I mentioned last week that my son recently started high school, and I can say with 100% certainty that the time and place in this world that gives me the most anxiety right now is the high school parking lot during morning drop-off. It’s chaos. There are all manner of signs and cones and every form of transportation you can think of: buses, cars, bikes, motorized scooters, skateboards, roller skates…even the maintenance guy is zipping around in a golf cart. And of course it goes without saying that the crowds of high schoolers are ignoring those aforementioned signs and cones and behaving unpredictably. I’m sure at some point I’m either going to hit something or get hit, so I’ve learned to take it pretty slow.

And learning and dealing with that made for a pretty frustrating first week of morning drop-off. See, my son is on the swim team and they practice before school and since we live a ways out of town, we had to develop a new routine to get him to practice and then showered, fed, and back to school on time (does your teenager eat as much and as often as mine?). Developing this new routine was a challenge relative to the established routine we had for middle school drop-off. That routine, honed over three years, enabled me to drop him off, write these missives, run, and shower all before 8am every day. 

The first week of high school drop-off was not nearly as productive. We were hurried, stressed, and late because neither he nor I were allocating our time efficiently and there was even one day when he had to wear my shoes to school and I went barefoot to the office because someone dropped the ball.

So he and I sat down at the end of the week and held a retrospective. I said, I don’t think this new routine is working well for either of us and here’s what I need from you for it to work well for me. Then I asked him what did he need from me for it to work well for him? With new agreed upon standards and procedures, we tried again the next week and it got better! We’re not a finely tuned machine quite yet, and I still need to figure out how to fit some things in, but we’ve both been consistently on time, less stressed, and wearing our own shoes, which I consider a win.

The lesson, of course, is that new systems and routines never work well right out of the gate and that if you expect them to, you might end up frustrated and barefoot. Instead, whenever you implement anything new, you also have to commit to putting in the time and energy to iterating and improving. And that’s the mindset we’re asking everyone involved to have with regards to implementing our new boards of directors and annual planning process at our portfolio companies. I think what we’re doing now is better than what existed before, but it’s certainly not perfect, and so we want everyone to feel empowered to speak up to help it work better and better for everyone over time. 

– Tim

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