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

In Episode 10 of Discussing Stupid, host Virgil Carroll is joined by co-host Cole from High Monkey to reflect on reaching their tenth episode 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 to maintain and grow digital projects like blogs, podcasts, or websites. They share personal experiences and lessons learned about adapting strategies based on analytics and listener feedback. The conversation highlights how even successful launches need follow-up actions to keep the momentum going and ensure long-term engagement.

As the episode progresses, they explore the importance of constantly evolving digital marketing tactics to meet changing audience needs. Insights are shared on how they've had to tweak their podcast's format and content to prevent listener drop-off, especially during the crucial first few seconds of each episode.

To wrap up, practical tips are offered on how to effectively use analytics to drive content improvements and audience retention strategies. Listeners will gain a better understanding of the necessity for resilience in digital marketing and how to make incremental changes that significantly impact their projects' success.

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
(0:47) - Let's hear it for Episode 10!!!
(1:56) - The work starts POST launch
(3:30) - Change is in the air for Discussing Stupid
(5:18) - Our takeaways after 10 episodes
(7:10) - Establish value RIGHT AWAY
(8:45) - Analytics. Analytics. Analytics.
(10:55) - A message for those who made it this far
(11:36) - Digital marketing is not just social media
(13:45) - Time to eat our own dog food
(14:40) - Cole is moving into a penthouse
(15:20) - Be intentional with your analytics & engagement
(17:00) - Discussing Stupid is now a live case study
(18:30) - Outro


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10 episodes into podcasting, here are our thoughts

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 Monkey, along with developer Chad, to tackle a common but frustrating issue—why web designs that look perfect in Figma often fall apart when built for real-world use.

They explore the biggest challenges of translating static designs into fully responsive websites, including:

✅ The problem with designing for just one screen size
✅ Why text, images, and layouts often break in development
✅ What developers wish designers knew about responsive design
✅ Lessons learned from their own website redesign mistakes

Chad shares a developer’s perspective on why rigid, pixel-perfect designs don’t always work and how to approach layouts with flexibility in mind. Through real-world experiences—including High Monkey’s own site rebuild—the team discusses the need for good communication between design and development and how to avoid the most common headaches.

To close things out, they share practical tips on designing for multiple screen sizes, working more effectively with developers, and ensuring that your website doesn’t just look great—it actually functions for all the devices browsing your website.

New intro, new look, new website, same crew ready to help you avoid dumb digital mistakes! Join us every two weeks for fresh 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
(2:06) Design is checkers… development is chess
(4:53) Common responsive design fails
(7:18) Unfortunately we are speaking from experience.
(11:09) How many breakpoints do you design for???
(15:40) Designers & developers need to talk
(18:07) - Outro


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The challenges of translating design into a responsive website build

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. That’s where the concept of the “metadata Goldilocks zone” comes in.
They unpack the most common metadata mistakes and what to do instead, including:

✅ Why under-tagging leaves your site relying on search engine guesswork
✅ How over-tagging renders metadata meaningless
✅ What makes a tag actually useful (and when it’s just noise)
✅ How to approach metadata as an evolving strategy—not a one-time fix

Virgil shares hard-won lessons from consulting across industries, explaining why metadata success depends on both the structure and the context of your content. From internal file systems to public websites, they explore how to build better tagging frameworks without falling into analysis paralysis.

To wrap things up, they offer a practical rule of thumb for anyone managing metadata: optimize for the 80% of user needs first—and let real usage data guide the rest.

For more conversations about digital strategy, search, UX, and all the ways we get it wrong (and how to get it right), visit www.discussingstupid.com and subscribe on your favorite podcast platform.

(0:00) - Intro
(2:27) - What even is metadata?
(4:10) - Metadata is not one-size-fits-all 
(7:20) - The dangers of under tagging
(10:00) - The dangers of over tagging
(12:43) - Finding the “Goldilocks” zone with metadata
(15:30) - Virgil’s verdict: Follow the 80/20 rule


Finding the metadata "Goldilocks zone"

In Episode 13.1, host Virgil Carroll is joined by co-host Cole and developer Chad to talk about something deceptively complicated: color. Specifically, the intersection of color palettes, visual design, and accessibility—and why getting it wrong can tank your user experience.

