Ep 6. What Are You Optimizing For?

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In this episode, we’re diving into a deceptively powerful question:

What are we optimizing for?

This question has shaped how I think about my work, how I collaborate with others, and how I make decisions in the chaos of scaling. It’s simple, but it’s transformative.

And as always, my hope is that you walk away with at least one thing to think differently about, and one actionable step to help you show up as a rad — or even more rad — human at work.

Speed, Price, Quality, Efficiency… What’s the Goal Here?

We default to getting things done.

We’re in a scale-up. There’s a backlog of priorities, everything feels urgent, and “done” becomes the holy grail.

But done doesn’t always mean done properly.

This is where our first Chaos of Scale guideline — Pause for Quality — comes back to save us from ourselves.

A great example: my team once decided to have one-on-one calls with all 190 of our highest-value customers.

If we were optimizing for efficiency, this would have been an awful approach.

But we weren’t optimizing for efficiency.

We were optimizing for relationships. For connection. For deep insight.

The way you work changes entirely when you shift the optimization lens.

Connection Over Speed

In one of my roles, I depended heavily on leaders across the business to deliver what I needed. The fastest route? A good old-fashioned group email.

And we all know what happens to group emails: Nothing.Because a group email is everybody’s noise and nobody’s work.

So instead, I sent individual messages with a reference to something meaningful:

a band they recommended, a great presentation they gave, a recent win, etc.

Was I optimizing for speed? Absolutely not. I was optimizing for connection while getting things done.

And it worked. People respond when they feel seen.

Knowing the Goal Helps You Shape the Plan

I do this in my personal life too. When I go running, I start by asking myself: What am I optimizing for today — speed or distance?

If it’s speed, I structure the run around ideal paces.

If it’s distance, I plan segments that keep the whole thing manageable.

The same principle helped us overhaul a company website once. We didn’t want to “tick off” a website review. We wanted the highest quality insights possible, so we divided the work page by page, device by device, browser by browser.

It was painstaking — but the results were exceptional.

Because we were clear on the optimization goal from the start.

Efficiency Isn’t Always Fast

Sometimes optimizing for efficiency means slowing down now to speed up later.

This is countercultural inside a scale-up, where everything feels like:

Go. Go. Go. Ship it. Get it done. Move quickly.

But sometimes the fastest way to the finish line is actually a strategic pause.

Use the Question in Team Conversations

One of my favourite moments to ask “What are we optimizing for?” is during brainstorms, especially when designing something new.

Because you’d be amazed how misaligned people can be:

I might be optimizing for sales. Someone else for speed to launch. Someone else for product lifecycle. If we’re all optimizing for different things, we’re solving different problems.

Another powerful partner question:

What does success look like?

Together, these two questions set the destination and the route.

Example: Getting High-Quality Input

Let’s say you need data or feedback from multiple teams.

If the goal is simply “Get it done,” great — send a short email, set a deadline, hope for the best.

But if the goal is “Get high-quality input,” you’ll approach it totally differently:

• Write a clear, detailed brief.

• Spell out exactly what you need.

• Explain the context.

• Remember guideline two: Beware the Curse of Knowledge. (What’s obvious to you is not obvious to them. They’re busy. They’re distracted. They’re skimming your message.)

If you want quality, you must set them up for success.

So, Before You Start Running… Ask the Question

What are we optimizing for?

Because the answer will dramatically change:

• The pace you move at

• The process you choose

• The way you communicate

• The level of quality you aim for

• The relationships you build along the way

Inside the chaos of scale, where a hundred things are coming at you at any given time, this question becomes a compass.

Your Action Item:

The next time you start a project, or you need something from someone, pause and ask:

What am I optimizing for?

If it’s:

• Getting it done → great, move fast.

• Building relationships → slow down and connect.

• Quality → write the proper brief, clarify the context, and help them help you.

Let your optimization goal guide your actions.

It’s one of the most valuable tools you can use in The Chaos of Scale.

If you found value in this, share it with someone navigating similar challenges. And if you haven’t subscribed yet, please do — it really helps others find these conversations.

Business growth is messy, but the human side doesn’t have to be.

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