The CTO Playbook

• 50: From Chaos to Clarity: Using KPIs to Protect, Persuade, and Prioritize as CTO

  Join The CTO Playbook Slack Community to connect with other CTOs!Your KPIs aren’t just underperforming—some of them are actively lying to you.In this episode, Adam sits down with Lior Gerson, co-founder and CEO of Target Board, a company that's redefining how tech leaders track and prove their impact. With two decades of experience leading both e-commerce and SaaS companies, and advising giants like Macy’s and Sephora, Lior brings a brutally honest take on why most CTOs are flying blind when it comes to metrics—and how to fix it.This conversation is a no-BS breakdown of the most overlooked lever in engineering leadership: meaningful, actionable KPIs. You’ll learn how to turn your data into a defensive shield, why most dashboards are vanity theater, and what it actually takes to align your metrics with strategic business outcomes. If you’re a CTO tired of being reactive—or worse, irrelevant—this is your wake-up call. Expect a tactical playbook for building real visibility, accountability, and leverage inside your org.You’ll Learn:How bad KPIs create blind spots—and how to replace them with metrics that drive resultsWhy most dashboards fail to align with business outcomes (and what to do instead)How to use KPIs as a defensive shield to prove your value as a CTOWhat engineering leaders can learn from consumer companies about data disciplineWhy many CTOs unconsciously resist accountability—and how that holds teams backHow to build a metric system that connects engineering output to revenueWhy founder-led companies often ignore metrics—and what fractional CTOs must do differentlyHow to identify whether your team is measuring for impact or just checking boxesWhat makes a KPI actually meaningful (hint: it’s not speed or story points)How to avoid the DORA trap and surface the metrics your exec team actually cares aboutTimestamps:[00:00] Introduction[00:52] Why KPIs are critical infrastructure, not just reports[01:28] Common CTO struggles with metrics and alignment[03:54] The shock of entering a $100M SaaS company with no metrics[05:32] The impact of analytical leadership on performance[06:18] Why understanding other C-level roles gives CTOs an edge[07:12] How fractional CTOs prove impact fast[08:48] Why engineering teams resist accountability and tracking[10:51] How internal pressure forces KPI adoption[11:23] Using metrics as a defensive shield in leadership[12:42] How lazy KPI systems fail ambitious CTOs[14:11] Why every team needs different metrics to improve[15:28] Why most BI teams can’t deliver what CTOs need[16:42] How Target Board replaces data teams in days[17:52] Why DORA metrics don’t move the business needle[19:07] Connecting metrics to revenue and business outcomes[20:26] Why paychecks depend on the metrics people ignore[22:13] What causes misalignment between execs and data[23:31] How OKRs can sabotage team performance[25:01] Why full metric visibility empowers better decisions[27:01] Automating metric modeling across platforms[28:13] The hardest part of using KPIs effectively[29:58] The mindset shift needed to use metrics well[31:09] What data can’t fix when politics blocks accountability[32:28] A step-by-step playbook for KPI-driven executionYou can connect with Lior and his company on Linkedin.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

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• 49: What’s the Point of Your Tech Team? Why Most CEOs are Missing the Signals

  Join The CTO Playbook Slack Community to connect with other CTOs!"Compliance doesn’t make you good—so how do you really know if your tech team is any good at all?"In this episode, Adam sits down with Andy Graham, former CTO with 30 years of M&A and enterprise tech leadership, and Dane Eldridge, serial entrepreneur and CEO of Stackup. Together, they’ve built a deceptively simple tool that’s flipping the script on how tech leaders assess their teams—and uncover hidden risks before they explode.You’ll learn why most CTOs are unknowingly flying blind, how to detect the silent killers of innovation (like misaligned architecture or fuzzy definitions of "automation"), and how a single 30-minute assessment can surface the unknown unknowns holding your business back. Whether you're a scaleup CTO, a board member trying to evaluate tech health, or a founder wondering if your dev team is as strong as they say—they break down the real reason so many companies move slow, and how to fix it. You'll walk away with a new lens on language, leadership, and the hidden liabilities inside most tech functions.You’ll Learn:How benchmarking reveals hidden risks and weak spots in your tech functionWhy compliance frameworks can create a false sense of confidenceHow to detect misalignment between your tech strategy and business goalsWhat most CTOs miss about the real cost of technical debt during scale-upWhy “automation” means different things to different teams—and why that’s dangerousHow to use Stackup’s 30-minute assessment to surface unknown unknownsWhat poor communication habits are silently sabotaging CTO credibilityHow to use objective scoring to drive strategic investment and track improvement over timeTimestamps:[00:00] Introduction[04:41] Common pitfalls in developer-turned-CTOs[06:33] Triggers for assessing your tech function[08:00] How Stackup surfaces unknown unknowns[09:23] Real-world horror stories that drive urgency[10:07] Why misaligned language leads to costly misunderstandings[11:56] When tech due diligence reveals million-dollar mistakes[13:35] What technical debt really costs in scaleups[14:20] Why early architecture choices are critical[16:14] Planning upgrades with trigger points[17:45] How Stackup supports smarter, faster decisions[20:39] Why slowness doesn’t show up on the P&L[26:15] Using storytelling to align leadership around tech[28:01] What Stackup assesses in just 30 minutes[29:47] Simple questions that reveal massive security flaws[31:08] Why shiny tools like AI won’t fix misalignment[33:22] How to counter hype with strategy and expectations[35:31] When to use Stackup as a new or evolving CTO[37:59] Proving your tech value with objective results[39:13] Why Stackup delivers reports in video and podcast formats[41:19] Running the assessment quarterly to track growth[43:12] Focusing on just four priorities for maximum ROI[45:10] How the scoring system ensures objectivity[47:31] Why most leaders want to improve—transparently[49:12] Upcoming AI-powered CTO assistant and benchmarking[52:06] Using Stackup data to shape strategy and performanceYou can follow Andy and Dane on LinkedIn and learn more about their work here.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

