91: The Hardest Upgrade for Technical Leaders: Leading Without Losing Your Edge

94: Execution Beats Strategy? Rethinking the CTO Role in the Age of AI

What happens when execution matters more than strategy? Build your own CTO Playbook at http://www.thectoplaybook.com/www.theCTOplaybook.com [http://www.thectoplaybook.com/] — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact. Adam Spector is a four-time founder and investor in over 200 startups. He has seen firsthand how quickly expectations have shifted, and why what worked even a few years ago no longer holds up. The bar for startups has moved. Companies that once raised capital on early traction are now expected to show real revenue, working products, and meaningful growth almost immediately. AI is beginning to change what teams can produce, even if it has not fully transformed day-to-day work yet. The pace is increasing, and the gap between what is possible and what most teams deliver is widening. Rigid strategy is becoming a liability. Founders who cannot adapt in real time are more likely to fail as conditions shift underneath them. Efficiency is under a new lens. Metrics like revenue per employee are becoming signals of how well a company actually operates. The underlying question is harder to ignore: what is your role when code is no longer the constraint? You’ll Learn: [00:00] Introduction [06:12] Why the bar for startups has changed faster than most founders realize [10:47] What investors expect now and why early traction is no longer enough [14:33] How AI is starting to affect workflows without fully replacing them [18:05] Why time is becoming the only truly scarce resource [22:41] What happens when startups grow fast but lack a real moat [27:18] Why rigid strategy increases your risk of failure [31:56] How revenue per employee is becoming a key efficiency signal [36:22] What breaks when competitors move faster than you [40:08] How to think about your role when code is no longer the constraint Find more from Adam Spector on LinkedIn [https://www.linkedin.com/in/adamspector2/] and the Chore Website [http://www.hirechore.com]. Find more from Adam Horner on https://www.linkedin.com/in/adamhorner/LinkedIn [https://www.linkedin.com/in/adamhorner/] and https://www.youtube.com/channel/UCGIBKIGGjsew2vGL3zVJQvwYouTube [https://www.youtube.com/channel/UCGIBKIGGjsew2vGL3zVJQvw], and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com [https://www.thectoplaybook.com/], helping you build your own playbook for your path at your pace.

93: From SDLC to ADLC: How Engineering Teams are Actually Adopting AI

A CTO hired a star engineer to push AI adoption forward, and within months, the team had lost its momentum, the new hire, and any sense of where they actually were. Build your own CTO Playbook at http://www.thectoplaybook.com/www.theCTOplaybook.com [http://www.thectoplaybook.com/] — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact. Almost every CTO Adam speaks to right now is carrying the same thing: exhaustion beneath loud pressure. The board wants speed. Investors want an AI strategy. The voice in their own head says everyone else has worked something out that they haven't. The pressure to go faster with AI is usually the signal that the real work is somewhere else. Adam has watched organizations try to leap from pure experimentation to mature AI practice through a single hire, and watched what breaks when they do. The fastest engineering teams aren't tuning the engine first. They're upgrading the brakes and tires, the testing automation, the review systems, and the people around the work, before they touch raw speed. Tune in to learn about the three-stage pattern of AI adoption, two contrasting examples that show what acceleration actually costs, and the three postures that separate the CTOs making real progress from the ones spending money to look busy. You’ll Learn: [00:00] Introduction [01:08] Why CTOs feel behind even when they’re moving fast [02:48] The three stages of AI adoption and where most teams get stuck [05:12] Why skipping stages creates friction that slows the whole team [08:34] How lack of standards turns fast progress into team-wide frustration [15:06] Why slowing down in the right way is what actually moves teams forward [23:11] How to spot your team’s real stage and decide what to do next Find more from Adam on https://www.linkedin.com/in/adamhorner/LinkedIn [https://www.linkedin.com/in/adamhorner/] and https://www.youtube.com/channel/UCGIBKIGGjsew2vGL3zVJQvwYouTube [https://www.youtube.com/channel/UCGIBKIGGjsew2vGL3zVJQvw], and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com [https://www.thectoplaybook.com/], helping you build your own playbook for your path at your pace.

