How Can We Learn If Decisions Are Disconnected from Impact?

Two years ago, there was a ballot initiative in California, Proposition 10, which would enable city governments to enact rent control on any buildings. I had no idea whether or not this was a good idea, and I was going to go to my default in situations like this, which is to vote no. But I decided to check with my friend, Steph, who works in affordable housing. She was thoughtful, knowledgeable, and even, and after my conversation with her, I decided to vote Yes.

This year, there was a similar ballot initiative, Proposition 21, which would enable city governments to enact rent control on buildings that was first occupied over 15 years ago. Once again, I had no idea whether this was a good idea or not. Once again, I turned to Steph. Once again, I voted Yes.

Here’s what troubled me about finding myself in almost the exact same situation two years later: I had learned absolutely nothing. I didn’t even remember whether or not Proposition 10 had passed. (It didn’t. Neither did Proposition 21.) Even if it had, I would have had no idea what the impact of that measure was.

I believe strongly in collaboration, democracy, and the wisdom of crowds. It’s why I do what I do. And I understand why folks don’t have faith in a population’s ability to govern itself. Our track record, especially recently, is terrible.

Here’s the thing: In order to act in intelligent ways, people need to be responsible for the impact of their decisions. If we don’t know the impact of our decisions, we are not going to make good decisions.

In his book, The Signal and the Noise, Nate Silver explains that pundits are terrible at predicting financial markets, but meteorologists are exceptional at predicting the weather. Why? For starters, we are more likely to remember a meteorologist’s track record, because the feedback loop is tighter. Last night, the weatherperson said it would be sunny. Today, it rained. You’re going to remember that.

If we could figure out better ways to tie decisions with impact, I think we would find society generally doing the right things. This is obviously incredibly hard, but I don’t think it’s impossible.

Polls as a Way to Measure Alignment

For the past few years, I’ve been thinking about developing a training called, “The Art of Aligning.” Aligning groups is fundamentally what my work is about. Like all things related to collaboration, I feel like folks can learn how to do it well by practicing.

I originally envisioned it as a face-to-face training, and I wanted to incorporate lots of somatic experiences to remind us of what alignment actually feels like. COVID-19 has pretty much put the kibosh on that for the time-being, but I think you can still develop a good training without it.

My approach to helping a group align is the Squirm Test, which consists of articulating what you think is the shared understanding of the group, and watching to see how much squirming happens while you talk. If no one squirms, you have shared understanding, which is a prerequisite for alignment.

Said another way, you help a group align by constantly testing for alignment and by making the results visible, so that the group itself can make adjustments accordingly. You’re essentially creating a tighter feedback loop than what normally exists when all you’re doing is tracking behavior.

I realized today that polling in elections is a manifestation of this same principle with all the same flaws. A poll is an attempt to measure alignment at various stages. Similarly, the Squirm Test is essentially a behavioral survey.

Polls are, by definition, imperfect. I continue to be baffled by people’s critique of polling in their post-presidential election analysis, because they seem not to understand this. Polls give you a guess as to where people are, so you can adjust your tactics and strategies accordingly, but at the end of the day, it’s still a guess. At least with elections, you have a clean measure in the end by which to see how off your polls were. In most things in life, we have to hand-wave those assessments also.

Bottom line: Alignment is hard.

A Quick Note on Probability and Strategy

As folks continue to monitor the presidential elections, I think it’s worth revisiting an important truth about probability and strategy.

If someone is given a 90 percent chance of winning something, that means if you replay the same scenario 100 times, that person wins on average 90 times.

Ninety is not 100. When you only get to play that scenario once, and the person favored to win 90 percent of the time loses, that doesn’t necessarily mean that the probabilities were wrong, and it doesn’t necessarily mean that the strategies that resulted in a loss were wrong either. They all could have been wrong, but it requires much deeper analysis to evaluate that.

If there’s a silver lining to the last two presidential elections, it’s that we’re collectively learning this in a very visceral way. The better we understand this, the better we’re able to make strategic decisions and prepare ourselves for different outcomes. It’s not just true in presidential elections, it’s true in business, and it’s true in life.

Professional poker players understand this. (I highly recommend Maria Konnikova’s The Biggest Bluff for more on what we could learn from professional poker players on strategy and decision-making.) Bill Belichik understands this. Nate Silver and the good folks at Five Thirty Eight are constantly trying to explain this to the rest of us. It’s very human not to understand this, but it’s helpful to keep trying.

The Uncanny Valley of Leadership

I’m a reasonably responsible voter. I vote pretty much every year, including off-years, and I do my best to educate myself on the issues. I’m lucky to be surrounded by folks who are extremely engaged, and I often “consult” with them on issues or candidates I don’t know well. Sadly, “consult” often means simply voting the way my friends tell me to vote.

Four years ago, disturbed by the direction our country was moving, I took a hard look in the mirror about my own level of civic engagement. Because I was already spending a good amount of my professional time working on national issues, I decided to focus my personal time on local issues. It was an easy decision, because I quickly realized how ignorant I was about what was going on in my own neighborhood, much less the city of San Francisco.

I started attending local meetings (which bear a shocking resemblance to the meetings on Parks and Recreation) and reading up on local issues. I met my Supervisor, whom I had voted for, but whom I had known nothing about. I learned that San Francisco has a $13 billion (!) budget, and that roughly half of this money comes from self-supporting services, such as public transportation (although this has changed dramatically, thanks to the pandemic). It seems like I should have known all this stuff before happily asserting my civic rights, year-after-year, but I was happy to finally start correcting this.

Flash forward to today’s election. About a month ago, I looked at my ballot, and I was troubled to discover that I was no better equipped to make decisions this year than I was in any other year.

For example, there were seven candidates running for Supervisor in my district. I tried to read up on all of them, which helped me narrow the field to three, but didn’t help me beyond that. San Francisco has ranked choice voting, which meant that I could vote for all three (which I did), but it didn’t help me with the order. I ended up voting for the person endorsed by the current Supervisor. I happened to run into her at a neighborhood restaurant (after already voting for her), and she left a good impression, but good impressions — while important — don’t seem like the best criteria for making these kinds of decisions.

In animation, there’s this concept known as the “uncanny valley.” When we see cartoonish versions of people, we are untroubled. We know they are meant to be representative, not realistic depictions of human beings, and we can appreciate them as such. We also react well to perfectly realistic depictions. However, we find depictions that seem almost human-like to be creepy, even revolting. (Think The Polar Express.)

I feel like there’s also an uncanny valley when it comes to assessing leadership. Federal and perhaps even state-level officials are the equivalent to the cartoonish representations of people. There’s no way for us to really know them, so we form opinions based on things that may not actually say much about whether or not they would make competent leaders, such as their opinions on various issues or how likable they seem to be.

On the other side of the spectrum, there are the leaders we actually know — our bosses, for example. We form our opinions of their leadership based on working with them, which seems like an appropriate way to make these kinds of assessments.

How, then, should we judge folks running for Supervisor or our local School Boards? These are folks I might run into at a local coffee shop and could actually have a conversation with if I have concerns or questions. Why is it so hard for me to assess who might be good for these positions? I think it’s because they fall into this uncanny valley of leadership, where they seem accessible, and yet there are aspects of them that seem fundamentally unknowable, and that feels unsettling.