A Woman’s Guide to Winning in Tech
By Caroline Dunn
Forget Fitting In. It’s Time to Win—on Your Terms.
👯♀️ Welcome, Brave Readers
So you’ve gathered a group of fearless, funny, tech-curious women (and honorary allies), and you’re ready to laugh, rant, and maybe even reprogram your workplace. This guide is here to help.
Whether you’re meeting in person or via Zoom, this page will equip you with questions, activities, and just enough sarcasm to keep things spicy.
🧠 Discussion Questions (For Each Chapter or General Use)
1. What moment in the book made you laugh out loud… and then scream inside?
2. Which stereotypes in tech have you personally encountered or internalized?
3. What part felt uncomfortably relatable?
4. How does this book challenge traditional advice given to women in tech?
5. What’s your favorite fake acronym or forum post from the book? Why?
6. Did any chapter change how you’ll approach your work or colleagues?
7. What’s your “Blake” story? (We all have one.)
8. What are you doing to kick down the door—or automate it?
✍️ Group Activity Ideas
🛠️ Build Your “Brag File” (Chapter: Imposter Syndrome)
Take 5 minutes for each person to write down 3 recent wins. Share one out loud. Bonus points if it includes fixing something someone else broke.
🖥️ Pink Keyboard Show-and-Tell (Chapter: Pink Keyboard? I Only Type on He-Boards)
Ask everyone to share their most “nontraditional” tech gear or favorite tool, regardless of gender-coded colors or aesthetics.
🎭 Skit Night: “Tech Bros in the Wild”
Have each group member re-enact a ridiculous tech interaction they’ve had. Others guess which stereotype it fits: Mansplainer? Blake? Wrong-Info-Charlie?
🎤 Alexa Reboot Challenge
Debate: Should all AI assistants default to male voices for a year? (Be ready for hot takes and sarcasm.)
🍷 Optional Extras (Because Book Club Should Be Fun)
- Dress Code: Business casual on top, Wi-Fi-enabled rage on the bottom.
- Snack Theme: “Non-Male-Dominated Munchies” — anything not named after a tech bro.
- Drinks: “Ctrl+Alt+Del Your Day” cocktails and mocktails encouraged.
- Background Music: Beyoncé, Lo-Fi beats, or a playlist called “Code Like a Girl.”
🔁 Sample Book Club Schedule (90 Minutes)
| Time | Activity |
|---|---|
| 0:00 – 0:10 | Welcome + Icebreaker: What’s your tech origin story? |
| 0:10 – 0:30 | Group Discussion (use questions above) |
| 0:30 – 0:50 | Activity: Brag File or Skit Night |
| 0:50 – 1:10 | Share from “From the Forums” – vote on favorite |
| 1:10 – 1:25 | Read a “Frequently Annoying Question” out loud. Respond with sarcasm. |
| 1:25 – 1:30 | Closing thoughts: What are you taking with you? (Besides rage and inspiration) |