Hello, I’m Joni

an excitable brand strategist

Daily Discussion Prompts, the Wiggle Work Way

15 November 2023

One of my favorite aspects of the Wiggle Work community so far is the daily discussion prompts in the general channel. Monday through Saturday, I post a prompt to kick off the day. Sometimes, the discussions stay within what’s posted, and better yet, sometimes, we end up on a weird path that at first glance, has no connection to the original prompt. For instance, one day, we started with “Friendly Fight” topics like dogs vs cats and landed on food safety guidelines. It’s a fun, unique way to get to know each other better fairly quickly since it brings up topics that would likely never come up organically–like someone sharing that they tape holiday cards to their ceiling.

Last Updated: 11/28/23

ChatGPT was pretty helpful in assisting with these at first and still can be with a lot of very specific directions in an attempt to break out of the repetitiveness that has taken hold. In doing general web searches, I find that posts about this are so riddled with ads they are rendered useless or are exclusively for elementary students–who decided only kids need icebreakers?!

Screenshot of prompts shared in Discord

I’ve been doing these since the beginning and have a couple of months worth of prompts as a result. I wanted to share some of my favorites here in case anyone is looking to start these or add some new ones to their discussion prompt bank. The best prompts, however, seem to come from listening to the community–what are folks interested in, what are common themes in terms of wins and struggles, and what could lead to fun revelations based on specific personalities. So, while I hope this list proves helpful, there’s still a lot of observation to do that will make yours even better for your group.

I aim to only present three specific questions a day, but some of these have more to account for multiple uses. I also try not to be overly prescriptive so that there’s wiggle room in responses. These are also all alliteration-based since that’s the Wiggle Work Way.








Mondays are hard for everyone, so I try to keep these as upbeat and lighthearted as possible.

Monday Motivation

  • What’s one goal you’ve set for yourself this week–personally or professionally?
  • Share a quote or mantra that’s motivating you today.
  • What project or task are you most excited about this week?
  • Discuss a mindfulness practice or technique you use to stay present and reduce stress at the start of the week.
  • Share something new you plan to learn this week.
  • Discuss a productivity tip or strategy that helps you stay focused and organized on Mondays.
  • Share a healthy habit or routine you follow to start your week right.
  • Share an act of kindness or connection you plan to undertake this week.

Masterpiece Monday

  • Share a project you’ve recently worked on or are particularly proud of.
  • Who is an artist (past or present) who deeply influences or inspires your own creative journey?
  • What is a unique piece of artwork you’ve come across recently that impacted you?

Manic Monday

  • What are your top priorities this week, and what plans do you have to make sure this is, in fact, not a Manic Monday?
  • What’s your go-to lunch on hectic days?
  • Share a GIF that perfectly captures your Monday mood or the week you’re about to have.

Maker Monday

  • What project are you currently working on or planning for this week?
  • Share your favorite completed project from the past.
  • What crafting hobby do you currently love or would like to get into?

Milestone Monday

  • Share a personal achievement or milestone you reached recently, no matter how big or small.
  • Discuss a recent professional milestone, such as a promotion, successful project, or new skill acquired.
  • Share a health or wellness milestone, be it related to fitness, mental health, or a new self-care routine.
  • Set a milestone you’d like to achieve in the upcoming months.

Maintenance Monday

  • What’s your strategy for keeping up with any side project maintenance?
  • How much of your job is related to maintenance and how do you address it?
  • How do you prioritize house/apartment maintenance? What efforts are you able to do yourself?

Mingle Monday

  • Share two truths about yourself and one lie.
  • How was your weekend? Share a highlight or something new you tried.
  • How do you take your coffee or tea? Or if you have another favorite morning beverage, let’s hear about it!
  • Share a fun or weird fact about yourself.
  • Share a movie you recently watched and loved.

Mend Monday

  • Do you have a personal project or goal that’s been neglected that you want to turn around?
  • Share a current challenge or obstacle you’re facing. What strategies or actions might help you overcome it?
  • Is there a relationship in your life that needs mending? What steps could you take to improve it?

