2023-08-27

Looking at this it looks like I failed to write anything yesterday - which ironically I thought about a lot yesterday but didn’t act upon because I had assumed that I had already written it in the morning. Which means that with two failures in the first two weeks that makes the whole thing rather more optional than I had initially desired.

But a long weekend is as close as I get to proper vacations these days so perhaps I should cut myself a break. Even the nightmare-fuelled Duolingo owl allows for you to save a streak occasionally to allow you to not fall off the streak wagon for the sake of life happening from time to time.

In this particular case I have to say that it has been a long couple of days. Certainly nothing in comparison to the start of August when we had some unexpected house guests. But long days with the kids outside of their natural environments is hard.

With the little one, it’s always incredibly hard to find a nap venue and to get him to sleep for as long as he needs. Yesterday, he slept for 40 minutes and then screamed directly into my face for the remaining 1h20 that he’d normally be asleep. Amazing!

The real challenge however is with the big guy. He just doesn’t listen. Or remember. Anything. Yesterday he thought it would be a good idea to start diving into a Jacuzzi. You know with ceramic edges just below the surface for people to sit on. His mother said not to, I shouted at him to listen to his mother and not to. He immediately dives in and misses a skull injury by a cm or two.

It’s just so exhausting. How are you supposed to have any fun with a kid if you’re going to spend half the day in a time out?

I genuinely don’t know how many times this week I’ve answered “What is an hour?”

Or had to correct a version of “Montreal is a country” “What country is this?”

I’m genuinely getting to the point of thinking that dog training with a clicker and treats would be more effective.

It’s getting harder too, when I can see the personality of the two year old coming in and being sharper. The two year old has worked out to reliably stop at intersections and look for traffic. The seven year old has been nearly taken out by a Porsche and a 7 ton truck this weekend alone.

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2023-08-25

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2023-08-28

How do you define successful engineering leadership?

The Philosophy

Many view technical leadership as being the “smartest architect in the room.” I see it as the opposite. My job is to build a room where I don’t have to be the smartest person because the systems, culture, and communication are so robust that the team can out-innovate me.

The Strategy

  • Alignment: Does every engineer understand how their sprint task impacts the company’s bottom line?
  • Velocity vs. Stability: We aren’t just “shipping fast”; we are building a predictable, repeatable engine that doesn’t collapse under its own weight at the next order of magnitude.
  • The Human Growth Curve: Success is when the engineering team’s capability evolves faster than the product’s complexity. If the team feels stagnant, the tech stack will soon follow.

What is your approach to scaling technical organizations?

The Philosophy

Scaling isn’t just “hiring more people” - that’s often how you slow down. Scaling is about moving from Individual Heroics to Organizational Systems.

The Strategy

  • The 3-Continent Perspective: Having managed global teams, I focus on “High-Signal Communication.” As you grow, the cost of a meeting triples. I implement “Asynchronous-First” cultures that protect deep-work time while ensuring no one is blocked by a timezone.

  • Modular Autonomy: I advocate for breaking down monolithic teams into autonomous units with clear ownership. This reduces the “communication tax” and allows us to scale the headcount without scaling the bureaucracy.

  • Automation as Infrastructure: At petabyte scale, manual intervention is a failure. I treat the developer experience (CI/CD, observability, self-service infra) as a first-class product to keep the “path to production” frictionless.

How do you balance high-growth velocity with technical stability?

The Philosophy

Technical debt isn’t a “bad thing” to be avoided; it’s a set of historical decisions that no longer serve you. Like any loan, leverage can accelerate growth when investments payoff. But if velocity and returns are slowing you need a payment plan before the interest kills you.

The Strategy

  • The ROI Filter: I don’t refactor for the sake of “clean code.” I don’t refactor a micro-service with no users. I refactor when the pain on that debt - measured in bugs, downtime, or developer frustration - starts to exceed the cost of the fix.

  • Zero-Downtime Culture: Especially at scale, stability is a feature. I implement “Guardrail Engineering” where the system is designed to fail gracefully, ensuring that a Series B growth spike becomes a success story rather than a post-mortem.

  • The 70/20/10 Rule: I typically aim to dedicate 70% of resources to new features, 20% to infrastructure/debt, and 10% to R&D. This ensures we never stop innovating, but we never stop fortifying either.