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• 48: Why CTOs Need to SLOW Down in Order to Speed Up

  Join The CTO Playbook Slack Community to connect with other CTOs!"Most CTOs spend all their time chasing rabbits—and miss the real future right in front of them."In this sharp, no-fluff episode, Adam cuts through the chaos CTOs face daily and reveals the underrated superpower every tech leader must develop: strategic foresight. Forget firefighting and sprint planning—this is about learning to think deeply and see the horizon others can’t. Adam shares why boredom (yes, boredom) might be your secret weapon for unlocking creativity and how slowing down can give you the attitude needed to lead confidently instead of just managing crises. You’ll get a clear three-step playbook to zoom out beyond the immediate, create deliberate mental space, and build a network that challenges your perspective. If you’re ready to escape the cycle of reactive firefighting and step into real leadership, this episode will push you to rethink what it means to lead technology—and how to spot the future before it’s obvious to anyone else.You’ll Learn:How strategic foresight shifts CTO leadership from reactive to visionaryWhy boredom can unlock breakthrough creativity and clear thinkingHow to create mental space for insight in a nonstop, distraction-heavy worldWhat the loneliness of leadership really means—and how to handle itHow to spot hidden risks and opportunities before they become urgent problemsWhy zooming out beyond the quarter accelerates better decision-makingHow to build a support network that challenges your perspective and expands your thinkingWhat deliberate stillness in your schedule does for creative problem-solvingHow small early mitigations prepare you for future challenges without wasting resourcesWhy acting with conviction on unseen signals separates leaders from managersTimestamps:[00:00] Introduction[00:20] Why CTOs need to prioritize strategic thinking[01:30] The loneliness of seeing the future before others[03:00] Overview of the CTO playbook coaching programs[04:10] Analogy of terriers chasing rabbits to explain reactive behavior[05:10] Why CTOs get stuck solving immediate problems instead of leading[06:00] The value of seeing what others don’t yet see[07:00] Example of cascading impacts from a tech stack decision[08:00] How thinking several steps ahead expands perspective[09:00] Why being ahead of the curve can feel isolating[10:00] Personal story about early career risks and mitigations[11:00] Importance of finding a thinking partner or mentor[12:00] How natural abstraction helps in leadership altitude[13:00] The power of stillness and boredom for creative insight[14:00] Example of deliberate boredom sparking creativity in kids[15:00] How adults avoid boredom and lose creative moments[16:00] Using walks and notebooks to capture ideas without distractions[17:00] Integrating stillness into calendars as a priorityFind more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

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• 47: The Future of Distributed Architecture and Durable Execution with Temporal CTO, Maxim Fateev

