December 1, 2022

the devil’s advocates

a section of the torn-down berlin wall covered in graffiti
photo caption: a section of the Berlin wall, covered in graffiti and screen printing, on display in Chicago. an image of Nelson Mandela (not a devil) and some other guys (no comment) line the concrete.

A personal note from me: Folks all over the Central District, Seattle, and beyond are mourning the tragic murder of D’Vonne Pickett, Jr. D’Vonne and his wife KeAnna started The Postman in 2018. They named their business in memory of D’Vonne’s grandfather, a letter carrier by trade. I don’t know the Pickett family personally but I know what they mean to the people and community around them. My heart goes out to D’Vonne’s family and everyone at The Postman. No amount of money is worth a life, but I encourage you to consider donating to support the Pickett family if you have the means to do so. You can also follow The Postman @thepostman_seattle.


I don’t like devil’s advocates. Someone will ask, “can I play devil’s advocate here?” The room always gives a resounding, “Sure, of course!” And then they deliver the grossest, most racist, dollars-over-people arguments anyone can make. Why do we tolerate this?

It’s a universal truth that people who sit at conference tables love making decisions. Those people make decisions without any connection to the consequences of their actions. Sometimes we get lucky and bring in an idea from outside the conference room’s echo chamber. Disconnected decision-makers will then debate the validity of ideas they didn’t come up with. In those rooms, there’s always someone who’s willing to take the contrary position. People call this ‘being the devil’s advocate.’ If we take an expansive position, they’ll take the restrictive one. It seems like their only goal is to be the “are we sure we need to do this?” person in the room.

The thing is, people rarely act as the devil’s advocate because of their own feelings about the issue. You might think you are doing everyone a favor by taking this contrary role, but you’re doing the opposite. Rather than discuss a proposal on its merits, the rest of us have to waste time telling you that you’re wrong. For a position you may not even care about.

The devil has too many advocates. Try being something else! Here are some roles you should try instead.

angel’s representative

It’s pretty basic to argue the contrary position. It’s unoriginal. It happens all the time and rarely breaks new ground. Instead, go further than the original proposal. Think bigger and bolder. We need more people who are willing to envision what justice really looks like. We need them to convince everyone else to do even more than they think is enough.

If you’re going to be the contrarian, “just ask questions” on the side of doing more. Suddenly the newly-watered-down proposal sounds pretty moderate and doable, doesn’t it? Best case scenario? People agree with you and support the expanded proposal. They might even feel empowered to dream bigger on their own!

Example sentence:
“Free public transit for people under 18 sounds great. Let me be an angel’s representative for a second here. What if we made transit free for everyone instead?”

[somebody’s] billboard

Did someone you know make a fantastic point? It happens more often than you think. When everyone is trying to make themselves heard, they don’t listen well to other people. This can cause ideas to hit the wall like spaghetti (if only the loudest spaghetti stayed stuck). We miss out on a lot of progress because people focus more on being right than finding the best solution to a problem.

Instead, try sticking your neck out for someone else’s good idea. Ask everyone to listen again to the person who just gave their idea. And this part is important: don’t restate the idea, or (gasp!) act like you came up with it first. Ask the person with the good proposal to explain it louder. Make sure they have the attention of the room before they say it again. Invite them into other rooms or discussions to continue fueling support for the proposal.

Example sentence:
“I’m going to be Jasmine’s billboard for a second. Jasmine, I think your point really got to the crux of the problem we were talking about. Would you please repeat it so that we can all hear it again?”

rotating prism

Improvisational comedy (improv) lives and dies by the concept of ‘yes-and’. For people unfamiliar with improv, don’t worry: I watched a lot of it in college. Improv is all about building on the ideas that others put down. Where a “no” might shut down conversation, “yes-and” will elaborate and add to the discussion. Someone might say, “The circus came to town, it has a fancy bear.” You might reply, “Yes, and they’re bringing along ten stinky clowns, too!” (Please note I did not say that I was good at improv). What if we said yes-and to others’ ideas rather than pooh-poohing them? Don’t shut down conversation, add to it.

If you’ve ever looked at a prism in the sunlight, you know that it changes color as it rotates. Take a lesson from this the next time you’re in dialogue with others. Devil’s advocating often implies that an idea in its current form will never work. Try building on the idea instead. Think about the person’s argument, especially the outcomes they describe. What other positive effects could this idea have? Ask questions that encourage others to build on the proposal as well. Bolster it with new perspectives that might lend more support or a thorough review.

Example sentence:
“I agree, installing a ramp at our entrance would be a huge benefit for people who are in a wheelchair or disabled. But can I play rotating prism here for a minute? It would also be helpful to people who are blind or vision-impaired. It would even benefit people like me who trip on the step every time I walk through the door. We should definitely do this.”

gender-neutral hype person

In rap and hip-hop of the 1990s, a hype man was an invaluable addition to the craft. Yona Marie of Yona Marie Music does a great job of breaking down the value of a hype man. She writes, “The hype man often throws out spoken words or small rap phrases that blend well within a song they’re performing for.” These interjections do more than add to the performance by exciting the crowd. They also give the rapper time to catch their breath without breaking their flow.

I’m probably not alone, but I would love to have someone like around this whenever I’m presenting. Try being someone else’s gender-neutral hype person! Praise or support them publicly when they have an idea that’s slow to gain traction. Excite the audience by talking up the positive outcomes that could emerge. Or try asking a supportive, non-gotcha question that can spark further discussion.

Example sentence (to say during a pause in the speaker’s monologue where they are starting to feel self-conscious about taking up space):
“I love where you’re going with this idea, Darryl. Please continue!” or, “Melina, thank you for presenting this idea to us on behalf of our community. What would you need to get started?”

sally field at the oscars

[Credit to James for naming this one 😘] We do too much decision-making with our heads, leaving our poor hearts behind. White-normative culture prizes neutrality and objectivity over everything else. They urge us to swallow our emotions and stick to cold rationality. But injustice should be hard to stomach. We should recoil from causing other people to suffer. We should feel horrible that we allow awful conditions to fester because it gets us cheap jeans.

Enter the actor Sally Field, who won the Best Actress Academy Award in 1985. While most people deliver stodgy or bland speeches, Sally Field laid it plain. While accepting the award she said, “I can’t deny the fact that you like me. Right now, you like me!” Her emotional speech added to her charm and resonates with people nearly 40 years later. I think we should appeal to emotions more. Let’s get super visceral with it.

Example sentence:
“Can I play Sally Field at the Oscars on this idea?” (from the room: “Sure, of course!”) “I hate this, I really hate this! We’re asking people to fill out a very long form to receive vouchers for diapers that they can only redeem on the other side of town? What kind of greedy amoral people came up with this? Why do we deserve any amount of power over other people? This plan is disgusting! You should all feel bad! YEAAARGHGHGHGH!”


Being the devil’s advocate doesn’t deepen a meaningful conversation. It derails it. Meanwhile, is the devil immune to horrible ideas? There’s apparently very little interest from contrarians in questioning those. It’s okay to be critical of a proposal or idea. Being critical, without having a point, makes it hard for people to navigate with you. If you object, say why. Open yourself up for inquiry, too.

It doesn’t have to be like this. The next time someone asks if they can “be Sally Field at the Oscars” for a minute, try saying, “Sure, of course!”

my name is josh martinez. i have always loved trying to understand systems, and the systems that built those systems. i spend a lot of time thinking about how to get there from here.

i own and operate a consulting practice, Future Emergent.

say hello: josh[at]bethefuture.space