Magic Moments
Entering Q2 2022, Rupa was around 60 people, and we had done a quarterly cadence of goal setting for the last two quarters.
This was my third “End of Quarter State of the Union” meeting (EOQ SOTU) where I built a presentation to celebrate the passage of a quarter and reflect on our goals.
The inaugural presentation a couple quarters prior had been a total surprise to the team. It was HYPE. I built a 70 slide slide deck and went through every win we had through the quarter and called out every team by name. It had confetti, music, and inside jokes scattered throughout. The team came in with zero expectations other than a 90 minute hold on their calendar, and they left the call crying laughing and STOKED about the future. That’s exactly what I wanted.
But now, after doing that two quarters in a row, suddenly it went from “wow, that was one of the best work moments of my life” to “oh it’s time for End of Quarter SOTU again”.
And just like that, what was once an unforgettable experience had become an expectation.
So I knew we had to mix it up. Keep it fresh. Keep people on their toes.
And I had an idea. 👀
The night before the Q2 2022 EOQ SOTU, my cofounder, Rosa, and I had a stealth project going on. We couldn’t stop laughing while making the slides. It was gonna be fun. (And if the team hated it, oh well. We had fun making it 😂)
The next day, the first hour of the SOTU went as normal. Wins, hype, music, confetti, shoutouts.
Then we got to the “Major Takeaways” section…
And the raucous began…
Rosa and I popped up on screen in full pirate attire (after the world’s fastest outfit change), blasted the Pirates of the Caribbean theme song, and told a hilarious story in pirate voices hyping everyone up for our next quarter’s mission.
(Except my costume didn’t make it from amazon in time and so I was wearing red leggings on my head, wearing my sleep mask over one eye, and holding a kitchen knife in my hand)
The team absolutely lost it.
That Quarter we were Pirates of the CaRUPAbbean.
Everyone had pirate names.
My slack handle was “TAARRRG-A” even to external partners & investors.
Slack turned into pirate memes.
We wrote and sang improv sea shanties.
(Imagine the head of engineering singing a song he wrote called “Gassy Sailor” to the entire company 😂)
We created a pirate poster with all of our goals and mailed it to everyone on the team.
It was a Magical Moment that I doubt anyone who was at that meeting will forget.
Most of life is forgotten. Magical Moments are remembered. If you can focus energy on creating outsized moments for your teammates, you’ll be in the top 1% of company cultures.
You don’t have to get everything right (you can’t get everything right), so creating these moments is high leverage.
But make sure to get the basics right (comp at a place where people aren’t stressing about money, benefits to support their lives, resources to support them accomplishing their work goals, etc.), and then focus the rest of your time on creating moments they’ll never forget.
Components of Magical Moments:
Unexpected. Magical Moments are unexpected. It’s the surprise factor that triggers an outsized reward in the brain. A surprise pirate theme works once, but if we did it every quarter, it would not be a Magic Moment. If a teammate expects it, the experience loses its magic. It’s become an expectation. Meeting an expectation is the opposite of a Magical Moment.
Different. Make it unique. People remember the moments that are different — the ones that stand out in their mind. People have ingrained expectations around certain rituals — “new hires get tshirts”, “all hands calls are stuffy and boring”, “the CEO is too busy for me”. Shake up their definition of “normal”. FaceTime the candidate the night before their first day and tell them how excited you are to have them start. Pick a great story you learned about the candidate and tell the whole team the story the day they start.
Personalized. Do what’s meaningful for the person. Please don’t send a person a cake for their birthday. First of all, it’s probably going to cost $50 all in. And they’re not going to remember it. It’s like saying “I don’t care enough to know what you like so I had my EA send you a cake”. With $50 you can create a custom piece of swag on Etsy that they’ll love, get them a travel yoga mat, feed a family in need, or do a million other things that will be more meaningful. (P.S. if they LOVE cake and it’s really special for them, by all means, get them a cake)
**Timely** Timing is key. Beginning of relationships (everyone remembers their first day on the job & this forever colors their experience at the company), during difficult personal moments, and monotonous or routine experiences (when you feel a meeting or general sentiment getting stagnant) when you need to shake things up are all key times to deploy Magic Moments. Also make sure to not do them on a “schedule” — if the team expects something once a week, quarter, year etc. it loses its impact. See point #1: “Unexpected”.
It’s usually inversely correlated with money. You can’t buy culture or loyalty — two things that Magic Moments unlock. It’s not about money. It’s about creating an experience they’ll remember. Everyone can send flowers if there’s a death in the family. What’s been more impactful is when I pick up the phone and call the teammate, listen to how they’re handling everything, and check in day after day to let them know they’re not alone. Showing you care can be a Magic Moment in itself.
One major point that ties in with “timely”. You can’t operationalize most Magical Moments. They don’t happen on a schedule that you can outsource to an EA.
Magic Moments must come from the heart and soul of the creator.
It’s about cultivating a mindset where you’re always thinking about this.
It takes intentional work and a commitment to creating these moments. But like anything, if you practice it, it’ll become second nature. You’ll start seeing the world through the lens of opportunities for Magic Moments.
Last crucial point: you alone as one person cannot scale this. It’s impossible to come up with a hyper-personalized gift for each team member’s anniversary as you grow. So you have to scale it through your team.
Our leaders deeply know my obsession with outsized Magical Moments. Everyone puts up a fight at first. “I don’t have time.” “I need to focus on my goals.” “These things are cheesy.” “I sent cupcakes, isn’t that enough?” (No, it isn’t.)
But once they experience their first taste of it — it’s hard not to get hooked.
The secret? Creating these Magic Moments ends up actually being a Magic Moment itself for the creator. The joy you feel when you deliver a meaningful experience for a teammate is unparalleled. Watching people’s eyes well up from gratitude (and also laughter) is one of my favorite parts of this job.
By creating Magic Moments for your direct reports, they’ll start doing it for theirs & so it cascades.
Now, I watch my team create Magic Moments in ways I couldn’t have dreamed of.
And it’s even coming back to me. 🥹
When we raised our Series A, our team surprised ME. Each person on the team hand wrote a letter to me about how much this company has impacted their life. My Chief of Staff collected the letters and put them in a box and surprised me with them.
I cried on the zoom call. (Something the team has never seen me do!) Immense gratitude, shock, overwhelm.
It was a Magical Moment I’ll never forget. 💙