From Executive Hackathons to Shadow IT: Making AI Normal at Work + Is Notion Mail replacing Superhuman?
- Author
- Work Less
- Published
- Mon 25 Aug 2025
- Episode Link
- None
Justin and Tom dig into the growing exec–team AI gap, and what actually works to close it.
From exec hackathons (yes, that's a thing now) and weekly “show your prompts” rituals, to putting bumpers on shadow IT before someone wires a weekend AI toy to your codebase, it’s a playbook for making AI normal at work.
We also side‑eye Apple’s latest Siri/Gemini rumor, explain why Notion Mail finally pried Justin off Superhuman, and kick the tires on Airbook, aka “cursor for analytics.”
What’s inside:
- Leaders who model the behavior win. Exec retreats turned into mini hackathons (with Replit) and “show your prompts” at all‑hands beat vague “use AI” mandates. Make it impossible not to use AI, set clear behaviors, cut red tape, and carve out time to tinker.
- Kill shadow IT with a “happy path.” The AI era version isn’t someone using Asana instead of Jira, it’s giving an AI wrapper to your codebase and CRM. Define approved tools and data guardrails so folks can experiment in the open. Bumpers on, bowling starts.
- Apple’s Siri situation. Rumors of Gemini as an option signal Apple still shopping for a story, and maybe for a model. Interesting strategy, messy execution.
- App of the Week: Notion Mail. Justin finally jumps from Superhuman: similar shortcuts and clean UX, but better AI‑assisted labeling + flexible custom views. (Gmail only, for now.)
- Tool test: Airbook (cursor for analytics). Connects data, writes SQL from chat, spits out charts. Nice power‑user flow (you can even copy code to ChatGPT), but the credit model bites and it struggles with messy, inconsistent spreadsheets. Verdict: shines with structured data; do your data homework first.
Tools & companies mentioned:
- StockX (exec hackathon), Replit, Headspace, Lenny’s Newsletter/Podcast (25 adoption tactics)
- Apple, Siri, Google Gemini
- Notion Mail, Notion Calendar, Superhuman, Gmail/Google Workspace
- Airbook (analytics), Fivetran, Google Analytics 4 (GA4), ChatGPT