Meet Up Monday

  • What’s a work-related meet up you’ve attended that stands out as one of the best?
  • With today’s hectic schedules, what do you find to be the best days and times to hang out with others?
  • If you had to start a new meet up today, what would it be about and what would it be called?


Tuesdays have proven the trickiest to match a theme with. Everything pairs better with Thursday, and ChatGPT is hell-bent on it always being Tech Tuesday!

Transparency Tuesday

  • What’s a tech tool or app you’ve recently discovered that’s been a game-changer for your remote work?
  • Design process insight?
  • How do you ensure clarity and openness in your communications within remote settings?
  • Share a personal life lesson that has had a significant impact on you. How did you come to learn it, and how has it influenced your perspective or approach to life?
  • How does your organization foster a transparent and open work culture?
  • Share a time when you faced a significant challenge or failure in your career. How did you overcome it, and what did you learn from the experience?
  • Reflect on your current skill set and share one area where you feel confident and one where you see room for improvement. How do you plan to enhance your skills in the identified area?
  • Share a travel experience that changed your perspective or taught you something new about the world or yourself. What was the journey, and what insights did you gain?

Transformation Tuesday

  • Reflect on a relationship in your life that has evolved or strengthened over time.
  • Who is someone you admire for their transformative journey, be it a public figure or someone in your personal life.
  • Discuss a significant career change or milestone you’ve achieved. What challenges did you face, and what kept you motivated?
  • Reflect on a change in your mindset or perspective that has positively impacted your life. What led to this shift, and how has it influenced your decisions or actions?
  • Share a goal you’re currently working towards and the transformations you’re making to achieve it.
  • Share a challenge or obstacle you’ve faced and how you transformed it into an opportunity or learning experience.
  • Reflect on a change in your mindset or perspective that has positively impacted your life. What led to this shift, and how has it influenced your decisions or actions?

Tidbit Tuesday

  • Share a tech tip, shortcut, or hack that you find invaluable.
  • Share an intriguing fact or origin story about a piece of technology or an invention.
  • Share an intriguing scientific fact or recent discovery that you’ve come across.
  • Share an intriguing fact about an animal, plant, or natural phenomenon.
  • Share an interesting tidbit about a famous author, book, or literary tradition.
  • Share a unique or lesser-known recipe or food item from your culture or region. What’s the story behind it?
  • Share a piece of folklore, legend, or an interesting historical tidbit from your hometown or country.

Teamwork Tuesday

  • Share a story of a recent team project or collaboration that was particularly successful.
  • Discuss a challenge your team faced and how you overcame it together. What lessons did you learn from the experience?
  • If you could assemble your dream team from any individuals (historical, fictional, or real), who would be on it and why?
  • Share your favorite team-building activity or exercise. Why do you find it effective, and how has it helped strengthen team bonds?
  • Reflect on your role within teams. What strengths do you bring, and in what areas do you rely on your teammates?
  • Share tools, strategies, or practices your team uses to ensure effective communication. How have they impacted team productivity?
  • How does your team approach feedback? Discuss methods or structures in place that ensure constructive and supportive feedback.
  • Discuss goals or projects your team is aiming for in the future. How are you preparing or strategizing to achieve them?

Tasty Tuesday

  • What’s your go-to weekday breakfast?
  • What’s a dish or technique you’ve always wanted to master?
  • What’s your favorite dessert?
  • What’s your favorite ingredient and how do you use it?
  • Share a kitchen tip or hack that has changed the way you cook or prep food.
  • What’s your ultimate comfort food?
  • What’s your favorite restaurant, and what do you order there?
  • Share a cookbook, food blog, or culinary-themed book you love.

Toasty Tuesday

  • What’s your favorite way to eat toast?
  • What’s your favorite kind of cozy attire?
  • What space in your home is the coziest?

Teaching Tuesday

  • If you could teach one thing as a career, what would it be and to whom?
  • In-person or remote or something else?
  • Who was your favorite teacher growing up or within professional development efforts?

