Watch people work

[name|Friend], we talk a lot about outcomes over outputs and how engineers are supposed to get us over the water, not blindly build a bridge because someone asked for a bridge. But how do you do that in practice?

Watch people work!

We tried this on my team and it has been wonderful.

Grab the person whose work you plan to improve
Sit in a room (or a call) with them
Just watch them work. As close to normal as possible. Ask them to narrate what they're doing

Does it feel annoying? I bet it does. Are they using a bunch of weird workarounds you didn't think of? Bet they are. Dealing with broken shit you long forgot was there? I can almost promise. Get every engineer nice and annoyed. Make them feel the customer's pain (user empathy). Frustration Driven Development is the goal.

Your job's not done until engineers could do this work without throwing their laptop out the window. 😈

Trying a new experiment:
At the beginning of a project (to automate a task), every engineer spends one hour doing the job.

then they keep doing this every week

project is done when your grumpy engineers don’t hate doing the work
— Swizec Teller (@Swizec) April 6, 2026

We ran 3 of these sessions last week and found all sorts of things:

users couldn't place a certain type of high value low frequency order. Fresh bug, first customer support request. We got lucky
a button went missing and for months support has been performing a workaround for users because they thought we removed it on purpose
support answers a lot of brain-dead easy questions because our site doesn't feed users the right info at the right time
having more info on support tickets is not the bottleneck we thought it was (our plan was to instrument this)
our support spends a lot of time doing expert work that users should be able to do themselves, but don't have the tools
support spends a lot of time writing very similar emails (templates exist but nobody likes or maintains them)
we found a miscommunication between support and product – we changed how something was supposed to work but forgot to change how support handles it, oops
our finance team deals with a lot of bad software and has built up a bunch of cargo culty beliefs – 4 clicks to run invoicing even though 1 click does everything
the finance team has a process that spans 6 different pages across 3 different tools. They do this multiple times per day. It takes hours. They're not sure how it all connects but if you do things just right, the company stays running
during this multi-hour process, if you scroll to the 2nd page of some tables, dropdowns stop working. You can work around this by opening yet another page and editing there ...

I wish we could fix everything [name|], but it's like spinning plates. One top priority at a time.

The trick is to find your biggest levers and focus on those.

We could fix the UI our finance team uses, sure, but that doesn't remove the problem. Why are we making them do this work at all? Automate.

We can give support more info on tickets and they'll be marginally faster at resolving. You know what really helps? Helping our users ask fewer questions.

Cheers,
~Swizec

PS: once you've got the frustration, find a way to measure. This lets you track progress over time.