| Website | https://kevingoldsmith.com |
Tech debt isn’t the enemy. Unexamined tech debt is.
Some debt is deliberate and healthy.
Some is benign.
Some constrains real business outcomes.
Some is a signal of broken incentives or structure.
Understanding why the debt exists matters more than fixing it.
https://kevingoldsmith.substack.com/p/tech-debt-is-a-signal-not-a-sin
Board meetings aren’t mysterious—they’re high-stakes performance reviews for the whole company. In this episode, I explain how they work, who’s in the room, and why they shape so many strategic decisions.
https://itdependspod.com/episodes/demystifying-board-meetings-a-ctos-perspective/
I’ve been thinking about how often engineering teams struggle simply because the strategy was never clearly written down.
So I tried to break down what a practical, grounded technical strategy actually looks like and how you know it’s working.
If your team is asking for more clarity lately, you’re not alone.
https://kevingoldsmith.substack.com/p/crafting-a-technical-strategy-that
A technical strategy isn’t a roadmap; it’s how you align your team to face the future together.
In this episode of It Depends, I discuss what makes a good strategy, how to document it effectively, and how to keep it alive as your company evolves.
🎙️ Latest podcast episode: The technical and business details of self-publishing "It Depends"
Covers the full stack: WordPress → Word → Amazon KDP + Ingram Spark, using ChatGPT for indexing, home audiobook recording setup, and the real economics.
Why self-publish vs traditional? What tools actually work? How much do you really make?
A case study in DIY business building that applies beyond books.
New newsletter: Why performance reviews kill collaboration, how to implement guilds that actually work, and advocating for accessibility as an IC. Real solutions for systemic problems.
New newsletter issue! Answers That Depend: Tech Leadership Q&A, pt 2
More of your questions from the newsletter and podcast...
In this issue:
* Fostering Learning Without Big Resources
* Building Your Personal Retrospective Process
* When Change Management Gets Stuck
* Balancing Urgent Fixes and Long-term Architecture
* Starting Out as the First Data Engineer
* When Product and Engineering Have Separate Roadmaps
https://kevingoldsmith.substack.com/p/answers-that-depend-tech-leadership-678
New Q&A episode of It Depends: Lessons in Technology Leadership is live! 🎧
Tackled six listener questions covering everything from building a learning culture on a shoestring budget to the hard realities of organizational change.
Kevin Goldsmith