While color choices often get made in design tools or branding meetings, they don’t always translate well to real-world implementation. The crew breaks down why the prettiest colors can create the ugliest accessibility problems once they hit the web.
They dig into key challenges and lessons, including:

✅ Why accessible design isn’t just about having the right colors—it's about using them correctly
✅ How contrast ratios break down across devices and screen sizes
✅ Why bright and “fun” color palettes often fail accessibility testing
✅ How to bring visual flair to a site without sacrificing inclusivity
✅ The difference between decorative vs. purposeful color use—and why it matters

From failed color combinations to misused font sizing, Virgil, Cole, and Chad share their own battle scars from High Monkey’s recent site redesign—and explain how inclusive design forces teams to think functionally, not just aesthetically.

If you’ve ever struggled to make your brand colors work on the web—or if you're tired of your site failing contrast tests but you still want some color pop—this episode’s for you.

For more conversations about digital strategy, UX, accessibility, and all the ways we get it wrong (and how to get it right), visit www.discussingstupid.com and subscribe on your favorite podcast platform.


(0:00) - Intro
(2:43) - Accessibility and your brand's color palette
(6:03) - Factoring in font sizes
(7:54) - I still want color pop on my website!!
(11:36) - The approach we took with our new site's color scheme
(15:13) - Outro

Keys to balancing aesthetics and accessibility in web design

In Episode 14, host Virgil Carroll and co-host Cole dig into a core truth behind most UX mistakes: people don’t pay attention. From accidental group chat leaks to confusing web forms, today’s digital missteps often stem from one thing—poorly designed experiences that expect users to be careful, focused, or even logical.
But here’s the hard truth: they’re not.

That’s why UX exists—to design for inattention, not perfection. In this episode, Virgil and Cole explore how small misjudgments in interface design can lead to big problems, and why it’s time to stop blaming the user and start designing smarter.
They dig into key lessons and takeaways, including:

✅ Why assuming users will “just pay attention” is a guaranteed way to fail
✅ The danger of designing tools for internal teams instead of real users
✅ How AI and other tools can mislead teams if used without critical thinking
✅ Why user feedback beats assumptions—every single time
✅ What it really means to design for the lowest common denominator

From confusing buttons and abandoned carts to real-world usability failures, Virgil and Cole share insights from decades of experience (and a few personal fumbles) that highlight how easy it is to get digital experiences wrong when we ignore how people actually behave.

If you’ve ever wondered why people keep screwing up your carefully planned interface—or if you’re trying to build something that works for real humans, not just ideal ones—this episode’s for you.

For more conversations about digital strategy, UX, accessibility, and all the ways we get it wrong (and how to get it right), visit www.discussingstupid.com and subscribe on your favorite podcast platform.

(0:00) - Intro
(2:10) - People don't pay attention
(4:41) - Are people bad at browsing or is tech too complex?
(6:49) - Will AI shape the future of UX?
(10:50) - The gap between internal assumptions and real user needs
(14:27) - Build for the lowest common denominator
(17:40) - Outro


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Want better UX? Expect less from your audience.

In this episode of Discussing Stupid, Virgil and Cole are joined by a new guest—High Monkey’s Project Manager and QA specialist, Seth Moline. Together, they dig into the often-overlooked world of quality assurance (QA) and why it can make or break a digital project.

From accessibility issues to ripple effects caused by last-minute code changes, Seth walks us through what great QA really looks like—and why it’s not just a checklist you run through before launch. The team discusses how QA needs to be methodical, repeatable, and fully integrated into your build process—not an afterthought.

They also explore:
	• Why QA isn’t just testing—it’s marketing
	• How staging environments save you from public embarrassment
	• The value of fresh eyes and non-developer perspectives
	• Common QA mistakes and how to avoid them
	• Why accessibility should never be separated from quality

Whether you’re a developer, content manager, strategist, or digital lead, this episode will change the way you think about testing and quality.

For more conversations about digital strategy, UX, accessibility, and all the ways we get it wrong (and how to get it right), visit www.discussingstupid.com and subscribe on your favorite podcast platform.


(0:00) - Intro
(3:04) - Seth's QA role at high monkey
(4:45) - Quality testing is best done by a fresh set of eyes
(6:47) - QA is about systems, not spot checks
(11:06) - Why you need a staging environment
(14:18) - How to stay methodical with your testing
(16:36) - Baking accessibility into your QA process
(18:06) - A quality site = top tier marketing
(19:52) - Outro


What separates good projects from great ones? Proper testing.

In this episode of Discussing Stupid, Virgil sits down with High Monkey’s Senior Developer, Chad Heinle, to break down one of the most debated choices in modern digital strategy: headless vs traditional CMS.

