WIN Spotlight: Sara Kalick

Welcome to the latest “WIN Spotlight,” our ongoing series that celebrates inspirational women in our community. Each interview features a member of WIN who is championing innovation at her organization. We dig into the diverse perspectives, influencers, missions, drivers, and dreams of these leaders, and of course, share practical tips.

We’re delighted to feature Sara Kalick, a founding member of WIN, and a leader in shaping how innovators work. Based in Lisbon, Sara is currently on a ‘global curiosity tour’ ( – incredible). When she’s not writing LinkedIn’s most compelling content (read her dispatches from Spain, prototyping a new OS for 2019, and dispatches from London, Johannesburg, and Kigali), she works to help start-ups tell their story and codify what makes them great & helps old-school orgs get their groove back.

We met up for coffee in Gramercy and walked around on a warm winter day.


Who are you and what do you do?

Hi, WIN ladies! I’m Sara. The short answer is: I’m a strategist, storyteller, coach, facilitator, wanderluster…curiosity junkie.

I spent 11 years at SYPartners, starting in SF and then moving to NYC to help open that office. I came up through strategy where I was battlefield trained and groomed under some amazing leaders, and then managed the strategy team for a number of years. My last three and a half years at SYP were on the product side of the house—launching and leading a start-up called Leadfully that was designed to ready the next generation of leaders to lead into the unknown.

However, I left in July and moved to Lisbon in August. I’ve got my own outfit (read: party of one) called The Possibilitarians. The gist of my work focuses on designing conversations and experiences that help individuals, teams, and organizations unlock their potential. On any given day, I might be helping a start-up or social impact organization tell their story to fund their future, helping an old school org figure out how to rekindle what made them great, or giving some tough love + coaching to an emerging leader. I like variety.

I’ve also got a personal curiosity project that has me meeting new people all the time to gather insights on the future of work, learning, and leading. This has given me an outlet to speak and write a lot more, which I love. Here’s a piece I wrote on some of what I’m learning from around the world – as well as one on my personal operating system.


What are the life moments that most influenced who/where you are today?

Ooof, so many (lessons from mom)…

Have a bag of tricks. Always be ready to improvise.

Second grade, and I was somehow sent to school on the day of the Halloween parade without a costume. This was an oversight that I did not handle well.

The school secretary typically knew to call my dad in these situations as he had a bit more flexibility to come to the rescue, but I insisted that she call my mom and have her assistant break through a call she was on.

In a rush, my mom drove back to our neighborhood, walked into school, asked where the art room was, and took me by the hand. She quickly surveyed the scene. Within seconds, she had eyed a ream of butcher paper. Taking two big pieces, she fitted them around my tiny body, placed some strategic staples, and fringed the edges. Then she whipped out her makeup bag, swiped my cheeks with lipstick, and said, “Great, I’ve got to go.”

While my costume was a bit of a mess, what I always admire about my mom is her ability to see possibilities and quickly solve problems with whatever resources are around.

Don’t get too comfortable.

Sophomore year of college, I was moving into my first apartment and desperately wanted to buy an unfinished wood dresser that I planned to stain using fabric dye (something I had seen on Todd Oldham’s House of Style—an early days MTV show which most of you will never have heard of).

While my mother finally acquiesced to this somewhat ridiculous request to buy heavy furniture, her advice to me was, “Pack light in life. You never know when you’re going to need to pick up and go.”

To be clear, my parents have been happily married for 45 years. My mother’s closet is chock-a-block with things from 30 years ago. Whole rooms are stuffed with nonsense that has no business nor place. And surely, there were no fly-by-night escapes.

But somehow this advice always stuck with me. It made it possible for me to make left turns easily and to not hold on too dearly to one reality.


If you had to choose one, who is the woman that most inspires you? Why?

Okay, so obvio I can’t say more about mom. (I mean, there’s also the time she threatened to sue my landlord for slander. Or the time she threatened to take legal action against an ex-boyfriend of mine…did I mention she’s a lawyer?…And let’s just pause for a moment and think about the hot water that, at least at some points in my life, I seemed to get myself into with relative ease.)

