72: Why OKRs Fail — and What to Use Instead (with Radhika Dutt)
Build your own CTO Playbook at 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.What if goals are the real problem?In this episode, I’m joined by Radhika Dutt, an engineer who studied electrical engineering at MIT. She wrote Radical Product Thinking and is now working on a new book exploring why goals and OKRs backfire, and what to do instead.Targets can look great on paper while the foundation quietly erodes beneath them, leaving leaders focused on green dashboards instead of genuine learning. Together we unpack how shifting from goal setting to puzzle setting can unlock motivation, creativity, and alignment, using a simple framework that turns experiments into smarter decisions. By the end, you’ll see why puzzle setting beats targets when progress actually matters.You’ll Learn:[00:00] Introduction[04:12] The story of how chasing perfect targets blinded a company to a crumbling foundation[05:47] Why leaders often get good news first and the truth too late[06:32] The hidden reason goal-setting traps teams in the wrong solutions[07:15] How puzzle thinking rewires teams to stay in the problem space longer[33:04] What happens when you replace optimization with exploration[35:41] Why surfacing bad news early helps leaders make smarter choices[37:18] How one company built real trust by modeling puzzle-solving from the top[38:21] The three questions that turn metrics into learning loopsResources Mentioned:Radical Product Thinking by Radhika Dutt | Book or AudiobookIt’s soul-sucking to chase arbitrary targets. OHLs—Objectives, Hypotheses, and Learnings—shift the focus to learning, experimentation, and real progress. These templates help you break up with OKRs (without a career limiting move) and reclaim meaning at work.If you want to connect more with Radhika, follow her on Linkedin.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.
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71: The Real Reason Digital Transformations Fail — It’s Not Technology or People
Build your own CTO Playbook at 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.What if the real bottleneck isn’t people or tech but the thing between them?In this episode, I’m joined by Michael Louis Schank, author of Digital Transformation Success. He’s spent years in the trenches at Accenture, Bank of America, EY, and Citi, then struck out on his own to codify what actually works. We dig into his process inventory framework and how it transforms complexity into clarity without wishful thinking.Most transformations stumble not because teams are bad, but because complexity breeds chaos. The fix starts with mapping what the business actually does, naming owners, and tying change to those specific processes. No buzzwords, just the hard work that kills the telephone game and keeps scope, design, and testing honest. And you’ll see why getting the map right beats chasing shiny tools.You’ll Learn:[00:00] Introduction[10:52] Why alignment and systems thinking are the two foundations every transformation depends on[13:17] What happens when business and tech speak different languages and how to finally bridge that gap[19:40] The real reason “easy buttons” and buzzwords keep derailing enterprise change[27:05] How a simple process inventory turns chaos into clarity across teams[31:14] What mapping COBOL systems taught one bank about risk and modernization[33:42] Why ignoring side effects in process change can quietly destroy entire workflows[43:05] How visualizing current state exposes waste and redundancy no one noticed before[45:11] The hidden danger of optimizing what should’ve been deleted in the first place[56:09] What transformation leaders get wrong about ownership, and the one fix that makes it lastResources Mentioned:Digital Transformation Success by Michael Schank | BookYou can connect with Michael on his LinkedIn.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.
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70: A Better Way to Explain Your Platform to Non-Technical Executives
Build your own CTO Playbook at 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.Ever tried to explain a technical decision and felt the room silently check out?Why do brilliant ideas so often get lost in translation? There is one simple metaphor that changes everything. In this episode, I share the story of a growth-stage CTO who could see a scale crisis coming, but couldn’t get his co-founders to see it too. It took one unexpected image, a floating city at sea, to finally bridge the gap.Why does the old “building” analogy fail? How does reframing your stack as something alive, modular, and adaptable change the whole conversation? The right metaphor doesn’t just explain your system, it earns you buy-in. Because oftentimes, leading isn’t about simplifying the truth, it’s about telling the right story.You’ll Learn:[00:00] Introduction[01:47] Why technical insight isn’t enough when your team can’t see the urgency you do[03:18] How one metaphor turned a frustrating explanation into an instant lightbulb moment[04:41] What happens when you frame your platform as a living, floating system instead of a fixed foundation[06:52] The reason most architectural metaphors fail modern software and what replaces them[08:36] How a single story helped a CTO win over skeptical co-founders and a cautious CFO[09:24] Why the right analogy frees you to teach complexity without losing the room[10:48] How to build metaphors that empower non-technical leaders to see real platform value[11:51] The mindset shift that turns architecture into leadership and communication into strategyFind more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.