Twisted Tuesday

  • What’s a weird “glitch in the system” thing you’ve seen and can’t forget?
  • What’t the silliest thing you’ve ever done by mistake?
  • Share a science experiment or discovery that seems too strange to be true.


Wednesdays are inherently Wiggle Work favorite–it starts with W and it marks a welcomed halfway point to the work week.

Wellness Wednesday

  • What work-life balance tools/methods do you find yourself leaning on this week so far?
  • Share a relaxation technique you use during work breaks.
  • What’s your go-to home workout or exercise routine?
  • What’s your favorite dopamine-producing snack this week?

Wear Wednesday

  • What sort of style do you find yourself settling into?
  • What’s one item of clothing that you splurge on in a “buy it for life” way?
  • What’s one thing that you’ll never give up, regardless of how “dated” it becomes?

Wordy Wednesday

  • What does your writing process look like?
  • Share a piece of writing (blog posts, books, poetry, a story, etc) that you especially enjoyed crafting and why.
  • If you journal, how has it helped? Do you use a special app?
  • What new word do you find yourself using more recently?

Well Done Wednesday

  • What’s something you’ve done especially well so far this week? Big or small!
  • Have you made a positive impact on someone recently?
  • Any healthy habits you’ve picked up?
  • Put any new skills to the test?

Wisdom Wednesday

  • Recommend a book that profoundly impacted your thinking or offered valuable wisdom.
  • Describe a challenging situation you’ve overcome and the wisdom you gained from it.
  • What’s a valuable lesson you’ve learned about maintaining healthy relationships?
  • Share a tip or lesson about managing finances or investments that you’ve found beneficial.
  • What’s a piece of advice you’d give to someone starting in your profession or industry?
  • Share a tip or practice that has positively impacted your physical or mental well-being.
  • Reflect on your educational journey. What’s something you learned outside a standard curriculum that’s been invaluable?
  • For those who’ve reached milestone ages (like turning 30, 40, 50, etc.), what wisdom or advice would you give to your younger self?

Wordsmith Wednesday

  • Share a poem you’ve written.
  • Share a piece of your writing that was either your favorite or most recent.
  • Write a mini-story in 100 words or less.
  • Share someone else’s writing that had a profound impact on you.
  • Take a well-known book title and change one word to give it a completely different meaning.
  • If you were to write a memoir, what would its title be?

Walking Wednesday

  • If you go for walks or hang out in nature, what time of day do you find is your favorite for this? What’s your primary motivation?
  • Do you prefer outside or a treadmill?
  • Any pics of a walk that especially stands out?

What-If Wednesday

  • What if animals could talk? How might our relationships with them change?
  • What if you could travel back in time, but only once? When and where would you go, and why?
  • What if you had chosen a completely different career path? What would it be and why?
  • What if everyone was born with a unique superpower? What would yours be, and how would you use it?
  • What if a fictional universe (from a book, movie, or TV show) was real? Which one would you want to live in?
  • What if money didn’t exist, and we returned to a barter system? What skills or items would you trade?
  • What if our dreams were a window into parallel universes? Share a recent dream and speculate on its alternate reality.
  • What if pets were in charge and humans were their pets? What do you think your pet would have you do?

Wildcard Wednesday

  • If you could teleport to any place in the world right now, where would you go and why?
  • Share a story about someone that you consider a hero or who has had a surprisingly positive impact on your life.
  • If you were stranded on a desert island and could only bring three items, what would they be and why?
  • Share a story about a random act of kindness you’ve either received, witnessed, or given.
  • Imagine you’ve received a box with three items from your future self meant to give you a hint about what’s to come. What do you hope is inside, and why?

Wacky Wednesday

  • Share the weirdest food combination you’ve ever tried (or want to try). Would you recommend it?
  • If you could have any unconventional animal as a pet (real or fictional), what would it be and why?
  • Imagine you’ve been tasked to create a wacky invention. What would it do, and what would you call it?

Watch Wednesday

  • What’s a show or movie you thought was very underrated?
  • What’s a show or movie you thought was very overrated?
  • What’s a show or movie you’d insist people get into over the holidays?