  Join The CTO Playbook Slack Community to connect with other CTOs!What if the most complex part of your backend system... just vanished?In this episode, Adam sits down with Maxim Fateev, CTO and co-founder of Temporal, a platform quietly revolutionizing how distributed systems are built at companies like Stripe, Snap, and Netflix. With a career spanning Amazon, Google, Microsoft, and Uber, Maxim brings a rare, battle-tested perspective to the chaos of modern infrastructure.This conversation unpacks why the old way of building event-driven systems is fundamentally broken—and how Temporal’s concept of durable execution makes reliability and scale feel effortless. You’ll learn why your devs are wasting thousands of hours on boilerplate, how workflows are being redefined by AI, and why most “modern” architectures are really just legacy spaghetti in disguise. If you care about developer velocity, rock-solid uptime, or building tech that doesn’t implode at scale, this one’s a must-listen.You’ll Learn:How durable execution eliminates retries, race conditions, and orchestration chaosWhy event-driven systems create hidden coupling—and how to break itHow Amazon’s early monolith shaped a new paradigm for backend scaleWhat makes step functions a step backwards in modern architectureHow to write workflows that survive failures, restarts, and region-wide outagesWhy most business logic doesn’t need YAML, queues, or 12 microservicesHow to scale from prototype to production without rewriting core systemsWhat AI agents reveal about the future of workflow orchestrationHow Temporal boosts developer productivity by 5–10x in real-world teamsWhy durable execution is becoming the backbone of enterprise AI systemsTimestamps:[00:00] Introduction[00:37] Why durable execution matters in distributed systems[03:36] The pain of monoliths and the shift to microservices[05:19] Why events create tight coupling in architecture[07:00] Amazon’s early attempt at workflow orchestration[07:50] Why AWS step functions fall short[09:08] How durable execution actually works[10:44] Open-source vs cloud-hosted Temporal[12:48] Multi-region replication and total uptime[13:58] Write workflows in code, not configs[15:50] Is Temporal just for big companies?[16:37] 5–10x productivity gains with durable execution[18:26] Durable execution as a new middleware layer[20:03] Replacing bloated cloud architecture with one function[21:10] When not to use Temporal[23:03] Netflix’s switch from Spinnaker to Temporal[24:15] Language support and runtime challenges[25:03] New features: priority queues and fairness[26:36] Nexus: long-running RPC calls with full durability[28:34] Getting started with Temporal[30:19] Why Max stepped down as CEO[32:14] Durable execution powering AI workloads[35:18] Why AI agents need orchestration[37:03] Saving state between agent calls[39:34] Durable execution vs traditional AI workflowsResources Mentioned:Amazon Simple Workflow Service | WebsiteAWS Step Functions | WebsiteTemporal (Open Source) | WebsiteTemporal Documentation and Courses | WebsiteAzure Durable Functions | WebsiteTemporal Slack Community | WebsiteIf you want to learn more about Max’s work, follow him on LinkedIn.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

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• 46: The CEO’s Playbook for Hiring the Right CTO with Warren Beazley

  Join The CTO Playbook Slack Community to connect with other CTOs!Most CEOs hire the wrong CTO—not because of a talent shortage, but because they don't know what they're actually looking for.In this episode, Adam sits down with returning guest Warren Beazley—known across the UK tech scene as The CTO Recruiter. With nearly 30 years in the industry and a track record of 96%+ retention rates, Warren specializes in helping founder-led and investor-backed companies make one of the most pivotal hires in their org: a world-class CTO.You’ll learn why most CTO searches fail before they begin, how top CEOs are quietly mapping their talent pipelines long before they’re hiring, and the exact behavioral tools Warren uses to identify true leadership fit—not just technical skill. Whether you’re a CEO hiring your first tech exec or a CTO positioning yourself for your next role, this episode reveals how high-stakes technical hiring actually works behind the scenes. Expect sharp insights on filtering through noise, diagnosing culture clashes before they happen, and why gut instinct is no longer enough.You’ll Learn:How elite CEOs reverse-engineer their CTO hires for long-term fitWhy mapping your talent market beats relying on inbound candidatesHow Warren’s “12-month success review” technique clarifies role expectationsWhat most CEOs get wrong about job specs—and how to fix itHow behavioral surveys predict executive compatibility before it’s too lateHow to test for strategic thinking without asking cliché interview questionsWhat to do when you’re not the candidate’s first choice—and how to tellHow to spot red flags in resumes that even experienced recruiters missWhy most hiring failures aren’t about skills—they’re about culture mismatchesTimestamps:[00:00] Introduction[00:37] Why the CTO hiring market is still tough in 2025[05:07] What makes hiring CTOs more like poker than chess[07:15] The difference between founder-led vs investor-led hiring[10:18] Why great CEOs pivot and redefine their own role[12:16] Why most companies don’t know who their top candidates are[14:03] Employed vs. unemployed CTO hiring strategy[15:00] How to pitch your company to elite CTOs[16:13] Why money isn’t the main motivator for great candidates[17:41] The “12-month success review” for defining your ideal hire[20:00] Why job ads fail and how to create story-driven ones[22:03] Mapping the market to uncover passive candidates[25:00] The challenge of filtering hundreds of resumes[27:00] How structured interviews speed up good hiring[29:16] What your resume should reveal—but probably doesn’t[31:14] Culture and compatibility: the real reasons hires fail[33:00] How behavioral surveys predict long-term fit[36:03] Using personality data to shape interview questions[38:06] Why a 3-day decision window makes or breaks offers[40:01] Setting salary expectations early to avoid breakdowns[42:15] Open feedback channels that improve CTO retention[45:03] What really happens when a great hire walks awayYou can learn more about Warren's work on his website. or you can book a FREE 10 Minute call to understand if his hiring blueprint would work for you.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

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