Welcome back + 4. All Systems Are Incentive Systems

June 19, 2025

Today is about accomdations and contiuning on from the previous topic

Yesterday I asked ChatGPT the question: “What are the top 10 things I should know?” and it really struck a nerve. Specifically 1. Compound Interest Applies to Everything, and 6. Writing Is Thinking. That helped me get back to writing.

Todays blog is going to be on “4. All Systems are Incentive Systems”. But first a word on why I’ve been away.


I’ve been having a hell of rollercoaster at work this last year.

Expanded responsitiblities, less accommodations, and a smaller team - from five down to three. And on the org chart our team just had a “?” for our immediate manager/team leader position.

It reminded me how important it is to have a direct manager to deal with all the bullshit and politics of work. I’m lucky my skip manager is good, but they’re stretched thin.

Anyway - I was hoping to write a bit more the last few months, but I was really treading water at work and I let my hobbies fall by the wayside.

I’d been asking to go back to WFH 3 days, in office 2 days. Had a few conversations with my boss that basically ended with “leave it with me, we’ll figure something out”.

Fast forward 3 months - nothing had been figured out, and I found out that instead we were all going to be back in the office 4 days per week. Well fuck.

I had a meeting with my boss, talked about trust, expectations, and everything we had already gone over. And made it clear that I was getting burnt out and this was the proverbial straw.

To my suprise - instead of not pushing the 4 in office, he flipped around and said I could go back to 3 days WFH, and if there was any issues from above that arose from it, the exception can be explained with the documentation I’ve already provided.

Bit of a shell shock. I guess there’s a lesson in understanding that what’s a massive deal to you - may or may not be that important to others, and if you really want to get what you need, you need to understand incentives.

Which brings me nicely to the point of this blog:


🤖💬 4. All Systems are Incentive Systems

Companies, governments, software, even friendships — follow the incentives to understand behavior. If it doesn’t make sense, you’re missing a motivator. /🤖

I tried to be aware of his incentives and motivators, but it’s all guesswork really. The first time I negotiated - I came at it from my needs. The second time - I came at it from a much more holistic place.

Where I need to improve is using calibrated questions and labels to uncover the truth inside the others head.

Anyway; Going into it: What were my motivators?

  • Looking after myself
  • A quiet space to be productive
  • Having energy left over outside work to live my life

What are my bosses motivators?

  • Not have a team under him collapse? Arrogant maybe - but we were already often down to 2 or 1 people manning the team due to sickness and annual leave. If I fell over or one of my two teammates left we’d be fucked.
  • Team cohesion and not having to explain why things are different for some people?
  • Liking the office being full of people?
  • Being afraid people won’t work if they aren’t visible?
  • ?

During the meeting:

  • I explained where I was at
  • Reminded that we’d left off the previous discussion with me to trust that he’ll figure it out
  • and I explained that my previous boss made similar promises and would backflip the next week.

I can’t recall the exact wording but it was something like: “My previous manager promised similar things, and then the next week would tell me the complete opposite - and that broke my trust. Here — it looks like the same thing is happening, and I trust you.”

Pretty shortly after that there was a moment of silence, and then he said three days WFH was fine.

I was a shell shocked to say the least.

I was already really struggling with 3 days in the office - and the bomb that it was going to be 4 dropped on me like a tonne of bricks. I wasn’t expecting to go into that meeting and get everything I was hoping for. I was just aiming for a reversal!

I know that sometimes the best thing to say is nothing at all - but it still stuns me a little bit each time I’m negotiating and I get hit by the extended silence followed by someone articulating everything you’ve been trying to get.

Sometimes you just gotta give people a momement to think. It’s not dead air. It’s space for them to move toward you.

It would have been fine to leave it there. But I didn’t leave it there.

I asked him if that was really okay - would it cause him trouble with other people demanding the same, or cause him issues with upper management who might put pressure to change?

He said it wouldn’t be a problem and then he explained why.

You might wonder why I asked that, instead of just taking the win. It was a little worrying for sure.

I didn’t want to risk making him second guessing himself; but even more than, I didn’t want someone else to either. I’ve learnt that when you open up and address someones concerns and look at it from their perspective and their needs, they tend to open up as well. And because no is the easiest word in the world, when you frame a question with “Won’t that cause a problem?” - if they’re on your side, they’ll say no, and often explain why.

Just be careful doing this if you don’t build rapport or haven’t actually empathised. If you’re fighting, they might throw it in your face, and say “yes it will, so I ain’t doin’ it!”

At the end of the day - as much as I’ve got my needs and my problems. He’s got his own to deal with - and I wanted to make sure this wasn’t an agreement that was going to be forgotten the second I left the room.


In the end, when I aligned what I was asking for with his motivators, and took an extra moment to address extra concerns at the end - the incentives lined up. And I think that’s why it worked.