The CTO Playbook

Duri's father holds more than 100 patents, filed his latest one at 96, and gave him a one-line philosophy that now drives how his teams approach every problem: most people don't try.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.Most CTOs think AI failures are technical problems. The data says otherwise, and the gap between a good idea and a great product is almost never where engineers expect it to be.My guest today is Duri Chitayat, CTO at CINC Systems, leading a 170-person globally distributed product development team across four continents with a background spanning AdTech, MedTech, Banking, and FinTech.What stood out for me in this conversation was how willing Duri is to question the assumptions other leaders treat as fixed. He grew up around an inventor with over 100 patents, and that shaped a way of thinking that strips problems down to first principles before touching a solution.The stakes here are real. Innovation tokens are finite. Spend them on the wrong assumption, and you lose the race before you knew it started.Our conversation moves through a six-part playbook for leading engineering in 2026, the leadership paradox that breaks most CTOs, and why measuring transformation honestly is harder than anyone admits. If you're leading through an AI shift right now, this one is for you.You'll Learn:[0:00] Introduction[3:00] What growing up around a 96-year-old inventor with 100+ patents taught Duri about first principles[4:54] The difference between writing code and delivering solutions, learned the hard way on an SAP rollout[7:29] Mount Fuji problems versus dancing landscapes, and how to spend your innovation tokens wisely[12:59] Why the customer hanging a picture frame isn't really trying to hang a picture frame[14:55] Finding the borders of the box you didn't know you were in[24:22] Duri's only juniors are named Claude and Codex, and how he hires senior talent globally[28:03] How the RFC process creates earned trust and stops Duri from running roughshod over smart engineers[32:07] Walking through the six-part playbook[40:33] Why tokens burned is the new lines of code, and what to actually measure insteadResources Mentioned:Your Strategy Needs a Strategy by Martin Reeves, Knut Haanaes, Janmejaya Sinha | Book or AudiobookFind more from Duri on LinkedInFind 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.

The reps that used to turn juniors into seniors are disappearing, and most engineering leaders won't notice until the senior shortage hits in three years.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.Your dashboards say velocity is up, your seniors are asking careful questions nobody wants to answer, and your juniors are getting confident faster than they're getting capable. I'm a coach for CTOs across startups and enterprises, and this is the pattern I've been hearing in coaching conversations for the last six months.It usually arrives as unease about velocity or quality. By the time we trace it back, it always lands in the same place. Does our boilerplate still earn its keep in an AI-accelerated world? One camp wants to lock it down further. The other wants to delete half of it. They're both right, and they're both wrong.The argument is a symptom. The real question is bigger, and almost nobody is pricing it in yet. Our most experienced engineers got their judgment from reps we can no longer reproduce. Our juniors aren't getting those reps. If we don't design a replacement, we'll wake up in a few years with a senior shortage and no good explanation for how it happened.This episode is about the scaffolding that fixes it.You'll Learn:[00:00] Introduction[00:22] The unease CTOs can't quite name yet[01:48] Three warning signals hiding inside a healthy-looking engineering team[03:45] Why both sides of the boilerplate debate are right and wrong at the same time[05:59] Why boilerplate is no longer just about code, it's doing three jobs now[08:44] The hidden dial between your code base and your AI that most teams haven't noticed[11:21] How senior engineering judgment was built and why AI has removed the mechanism[12:39] The senior shortage nobody sees coming and why your scaffolding is part of the answer[14:58] A five-step playbook for redesigning your scaffolding as a judgment toolFind 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 redefining one simple phrase could change how your entire organization delivers value?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.Why does the definition of ‘done quietly’ determine whether engineering effort turns into real business impact? In this episode, I share a coaching story from a CTO leading a busy organization where motion looked like momentum, but nearly everything stalled just before completion. The teams were working hard, yet features lingered in limbo, ownership blurred, and frustration built across engineering and product.There is a mental model that reframes software delivery using a familiar sports analogy, showing why writing code or merging branches doesn’t move the scoreboard. Impact only happens when work reaches production, is absorbed by the organization, and enables the next move. This lens exposes how excessive work in progress stretches timelines, fragments focus, and erodes fulfillment for senior engineers.I talk about what changes when leaders stop tracking activity and start insisting on outcomes. For anyone responsible for CTO leadership, engineering productivity, or scaling teams without burning them out, this conversation challenges how you measure progress and where you apply pressure.You’ll Learn:[00:00] Introduction[01:12] How teams stay busy yet fail to move the business forward when finishing is unclear[02:08] What happens when too much work in progress creates motion without results[03:07] Why writing code and merging branches do not equal business impact[03:56] How the basketball scoreboard analogy reshapes what done really means[05:14] The leadership question that exposes activity over outcomes[06:41] What changes when nothing new starts until something is fully done[08:27] How redefining done restores ownership, focus, and team satisfactionFind 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.

