I used to work somewhere where there was a very active and visible gaming culture. Some of the games were virtual, but a large portion of them were physical or based on physical games. Monthly game nights featured strategic board games which took several hours to play. Think Risk, but more complicated. At lunch every day, there was usually at least one table playing card or board games of some sort. Spades, hearts, and games most people have never heard of were standard fare. The players at lunch were all quite analytical. Card counting was common. If you weren’t aware that your six of diamonds was going to win the trick when it was played, the other three people in the game probably knew and could recall the last three tricks played. The games were quite competitive.

My game of choice was spades. I liked that it was a very strategic game. You could play the same hand several different ways depending on what other people had and bid, and what the progression of the hand turned out to be. In this environment, I probably won more games than I lost, so I fancied myself a good spades player.

One Saturday I sat down play me some spades online to pass the time. I had to sit at a beginner’s table because I didn’t have any sort of reputation. I got paired with some other “rookies”, and started playing. It turned out to be a huge exercise in frustration.

People would take forever to play out their cards. My partners would disconnect mid-round, leaving me with a loss. They would play abysmally, bidding far too high or low for the hands they had, and then going blind-nil in situations where it didn’t make sense to try to claw back. Unfortunately, while I tried my best, my reputation on the gaming site kept going down. Then the real pain started. Since my reputation was lower and I was out of the provisional period, I would get paired with partners of similar “rating”, which meant that I kept getting paired with worse and worse partners.

I stopped playing shortly after I recognized the death spiral going on, but was puzzled by the failing. Then I remembered one of my friends who was a competitive Halo player, and one of the keys to getting ahead in that game was to have a clan that could help each other train and compete together. He got really annoyed when his clan members didn’t show up to play or played poorly.

I immediately related these two. Imagine if I had taken a skilled player as my partner and we just sat at the same table and played together. Over time, we would get to know how each other plays, and start to be more strategic. We would trust the other person to not play stupidly, and have an underlying philosophy of what is going on.

Some takeaways

The lesson that I try to apply more broadly was: I have to take ownership of picking my teammates, or I will suffer the consequences.

If I am not proactive or intentional about working with people that are good at what they do and who I enjoy working with, I have only myself to blame and only I will see the negative effects of this. This is true if you are an employee, where you need to pick the organization that you want to be a part of. It’s a warning sign if you look around and aren’t excited about the prospects of who you can work with. This line of thinking is as or more applicable if you are on your own doing consulting or contracting.

Making “the awesome people list”

I think it’s useful to make a list of the people that you might like to work with some day. Maybe some of these are colleagues that you admire, others are people you’ve met, a role-model or two, or even people you just know through social media who seem interesting. More often than not, when I revisit my list, I realize that I have actually ended up associating with those people since the last time I looked at the list. Part of this effect just might be thinking about those people a little more and realizing when your paths cross. Sometimes they will be a little ahead of where you are in a certain skill, and other times it’s the reverse. I think the list helps me point out where I can grow, and to challenge myself to keep trying to get better.

I also think it’s pretty easy to mitigate risk by working with people informally before working “for real”. You can learn a lot about someone by working on a side project, picking their brain about sales in SaaS businesses, co-organizing a meetup, and so forth. I’m not sure that this strategy scales well, but it seems useful for finding good people to work with.