I Let Daily Pick Choose My Entire Week — Here’s What Happened
I handed over my calendar to Daily Pick for one week. No, I didn’t literally let it send emails or file requests, but I did let the app decide:
- which stand-up order would happen each day
- which blocker to tackle during synchronous sessions
- who should host the retro warm-up
- what question would jumpstart our async update
The result was not only wildly entertaining—it turned a painstaking ritual into a weekly experiment people actually anticipated.
Day 1: Chaos, then clarity
Monday started with a bold spin: Daily Pick paired “team courage” with Who’s holding a blocker? and assigned my least vocal teammate to explain what fell through the cracks. Instead of the usual autopilot updates, we dove into context, and the follow-up buddy system meant everyone knew exactly who would circle back on the solution. Later I used the Decision Wheel to randomize a creative prompt, and suddenly the stand-up felt like a shift into improvisational comedy instead of a checklist.
Day 3: Reset your blockers like a game show
Midweek I triggered a Trap! round to catch the blockers nobody wanted to say out loud. Daily Pick surfaced three potential problem areas, and the spinner cheerfully said “You’re up, Sam!” each time. The energy changed instantly—no more polite nods, just action. We paired the blocker with a Planning Poker Hub session to estimate how much time to carve out, and the deck even suggested a “technical debt” category so we could track cleanup progress.
Day 5: The reflection trick EVERY team should automate
By Friday, we asked Daily Pick to choose a retrospective “mystery guest”—someone outside the core team who should hear the takeaways. The result: our designer joined, loved the fairness dashboard, and shared a UX insight we never would have got otherwise. The recap had stats about how many people spoke, how often Trap! spun around a blocker, and our Decision Wheel history, which made writing the blog post you’re reading now surprisingly easy.
The surprise punchline
The experiment wasn’t about giving up control—it was about intentionally surrendering boring decisions so we had more energy for the interesting ones. Daily Pick didn’t replace us; it amplified curiosity. The Monday chaos became a ritual my teammates now volunteer to pilot. Want to try it? Spin Daily Pick, throw in your hottest blocker, and let the software keep score while the humans get creative.
Want more ways to gamify your stand-up? Tack on a few icebreaker questions from Remote Onboarding Icebreakers Your New Hires Will Love and see who laughs first.