Kevin Goldsmith
@kevingoldsmith.com
This is my account for technology leadership posts and announcements. For personal stuff, https://bsky.app/profile/kmg.bsky.social.
Author of "It Depends: Writing on Technology Leadership 2012-2022"
CTO @ DistroKid
https://kevingoldsmith.com
Author of "It Depends: Writing on Technology Leadership 2012-2022"
CTO @ DistroKid
https://kevingoldsmith.com
Tech debt isn’t inherently good or bad. It’s information.
Some debt is a smart trade-off
Some is safe to ignore
Some is genuinely dangerous
Some is a warning that leadership systems, not code, need attention
The problem isn’t debt. It’s unexamined debt.
kevingoldsmith.substack.com/p/tech-debt-...
Some debt is a smart trade-off
Some is safe to ignore
Some is genuinely dangerous
Some is a warning that leadership systems, not code, need attention
The problem isn’t debt. It’s unexamined debt.
kevingoldsmith.substack.com/p/tech-debt-...
December 14, 2025 at 2:25 PM
Tech debt isn’t inherently good or bad. It’s information.
Some debt is a smart trade-off
Some is safe to ignore
Some is genuinely dangerous
Some is a warning that leadership systems, not code, need attention
The problem isn’t debt. It’s unexamined debt.
kevingoldsmith.substack.com/p/tech-debt-...
Some debt is a smart trade-off
Some is safe to ignore
Some is genuinely dangerous
Some is a warning that leadership systems, not code, need attention
The problem isn’t debt. It’s unexamined debt.
kevingoldsmith.substack.com/p/tech-debt-...
Registered for the #ATmosphere conference! See you in March!
December 10, 2025 at 9:36 PM
Registered for the #ATmosphere conference! See you in March!
Just released a new episode on technical debt.
The truth? Healthy teams take on debt intentionally. The trick is knowing which debt matters and which doesn't.
pod.link/1724860326/e...
The truth? Healthy teams take on debt intentionally. The trick is knowing which debt matters and which doesn't.
pod.link/1724860326/e...
December 7, 2025 at 9:25 AM
Just released a new episode on technical debt.
The truth? Healthy teams take on debt intentionally. The trick is knowing which debt matters and which doesn't.
pod.link/1724860326/e...
The truth? Healthy teams take on debt intentionally. The trick is knowing which debt matters and which doesn't.
pod.link/1724860326/e...
A lot of the fear around board meetings comes from not knowing what they are. They’re direct, consequential, and heavily focused on judgment, not cleverness or technical depth. I dig into what actually happens, why it matters, and how leaders can show up well.
open.substack.com/pub/kevingol...
open.substack.com/pub/kevingol...
What Really Happens in a Board Meeting
Demystifying Board Meetings: A CTO's Perspective
open.substack.com
November 30, 2025 at 4:42 PM
A lot of the fear around board meetings comes from not knowing what they are. They’re direct, consequential, and heavily focused on judgment, not cleverness or technical depth. I dig into what actually happens, why it matters, and how leaders can show up well.
open.substack.com/pub/kevingol...
open.substack.com/pub/kevingol...
Reposted by Kevin Goldsmith
i’m not crying you’re crying
xkcd: Fifteen Years
xkcd: Fifteen Years
Fifteen Years
xkcd.com
November 25, 2025 at 1:58 AM
i’m not crying you’re crying
xkcd: Fifteen Years
xkcd: Fifteen Years
Reposted by Kevin Goldsmith
Reposted by Kevin Goldsmith
TIL that my colleague @rod.begbie.com wrote a fantastic article on a topic I struggle with occasionally. #keeplearning
Filtering your language as an engineering leader
The most painful lessons I’ve learned as an engineering leader have been when I have been imprecise with my language.
coaching.begbie.com
November 26, 2025 at 11:25 PM
TIL that my colleague @rod.begbie.com wrote a fantastic article on a topic I struggle with occasionally. #keeplearning
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.
itdependspod.com/episodes/dem...
itdependspod.com/episodes/dem...