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69: Breaking Free from Vendor Lock-In: A New Playbook for Modernising Legacy Systems
Build your own CTO Playbook at 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.When your CTO dies and no one can read the code, you realize the real problem was never the software.In this episode, I sit down with Matteo Di Battista and Marcello Modica, two Italian innovators who’ve spent decades helping companies escape the grip of outdated ERP systems. From IBM mainframes to cloud-native development, they’ve seen how technical debt and siloed knowledge can quietly strangle growth.We get into what happens when your tech stack outlives your people, why monoliths breed fragility, and how breaking systems into small, pluggable services changes everything. It’s not just about new tools—it’s about a new kind of teamwork that keeps knowledge alive even when key players leave.Because modernization isn’t just a tech upgrade—it’s a survival strategy.You’ll Learn:[00:00] Introduction[05:32] Why monolithic ERP systems quietly trap companies in technical debt[09:47] What happens when a CTO’s death exposes a company’s hidden knowledge silos[12:18] The moment you know it’s time to modernize your software before it collapses[15:44] How low-code and visual tools can close the gap between design and delivery[18:56] Why developers are becoming replaceable, and what that means for software teams[23:51] How building a shared development community protects both companies and clients[26:28] The real reason developers resist change even when innovation would make life easier[33:42] What the new network API standard means for identity, payments, and fraud prevention[45:37] How converting old databases into REST APIs transforms legacy systems into living platformsYou can connect on LinkedIn with both Matteo and Marcello, and their work though wavemaker.com and oneclickapp.it.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.
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68: Startups, AI, and the Funding Reset: What Investors Really Want in 2025
Build your own CTO Playbook at 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.What if the future of startups isn’t decided by who builds the flashiest AI, but by who solves the right problems?In this episode, I’m joined again by my friend Thorgeir Einarsson, almost a year since we last spoke, to unpack how AI funding and investor expectations have shifted from hype cycles to hard realities. Thor runs PGO, a service that helps founders get truly investment-ready with real pre-diligence instead of lipstick on a pig.Pre-seed and seed are brutal right now, and traction beats vibes. Investors are placing smaller, option-like bets at the AI application layer while steering clear of generic models. Hardware is back where it matters, from defense tech to medical devices, when firmware and software meet close to the metal. We trace the PE-ification of VC: rolling up vertical SaaS, “AI-firing” them, and rebuilding moats from customer bases and domain data. Thor flags a blind spot worth building for: AI safety and guardrails for agentic workflows. Then we get practical: preparation beats performative decks, checklist-driven pre-diligence forces the hard questions, and the playbook is simple… know yourself, know your co-founders, keep investors updated, and track the numbers.You’ll Learn:The reason many VCs focus on the AI application layerWhat happens when nobody knows what a great AI company looks like yetThe link between defense and medical devices and hardware-plus-software productsThe damage of skipping investor updates and simple monthly KPIsWhat it feels like to raise when only one to three percent get a checkThe reason pre-diligence and checklists come before the pitchWhat happens when agentic workflows scale without safety guardrailsTimestamps:[00:00] Introduction[05:42] Why AI investment has shifted from hype to hard reality[12:18] The brutal truth about pre-seed and seed fundraising in 2025[18:33] Why investors are betting smaller at the AI application layer[25:47] How defense tech and medical devices are bringing hardware back[32:11] The rise of “AI-firing” old SaaS companies and the PE-ification of VC[40:26] The missed opportunity in AI safety and agentic workflow guardrails[48:59] How founders can prepare for due diligence the right way[56:22] Why investor updates and clear KPIs determine long-term trustConnect more with Thorgeir on LinkedIn.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.
Join Adam Horner, a CTO with over 30 years in the tech industry, on The CTO Playbook — the podcast dedicated to helping CTOs excel. Perfect for CTOs and tech leaders navigating the complexities of their roles, each episode offers clear insights, innovative strategies, and practical advice from top leaders in tech.
With Adam’s extensive experience mentoring engineers and tech leaders, and over a decade as a CTO, you’ll gain the tools and knowledge to build and refine your own CTO playbook. Whether you're tackling complex projects, fostering innovation, leading teams, or shaping your company's tech strategy, this podcast is your go-to resource.
Adam’s journey from engineer to strategic CTO was challenging. He learned through the school of hard knocks, making avoidable mistakes and facing countless challenges. Often out of his comfort zone and wishing for more guidance, he created this podcast to provide the support and advice he once lacked.
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