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Interview with Phil Simon

by | Jun 10, 2021 | Interviews,

Phil Simon

Phil Simon

Owner & Founder of

Key Topics:Collaboration, Platforms, Big Data, Business Communication, Slack, Zoom

Phil Simon is a frequent keynote speaker, recognised collaboration and technology authority, and college professor-for-hire. He is the award-winning author of eleven books, most recently Reimagining Collaboration: Slack, Microsoft Teams, Zoom, and the Post-COVID World of Work. He helps organizations communicate, collaborate, and use technology better. Harvard Business Review, the MIT Sloan Management Review, Wired, NBC, CNBC, BusinessWeek, and The New York Times have featured his contributions. He also hosts the podcast Conversations About Collaboration.

How did you get to become an expert in your key topics?

Get in your time machine and get your popcorn ready.

I attended Carnegie Mellon University and studied Policy and Management with a minor in Political Science. The experience had a profound effect on me.

In December of 1993, I graduated. Unfortunately, I was clueless a bit unsure about what I wanted to do for a career. I settled in at Sony Electronics as a customer relations rep while I figured things out. I ultimately attended graduate school at Cornell University in August of 1995. For three semesters, I worked as a teaching assistant in labor economics and collective bargaining. I didn’t know it at the time, but this experience would serve me well down the road. #foreshadowing

During my summer internship in 1996, I began working with PeopleSoft, an enterprise resource planning system. I created reports and answered questions with data. It didn’t take long for me to learn new reporting applications.

After grad school, I started my brief career in corporate human resources. That wasn’t the best fit for me—a lack of match quality, as economists say. I quickly gravitated to work rooted in technology, data, and systems.

In 1998, I took my first quasi-IT job, traveling extensively to Latin America on a global PeopleSoft project for Merck. During that time, I taught myself advanced Microsoft Excel and Access, Crystal Reports, Structured Query Language, and a host of other applications. I became adept at manipulating enterprise data and identifying issues with it—something that my Merck colleagues either loved or hated. To paraphrase Walter White: I liked it. I was good at it.

The next step shouldn’t surprise anyone: I started working as a systems consultant in 2000. In 2008, I started writing my first book Why New Systems Fail. I got the bug and have scribed ten more books since then.

Aside from writing and speaking, today I advise all types of organizations on communication, collaboration, management, data, and technology. Along these lines, I like to think that I’ve been reasonably successful.

What sub-topics are you most passionate about?

These days, collaboration and business communication. To put it bluntly, most of us are doing it wrong.

Who influences you within these topics?

Oh, gosh. I cannot begin to cite all of my professional influences. I love what companies such as Basecamp, Automattic, and other distributed ones have done. The folks at Slack have redefined work—for the better. Josh Bernoff challenges his audience and clients to write and speak clearly. We can all take a page from his book. I could go on but you get my drift.

What challenges are brands facing in this space?

Again, where to begin? Hidebound organizations and managers are generally struggling to adopt to the new normal. If you look at most polls, employees don’t want to return to a Monday-Friday, 9-5 workweek. Brands must reimagine collaboration—hence the title of my new book. #shamelessplug

What do you think the future holds in this space?

As much as many people would like, you can’t unring the bell of Covid-19. The pandemic accelerated trends that were already underway like e-commerce, remote work, and online education. Follow, lead, or get out of the way.

What brands are leading the way in this space?

Again, Slack has done an amazing job not only building its core tech, but embracing platform thinking. Microsoft Teams is clearly thinking holistically about collaboration as well. I could name dozens of other companies that understand the concurrent need to embrace developer communications. Zoom’s up there as well.

If a brand wanted to work with you, which activities would you be most interested in collaborating on?

Podcasts, webinars, whitepapers, speaking opportunities, product innovation, video interviews, training, and advising come to mind.

What are your passions outside of work?

Reading, tennis, movies, golf, poker, good TV, running, weightlifting, Scrabble, and other word games.

What would be the best way for a brand to contact you?

Through my website.

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