what’s one thing that you think it's critical to know, in order to really understand your community?
TL;DR: there's not one thing, there are many. And your only way to understand the communities is to switch from back-office to front-office.
Back to some previous dark days, I remember someone1 mentioning staff "having panic attacks" when using the SE network. Because they were afraid of the way people "greeted" (read "attack") them. Others2 were talking with community members and, even on controversial topics, always had well-received messages, conversations and exchanges. With all due respect on both sides.
Face the everyday duties of the volunteering community members, such as welcoming new contributors, answering, editing, cleaning, tooling (flags and so on...)
People work hard, spend hundreds of (unpaid) hours every year in order to build a library of knowledge. Some of us surely do that elsewhere too. I give time and (little) money to Wikipedia. They too need some money. They ask for some financial help sometimes. So we can understand it's an important part to have money to survive, but we can't make it our top priority or main goal.
Why do we do that? Share, build and help. We don't need to monetize our time and work. On the other hand, SO/SE wants and does.
Yes, we can keep building, but we need help. Tools. How many discussions on meta about the tools? About every aspect of what that community needs for the volunteers to work, come back, and stay? You're treating us like a worldwide fast-food chain would behave with their customers. No matter the bad food, if they don't come back, some others will, and will replace them. Too big to fail? Sure? Or one day, someone will ring the bell and say: this is the worst restaurant ever, and it'll spread around like a bonfire?
We can't be heard by people who don't know what we mean when we ask for something because they can't understand it. Of course, these people don't understand it because they don't use it.
Sometimes, we feel like we're asking for something intended to make our work/life easier, and that it's understood as time-consuming and resources-consuming. On the other hand, some changes are made that have a (very) negative impact on our work. They may improve SO/SE for the eys of future investors, but they are impopular for the community because it doesn't help, sometimes, it even worsens the whole toolbox.
Why, when we're disappointed/upset about some changes (that happened without us, the end-users, being consulted), why does SO/SE focus on the criticism instead of the heart of the problem? Do you think that hiding the problems will solve them? Of course not. We are not the problem. Modifications that are done the wrong way are. How do you realize they're wrong? Use them. Everyday.
1. I do remember that person, but no name-calling.
2. Don't worry Yaakov, Shog, Robert, Jon, Catija (and many others), no name-calling either :)