“Please Please Please, don’t prove I’m right” about teams
A five-track masterclass in people-first tech leadership, courtesy of Sabrina Carpenter.
Sabrina Carpenter’s last 18 months read like a speed-run of pop milestones: two smash singles, a platinum album that opened at No 1, and a 72-date arena tour whose tickets vanished faster than a merch drop.90.5 WESApopfiltr.com
Yet the way she moves through those wins: equal parts candour, craft and fan obsession, offers a surprisingly crisp playbook for anyone trying to steer a product team in 2025. Below, five of her biggest songs become five habits that put people (users, colleagues, whole communities) ahead of ego or quarter-end dashboards.
1. Own the risk, invite the rescue — “Please Please Please”
Carpenter’s first Hot 100 No 1 is essentially a polite panic attack in 3-minute form: “Please, please, please don’t prove me right … don’t bring me to tears.”90.5 WESA
Great leaders channel the same honesty. Before a launch, say out loud what could go wrong: security slip, tone-deaf copy, DNS meltdown, and clarify that everyone has veto power when reputational smoke appears. Two practical tweaks:
The 🚨 rule: any teammate can tag a red-light emoji in Slack to pause the release while they investigate.
Save-sheet kudos: When someone catches the bug, celebrate the prevention publicly (release notes, stand-up, even LinkedIn). Catchers become heroes, not nit-pickers.
When risk is named and shared, a launch day feels less like Russian roulette and more like a win-together ritual.
2. Feed the energy in tiny bursts — “Espresso”
“Espresso” barely breaks the two-minute mark, yet it topped charts in 20-plus countries and clocked seven weeks at No 1 in the UK, all on the strength of an endlessly repeatable hook.
Translate that caffeine rush into management by favouring micro-recognition over quarterly sermon-fests: Short, frequent, specific praise keeps morale buzzing long after the flat whites are gone.
3. Adjust the outro to the room — “Nonsense”
At every tour stop, Carpenter rewrites the last three lines of “Nonsense” to roast or flatter that night’s city, spawning TikToks before the confetti even settles.
Adapting the message to the moment is people-first 101:
Local color → Swap boilerplate slides for references only; this client, cohort, or timezone will clock.
Iterate in public → Post-mortem the tweak next day: what landed, what whiffed, how to sharpen.
Build anticipation loops → Teammates start waiting for your personalised cold-open at stand-up—and you learn more about them to fuel tomorrow’s riff.
Personalisation isn’t extra sparkle; it’s proof you’re listening.
4. Lighten the load and level up — “Feather”
“Feather” floated to No 1 at Top-40 radio and double-platinum status on a chorus about shaking off dead weight: “I feel so much lighter like a feather.”Hashtag Magazine
Ask what would let your team feel feather-light:
Kill one ritual every sprint. If nobody can explain the Tuesday report’s purpose in 30 seconds, archive it.
Automate the nagging. Use CI gates and linting bots so humans stop policing style rules.
Document the exits. When a process dies, note the metrics that improved—speed, happiness, both—so nobody resurrects the zombie.
Removing friction is not laziness; it’s an act of respect for people’s craft.
5. Keep the vision short n’ sweet—“Short n’ Sweet”
Carpenter’s sixth LP rocketed to No 1 and hit platinum in barely a month, packaged in a baby-blue-and-lip-print aesthetic critics now call “Brinacore.”e
The lesson: concise story + cohesive styling = instant recall. Apply it to team comms:
Executive memo = one mobile screen. If it scrolls, it bloats.
Design tokens for culture. A palette of keywords (ours are focus, flourish, fail-forward) that governs docs, swag, even channel names.
Monthly “sweet spot” review. Audit every OKR: does it serve the headline story? If not, cut or condense.
Brevity is kindness. Consistency is relief. Together, they turn mission statements into muscle memory.
Encore: stitch the setlist together
Sabrina Carpenter’s catalogue proves that vulnerability, brevity and relentless audience attunement outperform fireworks and fear. For tech leads, the translation is simple:
Master those five tracks and you’ll run a team that feels seen, trusted and ready to sing your chorus back at full volume—no drama required.
