Retro Time // A Software Podcast cover art

Retro Time // A Software Podcast

Retro Time // A Software Podcast

By: Derek Seibert & Jeremy Miller
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About this listen

The Retro Time Podcast is all about retrospectives. Join your hosts, Derek Seibert and Jeremy Miller, as they talk about software — from product design to software development to the soft skills you need to make it in the industry. Using their long careers to kick off the conversation, they’ll drop a few nuggets of wisdom each episode… 96.7% guaranteed.© 2022 Retro Time. All Rights Reserved. Art
Episodes
  • In the Dark: The Infinite Usability Test
    Oct 30 2025
    The real horror? It’s not the prototype that’s broken… It’s her process.

    Today, we’re trading our usual interviews for a Halloween story straight out of every designer’s worst nightmare: The Infinite Usability Test.

    Meet Evelyn—a mid-level UX researcher running a morning of user tests that won’t quit. Every time she adjusts the design, another “Alex” walks in and repeats the same fateful words: “I can’t find the button.”

    As the day unravels, Evelyn realizes she’s stuck in more than a bad sprint—she’s caught in a validation loop. Each fix only pulls her deeper into the same mistakes, and each round of testing brings her face-to-face with the one insight she’s been avoiding all along.

    Because sometimes, the scariest thing in UX isn’t user feedback…
    It’s hearing something you didn’t expect.

    Join us for a hauntingly familiar tale about deadlines, doubt, and the difference between proving you’re right and learning that you’re not.

    Will Evelyn escape the room—or will she keep testing until the end of time?

    Tune in to find out… if you dare.

    —–

    Thanks for listening! We hope you enjoyed today’s episode. If you liked what you heard, be sure to like and subscribe wherever you get your podcasts! If you enjoyed today’s episode, please leave a comment and a five-star review. It helps us out a ton.

    If you haven’t already, sign up for our email list. We won’t spam you. Pinky swear.

    • Check out our website
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    The post In the Dark: The Infinite Usability Test appeared first on Retro Time.

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    16 mins
  • In the Dark: The Stakeholder from Hell
    Oct 31 2024
    What happens when your stakeholder is actually a demon from the darkest depths of UX hell?

    Listen for a wild ride through Silicon Valley’s dark side in our special Halloween episode. We’re trading our usual insights for incantations as we follow the misadventures of Sarah, Mike, and Emily, a UX team at the unicorn startup TechNova. Their world is turned upside down when they meet Mr. Deville, a new stakeholder who brings new meaning to the phrase “design from hell.”

    Our intrepid team faces challenges that would make even the most seasoned UX professional weep: interfaces that change on their own, product roadmaps possessed by demons, and stakeholder requests that defy the laws of physics (and good design). As they realize the true nature of their predicament, they must use every UX trick in the book – and perhaps invent a few new ones – to save their product and their souls.

    This episode is a tongue-in-cheek look at the sometimes hellish world of UX design, startup culture, and stakeholder management. It’s packed with laughs, gasps, and maybe even a few valuable lessons about staying true to good design principles, no matter how devilish the circumstances. Don’t miss this hilarious and horrifying journey into the dark side of UX!

    So go ahead and give it a listen… If you dare!

    —–

    Thanks for listening! We hope you enjoyed today’s episode. If you liked what you heard, be sure to like and subscribe wherever you get your podcasts! If you enjoyed today’s episode, please leave a comment and a five-star review. It helps us out a ton.

    If you haven’t already, sign up for our email list. We won’t spam you. Pinky swear.

    • Check out our website
    • Follow us on twitter
    • Find us on Facebook
    • Subscribe on Google Podcasts
    • Subscribe on Apple Podcasts
    • Subscribe on Spotify
    • Subscribe on Stitcher

    The post In the Dark: The Stakeholder from Hell appeared first on Retro Time.

    Show More Show Less
    12 mins
  • 78. A Thin Line: The Rough Reality of Enterprise Software
    Jan 18 2024

    No one likes one-play toilet paper. Yet it’s everywhere. It’s in just about every public or institutional toilet across the world.

    This begs the question, if no one likes one-play toilet paper, why is it everywhere?

    Well, I think it’s simple.

    The people who pay for the toilet paper aren’t the ones who have to use it.

    And it’s not too unlike enterprise software when you think about it.

    The people who get stuck using enterprise software have very little say in what tools they’re supposed to use every day. The people who pay for the software are rarely the ones who have to use it. Not to mention enterprise software is usually seen as a cost-center, not a profit-center. So there is very little incentive to bake quality in from the beginning.

    This week Derek and Jeremy dig into this conundrum and talk through some potential solutions to this unique problem.

    Topics:
    • 03:00 – The Analogy of One-Ply Toilet Paper and Enterprise Software
    • 20:00 – Building Better Software and the Importance of Empathy
    • 27:00 – Creating Empathy and Relationships in the Workplace
    • 31:00 – Turning Knuckleheads into Stallions
    • 31:28 – Building Great Software Requires Focus and Vision
    • 32:27 – Empathy and Skill are Essential for Solving Problems
    • 33:40 – Assuming Positive Intent and Encouraging Effort
    • 34:09 – The Challenge of Leadership Problems
    • 35:03 – Lack of Vision and Strategy as Leadership Problems
    • 36:38 – The Need for Empowering Employees to Speak Up
    • 39:30 – The Iceberg of Ignorance and Incentives for Silence
    • 41:40 – The Lack of Democracy in the Workplace
    • 48:26 – Leadership’s Role in Building Better Software

    —–

    Thanks for listening! We hope you enjoyed today’s episode. If you liked what you heard, be sure to like and subscribe wherever you get your podcasts! If you enjoyed today’s episode, please leave a comment and a five-star review. It helps us out a ton.

    If you haven’t already, sign up for our email list. We won’t spam you. Pinky swear.

    • Check out our website
    • Follow us on twitter
    • Find us on Facebook
    • Subscribe on Google Podcasts
    • Subscribe on Apple Podcasts
    • Subscribe on Spotify
    • Subscribe on Stitcher

    The post 78. A Thin Line: The Rough Reality of Enterprise Software appeared first on Retro Time.

    Show More Show Less
    46 mins
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