Generosity is a Flywheel
And other lessons I brought home from the Women in Retail Leadership Conference + plus a little Mother's Day advice too
I spent last week in Aventura, Florida, at the Women in Retail Leadership Conference, three days of women from every major brand coming together to discuss all the things currently affecting their careers and lives. Coming home from the summit meant walking straight back into the chaos of real life, and it took a minute to finally sit down, open my notes, and actually translate what I heard and experienced into something worth sharing. Now that I have, here we are.
I’ve been to a lot of industry events, and I have to say, this one is different. The women who show up aren’t there to collect business cards and post a photo of all the transactional networking. They’re operators, executives, and founders, and they actually came to connect. You feel the difference immediately.
This was my first year, and I was there in two capacities: attending as an industry person, and the IFP team was on the floor running a fit activation for our client, Wacoal, across three days. It was an interesting position to be in. I had an open door with anyone I wanted to meet: “Come get fit with Wacoal,” “Have you met the Wacoal team?”, and at the same time, I was absorbing sessions and keynotes while also watching what happens when you bring a genuinely great experience to women who are already in that headspace.
On the plane down, the woman who sat next to me and I bonded immediately over the lack of overhead bin space, which is honestly the great equalizer. Turns out she works at Etsy, right around the corner from me in Dumbo. By the time we landed, she had given me some of the most thoughtful feedback about what this conference had meant to her, how it helped her reconnect with her north star as a leader, how it gave her clarity she hadn’t found anywhere else. That set the tone for everything that followed.
Women Actually Showing Up for Each Other
The women at this summit were not there to network in the transactional sense. They were genuinely there to help each other, and as simple as it sounds, it’s actually rare these days at similar events.
Something that made it even more special was how many of these women I already knew, just not in person. People I’d emailed, people I’d heard about through mutual connections, people whose names had come up in conversations for years. Getting to finally put a face to all of that and just be in the same place together was its own kind of thing. It felt like a community that already existed, finally getting to meet itself.
One afternoon, I found myself sitting poolside with Rebecca Minkoff in the Florida sun, just catching up. I’ve known Rebecca for a while. We were neighbors at one point, pregnant around the same time, and I have been a fan and member of the Female Founder Collective since she started it. This catch-up was different because there were no kids, no chaos, no agenda, just two people in an industry being real with each other. Rebecca, if you don’t know her, is IMPRESSIVE in all caps. She shared what she’s building in this current phase. I told her what we’re doing at IFP, who we know, and how we can be useful to each other. Another thing about Rebecca is that she is one of the most genuine champions of women I have come across, and that’s not something she performs; it’s just how she operates. That conversation reminded me why I joined the Female Founder Collective in the first place and why communities built on that kind of generosity actually work.
It also reaffirmed a lot of what I already believe in operating. With kindness, with generosity, with showing up. The more present you are for your clients, the better your work gets, the more they trust you, and the bigger the opportunities they put in front of you. Hearing room after room of accomplished women say versions of the same thing was its own kind of validation.
Empowering Your Team is the Actual Job
Kelly Cook from David’s Bridal talked about rebuilding the brand, and one story stopped me. Her store teams didn’t feel empowered enough to approve printing costs for a deal that stood to generate significant revenue. They waited. They asked up. The moment almost passed.
She talked about teaching organizations to trust their people, and it immediately took me back to something I learned years ago from the Ritz Carlton school of thought. The $2,000 rule. Do whatever it takes, up to $2,000, to save the guest experience, no approval needed, no explanation required. Trust your people to make the call. I have believed in that principle ever since I understood it, and it was powerful to see how directly it translates to retail. When your teams feel empowered, they move. When they don’t, they wait. And waiting is expensive.
Kelly also shared the three Fs that guide her leadership: Faith, Family, and Forward. Simple, but the kind of framework that only lands when the person saying it actually lives by it, and she most definitely does. Those three might not resonate for everyone, but they reminded me that we should all have words that guide how we lead. Mine are Courage, Curiosity, and Community.
Investing in Your People Means Investing in Their Space
Kate Ridley, Chief Brand Officer of Stanley 1913, was recognized in this year’s Top Women in Retail report, and something she said has stayed with me. In a year when most companies were cutting costs, Stanley decided to invest heavily in their Seattle headquarters, upgrading communal workspaces and bringing their brand values to life physically, not to mandate people back, but to make coming in worth it. She also challenged us to get clear on what is nonnegotiable from your legacy and what needs to evolve to stay relevant. That tension between protecting what made you and being willing to change it is something every brand and every leader is navigating right now.
I have been a believer in return to office since before it was a debate. We were among the first to bring our team back, and I’ll tell you why. Humans need humans to be successful. That’s not a hot take, that’s just true. If you are going to invest in people, and I mean really invest, that investment has to include the ability to engage with each other in real time. The energy that builds in a room, the quick conversation that turns into a great idea, the mentorship that happens in the in-between moments of a workday, none of that happens on a Zoom call.
Look, human connection is only becoming more valuable. What Stanley did wasn’t about control. It was about creating an environment where people actually want to show up. There’s a difference, and most companies get it wrong by skipping straight to the mandate without doing the work to make the space worth coming back to
The Keeper Test
Mimi Swain, Chief Marketing Officer for Amazon Devices and Services, said something that caught my attention because it connected to a framework I’d heard about from Netflix called the Keeper Test.
If someone on your team told you they were leaving tomorrow, would you fight to keep them? Not would you be bummed, not would it be inconvenient. Would you genuinely fight for them?
