Lessons from re-organising a lot

Jason Yip
2 min readFeb 21, 2022


Prompt: “re-organizing a lot”

2 things that don’t work; 11 things that seem to work

What doesn’t work but still keeps popping up (especially when new leaders join)

Cargo culting FAANG

Any variant of “this is how I did it at my last job at [insert FAANG or other tech firm]” without any other rationale.

Going dark

Managers do all the thinking about org design, workers just follow, because “we don’t want to distract them” or “they’re not mature enough to deal with it” or “that’s why we have managers”. AKA Theory X.

What seems to work

Draft share decide

A smaller representative group initially drafts an org design which is then shared with a wider group for feedback.

I wrote more about this here.

Use everyone’s experiences, not just the leaders.

“The actual subject matter expertise and influence necessary for a successful re-org goes beyond the formal leadership team.”

I wrote more about this here.

Push autonomy as much as you can.

“No involvement, no commitment”

Dr. Stephen R. Covey

Having people actively sign up or express preferences avoids the “I didn’t sign up for this” problem.

I wrote more about this here.

Big announcements are just for show, actual feedback comes from small group discussions.

If you only make announcements, you are trying to not get feedback.

Approaches like Cindy Alvarez’s 6-person discussion are better.

If you wait for people to come to you to provide feedback, you don’t actually want feedback.

Office hours are waiting for people to come to you. Only the most active people will participate.

Team visits or scheduling small group discussions is actively seek feedback.

The first person everyone will talk to will be their manager and/or influential role models — make sure they’re ready in advance.

Use your managers and influencers. Make sure they’re ready, and not surprised.

Repeat the message until people complain about hearing it.

There is a reason why advertisers don’t just run ads once.

If you have coaches available, use them.

Because coaches are outside of the reporting line, people have a tendency to be more willing to share feedback. This is a useful way to learn about issues more quickly.

Use simple, direct language not corporate, weaselly language.

Less syllables, less words, get to the point.

Anticipate problems and prepare beforehand.

The more involved version of this is a pre-mortem. The less involved version is just thinking about what might go wrong and address those things in advance.

Structure should follow strategy

The first thing you should be concerned about in a re-org is not org structure. The first thing is product strategy. The second thing is technical architecture. The third thing is ways of working. The last thing is org structure.




Jason Yip

Senior Manager Product Engineering at Grainger. Extreme Programming, Agile, Lean guy. Ex-Spotify, ex-ThoughtWorks, ex-CruiseControl