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Retro Time // A Software Podcast

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Rating
★★★★★
5
from
14 reviews
This podcast has
105 episodes
Language
English
Date created
2020/01/17
Latest episode
2025/10/30
Average duration
33 min.
Release period
76 days

Description

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.

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In the Dark: The Infinite Usability Test
2025/10/30
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 • 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 Infinite Usability Test appeared first on Retro Time.
In the Dark: The Stakeholder from Hell
2024/10/31
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.
A Thin Line: The Rough Reality of Enterprise Software
2024/01/18
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.
In the Dark: The Tale of the Cursed Prototype
2023/10/30
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! —– 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 Tale of the Cursed Prototype appeared first on Retro Time.
In the Dark: A Cautionary Tale of UX Dark Patterns
2023/10/30
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 —– 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: A Cautionary Tale of UX Dark Patterns appeared first on Retro Time.
77. Sink or Swim: How to Survive Being Overleveled
2023/08/30
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. —– 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 77. Sink or Swim: How to Survive Being Overleveled appeared first on Retro Time.
76. Ctrl+Alt+Del Your Existential Dread: A Phoenix Will Rise Out of ChatGPT’s Ashes
2023/05/25
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. —– 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 Photo by Owen Beard on Unsplash The post 76. Ctrl+Alt+Del Your Existential Dread: A Phoenix Will Rise Out of ChatGPT’s Ashes appeared first on Retro Time.
From the Archives: Peak Software $#!% with Gojko Adzic
2023/05/11
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! —– 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 From the Archives: Peak Software $#!% with Gojko Adzic appeared first on Retro Time.
What Is the Network Effect?
2023/05/04
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 —– 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 Episode Thumbnail by Alina Grubnyak on Unsplash The post 75. What Is the Network Effect? appeared first on Retro Time.
Bursting the Multiverse Bubble or Stop It With the Status Quo Already!
2023/04/26
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. —– 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 Episode thumbnail by Israel Piña on Unsplash The post 74. Bursting the Multiverse Bubble or Stop It With the Status Quo Already! appeared first on Retro Time.
Who Do Software Teams Serve?
2023/03/09
Who the software teams serve is a great question and often gets conflicting answers, depending on who you ask. This week, Derek and Jeremy discuss this question and dive into some deeper questions about why the software team exists in the first place. What is the point of “the product”? Why do we even have a job in the first place? Check out this week’s episode for some deep conversation about these topics and find out if Jeremy finishes all of his king cake. —– 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 Episode thumbnail by William Krause on Unsplash The post 73. Who Do Software Teams Serve? appeared first on Retro Time.
When Important Decisions Become Ancient History
2023/02/23
Making decisions is hard. What’s harder is documenting those decisions. What’s often impossible is trying to figure out why a decision was made years before you joined the team. And all too often that decision lingers for a very, very, very long time. This week Derek and Jeremy discuss decisions, their long-term impact, and what happens when those decisions turn into ancient history that predates your modern era. Topics: • 10:25 – The Great Stink • 12:59 – Let the PSR commence • 14:06 – Teams often value speed over quality • 20:30 – Create a stakeholder map • 24:29 – Teams often have problems with decision making • 24:52 – Org charts don’t always tell the whole story • 28:13 – Visions can be great, but there’s a catch • 33:17 – You don’t have to be that wrong to still be wrong —– 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 72. When Important Decisions Become Ancient History appeared first on Retro Time.
A Couple of Miracle Workers
2023/01/19
When things go wrong at work, there’s usually someone to swoop in and save the day. But what about the folks who work hard to ensure nothing ever goes wrong? Sometimes they may get some recognition eventually, but usually, these are the ones who fly under the radar. We usually don’t know their names or their deeds. Because they fade into the background. What’s interesting is many organizations incentivize the hero mindset over incentivizing these nameless heroes who fly under the radar. Buckle up for the deepest, most philosophical software podcast episode you may ever listen to. Topics: • 00:36 – It’s Carnival Time! • 04:37 – A Star Trek Allegory • 09:50 – We often celebrate people who come to the rescue • 11:13 – Normal things shouldn’t be seen as exceptional • 14:41 – There is a social incentive to let things go nuts, so we can be seen fixing it • 18:58 – The less attention something receives the better it is managed • 21:43 – Boring usually means something works. But we celebrate the opposite • 23:47 – What’s the moral of the story? • 24:25 – What are our incentives? • 32:31 – Most people are terrible at estimating • 36:38 – Don’t focus on estimates. Focus on quality. —– 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 Episode thumbnail by Sander Sammy on Unsplash The post 71. A Couple of Miracle Workers appeared first on Retro Time.
70. The Endless Drive for the Perfect Program
2023/01/13
What does it mean to build perfect software? Is perfect software, or perfect anything for that matter, even attainable? Or is it a utopian dream? If perfection is nearly impossible, what options do we have? You’ve probably heard the old adage “Don’t let perfect get in the way of the good enough,” or something similar. But what does it mean to be good enough? Well, it’s likely hard to understand what any of this looks like without constant communication with your entire team. Topics: • 01:08 – The allegory of the “smart” dishwasher • 07:39 – We often start building before we know what to do • 08:32 – Think about the problem in simplest form • 08:44 – The UX team can help • 13:06 – “Good enough” is a conversation • 13:36 – Perfect looks different from Engineers and Designers • 17:05 – Communication is critical to know what “good enough” is • 19:52 – Reaching for perfection, within the context, is part of being successful • 20:59 – How much risk do you want to assume? • 21:39 – Look down the line for potential risks to “good enough” • 25:23 – It’s often about intuition and knowing what works • 33:16 – Perfection can be about anything • 33:46 – It’s not about being perfect its about finding the perfect balance —– 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 Episode thumbnail by Pablò on Unsplash The post 70. The Endless Drive for the Perfect Program appeared first on Retro Time.
Seasons Greetings: The Story of Barry Christmas
2022/12/15
Join Barry on the holiday adventure of a lifetime, a journey through space, time, and a kooky winter wonderland. Your hearts will be warmed by the colorful characters Morty the Head Elf, Emma and Mr. Weatherspoon (those goofs will laugh at anything), and most of all Barry, a man who learns all about the spirit of giving … Just in the nick of time. Coming this holiday season to home video! —– 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 Episode thumbnail by Isaac Martin on Unsplash The post Seasons Greetings: The Story of Barry Christmas appeared first on Retro Time.

