2023-09-15

Another day, another dollar. Yesterday turned out to a bit of one. It’s certainly felt like a long week this week. Enough for me to be reaching for a whisky on a Thursday night - which due immediate attention from the newly arrived in-laws about how it’s not a Friday. To which I retorted that it’s the whisky they brought from New Zealand, and it’s already Friday there.

Yes, Thursday was indeed a long day in the office. Perhaps foolish I decided to run to the office, which whilst only five and a bit km away, when you add in a backpack bouncing around with shoes, clothes and a laptop it makes for a very different experience.

City running is also very different. Dodging around the garbage cans, pedestrians walking down the middle of the sideway texting away with noise canceling headphones and that’s before the ruinous amount of traffic. I ran in reverse of my usual bike ride home so I got to see the road under the morning rush hour and school run traffic and was surprised to see the vast quantities of it. And it’s not like it’s even a fast option. Me jogging along at a very mild nine or so km/h, was clearly blowing past traffic, even with all the crossings and red lights.

All those crossings do make for some very challenging pacing though, when there’s a few seconds on the crossing and you know that these lights are long and you’ll stand there for a minute otherwise, you put the pedal down every time. Although my objective was to get to the office not as a sweaty mess, the watch told me that I’d be Z4 and practically red-lining it for 30 minutes by the time I got there.

After a quick, improvised shower with a wash clothe over the sink in the disabled toilet, I was ready to sit in a conference room for three hours with no windows. No coffee. No way out.

Executive planning for the next six months of the project you see. A noble task when considered at a high level, but the whole thing falls apart in the execution. Of the slide deck that my business guy had put together, we managed to get stuck on the first slide for the entirety. In a line I don’t think I’ve ever considered before, the problem really is that this organization truly has too many engineers and not enough visionaries. All of the technical folks are so open to everything being possible, but not wanting to be held accountable to it, and then boring you to death with outliers, edge cases and exceptions that you suddenly find yourself on a fifteen minute tangent completely lost as to where you were.

The problem really all stems from the fact that there isn’t a clear business case. They don’t know what they want. But there’s no escaping the fact that they are now 2 years and $7 million into a project with no tangible deliverable in the hands of the desired customers. If the customer has even been defined. The product team don’t want to make any decision that might come back to them, anything that might even be considered close to a decision. Which means our go-to-market strategy is very much a “we should have something for the end of Q1… unless Q1 is too soon, because we’d rather have something good and delay the timeline”. I mean, thanks for that, how am I supposed to work with that?

For a little, light relief then, still with a lack of coffee and non-croissant based nutrition I entered the mandatory training session. Which thanks to the company’s new found size being over Bill 96’s threshold, has to be in French. Challenging. Mandatory training in French.

I thought I was going to be okay, with the aid of slides and a general knowledge to the training area. I thought I was going to be okay. But then I was slapped in the face with the reality that most of my learning materials have been French French, specifically of a Parisian accent.

The facilitator of the course, instead was heavily of the Quebecois French variety. It felt like listening to a podcast at 1.5x, with all of the vowels being swallowed and merged together. It also occurred to me that most of my vocabulary has been around small talk or real-world stuff. How’s the weather? Talking to the taxi driver. That, is very different from talking about personal motivations and political beliefs in the workplace.

Further evidence and motivation that I need some business French ASAP - as if I needed further motivation.

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2023-09-13

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2023-09-17

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.