Making the hardest hire of my life the easiest
It’s not about cutting corners. It’s about cutting noise.
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In today’s issue:
How I used ChatGPT for my latest hire
Why brands are taking their customers on vacation
The founder that wants to invest in your antiaging startup
Notes from a messy desk
Moving to London has meant rebuilding my life from scratch. I knew I wanted to hit the ground running, and that meant finding a great Executive Assistant.
Not just someone to handle scheduling. I needed an athlete. A Swiss Army Knife. Someone who could manage my inbox, run my calendar, create invoices, pay bills, coordinate with CPAs, attorneys, household vendors across the world, and help me figure out how to get set up with water, power, internet, a UK phone number, broadband, a bank account, health insurance, and help me find a new GP, therapist, physiotherapist––the list goes on.
I received over 1,000 resumes, which was impossible for me to wade through manually — so I decided to hire the best recruiter in the world: ChatGPT.
To write the job description, I flattered it by telling it it was the best recruiter in the world and prompted it to interview me, asking questions like:
What’s actually weighing on you day to day?
What kind of decisions do you want this person to make without you?
Where have past assistant relationships broken down?
It pulled out things I wouldn’t have thought to include: how I like to communicate, how I delegate (or don’t), and what would make me feel truly supported. That conversation became the bones of a job post that AI helped with, but I ultimately rewrote because I care about words.
Then the applications rolled in. I gave ChatGPT a rubric — simple but targeted — and used it to score resumes on:
Job tenure: did they jump around or stick around long enough to show discipline and really learn the ropes of the job? I saw countless resumes with less than a year stints at every single role they’ve had. Major dealbreaker.
Complexity of past roles: were they coordinating across multiple stakeholders and have exposure to both the professional and personal lives of their former boss? That’s a unique relationship, and very different from pure EA and pure PA responsibilities.
Discretion: have they worked for executives or high profile individuals and been privy to sensitive information?
Proactivity: did they have decision-making responsibilities or were they purely task-oriented? I needed someone who hadn’t been so senior they delegated everything but also not so junior they didn’t know how to add something to a calendar.
Grammar: can they spell? The amount of typos and misspellings I saw was shocking — this is your one shot to make an impression!
Resume design (to a certain extent): because taste is important.
GPT then gave me a summary of strengths and gaps for each one, and flagged anything sketchy. It surfaced real insights, real fast, and ranked candidates against the job description, allowing me to narrow down the strongest candidates in half the time.
Then I used GPT again — to sharpen my interviews. It generated tailored interview questions for each candidate based on their resume, and then took it a step further. I asked it to simulate what a great answer vs. a red flag answer might sound like.
For example, I asked:
“What would a top-tier EA say if asked how they handle tasks that feel beneath them? What would a weak answer sound like?”
It helped me refine how I listened — not just to what they said, but how they framed their thinking. I could sense mindset, not just polish.
I found her.
After a handful of mostly disappointing interviews, we clicked. She had the experience, the chops, was able to answer my questions specifically, and ultimately had done the job. She started anticipating what I needed before I said it — and this was during the interview.
The only hiccup: I didn’t have a UK business entity set up. I didn’t want to wait months or jump through legal hoops to hire her, so I asked GPT what to do, and it recommended Deel, an HR & payroll platform that acts as the employer of record, essentially allowing my business to pay them to cut the checks with my money. Check, check.
If you want to take this further, here are other ways you could use ChatGPT in your own hiring or delegation process (I’ll be testing these next):
Train a custom GPT on your communication and decision-making style, so it understands what great support looks like for you
Use GPT to generate personalized 30/60/90 plans for your final-round candidates
Run simulations of how a great EA would handle your week, using your real calendar as input
Use GPT to ghostwrite a Delegation Operating Manual: how you think, what to escalate, what “done” looks like
Embed GPT inside a shared Notion workspace to co-manage tasks, updates, and even write simple comms for your assistant to send
I’ll report back on how these go.
In the meantime — if you’re already using AI in your hiring process (or want to try something you’ve read here), hit reply or drop a note in the comments. I’d love to hear how you’re experimenting with this too.
After two weeks working with her, I feel confident that I won’t have to go through this process anytime soon — but when I do, I know it’ll be even less painful and more sophisticated. Hats off to my new GPT buddy (I named her Nova)!
Wheels up,
Sophia
Collabs on my radar
The Devon Lee Carlson collection for Reformation is now live. Inspired by Carlson’s personal style (“which sometimes means wearing a milkmaid top to get coffee”), it’s very good. Eyeing this knit dress, this sheer tank, and these ballet flats to squeeze into my little London flat’s closet this spring. Designer Cydney Morris dropped six frame styles for Australian sunglasses brand Luv Lou. Band-Aid Brand and the Metropolitan Museum of Art… I love a collab that elevates everyday items. Imagine a classic metal tin package in your medicine cabinet adorned in a Hokusai painting. Fashion designer Aimee Song created a collection for Lulu and Georgia inspired by her Asian and Italian heritage. It’s gorgeous. Look at this solid wood floor mirror. Great for “I’m finally leaving the house and look cute” selfies. Vera Wang partnered with Jared Jewelers on her VOW collection, which is inspired by her own wedding. It’s 38 rings, and designed to be mixed and matched. Hard Candy dropped a limited-edition collection with Girl Scout Cookies. There’s even a Thin Mints-flavored lip scrub. The Starbucks x Peanuts collab is too powerful. The White Lotus celebrated its CB2 collection at Thai Diner. Leslie Bibb made an appearance. And I’ve been loving the C. Gonzalez x Velour self-stick lash clusters.
