『The Most Dangerous Phrase in Business: "It's Working Fine"』のカバーアート

The Most Dangerous Phrase in Business: "It's Working Fine"

The Most Dangerous Phrase in Business: "It's Working Fine"

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Every business owner has said it.
"It's working fine."
Sometimes that's true.
Sometimes it's the warning sign you only recognize after something breaks.

In this episode of Stack & Startup Al Fresco, I explore one of the most common mindsets that quietly creates operational risk inside businesses. Whether it's undocumented processes, aging technology, tribal knowledge, or a single employee who "just knows how everything works," these hidden dependencies can become expensive overnight.
This episode isn't really about IT.
It's about operations.
It's about leadership.
And it's about asking a simple question before your business is forced to answer it the hard way.
If you're building a business that you want to grow, sell, or simply sleep better running, this conversation is for you.
Connect with Jason Sherwood
🌐 https://stackandstartup.com
🌐 https://sdtechbaltimore.com
💼 LinkedIn
https://www.linkedin.com/in/jasonsherwood/
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Stack & Startup is a Baltimore-based business podcast focused on real conversations about building, running, and growing companies in Maryland.

If you’re serious about improving how your business operates—from technology to decision-making—follow the show for practical, experience-driven insights.

Watch and connect:

YouTube: https://www.youtube.com/@StackStartupBaltimore
LinkedIn: https://www.linkedin.com/in/jason-m-sherwood/

Need help with your business technology?

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