Clap for me, idiots

From the makers of “We’re Like a Family” and “We Value Your Feedback.”
Clap for me, idiots

Come on, old man.
We’ve done this a million times before.
I can’t believe we let them talk us into another one of these.

In principle, sure - quarterly all-hands sound like a good idea.
A chance to rally the troops, celebrate success.

But really?
We’re so close to retirement. Do I really need to keep showing up for these?

Shut up. Yes, you do. You can’t afford to retire. If you wanted peace and quiet, why’d you marry the second wife?
Five more years.
Five more years, and then we’re done.

Alright. Game time.
Big smile. Give ’em your trademark “Hello everyone!”
Tell them to interrupt you anytime with questions - and then let it hang, awkwardly, as you stare down anyone foolish enough to try.

I probably should’ve looked at the slides Amanda put together.
But how bad can it be? It’s your company. You’re the CEO. You know everything about your company… right?

Well, I should. I’ve been at all those weekly leadership calls.
Weird we keep calling it “leadership,” as if I’d ever let them decide how to execute by themselves. No, no - they’ll follow like their mortgage depends on it.
Can’t call it “management,” though.
What is this, IBM? Not doing that again!

Focus.

Right. Nearly the end of the year. Time to talk about “how we did” and “the road ahead.”
Ah yes - the old tightrope walk.

Things are great! Happy clients, exciting projects, bright future ahead.
Just - don’t leave. Don’t leave me. Please, God, don’t quit.

But not too great. Don’t want anyone getting ideas.
Every year it’s the same damn question: “What about pay increases?”
What about them? Start your own damn company. You try making payroll every. Single. Month.
Do they even know how hard it is?

Stay on track.

Tell them we’ve got a great sales team-our funnel… no, our pipeline - is looking healthy.
Complete confidence.
In fact, we’ve already got most of next year booked.
Well… almost.
Verbal commitments. Nothing on paper, per se, but you know… Strong growth signals.

Thread the needle.
Amazing results.
Exciting future.
Constant crisis - now’s not the time to be spending money on frivolous things like bonuses, raises, or a Christmas party.

I mean, it’s not like it’s my fault - it’s the market.
“External economic factors.”

“The federal government…” - a real crowd-pleaser.

“People just aren’t spending right now.”
Perfect. They’ll project their own little lives onto that.

We have to stay competitive. Keep prices low.
“We’re expensive in the market.”
No - better: “We’re expensive compared to our competitors.”
Nice and vague. Who are our competitors? Who cares?
Just wave your arms, say, “We shouldn’t compare ourselves to Big Tech,” and pivot.

Now, reaffirm that we “stay committed” to the company’s goals… we never did get around to defining them. But you know, everyone should know them by now.

Oh! Throw in that the leadership team has been “revisiting the strategic vision” and that “we’re tracking well against our five-year plan.”
Then keep. Your mouth. Shut.
Don’t add a number. Don’t give anyone something to remember later.
Just “we’re tracking well.”
As if there’s some sort of plan!

Better make a quick mention of all those seniors that left. Nope! Not doing that.
Er… nod to our “strong hiring” and how we’re “excited to see so many new faces.” Faces that can barely shave.
Interns are people too - half-price people.

Then it’s a quick sign-off.
Hand off to the VPs to “deep dive into The Plan.”

Then it’s drinks.
Dinner at that steakhouse you like.
Expensed, obviously.

Now I remember why I do this.
Big smiles.
Showtime!

Clap for me, idiots.

The Absence of Outrage
Hire like a CTO: three simple rubrics to save you from 'maybes'

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.