92: The CTO Playbook: How to Build Trust, Consistency, and Psychological Safety in Engineering Teams

The difference between a good CTO and a trusted one often comes down to a personal playbook. Build your own CTO Playbook at http://www.thectoplaybook.com/www.theCTOplaybook.com [http://www.thectoplaybook.com/] — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact. Sam Boswell is the CTO of Terralayr, an energy tech company focused on solving global energy storage challenges. With a background in high-risk infrastructure and scaling engineering teams, he brings a practical lens to how leadership actually works. At the center of that philosophy is a simple idea. Engineers don’t follow leaders because they’re the most technically brilliant person in the room. They follow leaders who are consistent. That consistency doesn’t happen by accident. It comes from a personal playbook. A set of lived principles that shape how decisions are made, how problems are approached, and how people are treated. We get into how that playbook forms over time, why documenting how you think matters more than most leaders realize, and what happens inside teams when that consistency is missing. The result is a grounded look at leadership that moves beyond theory. It shows what it takes to build trust, create safety, and lead in a way people actually want to follow. You’ll Learn: [00:00] Introduction [05:12] The shift from coding to leading people [07:45] Turning ideas into outcomes without touching the code [12:18] Why consistency earns trust faster than brilliance [15:42] Writing as a tool for clearer thinking and better leadership [18:36] What breaks inside teams when leadership is inconsistent [22:04] The power of a personal user manual for faster trust [26:31] There’s always a move, even when you feel stuck [30:12] Small principles that compound into better decisions [36:48] Psychological safety as the foundation of real performance Resources Mentioned: OODA Loop | Wikipedia [https://en.wikipedia.org/wiki/OODA_loop] The Joel Test: 12 Steps to Better Code | Website [https://www.joelonsoftware.com/2000/08/09/the-joel-test-12-steps-to-better-code/] Notion | Website [https://www.notion.com/] Knolling | Website [https://knolling.org/] Tom Sachs’ 10 Bullets | Website [http://tenbullets.com/] Time Enough for Love by Robert Heinlein | Book [https://www.amazon.ca/Time-Enough-Love-Robert-Heinlein/dp/0441810764] or Audiobook [https://www.amazon.ca/Time-Enough-Love-Lives-Lazarus/dp/B071VPXBRP/ref=tmm_aud_swatch_0] Joyful Militancy: Building Thriving Resistance in Toxic Times by Carla Bergman and Nick Montgomery | Book [https://www.amazon.ca/Joyful-Militancy-Building-Thriving-Resistance/dp/1849352887] or Audiobook [https://www.amazon.ca/Joyful-Militancy-Building-Thriving-Resistance/dp/B0F97C3J26/ref=tmm_aud_swatch_0] Eve Online | Video Game [https://www.eveonline.com/] Kanban Tool | Website [https://kanbantool.com/] Find more from Sam on LinkedIn [https://www.linkedin.com/in/samuelboswell/]. Find more from Adam on https://www.linkedin.com/in/adamhorner/LinkedIn [https://www.linkedin.com/in/adamhorner/] and https://www.youtube.com/channel/UCGIBKIGGjsew2vGL3zVJQvwYouTube [https://www.youtube.com/channel/UCGIBKIGGjsew2vGL3zVJQvw], and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com [https://www.thectoplaybook.com/], helping you build your own playbook for your path at your pace.

