How to (Help) Sell Girl Scout Cookies Like a Boss

My daughter was going to raise money for her troop, sure, but cookie-selling was also going to teach her some valuable life lessons.

by Brian Weisfeld
Originally Published: 

My oldest daughter was eight when the business world came knocking at her door — in the form of Girl Scout cookies. Her mission, as a somewhat shy, funny little second-grader, was to sell delicious baked goods, but her method? Well, that was still undetermined. She knew she wanted to sell and be successful. She just didn’t know how.

As a business exec who’s helped build several brands and companies throughout my career, I could have stepped in and given her a formal business plan or step-by-step instructions on how to get her fledgling cookie business off the ground. But not only would that have been way too advanced, it was unnecessary: she needed basic business skills. Very basic. And I was quite happy to stand back, let my wife take the lead on mentoring, and watch the situation all unfold.

I knew this selling experience was going to be a significant opportunity for my daughter to begin learning the important things I wanted her to know — lessons I want every young girl to know, really. That it’s OK to fail as long as you try your best and you get back up to try again. That basic business skills will help you succeed in life even if you don’t want to be a businessperson. That grit and a growth mindset are essential tools for success in life, no matter the path you choose.

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We taught our daughter three skills during her first foray into the business world that I would love for every child to learn, whether she goes on to become an entrepreneur or not.

Life Lesson No. 1: Say “Good Morning”

Have a script if you need to make conversations easier, but make conversation. This was my wife’s advice to my daughter as she stood at the end of our driveway, unsure of what to do while fumbling around with her boxes of Thin Mints, Samoas, and Peanut Butter Patties. She was a little wary of talking to strangers — it’s not necessarily a bad thing, but neither is it conducive to successful selling. Even when your product is cookies. Shyness is common among elementary-age girls, so encouraging them to initiate conversation and prepare what they want to say may be the first step in empowering them to get out of their shell and simply connect with others.

Life Lesson No. 2: Make Eye Contact

Translation: Be confident. This is a tough one, right? Making eye contact with an adult can feel intimidating to a child. Notice where many kids look when they’re talking to you — at their feet, at their parents, off to the side, maybe at a friend next to them. Making eye contact requires, among other things, self-confidence, which is something many elementary-age girls lack. But sometimes you have to fake it till you make it. By instructing our daughter to look people in the eye when she talked to them, my wife knew that, though it might feel unnatural for her at first, it would help her grow in her ability to communicate confidently and effectively.

Life Lesson No. 3: Know How to Appeal to Your Customers

In this case, that means telling people that the money goes to charity, and even if they don’t want anything, they can still make a donation. My daughter wasn’t just selling cookies; she was selling an opportunity to do good. Positioning your product and appealing to your audience is not a skill that’s necessarily innate for grade-school kids, but learning it is key for not only entrepreneurship but also convincing people to buy whatever you’re selling, be it a physical good or a something less tangible, like a point of view.

It also helps kids recognize when others are doing the same to them. It’s about articulating your position and convincing others to do what you want them to do. (It’s also an essential skill for savvy teenagers: “Dad, you wouldn’t be just buying me a new car. You’d be buying your independence. I’d be getting a car, but you’d be getting your freedom from having to cart me around.”) It’s a skill that could work against you, too, parents — just be aware. But if your child gets so good that they’re able to actually sell you, congrats! Your kid is poised for success.

This experience of watching my daughter fumble around with boxes of cookies, trying in earnest to sell her wares but not actually knowing how, was a big part of my inspiration behind The Startup Squad, an initiative dedicated to helping girls reach their potential, whatever their interests, through entrepreneurship. She may not grow up to start her own business, launch anything beyond a lemonade stand, or become a CEO. But the experience of entrepreneurship — learning those basic business skills, knowing it’s OK to fail, and learning the importance of pounding the pavement, with an eye towards growth — will help her succeed in life, no matter what her passions are.

Brian Weisfeld has always built businesses, from a childhood gummy bear business to adult gigs at IMAX Corporation and He’s the founder of The Startup Squad and lives in Silicon Valley with his wife and two daughters.

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