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The gift of leaving

Change is valuable, because it lets the oppressed be tyrants...
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(Like this article? Read more Wednesday Wisdom! No time to read? No worries! This article is also available as a podcast).

When I was younger, so much younger than today, I was already an insatiable reader. Unfortunately, I lived in a small village with a mediocre library that didn’t let kids borrow from the adult section (and rest assured: These were not “adult books” in the same way that there exist “adult movies”). The Internet didn’t exist yet and the book store in the village was not impressive. I therefore spent a lot of time going to the nearest big city which had a very good book store. At that time, the book store was located in some weird dungeon below the street level in the main shopping street of the city. Above the staircase that led down into the dungeon was an imprint of a truism by Jenny Holzer: “Change is valuable, because it lets the oppressed be tyrants”.

That sentence always fascinated me because so many things in our society seem ruled by this idea. First and foremost the political arena of course, where the cycle of elections throws one set of people out and brings the other people back into power. They then say (stupid) things like: “Elections have consequences” and “We have a mandate, and it’s time to get to work”, as if there is no overarching narrative of society that they are only playing a small part in. I always found the mandatory cycle of change in politics refreshing. If something good is going on, it might be a bit depressing to realize that it will inevitably end, but on the other hand, if there is something bad going on, you can rest assured that this too will come to pass. Sometimes, someone manages to cling on to power for too long (former Dutch prime minister Mark Rutte comes to mind), but all in all, politicians with that amount of staying power are an exception in functioning democracies.

Companies are clearly not democracies and often not functioning very well either, so there is no systematically mandated cycle of change going on. People can stay in power for decades and it is not at all clear that that is a good thing. CEOs specifically face regular criticism for staying too long; Jack Welch of General Electric comes to mind. When CEOs stay too long, there is often no shortage of a lack of innovation, a failure to adapt to changing markets, and internal scandals. Often, when they eventually do leave, things continue to go downhill.

There are of course examples of business leaders who stayed a long time and who are or were mostly phenomenal at their jobs. Warren Buffet, the renowned Oracle of Omaha, comes to mind. However, I would like to suggest that these people are the exceptions that affirm that there is in fact, a rule.

But, Wednesday Wisdom is not an article series for CEOs and heads of state. Instead, it seeks to be helpful to the 99% of us: The aspiring CEOs and aspiring heads of state who are currently toiling in the trenches, waiting for their big break. So let me shift my attention to the more mundane world that most of us live in.

When I joined YouTube in 2012 as a staff software engineer, looking to help build the SRE team in Zürich, I was quickly made aware of the existence of “OldTubers”. These were people that had been with YouTube for a long time, often from since before the acquisition by Google. As YouTube grew and grew, especially after said acquisition, they were spread out across the organization. They were a force to be reckoned with and it was quickly explained to me that if I wanted to get traction for my ideas, I would need to find a few OldTubers to support them. It was also explained to me that if my ideas were opposed by the OldTubers, they would be as good as dead in the water. Even directors and newly minted VPs often lacked the political capital to oppose the OldTubers.

The OldTubers were famous for clinging to old ideas. When I joined, YouTube was still mostly running in their own data centers instead of using Google’s hyperscaler infrastructure. It was completely obvious to me that this was not tenable, but the OldTubers resisted the move to Google’s ultra reliable and low cost infrastructure because they valued the level of control that their own data centers provided like not having to deal with Google’s data center division and its immovable change management and maintenance procedures. But, when hurricane Sandy hit, we spent one full day transferring essential services from our east coast datacenter to the one on the other coast and then another full day transferring services back when New York was not swept into the sea. Both of these actions took considerable effort and had user visible impact. This seemed to me a sterling reason for “moving to Borg” as we called it. However, it was not until the Snowden leaks prompted Google to increase all data center security that the YouTube data centers became impossible to defend and the migration eventually happened.

What we see at work here is the same thing that eventually catches up with overstaying CEOs: A lack of innovation and a failure to adapt to changing markets.

There were also internal scandals, but the less that is said about the Youtube ski trips, the better it probably is.

If you stay too long in a position of influence, your shadow grows long and you cast it far and wide. One of the consequences of that is that your hobby horses become holy cows, which stifles innovation. To add insult to injury, most of your knowledge is from the past and you are probably overindexed on things that are not true anymore or that at least have undergone significant change, which should prompt a re-evaluation. Many great things have been done by new people who didn’t know that something was supposed to be impossible, until they did it. As an influential person, you should not block them, but that is hard in a situation that is stressful and where you are absolutely sure that something is not possible.

Another problem of longevity is that it blocks new people from learning the ins and outs of the system. I have come across quite a few teams that were centered around a small number of senior people who had been there for a long time. Whenever there was a serious problem, one that needed in-depth knowledge to debug, the old-timers would swoop in and solve the problem. Unfortunately, problems like this also create unparalleled learning opportunities and by relying on the old guard to solve all really difficult problems, the new people only learn that when the shit hits the fan, they need to call in the heroes.

I wrote about the topic of heroism before in: Whatever happened to, all the heroes 🎶🎶: Unhappy the team that is in need of heroes…

The dependence on a small number of old-timers creates a cycle of dependence as everyone is affirmed in their belief that these people are critical for the team and cannot leave. Any new people come to believe that too and before you know it people crack jokes like: “If Wall Street finds out that Bob is on vacation, the stock drops.”

This situation gets worse over time as the once-new people get some tenure and even newer people come in. The even-newer people pretty quickly figure out that the old-timers are the real experts on the system and that it does not really matter what the now-somewhat-senior-in-terms-of-tenure people think. Really, nothing good can come from this sorry state of affairs.

Therefore, one of the best decisions you can make as a senior person is to make yourself dispensable. The moment you figure out that you are the senior technical person on your team, start working on succession planning and make sure that you afford learning opportunities for the more junior team members. Your value to the team should not be that you (consciously or unconsciously) hoard knowledge and (again: Consciously or unconsciously) block people from becoming experts too. Really, who wants to be the ops hero or right there in the critical path of everything that is going on?

Here’s a project management tip: As soon as you are on the critical path of anything, work to get out of it as soon as possible!

Not only will you be more valuable to your team by actively making yourself dispensable, it also builds a stronger and more durable network of professional connections that you can leverage for a long time. People will remember you anyway, the only choice that you get to make is how they remember you: As someone who jealously guarded their knowledge and expertise? Or as a mentor who taught them stuff and who was willing to take some risks to level up the entire team?

Ultimately, the best gift you can give your team is by eventually leaving. Not too soon, but definitely not too late either, thereby giving the people you helped grow the opportunity to be (hopefully enlightened) tyrants themselves for a while.

While you are in the gift-giving mood: Give yourself a free subscription to Wednesday Wisdom!

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