and subscribe to Thirty Minute Mentors on your favorite podcasting app.

Adam Mendler