November 23, 2025 at 10:57 PM
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.
itdependspod.com/episodes/dem...
itdependspod.com/episodes/dem...
I've just published a piece on building a technical strategy that people can use - not a wishlist, not a roadmap, and not a vague mission statement.
Strategy isn’t prediction. It’s clarity. And clarity scales.
open.substack.com/pub/kevingol...
Strategy isn’t prediction. It’s clarity. And clarity scales.
open.substack.com/pub/kevingol...
Crafting a Technical Strategy That Actually Works
Moving from disconnected decisions to a unified technical direction
open.substack.com
November 16, 2025 at 9:43 AM
I've just published a piece on building a technical strategy that people can use - not a wishlist, not a roadmap, and not a vague mission statement.
Strategy isn’t prediction. It’s clarity. And clarity scales.
open.substack.com/pub/kevingol...
Strategy isn’t prediction. It’s clarity. And clarity scales.
open.substack.com/pub/kevingol...
Anyone using this? Interested to hear how useful it is for you. Mozilla.ai releases universal interface to LLMs | InfoWorld share.google/pD8LMsPDGNxc...
November 9, 2025 at 9:58 PM
Anyone using this? Interested to hear how useful it is for you. Mozilla.ai releases universal interface to LLMs | InfoWorld share.google/pD8LMsPDGNxc...
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.
pod.link/1724860326/e...
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.
pod.link/1724860326/e...
November 9, 2025 at 9:22 AM
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.
pod.link/1724860326/e...
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.
pod.link/1724860326/e...
Every wave of tech promises transformation. Few deliver.
My latest newsletter, "Making Technology Choices That Last," is about leading with intent instead of impulse.
open.substack.com/pub/kevingol...
My latest newsletter, "Making Technology Choices That Last," is about leading with intent instead of impulse.
open.substack.com/pub/kevingol...
November 2, 2025 at 3:54 PM
Every wave of tech promises transformation. Few deliver.
My latest newsletter, "Making Technology Choices That Last," is about leading with intent instead of impulse.
open.substack.com/pub/kevingol...
My latest newsletter, "Making Technology Choices That Last," is about leading with intent instead of impulse.
open.substack.com/pub/kevingol...
The recording from my LeadDev NYC talk "From friction to function: Strengthening the product-engineering alliance" is now live! leaddev.com/communicatio...
From friction to function: Strengthening the product-engineering alliance
Learn practical strategies to turn product-engineering friction into alignment through better prioritization, communication, and shared decision-making.
leaddev.com
November 1, 2025 at 10:17 PM
The recording from my LeadDev NYC talk "From friction to function: Strengthening the product-engineering alliance" is now live! leaddev.com/communicatio...
Reposted by Kevin Goldsmith
Just having some innocent fun with Claude.
October 26, 2025 at 9:19 PM
Just having some innocent fun with Claude.
Every wave of tech promises transformation.
In the latest It Depends episode, I share how leaders can make thoughtful technology choices that last: balancing curiosity with caution, and learning before leaping.
Making Technology Choices That Last
itdependspod.com/episodes/mak...
In the latest It Depends episode, I share how leaders can make thoughtful technology choices that last: balancing curiosity with caution, and learning before leaping.
Making Technology Choices That Last
itdependspod.com/episodes/mak...
Making Technology Choices That Last - It Depends Podcast
Avoiding shiny object syndrome, encouraging curiosity, and building a system for smart adoption
Every few years, a new wave of technology arrives promising to change everything. Right now, it’s gene...
itdependspod.com
October 26, 2025 at 6:03 PM
Every wave of tech promises transformation.
In the latest It Depends episode, I share how leaders can make thoughtful technology choices that last: balancing curiosity with caution, and learning before leaping.
Making Technology Choices That Last
itdependspod.com/episodes/mak...
In the latest It Depends episode, I share how leaders can make thoughtful technology choices that last: balancing curiosity with caution, and learning before leaping.
Making Technology Choices That Last
itdependspod.com/episodes/mak...
