Working on other people’s projects: that’s how I’ve spent most of my working life. As a designer at Sliced Bread Design. As the course lead, accompanying many, many student projects at the Stanford d.school and the HPI School of Design Thinking. And at Superbloom, working with tech activist and human rights organizations all over the world.

Entering a new project is like entering a new world. My job is to notice things the people inside that world can’t perceive – a fish can’t see water. These are some of the questions I ask myself to discover this world as quickly, thoroughly, and creatively as I can.

  1. What have they already tried?
  2. What is a manual process that might work better if it was automated?
  3. What is an automated process that might work better if it was manual?
  4. What do new people think of it?
  5. What is their origin story – the publicity-friendly version?
  6. What is their origin story – the real, messy version?
  7. What are their third rails, ideas or issues they won’t touch because they’re too controversial?
  8. What is the question you wouldn’t dare ask them?
  9. What do you privately think about this work? No shame, what’s your honest opinion of it.
  10. What are they most proud of?
  11. If you were them, what would you do with this work?
  12. Does this remind you of anything else you’ve worked on? What’s the same? What’s different?
  13. What is the funniest part about this work?
  14. What is the saddest part about this work?
  15. What is the most confusing part about this work?
  16. Do you think they see their own problem? How do you know?
  17. Look at the work with gender goggles, even if it isn’t “related” to gender. Who’s active, who’s in charge, and what gender do they seem to be or tell you they are? Do you have any idea who the community is? Who the users are? What gender do they seem to be? Do they talk about gender, whether cis or trans? If you brought up gender how would they react? (If you are a cis person and/or a man, you might want to check the reaction of someone else to this question.)
  18. Look at the work with race goggles, even if it isn’t “related” to race. Who is in charge? What race do they seem to be, or tell you they are? Do you have the feeling that the community is mostly of a particular racial, cultural, or ethnic background? How do you know: are you guessing, or have they told you? Does the work seem like it’s “for” people of a particular racial background, or “not for” people of a particular race, and how do you get that sense? If you brought up race, how would people react? (If you’re white, you might want to check in with someone else who isn’t white about this question.)
  19. Look at the work with sexuality goggles, even if it isn’t “related” to sexual orientation. Does the work feel gay or straight or pan to you, does that even make sense to ask as a question? Is sexuality addressed in this work? Should it be? (If you are straight, you might want to check in with someone who isn’t straight to think about this.)
  20. If you ask them about accessibility, what is their reaction?
  21. What is it like to participate in this work with low vision?
  22. What is it like to participate in this work if you are hard of hearing?
  23. What is it like to participate in this work if you don’t know English very well? If you are a fluent speaker of English, you might want to check in with someone who isn’t.
  24. Do they talk about neurodiversity explicitly? If so, why do you think they are doing that? What does it tell you about their work?
  25. How would this work be different if it was on the exact other side of the globe from where it is? (For example, the opposite point to New York is in the Indian Ocean, southwest of Perth, Australia. The opposite point to Berlin is in the South Pacific, southeast of New Zealand. Find yours on antipodesmap.com.)
  26. If this work didn’t have to comply with any laws at all, would it be different? If so, how?
  27. If the people you’re working with could make new policy to help their work/their cause, what do you think it would be?
  28. How do they take notes? How do they seem to decide who takes notes? This can be an interesting symbol for power dynamics.
  29. Are you having a hard time understanding this work? List the reasons why (or why not).
  30. If you have been looking at this work on desktop, switch to mobile. If on mobile, switch to desktop. How is the experience different, better, worse?
  31. What is offline here? What would change if the offline parts went online?
  32. What is online? What would change if the online parts went offline?
  33. Not endorsing substance use, but is there any type of substance/drug that would make this work more effective or easier to use/understand? You can also make up a fantasy drug.
Two young children jumping in a leaf pile, blurry late afternoon picture, you can't see their faces, city street, with graffiti in the background
  1. What is the most expensive part of this work?
  2. What part of this work scales really well?
  3. What does not scale at all?
  4. What is the most renewable and sustainable part of this work?
  5. What is totally unsustainable and will get used up soon?
  6. What colors do they seem to like? Why do you think they like those colors?
  7. What famous person do you think the people here secretly want to be like, and might even think they are on the way to becoming, if they were to be really honest with you?
  8. Who hates this work? Why?
  9. Who loves this work? Why?
  10. Who doesn’t care about this work? Why not?
  11. If this work got a massive venture capital (VC) investment from a Silicon Valley firm, would they take it? And what do you think they would do with it?
  12. Would this work be useful in an apocalypse scenario? If so, how?
  13. What is a physical metaphor for this work?
  14. What is a smell or fragrance that represents this work to you?
  15. Would a child ever use this work or benefit from it?
  16. What is the half-size version of this work that would still be effective and interesting?
  17. What is this work’s closest nonhuman ally?
  18. What are the environmental effects of this work?
  19. If you had to describe this work on a protest sign, what would it say?
  20. If you had to describe this work as a wellness treatment, what would a spa menu description say?
  21. Is this work more strong, principled, and unyielding, or flexible and adaptable? Do you think that’s the right choice for them?
