CTO @ DistroKid, Principal @ Nimble Autonomy. Board Member & Speaker. Author of "It Depends: Writing on Technology Leadership 2012-2022." Let's talk on BlueSky.
Joined March 2008
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Pinned Tweet
4 Mar 2024
Today is the day! My book "it depends: writing on technology leadership 2012-2022" is now available everywhere!
amazon.com/Depends-Writing-T…
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Delivering well earns you more work, not more authority. You prove you can do the job, so you get more of the same job, not the next one.
New piece on the trap that creates:
kevingoldsmith.substack.com/…
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New ep of It Depends: The Reliable Team Trap.
Reliability buys you trust to execute. It does not buy you trust to decide. You can be rich in one and broke in the other.
itdependspod.com/episodes/th…
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🅺evin 🅶oldsmith 🇺🇦 retweeted
Jun 3
"Becoming a Business Leader, Not Just a Technical One"
Stop treating business fluency as someone else's job.
by @KevinGoldsmith
kevingoldsmith.substack.com/…
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🅺evin 🅶oldsmith 🇺🇦 retweeted
May 31
Self-driving cars are fun because you never see competing SaaS products having a literal standoff in the street
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New from It Depends: "The Conversation Before the Conversation"
Five signals a conversation is overdue: pattern, distance, workarounds, cognitive load, and inflation.
If two are present, you're not waiting for the right moment. You missed it.
kevingoldsmith.substack.com/…
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New ep of It Depends: "The Conversation Before the Conversation."
I lost a great engineer at Adobe because I kept avoiding a conversation with the rest of the team. By the time I acted, he'd already taken another offer.
🎧 itdependspod.com/episodes/th…
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🔥Hot off the press: Issue #352 of Level Up, a curated newsletter for leaders in tech #cto #vpeng #engmanager #techlead w/content from @KevinGoldsmith @josephgefroh @aleixmorgadas @lizziematusov @JustinReock & more! See sh1.sendinblue.com/3glfenxz5…
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This week's piece argued the AI transformation is in the org chart, not the IDE.
Earlier newsletter on why organizational design is the quiet variable that shapes what engineering teams can actually do:
kevingoldsmith.substack.com/…
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AI adoption is being treated like a tooling decision. It's a transformation.
We have tools for transformations. They're called change management. What we don't have is judgment about AI output quality. That's the actual leadership gap.
kevingoldsmith.substack.com/…
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If you're looking for the AI transformation, don't look at the IDE. Look at the org chart.
The technology adoption is the easy part. The organizational adoption is where everyone is struggling, and it's because almost everyone is making it up.
kevingoldsmith.substack.com/…
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AI adoption isn't a tooling decision. It's a transformation.
The four layers most engineering orgs aren't talking about: tooling, process, structure, judgment. Most companies are stuck on layer one.
kevingoldsmith.substack.com/…
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New ep of It Depends: "The Interesting Changes Aren't Happening in the IDE"
If you're looking for the AI transformation, don't look at the IDE. Look at the org chart.
🎧 itdependspod.com/episodes/th…
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🔥Hot off the press: Issue #351 of Level Up, a curated newsletter for leaders in tech #cto #vpeng #engmanager #techlead w/content from @jyhsu @kimballscott @KevinGoldsmith @theleoborges @emilybache & more! See sh1.sendinblue.com/3glb6ylz5…
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A CTO I mentor was prepping his technical due diligence deck for an acquisition.
The deck was fine. The problem: he was ready to give a technical presentation when he needed to give a business one.
kevingoldsmith.substack.com/…
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New ep of It Depends: "Becoming a Business Leader, Not Just a Technical One."
Most CEOs hire a CTO hoping for a business partner. Stay in the technical lane, and you're quietly disappointing them. Even when your teams ship well.
itdependspod.com/episodes/be…
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🅺evin 🅶oldsmith 🇺🇦 retweeted
Apr 21
"What Really Happens in a Board Meeting".
Board meetings aren’t actually mysterious, consequential. Understanding what happens in that room helps engineering leaders feel more confident and prepared for the responsibilities ahead.
@KevinGoldsmith
blog.kevingoldsmith.com/2026…
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Four mentees brought me the same problem in one week: how do you work with your CEO when the relationship isn't clicking?
New article on the four foundations of CEO trust, how to spot erosion early, and when it's a fit problem, not a fixable one.
kevingoldsmith.substack.com/…
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🅺evin 🅶oldsmith 🇺🇦 retweeted
Apr 18
Dario is wrong.
He knows absolutely nothing about the effects of technological revolutions on the labor market.
Don't listen to him, Sam, Yoshua, Geoff, or me on this topic.
Listen to economists who have spent their career studying this, like @Ph_Aghion , @erikbryn , @DAcemogluMIT , @amcafee , @davidautor
Anthropic CEO Dario Amodei: “50% of all tech jobs, entry-level lawyers, consultants, and finance professionals will be completely wiped out within 1–5 years.”
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🔥Hot off the press: Issue #349 of Level Up, a curated newsletter for leaders in tech #cto #vpeng #engmanager #techlead w/content from @avivby @bence_a_toth @ShaykeC @maybeFrederick & more! See sh1.sendinblue.com/3gkuc59z5…
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New ep of It Depends: "Working with the CEO: Close Enough to Influence, Independent Enough to Be Honest"
Surprised CEOs don't make good decisions. And if they've lost trust in your judgment, they're already interviewing your replacement.
itdependspod.com/episodes/wo…
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