Sherman On Software.

Knowing which features and changes are hard, and which ones are trivial is an evergreen source of friction between Product Owners and Developers. Navigating asking for something that sounds easy, but is actually hard, requires open communication and flexability. With agentic coding, no one knows how large a change is until they see the final result.

If you've ever been surprised by the difficulty of an "easy" task, this is the episode for you!

Watch on YouTube or listen to it at Spotify, Apple Podcasts, or your favorite podcast app.

Have a tricky problem that you think requires a rewrite of your software? Join as a guest on our podcast and we’ll talk you out of it.

Want some custom advice? Book a 2-on-1 call with Isaac and me today!

Do you need feature parity, or are you avoiding talking with your users? Are your application's boundaries there to free your users or protect you from them? Feature parity might be the correct choice, but it is always a big red flag.

If you've ever been pitched "feature parity" and suspected something was off, this is the episode for you!

Watch on YouTube or listen to it at Spotify, Apple Podcasts, or your favorite podcast app.

Have a tricky problem that you think requires a rewrite of your software? Join as a guest on our podcast and we’ll talk you out of it.

Want some custom advice? Book a 2-on-1 call with Isaac and me today!

The sunk cost fallacy is when past investment justifies future investment. It is hard for people to accept, but the past doesn't matter. What matters is how much value you'll get out of future investment.

If you've ever wanted to keep going on a project because of how much time you've invested, this is the episode for you!

Watch on YouTube or listen to it at Spotify, Apple Podcasts, or your favorite podcast app.

Have a tricky problem that you think requires a rewrite of your software? Join as a guest on our podcast and we’ll talk you out of it.

Want some custom advice? Book a 2-on-1 call with Isaac and me today!

A rewrite is a lot like moving homes. You pack everything up, take it somewhere new, and then struggle to set everything set up in the new environment. What changes when AI can do your metaphorical packing and unpacking?

If you've been wondering how our metaphors stand up in the age of AI, this is the episode for you!

Watch on YouTube or listen to it at Spotify, Apple Podcasts, or your favorite podcast app.

Have a tricky problem that you think requires a rewrite of your software? Join as a guest on our podcast and we’ll talk you out of it.

Want some custom advice? Book a 2-on-1 call with Isaac and me today!

Isaac and I preach iteration on small changes to get lots of small wins. Small wins are small, unremarkable, and forgettable. Yet, people need to celebrate wins; your team needs to celebrate to keep morale up. So, how do you create meaningful celebrations from small wins?

If you struggle to keep team morale high, this is the episode for you!

Watch on YouTube or listen to it at Spotify, Apple Podcasts, or your favorite podcast app.

Have a tricky problem that you think requires a rewrite of your software? Join as a guest on our podcast and we’ll talk you out of it.

Want some custom advice? Book a 2-on-1 call with Isaac and me today!

AI can rewrite your code. It is unlikely that this will solve any of your actual problems.

If your system is broken and you think an AI rewrite will solve your problems, this is the episode for you!

Watch on YouTube or listen to it at Spotify, Apple Podcasts, or your favorite podcast app.

Have a tricky problem that you think requires a rewrite of your software? Join as a guest on our podcast and we’ll talk you out of it.

Want some custom advice? Book a 2-on-1 call with Isaac and me today!

Isaac did a full rewrite using AI. Is the show over? Do we need to change the name to Sometimes Rewrite?

If you've been wondering about where AI makes rewrites ok, this is the episode for you!

Watch on YouTube or listen to it at Spotify, Apple Podcasts, or your favorite podcast app.

Have a tricky problem that you think requires a rewrite of your software? Join as a guest on our podcast and we’ll talk you out of it.

Want some custom advice? Book a 2-on-1 call with Isaac and me today!

Famous music producer Rick Rubin said "I have no technical ability. And I know nothing about music. My job is not to have any technical skill whatsoever, my job is to know what I like." Is the same true about software in the age of AI?

If you're interesting in how developer's skill sets are changing, this is the episode for you!

Watch on YouTube or listen to it at Spotify, Apple Podcasts, or your favorite podcast app.

Have a tricky problem that you think requires a rewrite of your software? Join as a guest on our podcast and we’ll talk you out of it.

Want some custom advice? Book a 2-on-1 call with Isaac and me today!

Transformation expert Sophia Rosa rejoins the show to deliver a master class on the human factors behind changing organization. Bad news for developers, changing code is the least important factor.

If you've ever tried to drive change by changing technology, and failed, this is the episode for you!

Watch on YouTube or listen to it at Spotify, Apple Podcasts, or your favorite podcast app.

Have a tricky problem that you think requires a rewrite of your software? Join as a guest on our podcast and we’ll talk you out of it.

Want some custom advice? Book a 2-on-1 call with Isaac and me today!

Can the hourly billing model survive Agentic coding? How is AI reshaping the software consultant career?

If you've been wondering how AI is impacting the developer's dream of going freelance, this is the episode for you!

Watch on YouTube or listen to it at Spotify, Apple Podcasts, or your favorite podcast app.

Have a tricky problem that you think requires a rewrite of your software? Join as a guest on our podcast and we’ll talk you out of it.

Want some custom advice? Book a 2-on-1 call with Isaac and me today!