  22. What does this work nourish?
  23. Could this have existed 10 years ago? 20? 50?
  24. What are some “error messages” (either actual or metaphorical) you, or others, get while trying to use or engage with this work? As in, dead ends that tell you you did something wrong and make you do a 180.
  25. If you speak a language that isn’t English, try explaining this work in that language.
  26. Literally turn the work upside down and see what you notice. If it’s a digital product, turn your screen upside down. If it’s a Miro board, you can do that too. If it’s more of an idea, I don’t know, try reading it backwards? That might not work so well.
  27. Some of you are into astrology, so what is the sign of this work? Sun sign, moon sign, rising sign? I, the writer of these questions, am not an astrology person, but I’m guessing this might be an interesting way to look at a project.
  28. If this work went extinct, what else does it drag under with it, and why?
  29. How do you feel when you think about this work? And how strong are your feelings about it?
  30. Is this project fast or slow? This means both, are we working fast or slow, and is the project’s theory of change fast or slow.
  31. If you could give this project the gift of a new team member who really helps them out, who would it be? Either a real person you know or a description of someone.
  32. Is this aesthetically pleasing? Should it be?
  33. In this project, do you feel more like you are an electrician fixing the lights, an interior designer rearranging a room, or a carpenter installing new cabinets? Or something else?
  34. Would you want to meet these people in real life, if you haven’t already? What would you want to ask them in real life that’s different from what comes up in virtual meetings?
Two young children jumping in a leaf pile, blurry late afternoon picture, you can't see their faces, city street, with graffiti in the background
  1. Does this project remind you of any sports? If so, more of a team or individual sport? A contact sport or not? Endurance or sprint?
  2. How do you describe this work to your family members who aren’t in our bubble?
  3. What are some similarities between you and the partners you are working with on this project? What are some differences?
  4. How quickly do they respond to your messages, and what does that tell you about them?
  5. What makes them laugh? (If anything)
  6. If you could matchmake them with another project you have worked on, what would you pick? Could they learn from each other, would they benefit each other?
  7. What is this work already doing the best at?
  8. Give this work a “Most Likely To…” headline, like in US high school yearbooks.
  9. What would be a cheer or chant for this work, if they were a sports team?
  10. If you got really sick for four weeks starting right now, have you told enough other people at Superbloom about what’s going on here that they could keep it moving, or would it stop until you got back? If not, is that ok?
  11. If your main contact in this work got really sick for four weeks starting right now, have they told others enough about what’s going on so that you could keep working, or would it stop until they got better? If not, is that ok?
  12. If this work absolutely had to have background/intro music – like, music that plays when you open the webpage, or when you start the workshop – what would be appropriate?
  13. Would this work be a good basis for a movie or TV series? A ballet? An opera? An experimental theater play? If so, why, if not, why not?
  14. If you were bodyswapped with the person you are working with on this project, Freaky Friday style, would you think that was fun or would you be horrified and want to switch back ASAP? What would you do while you were in their body? What do you think they would do while they were in your body?
  15. What do you think the people you are working with do for lunch? Eat at desk? Go out? Pack lunch?
  16. What do you think will still exist of this work in 1 year? 5? 10? 50?
  17. What is your favorite part of this work? What do you think just really works?
  18. Could you recreate this work with a Rube Goldberg machine? This is a hyper-complicated machine based on the cartoons of the cartoonist Rube Goldberg where many completely unnecessary (but super entertaining) steps enable a simple task to get done – for example, making toast, or turning on a light switch.
  19. Could you build this work from Lego? (This is an actual thing that is done in corporate workshops! It’s called Lego Serious Play.)
  20. Is anyone involved in this work scared or worried? Of what? I mean, we are all somewhat scared and worried these days, but anything other than the baseline?
  21. Do older people benefit from this work?
  22. How would the version of you from the beginning of your career have approached this work? What are you doing differently now?
  23. Are you scared, worried, or nervous about anything in this project?
  24. Where are you usually sitting when you are working on this project? Try sitting somewhere else.
  25. What are you usually listening to when you are working on this project? Try listening to something else.
  26. Have you asked for help on this work lately? Might be time to try that, even if you think you’re in a good place; it helps others know what’s going on, which is a plus.
  27. How can you make this work something that makes you feel good, not just something you have to do or some people you have to help? Doesn’t necessarily mean working more or harder on it.
  28. How would this work be different if there were no borders, no visas, no passports, no customs?
  29. Where is their center? Why? How strongly centralized is this work? Answer this however it makes sense to answer.
  30. Do most people use this work or project under their wallet/passport names? If not, why not?
  31. Who are the secondary users of this work: people who don’t use it themselves, but are impacted by others using it?
  32. If the project is digital, how is it impacted by physical infrastructure? By internet availability, server space, travel times?
  33. Describe this work like it is an infomercial and you are trying very hard to sell it for a low, low price while wearing a cheesy costume with lots of sequins on late-night TV.
  34. Is this work changing you? Even a little bit? This might seem silly, but there’s some truth to what Tennyson writes in “Ulysses”: “I am a part of all that I have met; / Yet all experience is an arch wherethro’ / Gleams that untravell’d world whose margin fades / For ever and for ever when I move.”