Jonathan Feldman

Digital Business, No Human Sacrifice. Chief Information Officer, IT rehab coach, award-winning writer, public speaker.

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Of Overlords and Organizations

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Here’s a post-mortem about my column, “Stop Being A Hated IT Overlord,” in InformationWeek on June 14.

My thought process as I was writing this: Most of the bad things that happen in the world of work are the result of disengaged employees. Most people feel like they’re slaves or prisoners working in a mineshaft, not free spirits who are working because they want to work. If we could fix this … wow.

I was inspired by three things in this column:

1. Fast Company contributor Mark Crowley’s excellent mental model of employee engagement in the US: “Imagine a crew team out on the Potomac River, where three people are rowing their hearts out, five are taking in the scenery and two are trying to sink the boat.”

2. My brilliant writer friend, Wade, wrote some vignettes about “Moloch13”, a dystopian dreamscape that I loved even before I knew he wrote it.

3. Spotify has done some really interesting work in terms of creating differently structured teams than the traditional workplace.

I tend to be guided by the Einstein principle (“The definition of insanity is doing the same thing over and over and expecting different results”), so I naturally came to the conclusion that if we want the situation to change, we probably need to do something differently.

My modest proposal: if we change our organizational structures, perhaps we’ll get different results. I’m interested in following Spotify and other startups as they grow.

One thing that I didn’t say in my column that probably needs to be said is that frequently, startups have this great thing going, and then all of a sudden, some VC decides that company XYZ needs to start being a real company.  Then they bring in a real CEO, and then they start acting like a real overlord, and people start getting real miserable.  We’ve seen that happen time and time again.  Small wonderful startup becomes gigantic horrendous company.  Exceptions like 37signals exist, but they are few in number.  (If you’ve not read Rework, do yourself a favor and do it.  Now.)

This propensity of “we’re not a real company until we start to make people miserable” kind of bothers me.  It should bother you, too.

Filed Under: Better Worklife, Writing Report

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Copyright © 2025 Jonathan Feldman. All opinions expressed are his, not those of his associates or employer.