Retro Time // A Software Podcast

Latest Episodes:

In the Dark: The Infinite Usability Test Oct 30, 2025

Show notes

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.

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The post In the Dark: The Infinite Usability Test appeared first on Retro Time.

In the Dark: The Stakeholder from Hell Oct 31, 2024

Show notes

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!

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78. A Thin Line: The Rough Reality of Enterprise Software Jan 18, 2024

Show notes

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

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In the Dark: The Tale of the Cursed Prototype Oct 30, 2023

Show notes

What happens when the quest for the perfect design goes too far?

Today, we’re stepping away from our usual interviews and discussions to bring you a special Halloween treat.

This is the story of Ethan. A talented UX designer so committed to creating the perfect prototype that he becomes consumed by it—so much so that he loses himself in his work… Never to be seen again.

😱

Two brave interns hear about Ethan’s tale and decide to unravel the mystery. What they discover is beyond anything they could have imagined.

Whether you’re a junior UX designer, a career shifter, or even a seasoned pro, this episode should serve as a cautionary tale. It’s a haunting reminder of what can happen when we lose ourselves in our work and the dangers of focusing on perfection at all costs.

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

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In the Dark: A Cautionary Tale of UX Dark Patterns Oct 30, 2023

Show notes

Sit right back and you’ll hear a tale. A tale of a woman who isn’t quite careful about what she does with her personal information while browsing the internet.

Do you think you’re safe online? Do you pay close attention to the websites you visit?

Unscrupulous UX designers might use some dirty tactics to trick you into doing their evil bidding.

Don’t fall for these dirty tricks. Find out how to protect yourself by listening to this cautionary tale of UX dark patterns.

We want to give a huge shout-out to Kat Richards for writing an awesome article about UX dark patterns that inspired this story. Thanks Kat!

Helpful Links:
• A Very Scary UX Halloween Story: Dark Patterns and Bad UX

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77. Sink or Swim: How to Survive Being Overleveled Aug 30, 2023

Show notes

Lots of folks have ended up in the position of being at a higher level than they maybe should be.

This sounds like a blessing, but it could quickly turn into a curse when you decide to move to a new job where you may be viewed as less experienced than other people at your level.

Overlevelling can happen for several reasons. It’s possible your current team doesn’t have a lot of rigor around promotions or hiring. It’s also possible a new company would offer a higher band to help give recruiters more wiggle room during compensation negotiations.

If you’ve been over leveled it means you may have a hard time making a lateral move and may have to think about making a more horizontal switch.

Whatever the reason, it’s important to ignore titles and focus on your experience level and the context of the team.

A great team will know your level and be able to get you up to speed.

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76. Ctrl+Alt+Del Your Existential Dread: A Phoenix Will Rise Out of ChatGPT’s Ashes May 25, 2023

Show notes

AI isn’t coming. AI is here.

There are two types of people in this world. Those who are chomping at the bit to embrace AI tools like ChatGPT, and those who are terrified the end is nigh.

Let’s face it, AI is pretty incredible. But it’s also kind of dumb right now. We’re not quite to the point of dealing with Skynet and Terminator-style robots looking to completely wipe out humanity… yet.

Is there any point in fighting it? Does it do any good? Or should you pop some popcorn, sit back, relax, and get ready for the end?

It all depends if you agree with Derek or not.

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Photo by Owen Beard on Unsplash

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From the Archives: Peak Software $#!% with Gojko Adzic May 11, 2023

Show notes

Most software teams don’t realize the power they have over our everyday lives. With the proliferation of smart technology and connected networks, when product teams miss seemingly little software bugs, the consequences can be astounding.

Where does the software industry start to draw the line between innocent oversight and criminal negligence? Will a licensing scheme similar to the law and medical industries help to hold people accountable?

This week Derek and Jeremy interview the esteemed Gojko Adzic. They talk about some examples of software gone wrong and offer some insights on how to address these issues.

Gojko is the author of Running Serverless, Impact Mapping, Specification by Example and a few more books… He’s now working on Narakeet – narakeet.com and MindMup – mindmup.com.

Topics:
• 03:00 – Very close to reaching Peak Software $#!%
• 04:24 – Software is starting to negatively affect people’s lives.
• 15:25 – Illegal vs unethical patterns
• 20:20 – “Automation helps to get things done faster, not better”
• 25:40 – Software that breaks is often meant to serve the underprivileged.
• 30:00 – Gojko’s state of the industry

Helpful Links:
• Gojko.net
• Humans vs Computers
• Narakeet
• MindMup

Order your Peak Software $#!% stickers!

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75. What Is the Network Effect? May 04, 2023

Show notes

You may have never heard of “The Network Effect” but you most certainly have experienced it.

If you’ve used social media, watched TV, or subscribed to a streaming service like Spotify, or Netflix, you’ve been a part of the network effect. Even if you didn’t realize it.

The Network Effect is when a system brings value to users because of the number of other users active in the system.

The more producers on a platform the more it is desirable for users. The more users on the platform the more desirable it is for the producers to join the platform.

This week, Derek explains The Network Effect and how this might influence your approach to planning out your system.

When we think about it in the context of software, this is something that can improve the experience of our users. Or it can have a negative effect and end up hurting the experience.

When you’re in the planning phase, it’s important to think about The Network Effect and make sure you’re setting your team up for success.

Helpful Links:
• The Network Effect on Wikipedia

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Episode Thumbnail by Alina Grubnyak on Unsplash

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74. Bursting the Multiverse Bubble or Stop It With the Status Quo Already! Apr 26, 2023

Show notes

Every once in a while, a great team will fall into an alternate universe. One where things don’t go according to plan. Where things could have gone right if only someone made a different decision. It might look a lot like the universe you’re used to, but it just doesn’t feel quite right.

The multiverse is often described as different bubbles. If you don’t like the universe you’re in. You might need to pop that bubble.

How do you get a team from a state of chaos to a state of enlightenment? How do we pull out the pin and pop the bubble? It requires time and energy to pop the bubble. If the leaders are unwilling, sometimes the leaders have to go.

When we reinforce and incentivize good behavior we get good results.

It’s often that simple.

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Episode thumbnail by Israel Piña on Unsplash

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