Our Research and Development team working on Teach to One Roadmaps at New Classrooms has had, admittedly, some crazy ideas. I tend to get a lot of latitude, but I’ve recently been subjected to weekly performance reviews where I’m told, multiple times, that my work isn’t good enough. On top of that, I’m accountable to multiple people, so even when I manage to eke a moment of delight from one of them, I still have to face the frustration of all the rest.

I treasure these times.

As a trained researcher, the first thought in my head is always: How would I know if I’m wrong?

As hard as it can be to see substantial amounts of work go unnoticed and unappreciated, I still think it’s much better to know that it’s a waste of my time to keep working on it rather than to keep trudging along on an idea that just isn’t worth the effort. And sometimes I learn something. Every time I’m surprised by the feedback I’m receiving, that’s a chance for me to realize that an assumption I made was wrong, to recalibrate my priorities, or to discover a new and important aspect of the problem I’m working on.

It also helps that my (many) bosses are so nice about it.

And that there’s snacks.

So every Wednesday afternoon, when schools are just letting out for the day, I mentally prepare myself for another brutally honest and honestly fun meeting with my seven bosses and their sixth-grade teacher.

We usually start with a review of the work that my team has done since our last meeting. I’ll pull up some data about student activity on our math education platform, and we’ll look at the amount of time it takes students to complete different activities and their pass rate on some of our hundreds of skills. We’ll workshop our current problem focus(es) and then break out a prototype or two.

That’s when things get unpredictable.

See, my bosses know the target user better than anybody. They know what “Labubu” is, all the hip anime, and what in the world is going on with “6…7…”. So I try not to tell them what I’m testing with a given prototype, because when they spontaneously comment on something else (like how the example text is confused with the current problem), I often realize that I was the one missing the point, not them. And in those rare moments they’re delighted by something, it’s usually a bug I didn’t have time to fix (like how some of the problems are randomly skipped), and I’m suddenly adrenaline-thinking about the implications of my shattered mental models.

That’s usually the point where I give up on doing my job and just ask one of my bosses to do it for me. We pull up some prototyping tools and I hurriedly assemble their rapid-fire feedback into an interactive experience we can both look at and react to. I’ll be honest, sometimes the vision gets lost in translation, and I get sent back to work for the week to figure out how all the pieces fit together to make what they actually wanted.

We’ve moved faster and had much better ideas ever since we started doing these regular check-ins with my multiple bosses. We’ve built over 50 prototypes and replaced core designs multiple times in the last 3 months, and we’re just getting started. But this would have been impossible without their sixth-grade teacher in the room to facilitate the meetings, to explain, to motivate, to inspire, and to give them hall passes when they need to go to the bathroom.

So really, I wrote this post to say thank you to all the teachers of the world, who enable the work of my bosses, myself, and my whole organization. Let’s keep working together to make this world a better place!

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