While flashy features and buzzwords like “omnichannel” dominate vendor pitches, the real decision comes down to your organization’s resources, structure, and long-term goals. Chad and Virgil dive into the practical realities of each approach, helping you cut through the hype and avoid the biggest mistakes teams make when choosing a CMS.

They also explore:
	• Why your internal team structure matters more than the CMS features
	• The rise (and reality) of content hubs and static site generators
	• What “freedom” really means in a headless setup
	• How traditional and headless CMSs are merging in unexpected ways
	• Why reuse and omnichannel content sound good—but rarely happen

Whether you’re in IT, marketing, or somewhere in between, this episode will help you make smarter, more grounded tech decisions.

For more conversations about digital strategy, UX, accessibility, and all the ways we get it wrong (and how to get it right), visit www.discussingstupid.com and subscribe on your favorite podcast platform.

(0:00) - Intro
(2:10) - It's not about the CMS, it's about your team
(4:44) - Headless gives you freedom - if you're ready for it
(6:36) - Traditional & headless are starting to look alike
(9:56) - Don't choose a CMS based on buzzwords
(12:00) - There's no perfect CMS - just the right one for you
(15:00) - Outro


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Listen on Apple Podcasts, Spotify, or Soundcloud:
https://podcasts.apple.com/us/podcast/discussing-stupid-a-byte-sized-podcast-on-stupid-ux/id1428145024
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Headless vs traditional CMS: Which one fits your organization?

In this episode of Discussing Stupid, Virgil and Cole tackle a quiet killer of user experience: layout inconsistency.

From university websites that feel like ten different brands stitched together to internal systems that change button locations with every page, inconsistent layouts confuse users, break trust, and derail digital goals. This episode dives into why it happens, what it costs, and how to start fixing it.

They also explore:
	• Why inconsistent layouts are often a sign of deeper organizational problems
	• How users feel bad design before they can explain it
	• The difference between visual theming and layout consistency
	• What a consistent structure looks like across homepage, sections, and detail pages
	• Why a style guide is your most underrated asset

Whether you’re building a public-facing site or an internal portal, this episode will help you recognize the hidden ways layout chaos is holding you back—and how to clean it up.

For more conversations about digital strategy, UX, accessibility, and all the ways we get it wrong (and how to get it right), visit www.discussingstupid.com and subscribe on your favorite podcast platform.

(0:00) - Intro
(2:22) - Where layour inconsistency happens the most
(4:57) - The difference between theming and consistency
(7:24) - Structuring consistency in layers 
(10:57) - Why inconsistency hurts your organization
(13:12) - Layout chaos as a symptom of deeper issues
(15:22) - How to start fixing this issue
(16:51) - Outro


Subscribe for Email Updates on Our Website:
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Why inconsistent layouts wreck your UX

In the Season 2 finale of Discussing Stupid, Virgil and Cole are joined by Ali Gillberg, a senior developer at High Monkey, to talk about one of the most broken (and misunderstood) parts of UX: form accessibility.

Using a real-world PowerApps project for the Minnesota Office of Accessibility, the team breaks down the invisible complexity of building forms that actually work for all users—including those using screen readers or assistive tech. Spoiler: most “accessible” forms aren’t.

In this episode, they dig into:
	• The most common accessibility fails in forms (labeling, tab order, cryptic errors)
	• Why Microsoft tools like PowerApps and SharePoint often work against accessibility
	• How poor form validation breaks user experience and trust
	• What it really takes to make dynamic forms work properly
	• The tedious but necessary work behind making forms usable for everyone

Whether you’re designing a public-facing form or managing internal workflows, this episode will change how you think about accessibility—and show why most tools still fall short.

This wraps up Season 2 of Discussing Stupid. We’ll be back in September with new episodes, fresh rants, and more stupid digital decisions to unpack. Thanks for listening!

For more conversations about digital strategy, UX, accessibility, and all the ways we get it wrong (and how to get it right), visit www.discussingstupid.com and subscribe on your favorite podcast platform.

(0:00) - Intro
(3:13) - The form looks fine… but is it usable?
(4:57) - The false promise of built in accessibility
(6:08) - Inside a real accessible PowerApps build
(10:15) - What screen readers see (that you don't)
(12:12) - The workarounds nobody talks about 
(16:33) - Why this problem isn't just Microsoft's fault
(17:38) - Outro


Subscribe for Email Updates on Our Website:
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What it really takes to build accessible forms

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.

Discussing Stupid

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