3 Mistakes I’ve Made When Starting Up (and will probably make again)

I have the privilege of meeting a lot of highly effective people who are early in their career, and in the process of joining a new company or team. One of the most interesting parts of this experience is watching them make the same mistakes that I’ve made when I’ve been in the same sitation before.

Here are the top three that seem to jump out at me the most often:

Conforming to the average schedule of the team

I’m naturally a morning person; if I haven’t started on something productive by 6:30am, it’s going to be a bad day for me. As a general rule, I like to have my most important work done by 11am.

Some of the most unproductive times in my life have been when I let myself be dragged into the work schedule followed by the rest of my team. I definitely think it’s important to have 3-4 hours of overlap in working hours, but I often see people new to the game sitting around on their laptops “reading articles” way past when their brain has shut down and they don’t want to be the first to leave.

I learned to fight that urge. I still lose the battle once in a while, though, and I always pay for it the next day.

Refusing to set boundaries

When you first start on a new project or join a new team, there is a period of time where you’re learning what everyone else’s working habits are. It’s tempting to be “on call” all the time during this period. This can mean allowing interruptions at any time, or being connected to email / IM from the moment you wake up until the moment you go to sleep.

It’s also very easy for this “adjustment period” to stretch onwards into infinity.

This is another thing that has been disastrous for me in the past. I’ve actually found the inability to set “do not disturb” times during the day to be even worse for me than staying having to stay connected all night, since the former often necessitates the latter.

I’ve also found that certain personalities won’t ever respect these boundaries. It took me a while to accept that this is my problem, not theirs, in the sense that trying to change someone like that is going to be a fruitless battle. I’ve had this behaviour crop up in supervisors, clients, etc., and I’ve had to develop strategies in each case for dealing effectively with such people. This is a whole topic on its own, though, so I’ll leave this one for another time.

Trying to change things too drastically, too soon

Here’s a scenario I see pretty often: Let’s say you’re an engineer who has had the opportunity to learn the best engineering practices from your previous job experience at places like Facebook, Google, Twitter, etc. You decide to join a smaller company with maybe 10 engineers on the team where you can “make a greater contribution.”

So you sit down on the first day, check out the code, and build it… only to find that the build is a manual, 7 step process. All the “unit tests” are broken, but still take 16 minutes to run. You take a deep breath, go to your first scrum meeting… which drags on for over an hour.

And so on.

If you’re especially optimistic, your first instinct might be one of elation. “I have so much I can help them with!” you may think. And it’s true; there probably is a lot you can help them with.

But not right now.

Unless you’ve been specifically tasked with the job of “fixing things”, take your time with it. Get to know your teammates first. Go for coffee or lunch with them; learn about their lives as human beings first, and as coworkers second. My general rule of thumb is that I’ll know I’m in a position to tentatively suggest real changes to someone when I can first comfortably call them an asshat and not get in trouble for it.

I’m sure there have been exceptions to this rule in the past, but I personally haven’t witnessed any. Trust has to come before change. If only I’d learned this a decade ago, I could have my past teammates and myself a lot of unnecessary angst.

I know I’ve made these mistakes before, and I’ll probably make them again. But at least next time around, I’ll recognize when it’s happening.

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