Automate toil away

I think there’s an immense compounding return to automating away the toil in daily work.

What is toil?

Basically “paper cuts” or “pebbles in your shoe”.

These could be processes that are needlessly complicated — like having to click around a whole lot to accomplish something simple.

Or it could be something slow, like a search bar that makes the whole page lag with each keystroke.

Or it could be something that’s error-prone and often requires rework.

Ultimately, toil is the feeling of friction in your daily work.

The ugly snowball

Unfortunately, mess begets mess.

When processes are time-consuming or annoying, we’re less likely to go through them. That’s just human nature.

The problem is that often times going through these processes is a part of improving daily work.

For example, if the process for getting code into production is toilsome, you’re less likely to make small improvements.

You’ll find yourself saying “Eh, this small thing doesn’t warrant the whole song and dance of our deployment process.”

And, over time, the lack of maintenance will add up.

The organization will likely end up with weird work-arounds to make up for quirky behaviors. Learning all of these quirks will take newcomers more time, and it’ll take longer for them to become productive contributors to the team.

Noticing toil

Before you can automate toil away, you need to know about it.

Ask folks to highlight the toil that comes up in their daily work. Big or small.

At Clever, a lot of our engineering efforts went into helping our sales and customer success teams be more efficient.

I created a slack channel called #toil and asked folks to write down all the pebbles in their shoes.

This surfaced things that might have otherwise gone unnoticed and were actually quite easy to improve.

For example, a lot of time was spent clicking through to different pages and gathering information about customers and real estate agents. (Clever provides a matching service.)

Building a single page that summarized all of this information was an easy win.

This kind of thing happened all the time, and it made the team more productive and the work more enjoyable.

Rolling up sleeves, not complaining

Highlighting toil and complaining are dangerously close to each other.

The key difference, in my experience, is a willingness to roll up your sleeves — and it has to come from everyone on the team.

At Clever, our engineering team was quite small. That meant that we couldn’t fix every pain-point.

A big part of my job was doing cost/benefit analyses for potential improvements.

Our stakeholders were awesome about this. They understood the constraints and helped us prioritize.

For lower-priority pain-points, they helped each other out and documented their work-arounds and processes, until we eventually got around to improving the tooling.

Writing as “automation”

In fact, we discovered that — if you squint — writing can be a powerful form of “automation”.

Documenting the toil and workarounds often gave rise to: “Hey, actually I have a faster way to do this!”

Having a written down processes helped us teach newcomers more quickly, surface improvements, and understand the problem in detail when we eventually had the engineering resources to deal with it.


I was honestly astounded by how much we managed to automate at Clever.

In some cases, they were quick improvements. In other cases, large projects.

The through-line was identifying an extremely critical process — connecting customers to real estate agents — and continually finding ways to streamline it further.

Throughout, having a clear understanding of what made us special was important: the human touch — the concierge feel. We aggressively automated, but never at the expense of that core value proposition.

That combined focus and clarity was addictive.