Collab report: Last week, subscribers were most into the Barbour x Crocs collab and Puma’s Harry Potter collection.
Shopping roundup, feeling like a spring chicken edition
Links to make you smarter and more interesting
Brands are investing in customer trips instead of influencer ones, because 9k diehard followers can be more impactful than 1M so-so ones. And it’s smart – brands like Cocokind, Vita Coco, and Refy are redirecting budgets typically reserved for things like creator mailers, and instead treating their most loyal customers to their own version of an influencer trip. Cocokind’s founder Priscilla Tsai even picked up guests from the airport to better connect with them. It’s always a good idea to reward your most engaged consumers. They’re the ones telling their friends about the products they love and actually adding stuff to cart. It’s hard not to view this as a counterresponse to the consumer backlash around lavish influencer gifting (see: Poppi’s vending machines).
Paris Hilton’s nonprofit is giving $25k recovery grants to women entrepreneurs impacted by the LA wildfires. Icon.
At Coach’s playful, immersive concept stores, shoppers are hanging out for 4-8 times longer than in regular Coach stores. They’re called Coach Play, and they’re really resonating with Gen Z shoppers. Likely because they’re centered less around just shopping, and more on community, discovery, and having a cool experience (like customizing a Coach Tabby bag or getting a scoop of ice cream). A cool piece of trivia: Coach ditched 3D store window displays for storefronts with “found items” to appeal to younger consumers’ desire to support sustainable brands.
Highly recommend this visual tour of Coach Play’s Singapore store, which includes a dessert item with a chocolate Coach tag.
Rare Beauty, Selena Gomez’s makeup brand, is now on Substack. We wrote about Allure joining the platform in last week’s newsletter, and they’re following the lead of other beauty and fashion brands. It’s a strategic way to avoid algorithm fatigue on TikTok and Instagram in favor of cultivating more meaningful, engaged communities. That being said, it’s not just another funnel for promo emails – if you’re a brand joining Substack, you need to think about your niche and the value you’ll add for readers. Dianna Cohen, the founder of Crown Affair, nails it with her Substack Take Your Time – it’s about providing creative thought leadership to build trust and brand awareness. It’s a new era of free marketing, and the best Substacks center founders and creators over brand.
The Ordinary sold eggs not to sell more skincare, but to create a conversation. It didn’t hurt that the egg post on Instagram got more than 100,000 likes compared to its usual 2,000ish.
Unilever just acquired refillable body care brand Wild for a reported $286 million. The move further cements Unilever’s stated commitment to sustainability and eliminating single-use plastic. They’re reportedly focusing their portfolio on premium and high-growth brands. Wild’s founders – childhood friends who launched the company six years ago – are now millionaires.
71% of businesses are using generative AI in some way. But less than a third are employing best practices to get a return on investment. Those include things like having a dedicated team to deploy AI into the workflow, tracking KPIs, and having a roadmap – one that, ideally, communicates the plan in a way that puts workers at ease.
ShopMy’s founder says that you don’t need 500,000 followers to move product, just a few thousand locked in ones. Tiffany Lopinsky said in an interview with Beauty Independent that ShopMy’s top 100 sales drivers each month might have anywhere between 1,000 followers to millions, with a lot in the 10k to 500k range. She noted that just because someone’s really good at Reels, doesn’t mean they’ll convert on the affiliate platform. “We have over $50 million a month in sales flowing through the platform. The brands are able to see, oh, she only has 2,000 followers, but she moves $30,000 a month in product sales.” It truly is about quality not quantity, and that applies not just to affiliate marketing, but to getting any audience to convert, whether it’s buying a product or signing up for your new service.
A third of Pinterest shoppers make more than $100k a year. If your company isn’t thinking about how to tap into that audience, that stat alone should make you reconsider.
Kind Snacks founder Daniel Lubetzky wants to invest in your antiaging startup. His venture firm Camino Partners has already invested in Barry’s, Cava, and medical spa acquirer WellLabs. The firm’s focus is on growth-stage investments, with brands providing solutions backed up by data. In short, not a fad and not the next Theranos.
Link report: Last week, subscribers were most into Emma Chamberlain’s leaked pitch deck and Rimowa selling beautiful beat up suitcases.
More from my rich universe of endeavors
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Could not love this more. Thank you for the love— in awe of all that you're doing, always. x
I love your news, but this post is something else!! 😍😍😍