But seriously, the two women that come to mind for me are Jessica Orkin and Susan Schuman at SYPartners. These ladies embody what it means to be a leader. Not a woman leader, but a leader. They bring brains and vulnerability, passion and creativity, irreverence and discipline. In different ways, they’ve both pushed me to be a better version of myself—and I have eternal gratitude for that!

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What is the best advice someone has given you?

We all know what it looks like when it works. My friend Laura and I used to say this a lot when we were younger. When we all chased the wrong lovers, the wrong relationships, the wrong jobs, the wrong [insert whatever]…When we still did things for other people’s reasons, not because they were right for us. It became a touchstone to get clear on whether we were suffering unnecessarily or simply needing to walk away.

What is your creative ritual?

Post-it notes? Duh.

Lead with curiosity. I find that when I am facing a big messy problem, the best way to get unstuck is to go get inspired. Go talk to people and mine them for their insights. Go let your eyes feast on something new. Without new inputs, you’re just going to regurgitate old outputs. Or, as I once heard someone say, it’s like eating your own poop and making new poop.


As a leader in this field, what is your advice for any woman in innovation?

Don’t tell people your biggest strength is your energy—not unless you know how to explain how it helps you be more innovative.

Listen, I’m not saying energy isn’t a strength. It is. But, I’ve honestly met too many well-meaning, fresh-faced young women who wield their effervescence like a magic wand. It can be, believe me, but it’s often not enough. Not in the work that we do—which requires things like empathy, insights, framing, generative and systemic thinking, storytelling, grit, etc.

Work is going to become increasingly about diverse, collaborative, mission-based teams. The more you can understand your superpowers, how you show up at your best, how others can activate you, and how you can contribute, the better. If you don’t know the answers to these questions, ask for feedback from others. What do they see and believe about you? It’s a starting point.

Once you have an idea, my advice, focus on the problems you like to solve, how you like to solve them, and the types of people you like to solve them with. In that context, think about what you uniquely bring to the mix. And always, always, lead with a point of view.

Do you have any rituals or routines?

Wash face. Floss teeth. Moisturizer (face, not teeth). Twice daily.

What do you never leave the house without and why?

There’s a steady collection of fine-tip Sharpies at the bottom of every one of my bags.

Half of my meetings, lunches, drinks, dates (formal and informal) end up in some type of brainstorming/coaching session. I find that I can think better with a pen in my hand. It helps me see and sketch the forces at play, cut through the clutter, weigh options, make choices. For me, and for whomever I’m engaging with.

What is your favorite book and why?

Last time I was asked this question I would have circled around The Story of O, Lady Chatterley’s Lover, Henry and June, and Tropic of Cancer…I was 20. Enough said.

I’ll be honest (nod to the editors), I don’t love questions like this. I love lots of books. I also love buying books and not reading them (and then giving them away when I move to new countries and realize I can’t keep shipping stuff across the world that doesn’t give me joy. Thank you Marie Kondo).

That being said, two books I’ve loved in the last year. First, A Little Life by Hanya Yanagihara, because it is heart-wrenchingly human. The second is A Finer Future because unlike a lot of the other doomsdaying about the environment, this book paints a picture of a future where we have (and we can) saved the environment. If you’re an optimist, read it. If you’re a pessimist but a problem solver, read it. While you’re at, get obsessed with Hunter Lovins.


What is your favorite app and why?

Things. My head is full. I need a place to keep track of the half-thoughts and reminders that would otherwise clutter my brain if I was trying to actively remember them.

Fast follow up with Hotel Tonight.

Name a fundamental human truth you recently realized.

This may be more a fundamental Sara truth—and the jury’s still out on it being a truth at that—but let’s go with it: While I am attracted to Alpha men, I think it’s my own reflection I’m chasing.


What is your favorite quotation?

“You get what you get and you don’t get upset.” I don’t know that I agree with it, and I definitely don’t think it applies to me, but I love saying it to other people.

I also like “Focus and finish” which works great for people like me with mild (self-diagnosed) ADD.

Photos & interview done by Katie Burwick

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