It's amazing what you can learn watching someone else do their job.

We just switched accounting systems at my HOA: 350 monthly invoices, 19 employees, hundreds of vendor payments flowing out from a half-dozen bank accounts.

All in Cantonese, English, Mandarin, even some Spanish. It's an operation.

One of the other board members stormed in. He seemed surprised I was sitting at the table with the staff, "wasting time" folding invoices—why wasn't I working on something higher-value?

I didn't want to get into a big argument, so I sort of ignored him, and he left. But it's been on my mind ever since, and I realized I've lived through a lot of these big change projects, and have learned a thing or two.

First, before you automate or change anything "broken" or "stupid", you'd better have a little humility and understand how things work now, and why it got that way. In my hotels work, I often found "stupid" things, that turned out to be clever workarounds for problems that came up doing the job. There's no way to see this stuff from behind a monitor; you have to get into the environment—go do the job. Before you make any kind of technology system, go stand shoulder-to-shoulder with your users; go experience the fast pace of a commercial kitchen, the noise of a construction site, or the chaos of a hotel's front desk. You'll learn more than you can imagine.

Second, once you understand the process, do it once or twice by hand. You'll learn a lot about what's hard and what's easy, and where the errors crop up. Often, things that seem "easy" are impossibly difficult, and those that seem hard almost never happen, meaning it's not worth handling them in code/automation; humans are slow, but they're great at dealing with weird cases you didn't anticipate.

And finally, as a leader, showing your face is powerful. In times of difficulty or stress, knowing the leadership has your back—seeing them shoveling right with you—can be a tremendous morale-enhancer. Management by wandering around really works.

Hard, important things take a long time and have lots of little steps. You have to play the long game, and sometimes that means taking a bit of time to thank people, and help them, when you know they're doing something hard. For my part, I make sure to notice when people go out of their way to help me, or make my life easier.