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
The hardest leadership transitions aren’t about learning new skills.
They’re about unlearning the ones that used to work.
Managing managers means moving from decisions to context, from comfort to leverage.
kevingoldsmith.substack.com/p/the-shift-...
They’re about unlearning the ones that used to work.
Managing managers means moving from decisions to context, from comfort to leverage.
kevingoldsmith.substack.com/p/the-shift-...
February 8, 2026 at 8:34 AM
The hardest leadership transitions aren’t about learning new skills.
They’re about unlearning the ones that used to work.
Managing managers means moving from decisions to context, from comfort to leverage.
kevingoldsmith.substack.com/p/the-shift-...
They’re about unlearning the ones that used to work.
Managing managers means moving from decisions to context, from comfort to leverage.
kevingoldsmith.substack.com/p/the-shift-...
The hardest part of managing managers? Realizing that feeling indispensable is a warning sign, not a success metric.
New episode of It Depends: how to shift from being a decision-making bottleneck to providing context and leverage. itdependspod.com/episodes/the...
New episode of It Depends: how to shift from being a decision-making bottleneck to providing context and leverage. itdependspod.com/episodes/the...
The Shift to Managing Managers - It Depends Podcast
Moving from managing individual contributors to managing managers requires a fundamental shift that many leaders struggle with. In this episode, Kevin shares lessons from his own difficult transition,...
itdependspod.com
February 1, 2026 at 8:55 AM
The hardest part of managing managers? Realizing that feeling indispensable is a warning sign, not a success metric.
New episode of It Depends: how to shift from being a decision-making bottleneck to providing context and leverage. itdependspod.com/episodes/the...
New episode of It Depends: how to shift from being a decision-making bottleneck to providing context and leverage. itdependspod.com/episodes/the...
At some point in leadership, you outrun your own resume.
You’re responsible for systems, teams, and domains you’ve never personally worked in. Trying to stay the expert doesn’t scale. Ignoring the work doesn’t either.
kevingoldsmith.substack.com/p/leading-wh...
You’re responsible for systems, teams, and domains you’ve never personally worked in. Trying to stay the expert doesn’t scale. Ignoring the work doesn’t either.
kevingoldsmith.substack.com/p/leading-wh...
Leading What You’ve Never Done Before
What happens when your role outgrows your technical background
kevingoldsmith.substack.com
January 25, 2026 at 8:38 AM
At some point in leadership, you outrun your own resume.
You’re responsible for systems, teams, and domains you’ve never personally worked in. Trying to stay the expert doesn’t scale. Ignoring the work doesn’t either.
kevingoldsmith.substack.com/p/leading-wh...
You’re responsible for systems, teams, and domains you’ve never personally worked in. Trying to stay the expert doesn’t scale. Ignoring the work doesn’t either.
kevingoldsmith.substack.com/p/leading-wh...
Did I just invent this, or did someone else already come up with this idea?
"Zoom Chicken": Show up to the meeting as late as you can without being the last one to arrive. Alternate rule: Show up as late as you can while still being the first to show up. Company culture dictates which rule you use.
"Zoom Chicken": Show up to the meeting as late as you can without being the last one to arrive. Alternate rule: Show up as late as you can while still being the first to show up. Company culture dictates which rule you use.
January 21, 2026 at 9:08 PM
Did I just invent this, or did someone else already come up with this idea?
"Zoom Chicken": Show up to the meeting as late as you can without being the last one to arrive. Alternate rule: Show up as late as you can while still being the first to show up. Company culture dictates which rule you use.
"Zoom Chicken": Show up to the meeting as late as you can without being the last one to arrive. Alternate rule: Show up as late as you can while still being the first to show up. Company culture dictates which rule you use.
Was planning my day tomorrow and may have come up with the title of my next book. "6 meetings before lunch: the job of the CTO"
January 21, 2026 at 7:43 AM
Was planning my day tomorrow and may have come up with the title of my next book. "6 meetings before lunch: the job of the CTO"
New episode of the It Depends: Lessons in Technology Leadership Podcast - "Leading What You’ve Never Done Before"
Your scope will eventually outrun your resume.
The job isn’t to become an expert in everything; it’s to lead the system around it.
itdependspod.com/episodes/lea...
Your scope will eventually outrun your resume.
The job isn’t to become an expert in everything; it’s to lead the system around it.
itdependspod.com/episodes/lea...
January 18, 2026 at 4:54 PM
New episode of the It Depends: Lessons in Technology Leadership Podcast - "Leading What You’ve Never Done Before"
Your scope will eventually outrun your resume.
The job isn’t to become an expert in everything; it’s to lead the system around it.
itdependspod.com/episodes/lea...
Your scope will eventually outrun your resume.
The job isn’t to become an expert in everything; it’s to lead the system around it.
itdependspod.com/episodes/lea...
Experience makes the job easier.
That’s also when growth quietly stalls.
This week’s newsletter is about reflection as a leadership skill. Not journaling for journaling’s sake, but deliberate time to avoid running the same playbook forever.
kevingoldsmith.substack.com/p/reflection...
That’s also when growth quietly stalls.
This week’s newsletter is about reflection as a leadership skill. Not journaling for journaling’s sake, but deliberate time to avoid running the same playbook forever.
kevingoldsmith.substack.com/p/reflection...
January 11, 2026 at 9:55 PM
Experience makes the job easier.
That’s also when growth quietly stalls.
This week’s newsletter is about reflection as a leadership skill. Not journaling for journaling’s sake, but deliberate time to avoid running the same playbook forever.
kevingoldsmith.substack.com/p/reflection...
That’s also when growth quietly stalls.
This week’s newsletter is about reflection as a leadership skill. Not journaling for journaling’s sake, but deliberate time to avoid running the same playbook forever.
kevingoldsmith.substack.com/p/reflection...
New podcast episode for the new year! Why a reflection practice is critical as you move into senior leadership (because no one else is going to be focusing on developing you). You can’t lead others to grow if you’ve stopped growing yourself.
pod.link/1724860326/e...
pod.link/1724860326/e...
January 5, 2026 at 12:02 AM
New podcast episode for the new year! Why a reflection practice is critical as you move into senior leadership (because no one else is going to be focusing on developing you). You can’t lead others to grow if you’ve stopped growing yourself.
pod.link/1724860326/e...
pod.link/1724860326/e...
Most engineering orgs don’t struggle because they lack process.
They struggle because the process they have doesn’t match the problem they’re trying to solve.
This week’s issue is about treating process as a coordination, pruning it when it stops helping.
kevingoldsmith.substack.com/p/process-is...
They struggle because the process they have doesn’t match the problem they’re trying to solve.
This week’s issue is about treating process as a coordination, pruning it when it stops helping.
kevingoldsmith.substack.com/p/process-is...
Process Is a Tool, Not a Virtue
Making Deliberate Choices About Process, Autonomy, and Scale
kevingoldsmith.substack.com
December 29, 2025 at 1:26 AM
Most engineering orgs don’t struggle because they lack process.
They struggle because the process they have doesn’t match the problem they’re trying to solve.
This week’s issue is about treating process as a coordination, pruning it when it stops helping.
kevingoldsmith.substack.com/p/process-is...
They struggle because the process they have doesn’t match the problem they’re trying to solve.
This week’s issue is about treating process as a coordination, pruning it when it stops helping.
kevingoldsmith.substack.com/p/process-is...
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...