You cannot kill the sidekick

I have spent quite a bit of time discussing end-game wisdom for the high level engineering leader. I am going to change gears this week and talk a little about some of the things that are more helpful in the early half of your career.

When I first started my career, I will confess that I had a pretty myopic view of work. Ideas go in, code comes out, and profit taking ensues. The value chain looked short to me; we were entering the age of meritocracy in the very heart of silicon valley. Fully decked out in nerd apparel and armed with role-playing dice and leftover pizza, this was the coming of age of My People. There was no better time to be alive!

I could not help but notice that my view of the giant rose-strewn field that was Startup America had some kind of minor irritant; some kind of pollen that made my nose stuffy and my eyes water. What was this? Why did it mar this near-perfect experience?

Slightly confused, and incredibly curious, I decided to dissect the very world around me in real time, much like a lonely surgeon on a desert island needing to disinfect a small but insidiously deep wound. Much like said surgeon, my diagnosis and correctional tools were crude and medieval.

What I found should come as no surprise: The teams that I worked on had flaws. Not everyone was up to par with the high level of work output some of us were producing, and this meant that there was inefficiency. The internal alarms sounded! It was time to take action! How did this impostor get into our midst?

I am going to take a moment here to pause for a second. Younger John Szeder was very quick to protect his teams and his products. The Older, Wiser John Szeder of today looks back on that time with more than a little regret. By no means should anyone take this as a playbook on “what to do when confronted with team inefficiency”, but a cautionary tale. Let’s continue.

Naturally, I went on the offensive. It is easy to look at the numbers and the output and demand accountability. I really enjoyed seeing the ROI on projects I was associated with; I wanted everyone to participate in such a wondrous financial reaping. In some cases, there were people who were in the company who struggled to get good results on their projects, and I felt like they had no place in the merit-based paradise we were trying to build. I would try to “help” them. This had varying degrees of success. As someone who specialized in computer science, and saw college electives as a great way to pad one’s understanding of Arthurian Legend and Shakespear, I did not take many management science classes. The fault here is mine, honestly, even though nobody told me better.

One pattern that invariably emerged through all of these attempts at team optimization is that a form of resistance manifested itself. In between my best work of creating things and disassembling teams that were not producing, I had met an immovable object that I slammed into with my unstoppable force.

Let me introduce you to The Sidekick.

This is a dark pattern that I have observed over a few decades now; I still truly believe this. I understand it better now that I am closer to a functioning adult than ever, but I want to make sure that you understand this pattern in its entirety before you throw away years like I have.

I have been blessed to work with many successful visionaries and leaders over my career. They are all human. They all have their strengths and their weaknesses. Sometimes their weaknesses manifest themselves in the form of an individual who follows them along from opportunity to opportunity. Maybe they see this as a strength, maybe they see this as training their successor, maybe someone has incriminating photo evidence. I don’t know. All I know is that sometimes you will find that they will have themselves a Sidekick.

They may have marginal utility, if you are lucky, but often they resemble a home improvement project in one very specific way. They are an unfinished eyesore that requires love and attention to turn into a beautiful part of the house. I did not always have that vision, nor did I have the patience to deal with that sort of thing. I generally traded high on the “take equity” side of startup compensation; the presence of a Sidekick interfered with my desire to create high ROI on said equity.

So what did I do? The thing that most super-villains naturally do. I went after The Sidekick.

I am going to get to the outcome here before going further. TL;DR: This is a Bad Idea. Do not do it.

I do not know the full extent of the relationship that exists between a boss and their useless sentient appendage, all I know is that the The Sidekick possesses unnatural powers; You cannot kill The Sidekick.

There is a certain amount of Dilbertian truth to some of my professional career, and this is one of those moments; I can only look back at it and laugh because the alternative is to cry.

When confronted with this moment, and you clutch your high amounts of equity in one hand, and your sword of self-righteousness in the other, all I can do is ask you to stop. Breathe. Reconsider.

This battle will go poorly for you, and probably for everyone around you.

Take a moment to reflect on why this person is here. In the rare case where this person winds up being your boss, you may feel a need to run, and promote yourself to Not Working Here Anymore. Regardless of that feeling and your relationship to The Sidekick, you should not take sudden action. Whatever you do in your manufactured urgency, you will probably regret when you get to my age.

So what should you do? Welcome to the silver lining moment of this particular dark cloud. For starters, have a little faith in your leadership. They have reasons for hiring people, and even if you cannot see them, it is worth learning what they are. Resist the urge to weaponize them. One of the things I did not do in early experiences with The Sidekick is spend enough time working with them or attempting different ways of helping them.

The nice part about a startup is that it is a twisted sort of laboratory experiment. You can try things, and get paid for it at the same time! Use this situation for what it is; an opportunity to refine your tools for overcoming roadblocks, rather than screaming, stepping on the gas, and closing your eyes. As much fun as it was at the time, you mostly wind up just wrecking things.

The one thing you are not likely to wreck with that strategy? The Sidekick. That person is invulnerable. Please identify them as early as possible, and whatever you do, please do not attack them. You. Cannot. Kill. The. Sidekick.

Thanks again for reading. This was probably the most therapeutic article I have written out of all of them. I hope it hit you in the feels, and you feel compelled to socials. I like your likes. I read your comments. Thank you for reading along this week and I look forward to sharing continued learnings with you all!