2023-08-20

Sunday morning writers block. It was going to happen sooner or later, but I assumed it would be a little later than three days into the exercise. Then again, this is sort of the whole point of the exercise - to write even when there’s nothing to write. Perhaps, just maybe, these are the days that turn out to be the most valuable. As, when there is nothing in the front of mind it actually yields an opportunity for the more important stuff to come forward.

Yesterday, for instance, I started with some simple observations about a supermarket and that quickly turned into an internal reflection on happiness in 500 words or less.

I think that reflection is warranted and long overdue. I’ve been asking myself a lot recently about what I want - but haven’t taken the time to really sit down and inspect those feelings. Which means that my brain defaults to the same worn out paths. Walking the same circles and loops, without ever progressing very far before something interrupts and resets the whole process over again.

I remember, one weekend finding a quiet bench in a park outside of Rehovot and taking an afternoon to really take my time in assessing whether I was leaving academia. What was it that I really wanted to do.

Once I moved to Canada, and had essentially no luck in finding a job for six months, I took an afternoon and found myself a quiet corner of the local community centre to sit down and write out three scenarios of what I wanted my future career to look like.

I guess I have responded well to setting out a vision in the past, as it allows me to have a tangible plan to execute against. When I’ve discussed this with mentees, I’ve approximated the advice to once you have a destination, every decision becomes binary - it either takes you closer or further away from your goal.

Perhaps this is as true as it has ever been. Perhaps I’m just wired to require a goal to pursue.

But I can’t help but feel maybe this time it’s different.

Maybe I should be pivoting my outlook on life.

By every tangible metric, I’ve got a very successful life. It’s everything that I had ever envisaged as a teenager. I have the loving life. I have the two amazing boys. The mortgage on a place with a view of trees (that I’ll pay off before I’m 60). Heck, I’ve even got a job that pays me well, doesn’t feel like an oppressive corporate prison, where people respect and trust my opinion.

It just sucks that I’ve been so conditioned to be moving on to the next thing, rather than to stop and smell the roses.

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2023-08-18

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2023-08-19

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.