High Monkey
Discussing Stupid: A byte-sized podcast on stupid UX
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, o...
Author
High Monkey
Category
Podcast website
Latest episode
Jun 16, 2026
Where to listen?
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Episodes
S2E12: Finding the metadata "Goldilocks zone" 01.04.2025 18:05
In Episode 12, host Virgil Carroll is joined by co-host Cole from High Monkey to dig into a deceptively tricky topic: metadata—what it is, how it works, and why getting it right is more about balance than perfection. Metadata plays a huge role in findability, search accuracy, and content structure. But when it comes to tagging your content, more isn’t always better—and less definitely isn’t enough...
S2E11: The challenges of translating design into a responsive website build 18.03.2025 19:05
Discussing Stupid has a new look! This episode marks the beginning of our refreshed brand—featuring a brand new website, sleek color scheme, updated album cover, and a restructured intro sequence. While our look has evolved, our mission remains the same: breaking down the biggest digital mistakes so you don’t have to make them. In Episode 11, host Virgil Carroll is joined by co-host Cole from High...
S2E10: The real work starts AFTER your project launches 04.03.2025 19:32
In Episode 10 of Discussing Stupid, host Virgil Carroll is joined by co-host Cole from High Monkey to reflect on reaching episode 10 and the ongoing journey of digital marketing beyond just launching a project. As they celebrate this milestone, they dive into why the launch is only the beginning of a much longer journey in the digital world. Virgil and Cole discuss the continuous effort required t...
S2E9: The chaos of modern workplace collaboration 18.02.2025 16:40
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 abund...
S2E8: Bad mobile button design is driving us crazy 04.02.2025 18:02
In Episode 8 of Discussing Stupid , host Virgil Carroll is joined by co-hosts Chad and Cole from High Monkey to tackle a common yet overlooked frustration: poor mobile button design. The trio dissects why mobile usability remains such a challenge and explores how bad design impacts user experience on mobile devices. Virgil, Chad, and Cole highlight the pitfalls of prioritizing aesthetics over func...
S2E7: AI alone won't fix your crappy content 21.01.2025 14:09
In Episode 7 of Discussing Stupid , host Virgil Carroll and co-host Cole Schlotthauer from High Monkey tackle the buzz surrounding artificial intelligence (AI) and its implications for technology, marketing, and content management. This episode explores the reality behind AI’s hype, focusing on the importance of high-quality content and structure to make AI truly effective. Virgil and Cole delve i...
S2E6: Are websites evolving or devolving? 07.01.2025 14:59
In Episode 6 of Discussing Stupid, host Virgil Carroll and co-host Cole from High Monkey reflect on the evolution of web design and discuss how websites have grown increasingly complex over the years. This episode delves into the challenges of balancing form and function in web design, examining how trends have influenced modern websites—often at the expense of user experience. Virgil and Cole exp...
S2E5: Font mistakes that are costing you big time 17.12.2024 15:47
In Episode 5 of Discussing Stupid , host Virgil Carroll and co-hosts Chad and Cole from High Monkey explore the often-overlooked mistakes organizations make with typography and the significant impact it can have on user experience and performance. From excessive font usage to unreadable design choices, this episode dives into the dos and don’ts of effective typography. The team discusses: Why usin...
S2E4: Why search systems fail without semantics 03.12.2024 13:35
In Episode 4 of Discussing Stupid, host Virgil Carroll and co-host Cole from High Monkey dive into the complex world of search systems and the importance of semantics in delivering relevant results. This episode explores the frustrations users often face when search systems fail to recognize variations in spelling, synonyms, and context, which can drastically impact user experience. Virgil and Col...
S2E3: If you want people to read your content, make your content readable!! 12.11.2024 17:22
In Episode 3 of Discussing Stupid Season 2, host Virgil Carroll, along with Cole from High Monkey, dives into the topic of content readability. They focus on how overly complex or technical language can turn users away and make it harder for people to understand. The team discusses common readability mistakes like using too much jargon, confusing sentence structure, and not keeping the audience in...
S2E2: Big images, slow loading 29.10.2024 16:46
In Episode 2 of Discussing Stupid Season 2, host Virgil Carroll, along with Chad and Cole from High Monkey, dives into the topic of page performance and SEO, specifically focusing on how oversized images can slow down your website. They discuss common mistakes people make with large images—like shrinking images in HTML without optimizing file size—and how these errors can negatively impact both th...