Podcast reviews

Read Retro Time // A Software Podcast podcast reviews


5 out of 5
14 reviews
★★★★★
stephen dunford 2022/08/08
Love this show
At first glance folks will think… is this about retro music or retro software or retro… something?? Nope nope nope , I find this podcast is chock ful...
★★★★★
dougp_123 2022/03/26
Dynamic Duo
The episodes with guests are outstanding, but my favorites are the ones where Derek and Jeremy tackle issues themselves. Their rapport and ability to ...
★★★★★
Seauxcrazy 2022/03/02
Best in the Biz Ya Heard
Yo! These two have such a hot pod it makes the “D” key on my keyboard rise up, if ya know what I mean. Great knowledge, glad I found then 😎
★★★★★
Dmwkunewsie 2022/02/05
Derek & Jeremy Rock!
I love listening to these two! They give really great advice and drop serious gems with thier guests. I was told there's a dedicated jingle to each re...
★★★★★
6327853585 2022/02/01
Infotainment at its finest
Derek and Jeremy tackle hard-hitting issues facing modern software developers, with a sense of humor that lightens the tone and emits an effervescent ...
★★★★★
JMillsPaysBlils 2021/11/03
What a show!
Two of the most handsome podcast hosts I’ve every listened to. Retro Time is a wonderful, engaging podcast that doesn’t go too deep into the weeds wit...
★★★★★
DerekSeibert 2021/11/03
Funny and Informative Software Podcast
The two hosts of this podcast are some of the more insightful software people I’ve listened to. It’s neat how they are both from different fields with...
★★★★★
_RED*STAR_ 2021/07/29
Expert Insight into the Industry
I have been listening to this podcast from the start and absolutely love hearing Jeremy and Derek talk about working in the industry. They keep things...
★★★★★
summittbb 2021/04/10
Fun and informative
Jeremy and Derek have created a fun and informative way to discuss all the ups and downs around building software. Often times building software can b...
★★★★★
bigbrother82 2020/05/29
Software super hero’s with a sense of humor
These two guys are pretty special. They always have an interesting take on software development but instead of just stating facts, find an entertainin...
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