91: The Hardest Upgrade for Technical Leaders: Leading Without Losing Your Edge

What if leadership isn’t about managing people, but about owning decisions? Build your own CTO Playbook at http://www.thectoplaybook.com/www.theCTOplaybook.com [http://www.thectoplaybook.com/] — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact. I’m joined by Michael Di Prisco, who describes himself as “a software engineer struggling to realize that he became a tech leader”. Michael was pretty reluctant to become an engineering manager and leave the keyboard, but he started moving outside his comfort zone one step at a time. He gradually found a balance where he still writes code, but it is not expected of him. We explore how authority and responsibility actually work inside a team. He explains why every engineer should understand the business, and what changed when he started delegating code instead of doing everything himself. That shift did not slow the team down. The quality of their coding was becoming better, and people could focus on what they wanted to do more. We also get into documenting technical debt and how his team reached a point where they solved more debt than they created.  If you are thinking about the move into leadership, this is a grounded look at what that shift might actually involve. You’ll Learn: [00:00] Introduction [02:05] Stepping into leadership felt like losing his edge as an engineer [06:45] A small move outside your comfort zone can shift your entire career path [08:30] Coding stopped being expected and started becoming a deliberate choice [12:10] Teams can improve when a tech lead stops doing all the coding and starts delegating [16:20] The hidden gap between responsibility and authority most teams never fix [20:15] Engineers make weaker decisions when they don’t understand the business [24:40] Letting go of best practices can reveal what actually works in your context [27:10] Documenting technical debt can lead to actually reducing it over time [31:25] Small steps and honest feedback often outperform big career moves Resources Mentioned: The Software Architect Elevator: Redefining the Architect's Role in the Digital Enterprise by Gregor Hohpe | Book [https://www.amazon.ca/Software-Architect-Elevator-Redefining-Architects/dp/1492077542] Architectural Decision Records (ADR) | Website [https://adr.github.io/] GitHub | Website [https://github.com/] Astro | Website [https://astro.build/] CodeMotion Conference | Website [https://www.codemotion.com/] jsday - The Italian JavaScript Conference | Website [https://www.jsday.it/] Italian Agile Days Conference | Website [https://www.agileday.it/] Dive deeper into Michael’s ideas on software engineering and leadership on his blog [https://cadienvan.github.io/]. Find more from Michael on LinkedIn [https://www.linkedin.com/in/mdiprisco/]. Find more from Adam on https://www.linkedin.com/in/adamhorner/LinkedIn [https://www.linkedin.com/in/adamhorner/] and https://www.youtube.com/channel/UCGIBKIGGjsew2vGL3zVJQvwYouTube [https://www.youtube.com/channel/UCGIBKIGGjsew2vGL3zVJQvw], and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com [https://www.thectoplaybook.com/], helping you build your own playbook for your path at your pace.

90: Data Is a Leadership Problem, Not a Technical One — A Playbook for CTOs

Most teams don’t have a data problem; they have a decision problem. Build your own CTO Playbook at http://www.thectoplaybook.com/www.theCTOplaybook.com [http://www.thectoplaybook.com/] — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact. Nic Granger, Chief Information and Financial Officer at the North Sea Transition Authority, joins me to share her perspective from the intersection of data, finance, and transformation in a highly complex, regulated industry. Nic leads a multidisciplinary portfolio spanning digital, data, and core services, with a focus on enabling better decisions across the energy transition. We get into why data strategy is fundamentally a human challenge, not just a technical one, and how data-driven decision making only works when people can actually access and trust the data. You’ll hear how data leadership shifts when the goal isn’t dashboards, but real-world outcomes like energy security and decarbonization. We also unpack why jumping straight to AI in business often misses the point, and what it really takes to build strong data foundations that support scale. If you’re responsible for digital transformation or shaping CTO strategy, this will likely reframe how you think about value, not just volume. You’ll Learn: [00:00] Introduction [03:15] The value of data has nothing to do with the data itself, and what it actually comes down to [07:30] Nic's realization that turning petabytes into value is a people problem, not a technology problem [10:05] The mistake most organizations make with data is jumping to AI before they've solved anything [13:00] What decades of vital data trapped in unreadable PDFs look like, and what AI is doing about it [16:45] Making industry data freely available unlocked competition from smaller players and academia in ways nobody expected [21:20] Your team is probably already asking the right data questions; you just have to listen for them [27:45] The reason Nic's team swapped the word "process" for "workflow" and what the language shift actually changed [31:20] Digitizing a paper trolley process revealed hidden data that now predicts industry trends [37:00] The one thing Nic says every CTO should prioritize in the next 90 days to unlock data value If you want to support the work Nic mentioned, become a member of the Bat Conservation Trust [https://www.bats.org.uk/membership/scheme]. Resources Mentioned: CTO Craft | Website [https://ctocraft.com/] UK National Data Repository (NDR) | Website [https://ndr.nstauthority.co.uk/] Bat Conservation Trust | Website [https://www.bats.org.uk/] Falklands Conservation | Website [https://falklandsconservation.com/] Lovable AI | Website [https://lovable.dev/] Base44 | Website [https://base44.com/] If you want to support the work Nic mentioned, become a member of the Bat Conservation Trust [https://www.bats.org.uk/membership/scheme]. Find more from Nic Granger on LinkedIn [http://www.linkedin.com/in/nicgranger]. Find more from Adam on https://www.linkedin.com/in/adamhorner/LinkedIn [https://www.linkedin.com/in/adamhorner/] and https://www.youtube.com/channel/UCGIBKIGGjsew2vGL3zVJQvwYouTube [https://www.youtube.com/channel/UCGIBKIGGjsew2vGL3zVJQvw], and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com [https://www.thectoplaybook.com/], helping you build your own playbook for your path at your pace.