Thursday! Throwback Thursday is a classic, but there’s more.

Throwback Thursday

  • Share a photo of your first remote workspace vs your current setup.
  • Anything weird/funny/scary/etc about your early remote working experience in general that you’d like to share?
  • Discuss a book, movie, TV show, or game from the past that had a significant impact on you.
  • Share a favorite pastime or hobby from your past that you no longer pursue. What did you love about it, and would you consider picking it up again?
  • What was the first tech gadget you owned or were obsessed with?
  • Discuss what you aspired to be when you were a child and how it compares to where you are now.
  • Post a photo or describe a fashion trend you once loved (and maybe now cringe at).
  • What TV show, cartoon, or movie did you love as a kid? Would you re-watch it now?
  • Discuss a piece of technology or software that you used early in your career but is now obsolete or outdated. How did it shape your understanding of technology?
  • Share a song or album that takes you back to a specific time in your life. What memories are associated with it, and why does it hold significance for you?
  • Share a memorable story from your school days – a favorite teacher, a school trip, or a funny incident.
  • Share a memory from the early days of the internet.
  • What was your favorite board game growing up?

Thoughtful Thursday

  • Reflect on a technology that has evolved significantly during your career. How has this evolution impacted your work, and what do you anticipate for its future development?
  • Share a learning resource or platform you find invaluable for professional development in tech. How has it helped you in enhancing your skills or knowledge?
  • Share a life philosophy or quote that resonates with you and has influenced your perspective or decisions. How do you incorporate it into your daily life?
  • Discuss a simple pleasure or ritual in your daily life that brings you joy or peace.
  • Reflect on a personal challenge you’ve overcome in the past year. What did you learn about yourself in the process?
  • Describe a moment in nature that was especially meaningful to you.

Tales & Traditions Thursday

  • Reflect on a tradition or practice that has faded or evolved over time in your family or community.
  • Introduce a tradition from your culture/family that you believe others might not be familiar with.
  • Share a story or legend that you were told as a child.

Tune-in Thursday

  • What song has been stuck in your head this week?
  • Share a podcast episode that you recently found enlightening or entertaining.
  • Describe the best concert or live music experience you’ve ever had.

Thermometer Thursday

  • What’s your favorite weather? Got a pic that represents it?
  • What weather did you grow up with?
  • What weather can you not stand, even for a day?

Thankful Thursday

  • Share a trait or quality about your family that you’re grateful for and why it means so much to you.
  • Recall a teacher or mentor who made a significant impact on your life. Express your gratitude for their guidance.
  • Share something about your job or career that you’re thankful for.
  • Reflect on something you’re looking forward to in the future

Thrive Thursday

  • Share a recent “small win” in your life.
  • Reflect on a piece of constructive feedback you’ve received. How did you use it as a catalyst for growth?
  • How do you prioritize self-care in your busy schedule?
  • Think back to where you were a year ago. What’s one significant area of growth or change you’ve noticed in yourself since then?
  • Discuss the importance of setting boundaries in personal and professional life. How has establishing clear boundaries helped you thrive?

Thinking Thursday

  • What’s a regular problem in your everyday life that you wish you had time to develop a solution for?
  • If you could move anywhere, where do you think you’d go and why?
  • What does happiness mean to you, and do you think it has changed with age or certain experiences?


Generally, Fridays are the best days–the weekend excitement is in the air, and anything is possible.

Friendly Fight Friday

  • Dogs or cats; which is best and why?
  • Morning bird vs night owl; which is superior?
  • Chocolate vs vanilla, cake vs ice cream; which one would you strictly choose forever over the other?
  • Choose your own friendly debate question to ask the group!

Future Forward Friday

  • How do you see your profession or industry changing in the next decade?
  • Share a personal goal or aspiration you’re working towards for the next year.
  • Share a specific thing you’d like to learn more about in the next year.