Are you running faster with AI, or just running blind?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.Most teams don’t lack data, they lack understanding. Today, I sit down with CTO Jason McGhee, who has spent years inside analytics, machine learning, and product teams asking the hard question: why is the data changing?AI in analytics works best when it supports human judgment instead of replacing it. A hybrid approach keeps people involved while AI assists with complex tasks, making decisions clearer and systems easier to reason about. Moving faster with AI increases risk when teams cannot explain why the data is changing.Both recurring reports and one-off investigations break down without context. Dashboards often fail as real deliverables because they separate numbers from explanation. Insight becomes more actionable when it is shared alongside the data itself. Screenshots, slide decks, and disconnected tools add friction, making validation harder and discouraging deeper questions from leaders.If you care about data-driven decision making, want a more honest relationship with machine learning outputs, or are figuring out how generative AI fits into real-world business analytics, this conversation sharpens how you think about data, trust, and momentum as a technology leader.You’ll Learn:[00:00] Introduction[02:45] Why more data doesn’t help if you can’t explain what changed[05:12] How keeping humans in the loop changes AI analytics failure modes[09:48] Why dashboards break down once they leave the builder’s hands[14:32] How AI turns big analytical questions into auditable steps[20:41] Why one-off and recurring reports need shared intuition to work[27:18] How screenshots and slide decks quietly block data validation[34:55] Why faster AI increases the risk of running in the wrong direction[43:07] How mixing structured data with Slack adds missing business context[57:26] The leadership cost of treating analytics as outputs, not understandingFor more information you can also visit writ.so.You can connect with Jason on his personal LinkedIn or his business 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.

Your most powerful decision engine isn’t your data, your dashboards, or your AI, it’s your gut.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.There is a topic that most technical leaders quietly wrestle with: gut instinct. Not as mysticism. Not as guesswork. But as a real decision-making tool for modern CTO leadership.This episode is all about why your instincts are often your experience compressed into a feeling, when you should trust that signal, and when you absolutely shouldn’t. You’ll hear real coaching stories from seasoned CTOs navigating technical leadership, roadmap trade-offs, scaling engineering teams, and high-stakes calls where the data wasn’t enough. We’ll talk about how engineering leadership changes when you treat instinct like a cached function, fast, powerful, but sometimes stale, and how to validate it without killing its speed. This episode is for startup and enterprise technology leaders who want sharper judgment, fewer regret-filled postmortems, and more confidence saying, “Something about this feels off, and here’s why.”If you’ve ever ignored your gut and paid for it later, or trusted it blindly and been burned, this conversation will give you a practical way forward. It’s about building better instincts, not just better systems.You’ll Learn:[00:00] Introduction[01:02] Why seasoned CTOs sense problems before they can explain them[03:18] How ignoring gut signals leads to overcommitment and roadmap failure[05:07] What gut instinct really is — experience compressed into a signal[07:26] When instinct fails in new or emotionally charged situations[09:41] How to spot where your instincts are strong, weak, or distorted[12:12] Treating instinct like a cached function — fast but fallible[16:34] Using gut instinct as a warning without turning it into dogma[20:18] How data can validate instinct without slowing decisions[24:47] A playbook for sharpening instinct under pressureFind 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.

The real reason invoices don’t get paid has nothing to do with accounting.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.Late payments aren’t just annoying, they quietly drain focus, energy, and leadership bandwidth. In this episode I sit down with entrepreneur Maximiliaan van Kuyk to discuss why trust in business payments is breaking down, and what CTOs can do about it.Drawing on years of experience across startups, agencies, and global markets, Maximiliaan explains why accounts receivable is no longer just a finance function, but a leadership and systems problem. They explore how late invoice payments persist not because people are malicious, but because incentives are misaligned, and accountability is invisible.You’ll hear why consistency beats confrontation, how social accountability in business can outperform legal threats, and why CTOs should care deeply about cash flow management even if they never touch invoicing.If you’ve ever felt the quiet frustration of waiting to get paid, or watched payment delays impact runway, morale, or growth, this conversation will reshape how you think about trust systems, AI in accounts receivable, and the future of getting paid on time.You’ll Learn:[00:00] Introduction[02:18] Why getting paid is really a trust problem, not a money problem[06:41] How chasing payments drains founders emotionally and why it usually lands leadership[10:52] What happens when small businesses become accidental lenders, and why the system works against them[15:37] Why consistent follow-ups beat confrontation and legal threats when recovering unpaid invoices[21:04] Why late payments persist even with contracts and how incentives shape behavior[27:56] How social accountability changes payment behavior faster than reminders or credit scores[34:48] Why reputation only works when it’s visible, and what hidden payment history enables[41:22] Why CTOs need to understand cash flow risk even if they never touch invoicing[48:09] How tracking payment behavior could reshape trust, partnerships, and who gets hiredYou can connect with Maximiliaan on Instagram or find his work on his website 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.