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Are you getting the most out of your individual contributors?
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.
In this episode, I sit down with Matan Kubovsky to dive into the art of managing individual contributors through weekly one-on-one meetings. Matan shares his experience and a proven system for leading teams with consistency, clarity, and alignment. This method isn’t just about project updates—it’s about shaping growth and connecting each person’s role to the broader organizational mission.
We cover how to structure meetings, build trust, and set the right cadence to keep momentum going. Matan also discusses how to track progress with a rolling agenda and how to use the VARK learning model to tailor coaching to the team’s learning styles. Whether leading a small team or guiding team leads, this episode is packed with actionable insights to make performance management smoother and more effective.
You’ll Learn:
Timestamps:
[00:00] Introduction
[06:30] Why many engineering teams lack performance management skills
[08:05] The problem with annual performance reviews
[09:35] How feedback frequency impacts team performance
[11:10] The Start/Stop/Continue framework explained
[13:25] The need for weekly one-on-one meetings with individual contributors
[16:05] Why silence in meetings can drive more meaningful conversations
[19:15] How to help engineers improve their listening and communication skills
[21:40] The importance of shifting focus from output to experience in meetings
[25:00] Why keeping a rolling agenda document is essential for tracking progress
[30:20] How to structure quarterly reviews and set goals for the next quarter
Resources Mentioned:
McKinsey Research | Website
You can connect with Matan through his Linkedin or schedule a meeting to learn more here.
Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
Being busy isn’t your problem—being absent is.
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.
In this special episode, Adam dives into the hidden cost of not showing up—at work, at home, and especially as a leader. If you’ve ever coasted through a Zoom call, half-listened to a teammate, or checked your phone while spending time with your kids, this one will hit hard.
Adam pulls back the curtain on what it really means to lead with presence—not perfection—and how that simple act can radically transform trust, engagement, and team performance. You’ll hear personal stories, hard-won lessons, and five tactical steps to build a leadership style grounded in consistency and connection. Whether you're burned out or just trying to level up, this episode delivers the wake-up call (and the playbook) you didn’t know you needed.
You’ll Learn:
Timestamps:
[00:00] Introduction
[02:20] Why presence matters more than perfection
[03:08] The real meaning of “showing up”
[03:47] Story: daughter calls out her dad for not watching
[04:29] Story: child notices when phone is put away
[05:07] Why absence creates disconnection—even in the same room
[05:35] What presence looks like in a professional setting
[06:10] How presence builds or destroys trust
[06:45] Story: transforming a demoralized team through consistency
[07:56] The role of showing up in changing team culture
[08:25] Why presence includes celebrating wins
[08:58] Story: the 15-minute celebration that stuck
[09:50] Why being noticed beats being rewarded
[10:36] What makes consistency so difficult
[11:05] The support systems that enable presence
[12:02] Step 1: know where presence matters most
[12:22] Step 2: create friction for distraction
[12:45] Step 3: celebrate outcomes deliberately
[13:04] Step 4: practice active presence in 1:1s
[13:30] Step 5: acknowledge your misses and recommit
Resources Mentioned:
The CTO Playbook Platform | Website
Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
You’re leading everyone else—but are you quietly abandoning yourself?
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.
This episode features executive coach and former engineer Natalya Tarasova, who brings a rare blend of technical credibility, Eastern philosophy, and mountaineering metaphors to the world of tech leadership. With a background in physics, machine learning, and organizational coaching, Natalya doesn’t just talk about change—she’s lived it through multiple career pivots and international moves. Her perspective is especially powerful for high-performing CTOs who’ve built their careers on delivering results but feel disconnected from their own needs.
In this conversation, Adam and Natalya break down why so many senior tech leaders are brilliant at leading others but terrible at leading themselves. You’ll learn how to recognize when you’ve put yourself last for too long, how to approach inner transformation with the same strategy you’d use for scaling a system, and why burnout often hides behind high output. Expect unconventional insights on emotional regulation, breathing as a leadership tool, the myth of waiting until you’re “ready,” and how to rewire your mental architecture for sustainable impact. This episode is a must-listen if you’re ready to stop sprinting and start leading from stillness.
You’ll Learn:
Timestamps:
[00:00] Introduction
[04:58] What constant career change reveals about personal adaptability
[06:36] The hidden cost of being too externally focused
[09:08] Are you a victim of change or a driver of it
[10:18] How to take control of your state and response
[12:30] Why CTOs say they don’t know how to put themselves first
[14:56] Using a mountain metaphor to visualize growth
[17:05] Why high achievers struggle to slow down
[18:16] The role of stillness in understanding motion
[20:12] Why breathwork is the fastest reset for high performers
[23:12] How to prepare for the next phase of your leadership
[25:11] How to know when it’s time to move
[27:09] What leaders need to leave behind to grow
[28:12] Change is not linear—it’s a spiral
[30:01] What most high performers miss when working on themselves
[31:07] Why change starts with rewiring your identity
[33:00] Giving yourself permission to fail and learn
[35:03] Why emotional empathy can’t be intellectualized
[37:06] How embodied wisdom changes your leadership presence
[39:04] The hidden power of integrating personal and professional growth
[41:05] How self-leadership creates ripple effects across teams
[42:12] The 4-step change framework for CTOs
[44:05] Why timing your next change is a skill, not luck
You can connect with Natalya on LinkedIn and learn more about her company, Tarasova Coaching on its website.
Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
Your KPIs aren’t just underperforming—some of them are actively lying to you.
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.
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:
Timestamps:
[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 execution
You can connect with Lior and his company on Linkedin.
Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
"Compliance doesn’t make you good—so how do you really know if your tech team is any good at all?"
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.
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:
Timestamps:
[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 performance
You can follow Andy and Dane on LinkedIn and learn more about their work here.
Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
"Most CTOs spend all their time chasing rabbits—and miss the real future right in front of them."
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.
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:
Timestamps:
[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 priority
Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
What if the most complex part of your backend system... just vanished?
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.
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:
Timestamps:
[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 workflows
Resources Mentioned:
Amazon Simple Workflow Service | Website
AWS Step Functions | Website
Temporal (Open Source) | Website
Temporal Documentation and Courses | Website
Azure Durable Functions | Website
Temporal Slack Community | Website
If you want to learn more about Max’s work, follow him on LinkedIn.
Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
Most CEOs hire the wrong CTO—not because of a talent shortage, but because they don't know what they're actually looking for.
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.
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:
Timestamps:
[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 away
You 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 explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
What if the part of you causing burnout is the same one that got you where you are?
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.
In this episode, Adam sits down with Rob Kalwarowsky—executive coach, TEDx speaker, and author of Capitalizing on Chaos—to explore how high performers can stop white-knuckling their leadership journey and start transforming from within. Rob has helped tech execs and founders all over the world how to fast-track deep change through his FIRE method, a unique four-step framework that rewires how we lead, scale, and relate to chaos itself.
If you’ve ever looked “successful” on the outside while feeling stuck, burned out, or quietly miserable on the inside, this conversation will hit home. You’ll hear Rob’s deeply personal journey from MIT engineer to global coach, how internal family systems reshaped his leadership philosophy, and why chaos might be the exact catalyst you need. Expect mindset rewiring, counterintuitive truth bombs, and tools to break through the next ceiling in your growth.
This one’s not just about business. It’s about the human behind the title.
You’ll Learn:
Timestamps:
[00:00] Introduction
[06:13] The cost of a “perfect” life
[08:42] The role of coaching and therapy in real growth
[11:41] What Internal Family Systems therapy reveals
[13:21] Why mindset hacks don’t solve deep issues
[15:11] Even destructive inner voices have a purpose
[16:27] Rob’s 6-minute self-leadership exercise
[16:53] Step 1 of the FIRE method: find your reason
[17:32] Step 2: ignite the masks and uncover inner blocks
[21:56] Step 3: rapidly transform your identity
[25:04] Step 4: expand and evolve your leadership
[26:17] Why fear shuts down innovation
[28:00] How to lead teams through disruption
[30:10] Chaos opens new possibilities for growth
[31:33] Summary of the FIRE method
[32:57] The importance of guided transformation
[35:55] Why leadership growth is deeply personal
Resources Mentioned:
How to Handle a Bad Boss | TEDx Talk
Saboteur Assessment | Website
Internal Family Systems by Dr. Richard Schwartz | Website
Movie: Inside Out
If you want the first 2 chapters of Capitalizing on Chaos for FREE, sign up for Robs newsletter!
Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
Ever wondered what it really takes to produce a high-quality tech podcast from scratch—while wrangling kids, late nights, and a studio in your basement?
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.
In this rare behind-the-scenes solo episode of The CTO Playbook, Adam pulls back the curtain on the exact gear, workflows, and production team that bring each episode to life. You’ll get a candid tour of his setup—from boom mics and soundproofing hacks to lighting rigs, software automation, and the husband-and-wife editing duo who shape the final sound. Whether you're a tech leader curious about content creation, or just a gear nerd wondering how to level up your own audio-video presence, this episode delivers a crisp, tactical walkthrough of what goes into building a professional podcast from the ground up.
You’ll Learn:
Timestamps:
[00:00] Introduction
[00:25] Purpose of this behind-the-scenes episode
[01:27] Who produces the podcast
[02:19] Why episodes are recorded at night
[03:00] Microphone and audio gear overview
[04:00] How the audio is routed and optimized
[05:05] Acoustic treatment in the room
[06:00] Webcam, monitor, and lighting overview
[07:15] Lighting gear and why it's travel-friendly
[08:25] Background lighting setup
[09:25] Software used to control lighting
[10:22] OBS setup and live scene switching
[11:45] Using Riverside and production handoff
[13:08] Desk setup and standing comfort
[14:10] Music used and its personal connection
[15:00] Using the setup for coaching calls
Want to start a podcast like this one? Book your free podcast planning call here.
Resources Mentioned:
Shure SM7B Microphone | Website
Elgato Low Profile Wave Mic Arm | Website
Sennheiser IE 200 In-Ear Monitors | Website
RØDECaster Duo | Website
Amaran 100X S | Website
Aputure Light Dome Mini III | Website
Keep It by Justin J. Moore and Mortiz Houwen | Spotify or Apple
Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
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