New newsletter: The Hidden Architecture of Engineering kevingoldsmith.substack.com/p/the-hidden...
October 20, 2025 at 4:46 PM
New newsletter: The Hidden Architecture of Engineering kevingoldsmith.substack.com/p/the-hidden...
I've heard "Code Survivability Rate" come up as a useful metric for measuring AI-assisted developer productivity. I'm not sure it is a great metric as it highly depends on your workflow. I tend to use AI as a pair programming partner and follow XP processes of progressive improvement. ->
October 19, 2025 at 5:48 PM
I've heard "Code Survivability Rate" come up as a useful metric for measuring AI-assisted developer productivity. I'm not sure it is a great metric as it highly depends on your workflow. I tend to use AI as a pair programming partner and follow XP processes of progressive improvement. ->
Reposted by Kevin Goldsmith
Interesting impact of Claude Code:
I dabble with frontend, but not a frontend expert. I always reached for etiher some templates or something like Webflow to put together some landing page.
Now I started to... ask Claude Code to build me as per my spec.
A big reason for it:
I dabble with frontend, but not a frontend expert. I always reached for etiher some templates or something like Webflow to put together some landing page.
Now I started to... ask Claude Code to build me as per my spec.
A big reason for it:
October 18, 2025 at 4:28 PM
Interesting impact of Claude Code:
I dabble with frontend, but not a frontend expert. I always reached for etiher some templates or something like Webflow to put together some landing page.
Now I started to... ask Claude Code to build me as per my spec.
A big reason for it:
I dabble with frontend, but not a frontend expert. I always reached for etiher some templates or something like Webflow to put together some landing page.
Now I started to... ask Claude Code to build me as per my spec.
A big reason for it:
So used to seeing Meri Williams as a conference host, I forgot how good a speaker Meri is! #LeadDevNYC
October 16, 2025 at 6:39 PM
So used to seeing Meri Williams as a conference host, I forgot how good a speaker Meri is! #LeadDevNYC
Kudos to Pooja Varshneya for the prettiest slides so far. #LeadDevNYC
October 15, 2025 at 7:28 PM
Kudos to Pooja Varshneya for the prettiest slides so far. #LeadDevNYC
Really liked the talk from @addyosmani.bsky.social on leadership supporting AI coding. #LeadDevNYC
October 15, 2025 at 4:05 PM
Really liked the talk from @addyosmani.bsky.social on leadership supporting AI coding. #LeadDevNYC
Hello #LeadDevNYC! @yee.camp starting things off!
October 15, 2025 at 1:48 PM
Hello #LeadDevNYC! @yee.camp starting things off!
new newsletter: Values->Culture->Everything
open.substack.com/pub/kevingol...
open.substack.com/pub/kevingol...
October 5, 2025 at 9:10 AM
new newsletter: Values->Culture->Everything
open.substack.com/pub/kevingol...
open.substack.com/pub/kevingol...
Most company "values" are BS. Real test: Can you tell your boss "no" when they ask you to violate a core value without getting fired?
Culture = what gets rewarded, not what's on the wall.
If you're constantly fighting your workplace culture find one that fits instead
itdependspod.com/episodes/val...
Culture = what gets rewarded, not what's on the wall.
If you're constantly fighting your workplace culture find one that fits instead
itdependspod.com/episodes/val...
Values → Culture → Everything: Why Company Culture Actually Matters - It Depends Podcast
Kevin Goldsmith revisits his influential 2013 keynote on engineering culture, expanding the conversation beyond just engineering teams to address anyone navigating workplace dynamics. This episode bre...
itdependspod.com
September 30, 2025 at 5:19 AM
Most company "values" are BS. Real test: Can you tell your boss "no" when they ask you to violate a core value without getting fired?
Culture = what gets rewarded, not what's on the wall.
If you're constantly fighting your workplace culture find one that fits instead
itdependspod.com/episodes/val...
Culture = what gets rewarded, not what's on the wall.
If you're constantly fighting your workplace culture find one that fits instead
itdependspod.com/episodes/val...