The CTO Playbook

Quantum computing may not be breaking your security today, but the decisions you make now could determine how exposed your organization is when it does. Conor Deegan explains why CTOs need to start preparing before Q Day arrives.

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.

My guest this week is Conor Deegan, a security engineer, cryptographer, and co-founder of Project 11, focused on helping organizations prepare for the transition from classical cryptography to post-quantum cryptography.

The quantum threat goes far beyond Bitcoin and digital assets. Conor explains how quantum computing could eventually affect the cryptography behind banking, communications, cloud infrastructure, authentication, health records, and everyday internet security.

He breaks down what "Q Day" means, why organizations cannot simply wait until a powerful quantum computer exists, and how "harvest now, decrypt later" could put sensitive information collected today at risk in the future.

The transition also comes with real engineering challenges. Post-quantum cryptography can require more computing resources, memory, storage, and bandwidth, while legacy systems and constrained devices such as IoT hardware can make migration even more difficult.

Conor then shares a practical framework for CTOs: understand the threat, put someone in charge, identify critical systems and data, take the easy wins, put pressure on vendors, and stop creating migration debt.

You'll Learn:
[0:25] The Quantum Threat and Why It Matters
[3:54] Understanding Q Day
[7:52] How Quantum Computing Impacts Security
[11:22] The Mission Behind Project 11
[18:58] Harvest Now, Decrypt Later
[21:30] The Challenges of Post-Quantum Cryptography
[27:29] From Engineer to CTO
[30:20] A Practical Quantum Security Plan for CTOs
[36:56] Identifying Critical Systems and Data
[41:03] Taking the Easy Wins
[43:12] Preparing Vendors for the Quantum Transition
[43:57] Avoiding Migration Debt
[45:59] Building Crypto Agility
[48:35] The Quantum Challenge for IoT
[54:50] Preparing for Q Day

Find more from Conor Deegan and learn more about Project 11 through his professional channels: projecteleven.com, X, and LinkedIn. Conor welcomes direct contact on post-quantum migration questions.

Find more from Adam on https://www.linkedin.com/in/adamhorner/ and https://www.youtube.com/@TheCTOplaybook, and explore coaching, cohorts, and how you can stay up to date at the https://www.thectoplaybook.com/, helping you build your own playbook for your path at your pace.

If you prefer listening, check out the podcast at https://bit.ly/thectoplaybook.

Twenty years at one company should have made my guest predictable, and that is exactly the trap he built a method to escape.

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.

Krystian Kolondra runs the browser portfolio at Opera, a set of products used by more than 300 million people, and he has spent two decades watching what happens to technical judgment when the work that built it starts to disappear.

His argument is uncomfortable. Your judgment was earned through execution, and AI compresses execution. So what is training your judgment now?

His answer starts somewhere I did not expect: an audit of the questions you stop asking. He calls it the shape of your curiosity, and he thinks most leaders have never looked at theirs.

We get into why he refuses to check AI's output and flips the task back on the model instead. There is a sniper analogy that reframes what "learning from failure" actually requires. There is a story about Opera GX where the first questions his team asked turned out to be the wrong ones, and the right ones only appeared once they went somewhere uncomfortable.

If you lead engineers, and you have felt the ground shift under what "senior judgment" means, this conversation gives you something concrete to practice tomorrow morning, before your first coffee.

You'll Learn:

[0:00] Introduction
[5:46] Twenty years at Opera and the business behind free browsers
[7:18] Why leading five hundred people is a different job entirely
[9:39] The temptation to stick with what already worked
[12:39] Curiosity as a counterweight to accumulated experience
[17:44] How the gamer browser came from asking the wrong questions
[23:26] Learning from failure means planning the shot before firing
[29:06] How AI compresses execution but never the judgment
[36:14] Auditing the questions you never ask to find blind spots

Resources Mentioned:

A Beautiful Constraint by Adam Morgan and Mark Barden | Book
Theory of Constraints by Eliyahu M. Goldratt | Book
Really Achieving Your Childhood Dreams (aka The Last Lecture) with Randy Pausch | TED Talk
Eric Ries, Validated Learning | Wikipedia
Igor Grossmann | Website
A route to well-being: intelligence versus wise reasoning by Grossmann, I. et al. | Article

Unlock more ways to make your browser yours with deeper personalization and an expanded modding universe with the Opera GX Gaming Browser here.

