I spent nearly all of my 30-year tech career in middle management. I managed teams that built and delivered web and mobile business applications.
I intentionally stayed in the middle management bracket, where I was paid well and typically worked 40 to 45 hours most weeks. This meant I had enough time to build a real-estate side business. Doing that helped me achieve my goal of early retirement.
In 2024, I left my corporate job and live off my real-estate passive income.
My retirement at 59 came as the wider tech industry began eliminating many middle management positions.
Big Tech companies like Microsoft, Amazon, Meta, and Google have been trying to flatten their company structure by removing managers. Google’s CEO, Sundar Pichai, has said this is to increase efficiency, while Amazon’s Andy Jassy, who has said he wants the company to run like the “world’s largest startup,” has suggested that removing management layers can cut bureaucracy.
Although I really enjoyed working and learning as a middle manager, I did occasionally question the value I was bringing at that level.
I worked in startups and bigger companies alike
Beginning in the late 1990s, I worked in both engineering and middle management roles for a few small startup companies.
These startups maintained a flat management structure where the CEO worked directly with individual contributors to quickly make key decisions and deliver software products. There were few middle managers, and little bureaucracy. This leaner model meant we had fewer scheduled meetings and fewer roadblocks to building out products.
In the startups I worked for, everyone was focused on rapidly solving problems to reach the objective. Your job and future stock awards were based on the team’s ability to focus and deliver quickly. Teams could make and execute plans more rapidly without the bureaucracy of a middle management layer — the reviews and approvals that middle managers tend to oversee in larger companies often only slow things down.
When I worked in tech roles at larger companies, my role often involved monitoring progress and confirming that software development teams were meeting the project timelines. I was responsible for explaining the delays to senior management and recommending improvements to avoid future hold-ups.
I spent significant time relaying status updates to the leaders above me and directives to the individual contributors below me. From working at startups, I knew that this back and forth could be reduced in a leaner management environment.
While working at larger companies, I also noticed that fiefdoms began to thrive due to the large number of middle managers.
Fiefdoms, a well-known phenomenon in tech, are essentially siloed groups of workers who are closely controlled by middle managers. These managers oversee what information about the group they share with the rest of the company.
I noticed that fiefdoms often benefited managers. By overseeing a larger head count, they had a greater perceived value. However, it unfortunately ended up isolating teams and departments from one another, leading to duplicated efforts across the company due to limited communication between groups.
On several occasions, my team and I would spend months building out a new software solution only to learn upon presenting our work that another manager’s silo of engineers had already built out a similar one.
This is a management fiefdom scenario at its worst, and it negatively impacted morale. My team members were furious that their efforts had been wasted because of the lack of communication.
I’m not sad to see middle managers go
I built my tech career in middle management, so it may seem odd that I recommend removing the very role I once performed.
But after working in tech for over 30 years, I’ve witnessed significant wasted effort, duplicated results, and territorial management practices in the traditional, heavier middle management model.
There may be disruption and some confusion until the new model has fully worked itself out, but I expect that flattening companies will ultimately create leaner, better working environments.
Do you have a story to share about middle management in tech? Contact the editor, Charissa Cheong, at [email protected]
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