In Episode 9 of Discussing Stupid, host Virgil Carroll is joined by co-host Cole from High Monkey to break down a frustrating reality of modern work: the overwhelming number of collaboration tools that don’t actually improve teamwork. With so many platforms—Slack, Teams, ClickUp, Figma, email, and more—why does collaboration feel more chaotic than ever?

Virgil and Cole explore how the abundance of tools often leads to scattered conversations, lost information, and inefficiency, rather than better collaboration. They discuss real-world examples of how context gets lost in endless message threads, how teams juggle disconnected platforms, and why no single tool seems to solve the problem.

As the conversation unfolds, they dig into why the issue isn’t just the tools, but also the processes behind them. They explore what effective workplace collaboration really looks like, sharing insights on how teams can reduce tool overload, set clear communication guidelines, and establish a single source of truth to prevent chaos.

To close, they offer practical takeaways on improving collaboration—whether through better workflows, tool integration, or just picking a platform and sticking to it. Listeners will walk away with a clearer understanding of why collaboration is broken and what steps can actually make it better.

Join us every two weeks for new episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com.

(0:00) - Intro
(1:24) - Modern collaboration: Many tools, little clarity
(4:00) - Why the "perfect collaboration tool" is a false promise
(7:30) - The path to streamlining collaboration
(12:00) - It's about strategy, not just software
(15:00) - Outro


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The chaos of modern workplace collaboration

Discussing Stupid returns to the airwaves to transform digital facepalms into teachable moments—all in the time it takes to enjoy your coffee break! Sponsored by High Monkey, this podcast dives into ‘stupid’ practices across websites and Microsoft collaboration tools, among other digital realms. 

Our "byte-sized" bi-weekly episodes are packed with expert insights and a healthy dose of humor. Discussions focus on five key areas: Business Process & Collaboration, UX/IA, Inclusive Design, Content & Search, and Performance & SEO. 

Join us and let’s start making the digital world a bit less stupid, one episode at a time.