Friday Favorites

  • What’s your favorite book you’ve read recently?
  • What’s your favorite new recipe?
  • What’s your current favorite video or board game?
  • Share a favorite outdoor spot or nature activity you love.
  • What are you most looking forward to this weekend?

Friendship Friday

  • Share a memory of your very first friend.
  • Who are the most significant acquaintances in your life?
  • Share a story about a friend you made in an unexpected place or under unusual circumstances.
  • Have you ever lost touch with a friend and then reconnected years later?
  • Share a quote or saying about friendship that resonates with you. Why does it hold significance?
  • Discuss the experience of maintaining a long-distance friendship. What tools or practices help you stay connected?

Freestyle Friday

  • What have some of your nicknames been, and who gave them to you?
  • If you had ZERO obligations this coming weekend, what would you choose to do?
  • If you had a sandwich named after you (or maybe you already do?!), what would it be called?

Fun Fact Friday

  • What’s a fun fact about the tech or coding world that many might not know?
  • Discuss an unusual or little-known fact from history.
  • Discuss an unusual geographical feature or location. What makes this place so special or different?
  • Discuss an unusual or unexpected fact from the world of sports.

Feel-Good Friday

  • Share any uplifting stories, positive news, or personal achievements from the week.
  • Share a piece of positive feedback you received this week.
  • Share a song that lifted your mood.

Finally Friday

  • What was your favorite part about this past week?
  • What’s one thing you wish you had done differently?
  • What are you most looking forward to this weekend?


I find that Saturdays are quieter but can lead to more in-depth discussions.

Social Saturday

  • What’s a virtual event or webinar you’re looking forward to?
  • Cooking or baking anything special? Share a recipe!
  • Working on a side project? Show us!
  • Share a hidden gem in your local area–it could be a café, park, museum, or any special spot you love.
  • Show off a photo of your pet or share a cute or funny story about them. No pet? Share an animal you’d love to have!
  • What book are you reading this weekend?
  • Describe your ideal Saturday adventure.
  • Recommend a movie or series perfect for a Saturday binge-watch.
  • Share a fun DIY or craft project you’ve tackled on a Saturday.
  • For those with a green thumb, share your gardening tips, successes, or even your plant wish list.
  • Whether you’re a player or a fan, share your favorite sport or sports moment. Who’s your all-time favorite athlete or team?
  • Are you cooking or baking something delicious today? Share a before-and-after snapshot.
  • Are you working on a project, hobby, or craft this weekend? Share a snapshot of your progress or the tools you’re using.

Snapshot Saturday

  • What’s your favorite snapshot from the week on your camera roll?
  • What’s the best snapshot you’ve taken of all time?
  • Share a snapshot of something beautiful you’ve observed in nature this week.

Sleepy Saturday

  • What’s your bedtime routine look like, and how has it changed over the years?
  • What special sleep devices do you need?
  • Do you take naps?

Shelfie Saturday

  • What do you find filling up most of your shelves?
  • What do you need a new shelf for based on what you have piling up?
  • Got any pics of your setup?

Science & Space Saturday

  • Share a recent scientific discovery or advancement that caught your attention.
  • If you could get an answer to any unsolved mystery or question about space, what would it be?
  • Think of a science fiction movie, book, or show you love. Which of its futuristic concepts do you think might become a reality, and which ones seem purely fictional?

Silly Saturday

  • If you were forced to choose one domain from the list of ones you currently own and do something with it today, which would you choose and what would you do with it?
  • What’s a silly mistake you’ve made that you can laugh about now?
  • What’s a harmless but silly secret you’ve never told anyone?

Stories Saturday

  • What book are you reading this month?
  • Tell us a fictional story within 200 characters.
  • Tell us a real story about a past winter/spring/summer/fall.

Wiggly Wrap Up

If participating in any of these prompts sounds like a fun and energizing way to spend time, we’d love for you to join us. You can fill out the little application here, or ask me questions on Mastodon or via email. It really is what all the best parts of having coworkers and friends could and should be like, except we don’t have to resent each other for burning coffee in the break room.

I can’t wait to hang out and learn important things about you, like if you eat toast.