The Keeper Test is about identifying who is exceptional, and being honest about the difference between someone truly great and someone just fine. Comfortable. Competent. Fine. And fine is the enemy of any great team.
Leaders avoid this because it is easier to keep someone who is good enough than to have the hard conversation. But small businesses, especially, cannot afford it. Keeping people out of obligation or guilt is how small businesses go under. And letting someone go is rarely a reflection on your leadership. Sometimes it is just honesty about fit.
If someone passes your Keeper Test, tell them. Exceptional people should know they are valued. The most powerful leadership move is sometimes just saying it out loud.
On AI, Taste, and the Thing the Robots Don’t Have
A lot of the summit touched on AI, as every industry conversation does right now. My position hasn’t changed, and many of the leaders at the conference said the same thing, so I’ll keep saying it. AI doesn’t have taste or discernment. You can automate a lot, but you cannot automate those two things, nor can you automate the nuance that comes with them. As long as we, as humans, stay sharp, stay opinionated, and stay specific, there will always be a need for people who can tell the difference between what is good and what just looks good. That’s not going away.
More from The Ballroom
There was so much more that resonated for the team and me across the three days, and I want to make sure these women get their flowers.
Jen Hatmaker reminded us of the power of vulnerability, of accepting generosity, and of learning to mother yourself. That last one hit differently in a room full of women who spend most of their time caring for everyone else.
Shakaila Forbes-Bell explored the connection between our emotions and what we buy and wear, reframing consumer behavior as rooted in identity rather than impulse. As someone who works in brand every day, I felt that was an important thing to sit with.
Reba Hatcher of ButcherBox shared something simple and true: what you want to be true externally starts with what’s true internally. You cannot build a brand that stands for something if the people inside the organization don’t feel it first.
Daria Burke left us with this: the most powerful thing you can do as a leader is to keep becoming more of yourself. Not a polished version, not a safer version. More of yourself.
Corie Barry, CEO of Best Buy, spoke about the importance of who you surround yourself with, because the strongest leaders know they are not supposed to do it alone.
If You Build It They Really Will Come
Last year, the IFP x Wacoal team showed up with two fitters and a two-day activation, fitting 102 women. This year, we added a third fitter, brought product to sell, and ran it for almost three full days. We were fully booked from day one and stayed that way, with word spreading through the summit fast enough that walk-ins filled every gap.
What kept coming up from the women we fitted: most hadn’t been professionally fit in years. Many were in the wrong size and didn’t know it. The fitting experience kept getting named the highlight of the summit. The reactions in that room were something I genuinely wish we had recorded.
This activation got bigger and better because we had a client willing to push with us. And what it proved is simple. When you bring the right experience directly to the right people, in a context where they are already open and already investing in themselves, meeting the customer where she is stops being a strategy and takes on a whole new meaning.
Business Lessons from my Mom
This weekend, we celebrate mothers, and I couldn’t close this out without saying that the summit was full of women at every stage of leadership, in their careers, and in their personal lives. Mothers, daughters, mentors, mentees, women figuring it out, and women who figured it out and came back to show someone else the way. That energy was everywhere.
My mother was an entrepreneur her whole life. She even sold her own company a few years back. I guess it’s genetic. Over the years, she’s given me some excellent advice, even when I’ve resisted.
The best piece of business advice I have ever received came from her.
Don’t show up if you’re not willing to play. I’ve heard Serena Williams say a version of this, too, but I’m attributing it to my mom because, hi, she said it first. Show up ready, show up fully, or make room for someone who will.
I watched that principle in action all week, on stage, poolside, on the floor of a fit activation, and on a plane before any of it even started.
Happy Mother’s Day to all the women who taught us how to play.
The Fine Print
Find your north star and keep it simple. Know who you are at the root, let that define how you lead, and build your principles around it. Courage, Curiosity, Community. Three words. That’s all it takes.*
Generosity is something you do for yourself, not for others. In a world that tells you to hold everything tight, giving freely and doing it without keeping score is one of the most important things you can do. Keep doing it selflessly.*
And on the other side of that, be mindful and make your ask meaningful. There is a difference between accepting generosity graciously and taking advantage of it. Know the difference and don’t be greedy with people’s time, energy, or goodwill.
So I’m honestly exhausted this week, which is why this newsletter is late.
As I said in my note earlier this week, life has been life-ing, and since I got back from the conference, I’ve been to a funeral AND a celebration of life. Attended the Pokémon x Target Launch with a Jonas Brother. Had friends in town all weekend. Went to an all-day client sales meeting, followed by watching the Met Ball with a bestie who was visiting. Attended a PR Net event. And saw The Rocky Horror Show on Broadway!
For this week’s listicle
Also, if you want to go for a fitting with Wacoal (and you should), you can find more information about their fittings HERE and do a little good too.
My mom also says “Your handbag should never be more than your fee. People pay you a lot of money, don’t let them think you’re being paid too much because your stuff is fancier than theirs.” Well, here is a list of some of my favorite, less-fancy handbags, plus a few extra ones just for fun.
That’s it from me, as always, thank you for being here, for reading, and for sending me words of encouragement. And don’t forget to tap the lil heart so I can make more internet friends.
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loved this, melissa! esp the subj line: hard agree. xx
Love this. And know Kirsten will also hard agree. There’s a shift happening in female leadership and I’m very here for it. Excited to catch up in Cannes!