Hi Reader,

(If you're just joining me—welcome—and want to catch yourself up, here's a link to all my past newsletters. The first one in this series was called "A brief project(ed detour)")

One of the perks of being a parent of young kids is getting to see a lot of learning happening firsthand. That's a challenge sometimes, but it's been helpful when reflecting on this batch of newsletters.

Some things are easy to teach because you can point to them or touch them or otherwise easily have someone else experience them. My kids haven't burned themselves on the stove yet. In part that's because of our vigilance, but it's also due to the fact that they know what hot is from trying food that's too hot, and from watching us cook and having us put their hands above the burner or in the steam and pull them back quickly saying, "hot!" They can easily associate (or at least I imagine they can) an experience with a concept, and quickly learn to avoid burning themselves.

Other things are harder to teach. The other day my wife used the word trust and our toddler asked what that meant. Take a minute to think how you'd answer that question for a two-year-old. You can't force someone to experience trust. It occurred to me, though, that you CAN look for situations where someone is already experiencing trust. Later we told her (the toddler) that she feels trust when daddy throws her up in the air, because she knows he's going to catch her.

As we go down the stack in my model, things get harder to teach because they're harder to point to:

It's easy to point to how the platform is supposed to behave. It's like showing a first grader one apple plus one apple. Surely we can do better than that in our corporate training, though!

But it gets significantly trickier even just one level down. I'm often surprised, for instance, when I ask one of my junior teammates to look at a screenshot of an issue and tell me what they see. They often miss things that are completely obvious to me. (I am just as susceptible to this, by the way; just ask my wife how bad I am at finding things around the house.) The tricky part in training isn't pointing out the thing they missed on that individual screenshot. It's getting them to generalize the kinds of things they could look for in any screenshot. The only way I've ever learned to do that is through repetition.

I was fortunate to have a dad who's an engineer, so from a very young age I was being handed stuff and encouraged to tear it apart to figure out how it worked. So I had a big head start. But really I think the trick here is developing a troubleshooting curriculum. There are some out there, and in the interests of being informed I should probably make the time to explore them. What I mean, though, is that there's certainly nothing like a degree in troubleshooting. And the skills one needs to be a good troubleshooter can be subtle. There is a process to it, sure, but there's also observation and creativity. Thinking about how to teach those hasn't given me any easy answers so far.

A non-comprehensive list of some of the subtle basic skills I employ when troubleshooting, that I've noticed other people struggle with:

• Compare and contrast: looking at two similar things and pointing out the differences.
• Ordering: given a list of things, how many different orders can they be put in? How can it be done systematically?
• Specificity: putting a given list of things in order from general to specific
• Connectedness: how interconnected is a thing? What might it impact or be impacted by? This also relates to...
• Likelihood: how likely or unlikely is some effect related to some cause?
• Seriality: what order might things have happened in versus what they should have?

I don't have any magic tricks for teaching this stuff, other than patience and repetition, and letting people make mistakes so they can learn from them. If you have any ideas or stories about how you learned some of these kinds of skills, I'm super interested to hear them!

Alright, I had planned to do all four boxes in this newsletter, but it's already longer than I expected. I had hinted that there was good and bad news. Most of what's above is the good news: this stuff CAN be taught. I'm not so sure about the next two boxes (other-awareness and self-awareness). They seem much more like trust to me: not so much teachable as they are point-outable experiences. Maybe that's bad news.

Or maybe we'll see something new in next week's newsletter!