Some of you have heard the story of Monique's first sales call. I love telling this story and this is me finally writing it down. For those who haven't heard it, some context first -
Whenever I meet someone just starting their entrepreneurial journey, they'll inevitably ask me to share my own story. I've found this to be a highly inefficient activity for both parties. Instead of launching into a story about my "lightbulb" moment and rollercoaster ride, I try to ask them about their company's next milestone.
When they share, it's so, so tempting to say "oh! here what's you should do next" or "yes yes, here's what I did in that situation." I've been training myself not to do that, to remind myself it's actually counter-productive if I want to be helpful.
Instead, I think about optimizing for startup skill acquisition over well-intentioned but misguided advice.
Enter the roleplay. Why tell someone what they should do, when you could help them actually practice the skill they'll need to reach the next milestone? Teach an entrepreneur to fish, as the saying goes, you know?
The value of my own experience is not found inside my stories of success and failure and perseverance. Rather, my experience affords me an ability to recognize the skills and mindset a founder will need to reach their very next milestone, because there's a good chance I had to develop the same skills to reach a similar milestone.
The most memorable company milestones are the "firsts" because going from 0 to 1 is always more exhilarating (read: scary) than going from 1 to n. The most memorable of the memorable, of course, is closing your first sale.
Especially if you're a first-time businessperson coming directly out of the classroom, like me.
And like Monique, who I had the good fortune to meet this summer. Monique is a former teacher and business school graduate who is passionate about equipping parents with high-quality resources to help their children become great readers. Her company, Parents as Partners, provides annotated leveled books to schools. By annotated, I mean the books include questions that parents can ask their children as they read together, to encourage and model good reading habits.
The day that Monique had scheduled her first in-person sales presentation, she asked my advice.
Instead, we sat down to role-play.
The mock conversation started out as you'd expect: intro to the company, its value proposition, a couple pilot success stories. Fast forward to the ask -
Me, playing the role of a school district's Director of Family Engagement, "It definitely sounds like your product could help us reach our parent engagement goals, but you know, budgets are really tight right now, so tell me how much this will cost."
Monique paused, but only slightly.
"Well, each book is $5.00," she responded confidently.
"Time out, time out, time out," I said. "You're asking the customer to do the math. Don't be afraid to ask for the sale. Let's walk through this with some back-of-the-envelope math. How many different book titles do you recommend having in each classroom?"
"Well, average class size in early elementary classrooms is 25, so a classroom set would be 25."
"And how many copies of a title do you recommend in a classroom?"
"At least 3 to form a guided reading group."
"Ok, so 75 individual books per classroom, times 3 classrooms per grade level, times 3 grades (K - 2), times $5/book means you're basically asking for an $3,400 order."
Monique's mouth dropped open. She looked visibly surprised.
"Monique," I said, "Don't take this the wrong way. But $3,400 is a drop in the bucket for a district school. They can afford this, your role is to make them see the value."
"Got it. Let's rewind and play it again," she said.
Couple more rounds of tweaking the phraseology and tone, and Monique was out the door to make her appointment.
The next morning, Monique comes bounding into the office. "So???" we all ask.
"We got to the part about pricing and I explained what was included in the $3,400 package. The Family Coordinator - she didn't even blink! In fact, she responded with 'That sounds great. We'll also want some professional development, so that our teachers know how to roll this out and invest their families. Talk to me about your PD options.'"
"Annnnd?" we all chorused, literally sitting on the edges of our seats.
"Well, I said I'd have to check with my team of course, but we, meaning the Royal We, could probably deliver a half-day session for around $50."
I smiled. I cringed. "Oh, Monique, you didn't! Industry standard rate for PD is $2500/day! But hey, you got the sale!"
Moral of the story? Roleplay is a great way to build skill and confidence. But just remember, you can't rehearse everything - there's no better way to learn than getting out there and making it happen.
Kudos to Monique on her first sale, and many thanks for allowing me to share this story.
Next time, I'll continue the theme of recognizing the skills and mindset needed to reach your next milestone with a story about embracing the CEO identity as a first-time founder...