Find more from Krystian Kolondra 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 CTOs think adopting AI means picking the right tools, but Sumeet argues the real work is closing the accountability gap between agents and engineers.

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.

My guest this week is Sumeet Vaidya, co-founder and CEO of Crafting, who spent years at Facebook, Uber, and Discord before building the infrastructure enterprise engineering teams now use to put agents to work safely.

His perspective matters because he sees what CTOs say publicly, and what their teams are actually doing internally, and the gap is bigger than most leaders want to admit.

Roughly 80% of enterprise engineering orgs, he estimates, are doing close to nothing meaningful with AI. The rest are either reacting to hype or trying to build something durable, and the difference is not the tools they pick.

One partner running 3,000 agents against 250 engineers changed how he thinks about capacity entirely. That number is where his six diagnostic questions come from and where the cracks appear first: brittle CI/CD, accountability gaps for agents, and a hiring pattern that's storing up debt for the next downturn.

If you're under pressure to show AI gains while cutting token spend, this one is aimed at you.

You'll Learn:

[0:00] Introduction
[2:25] The disconnect between what companies say and what teams do
[4:38] Why 80% of enterprises watch and wait on agents
[9:31] Chasing the latest model as a vanity metric
[14:14] Resilient cultures survive shocks that short-term thinking cannot
[15:46] The engineering cultures that shaped Sumeet's career
[28:51] Silicon Valley is not the whole world
[33:02] What breaks if you 10X the team today
[42:31] Hiring only senior engineers stores up hidden debt
[47:11] Turning engineers from code writers into builders

Find more from Sumeet Vaidya on LinkedIn, X, or explore the Crafting 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.

Ask a CTO which executive relationship matters most, and they'll name the CEO, but my guest today would send you to the CFO instead.

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.

Anoop Tripathi is 32 years into a career that spans from writing firmware for telephone exchanges to sitting as CTO at Sauce Labs, and he's unusually direct about what decides whether your technical work gets funded.

Most of us step into this role believing the job is to be the strongest technologist in the building. Anoop thinks that's the fastest way to build an organisation of people waiting for commandments from the top.

The conversation gets sharper when he talks about scaling an engineering team from zero to over 100, then having to bring it back down to 70 in a tough market. His lessons from that period are not the ones I expected.

There's also a serious defence of laziness as an engineering virtue, a story about resellers walking out of a Citrix demo because the product was too good, and a framework he calls SHAPE that he uses to run his own career.

Fear is the dominant feeling across my coaching practice right now. Anoop's take on what that fear is costing tech leaders is worth contemplating.

You'll Learn:

[0:00] Introduction
[2:51] The double-edged sword of laziness as an engineering trait
[7:18] Reframing tech debt as a business outcome your CEO hears
[10:24] How investor pressure and a faster POC upended the Citrix integration story
[18:01] What he learned cutting a team from 100 to 70
[26:19] Spotting an inflection point before hindsight makes it obvious
[29:50] Fear you plant in your head tends to come true
[32:52] The SHAPE framework for tech leadership
[47:44] One piece of advice for a first-time CTO

Resources Mentioned:

Sauce Labs | Website

Find more from Anoop Tripathi 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.

I nearly turned my own summer into the cautionary tale. The thing that saved me was a last-minute week in the Swedish mountains.

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.

I came home with a small number of clear thoughts about my business that I couldn't have produced at my desk, and they fade fast once you're back. This episode is for anyone heading back into work in the next fortnight, because how we come back in late August shapes the rest of the year more than almost anything else in September.

Real intent goes in on day one. The stack gets attacked head on. Two or three weeks later, we're extremely busy and have moved nothing forward.

There's a spaceflight analogy in here about why the most dangerous part of any return is the descent, and the one small decision that sets the angle for everything after it. Most of us come in too steep, and the queue gets to decide what matters so we don't have to. The cost is specific: the decisions only you could have made never surface, because they're never the loudest thing in the queue. There's a practical exercise at the end.

You'll Learn:

[0:00] Introduction
[2:05] The summer move that nearly made me the cautionary tale
[4:16] How spacecraft reentry explains a bad return to work
[6:52] Why late August beats January for real resolutions
[9:36] Career trains every leader to choose the steep angle
[10:52] Heavy first week is the friction doing its job
[12:37] Naming your own re-entry angle before the queue decides
[17:14] A controlled re-entry playbook in four steps

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.