The worst, still good example
There's a conversational move that I discovered recently: when explaining a perspective with examples, use the worst-yet-still-good example. One that's still representative of your position, but isn't the strongest you can think of.
This may seem counterproductive: it's normal to give extreme examples to prove a point. However, these examples are often not all that typical of what the disagreement actually may be. When you're trying to convince someone of something, you're often offering a somewhat subtle perspective that's a bit lossy.
Sensationalist news fails this. It chooses stories that polarize people into believing things are obviously good or obviously bad, without any recognition of the messiness of it all. Many political debates miss this: the most egregious cases of your political cause are highly likely just bad outcomes of the current system, but are also atypical.
It's useful to come up with an example that's actually fairly common, so that you're able to talk about how the principle you believe in can be seen in marginal cases. Typically, arguments aren't extremes. They acknowledge that the world is messy and points to a legible trend or theme, rather than absolute rule. It's often counterproductive to treat extreme examples as representative of your perspective, because it can feel that you're not offering empathy to the other side. People who disagree can easily dismiss your principle because they can contrive more reasonable counter examples.
Imagine your perspective is of the red variety, above, and you perceive the opposing side as the blue variety. Of course, the extremes on the blue side have good points (i.e., are actually blue!), but those aren't typical. Arguing from exclusively the red side can feel stable, but also doesn't address the blue-believer's perspective at all. They also, likely, see that the extreme red examples are valid, but that the typical example is far more blue. Notice the subtle shift in their perspective:
You resonate with the red side. In practice, this could be issues that relate to personal freedoms, injustice, cultural systems, etc. They resonate with the blue side. What matters is the purple region in between — you see the middle as mostly red, and they may see the middle as mostly blue. Addressing examples here let you both embrace the messiness of reality and consider the redness and blueness of common cases.
In Value creation vs capture, I wanted to show how capturing value isn't always perfectly correlated with value creation: it's possible to capture value while just transferring existing value to yourself, or even while overall destroying value. And there's several cases when this is clearly true, like fraud. But these cases won't convince you of my underlying point because most situations are messy. Companies create some new value, transfer some value towards themselves, and offload some externalities to the commons.
So, a good "worst, still good" example is Uber. They clearly captured tons of economic value for founders (billionares), early investors (100x returns), and employees (high compensation). And some net value was definitely created: the flexibility of gig-economy driving is a net positive for some people who otherwise wouldn't have had access to this income stream, and the user experience is indeed better than previous alternatives. Yet, if we took an expansive view, it's not nearly as clear how much of the captured value was new, and how much was transferred from taxi companies and drivers, and investors. The median dollar invested into Uber has lost money (investments since 2016, including their IPO), and the taxi industry is a shell of its former self.
We see this commonly with political issues. American progressives resonate with systemic issues of injustice, and often raise the strongest examples of people treated unfairly — where "strong" is defined by cultural preferences and appetite. American conservatives resonate with personal autonomy and responsibility, and often raise strongest examples of people working hard and overcoming adversity. Neither side spends much energy towards more typical cases, where justice and and work ethic are hazy. And why would they? These are bad examples.
Yet, some of the most impactful political conversations I've had with people center around focusing on how both sides see something reasonable that needs to be balanced. In these conversations, we focused not on the strongest examples, but typical examples of injustice and work ethic; of base cases, and the messiness caused by real policy. And I often leave feeling that I was able to shine a light on something I care deeply about, and hear about things I value less but others value highly.
Borrowing from a blurb I wrote nine years ago, here are some beautiful examples of people plainly realizing the complexity and non-polarization of complex issues:
Pro-life, pro-choice, pro-dialogue, On Being. David Gushee and Frances Kissling, diametrically opposed about abortion, discuss what “their side” is doing wrong. Of interest, Gushee argues that we cannot illegalize abortion without first building a strong social support structure for women.
A School of Life for Atheists, On Being. Atheist Alain de Botton argues that rejecting religion should not mean we reject everything it brings. Particularly, after wrestling with the meaning of religion and faith, he realized that humans shouldn't navigate through life alone, and that we need help. So, as any respectable atheist would, he started a church.
Red state, blue state, This American Life. In Act Two, Sarah Koenig explores moderation, and how polarizing politics makes it hard to not get swept to one side.
So, when discussing difficult topics, center examples around areas that are still good, but about as bad as it could be to still illustrate your perspective. This leaves room for other perspectives to breathe and be heard. You can admit up front that it's not a great example, so you're not forcing them to argue against what feels like a strawman. It's a move of offering empathy — there's natural bridges with your perspective and opposing ones. Polarization of arguments almost guarantees that no progress will be made, because energy is taken away from the common, "middle" cases that actually need to be improved.