S2E1: Your poorly written alt text doesn't go unnoticed... 15.10.2024 16:05
Welcome to the first episode of Discussing Stupid Season 2, where your host Virgil Carroll, along with Chad and Cole from High Monkey, dive into the importance of inclusive design. In this episode, they focus on the often overlooked but crucial aspect of alt text for images. Virgil, Chad, and Cole discuss the significance of alt text in creating an inclusive digital experience. They emphasize that...
Season 2: The Teaser 01.10.2024 4:56
In this highly anticipated return of the Discussing Stupid podcast, host Virgil Carroll welcomes new co-host Cole Schlotthauer to kick off Season 2. After a five-year hiatus, they're back with a fresh approach, focusing on shorter, more targeted episodes that delve into specific UX and digital practices. Virgil and Cole discuss the shift from long-form interviews to concise, 10-15 minute episodes...
The Semantics of Search | Brett Matson, Funnelback 15.05.2019 46:20
In this episode of the Discussing Stupid podcast your host Virgil Carroll has a conversation with Brett Matson, the Managing Director of Funnelback Search Technology , about search, semantic search, knowledge graphs, artificial intelligence in search, and the related leverages and pitfalls. Brett shares that there are several big things coming in the area of search, after reaching a plateau...
Consistent UX across multiple channels | Kanwal Khipple, 2toLEAD 13.03.2019 44:48
In this episode of the Discussing Stupid podcast, your host Virgil Carroll has a conversation with Kanwal Khipple about successful and consistent user experience (UX) across multiple channels. The question is how to design consistent user experience for people across different interfaces developed by different companies to provide different experiences. Kanwal is the CEO at 2toLEAD, and great UX i...
What's Old is New Again | Chad Heinle & Joel Baglien, High Monkey 30.01.2019 44:41
In this episode of the Discussing Stupid podcast, the first in 2019, host Virgil Carroll and Principal Solutions Architect at High Monkey, has a conversation with Chad Heinle and Joel Baglien about how technology has changed due to people’s needs changing and how certain technology has been recycled to reflect a market that’s now ready to utilize it. Chad Heinle and Joel Baglien are bo...
Reducing friction in your digital content creation | Martin Michalik, Kentico 24.10.2018 43:46
In this episode of the Discussing Stupid podcast, host Virgil Carroll sits down with Martin MacCulloch from Kentico Cloud. Martin is a product manager at Kentico Cloud. Kentico Cloud is a cloud-based environment for content management and delivery. Martin joins Virgil to discuss content friction, common workflow problems, and how Kentico Cloud is harnessing technology to improve conten...
Making sense of diversity in digital messaging | Heather Newman, Creative Maven 19.09.2018 51:17
The digital world of today challenges marketers to carefully craft their messaging or risk causing the type of public relations nightmare most don’t want to think about. Now, digital marketers have to not only appreciate the power of the words and imagery they use (or choose not to), but also recognize the need to elevate their messaging to tell a much broader, more diverse story around our brands...
Creating inclusive digital experiences – getting your content contributors onboard | Doug Burgett, University of Illinois 23.05.2018 38:26
In today’s digital world, creating an inclusive visitor experience is often discussed but never really implemented. One of the biggest challenges facing successful implementation is taming the behaviors of a large base of content contributors. In this episode, Virgil is joined by Doug Burgett of the University of Illinois, to discuss his first-hand experience with this topic. Doug is the Creative...
Being a HERO with your customer’s data (and understanding what you have) | Liam Cleary, SharePlicity & Rencore 09.05.2018 36:04
Since Virgil knew you couldn’t get enough about good data practice regulations, he decided to do another episode on GDPR . . . yay! Where Episode 2 dealt with the collection of private data, this Episode focuses on how you handle your customer’s private data after you collect it. To assist him in telling this exciting story, Virgil recruited his long-time friend Liam Cleary. Liam is a well-respect...
Preparing your website for GDPR (or just because privacy matters) | David Komarek, Kentico 25.04.2018 30:24
Join Virgil Carroll as he hashes over what has been one of the most over-talked about changes in global digital marketing in a very long time - the implementation of GDPR. The European Union’s General Data Protection Regulation rewrites the book on digital personal privacy and creates a new mandate for how organizations need to respect and protect individual’s data. While this topic has been talke...
The hype and sensibility of Artificial Intelligence in Search | Ben Tilley, Funnelback 11.04.2018 34:34
On our very first podcast (episode 1 YEAH!!!), Virgil is joined by Ben Tilley from Funnelback, an Australian-based search company, to break through all the hype around the use of artificial intelligence in search and talk about real world implementations and pitfalls. Listening to this discussion, you will discover that implementing AI in search is not all that easy (shocker!!) and still requires...
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