Making It Rain: A Starter Kit

“Wait—there’s a job where you can get paid to talk to strangers? Sign me up.”

That’s the true story of how I accidentally fell for my first (professional) love in a chance encounter. As a fundraiser and sales executive, I loved the relationship building, the great conversations, the thrill of closing the deal, and the mandate to solve tough problems all day everyday. 

I won’t be shy: I also loved making it rain. 

The skills I had learned--handling tough conversations, negotiating, and managing complex groups of stakeholders--felt like my professional superpowers. As I left my business development career to take my executive coaching business full-time, a part of me worried: what would happen to my super powers? Did this mean I was hanging up my cape?

Quite the contrary, I quickly learned. People hunger to make it rain in their work lives and not just financially--though that’s often part of the equation. They’re hungry to make the universe rain down on them with the clarity, skills, and opportunities they’ve been longing for to make their professional dreams their career reality. Even, and dare I say especially, at the senior-most levels of leadership. 

So are you ready to make it rain? 

Regardless of your sector, seniority, role or profession, you can also take the skills of great sales leaders and use them to “close the deal” on something big in your work life. Here are four places to start and don’t worry: my colleagues and I have already done that pesky work of talking to strangers for you. 

1. Holding your own. In my 20s I worked for a company called The Advisory Board Company. Kudos to them: I knew nothing about healthcare but they hired me anyway on pure potential (and a strong referral—thank you, Laura Herman!). Three weeks into my job I was on a plane to pitch a room full of hospital IT execs in North Carolina. I was scared, but I was prepared. Another client once invited me up to Boston to pitch his team of 15. When I asked him to kick off the meeting he announced to the room that I was “here to audition for his business.” If those experiences didn’t teach me how to hold my own (even when I was scared as hell on the inside), and to be confident about who I am and what I have to say, nothing could.  

   One question to ask yourself: what could transform in your work life if—in high-stakes situations—you replaced imposter syndrome with self-assurance? 

2. Understanding how to articulate value: Years ago I worked on a sales team with a superstar saleswoman. We were consistently among the top performers and shared a fundraising background. While we got along really well, that was about all we shared in common. Remarking one day on our striking differences but shared, consistent performance, our Chief Revenue Officer asked me what we were doing in common that the rest of the team wasn’t. The answer was simple, I told him. Here’s what all those sales managers who had initially rejected us when we were “just fundraisers” for jobs on their sales teams hadn’t understood: while their teams were trained to sell products, we didn’t have products. We had been trained in fundraising to exclusively sell value and impact--which is actually the key to success in sales. 

   One question to ask yourself: what could transform in your work life if you could better communicate your unique and inherent value? 

3. Talking about money. After holding your own in the pitch and articulating value during the sale comes the negotiation. So why are salespeople so great at talking about money? They do it all day, every day, and here’s the secret any good salesperson knows: during a negotiation, when you believe in the integrity of your pricing, deadline, and terms so does the other party. They might not agree with them, but they respect your confidence and respond back accordingly. Show one sign of weakness or waffling and those terms (if not the deal itself) are dead. The foundation of great negotiating isn't trickery, it’s confidence.  

   One question to ask yourself: what could transform in your work life if you could speak more confidently about money… and what you’re worth? 

4. Learning how to lose… and keep going. Losing in sales is just plain math. Sales teams use a “conversion rate” to determine what percentage of initial client conversations will convert to closed deals: for a company with a 20% conversion rate, that means for every 5 initial client conversations you have, you’ll hear 4 “no’s” and close 1 deal. Winning is the fun part but it takes a lot (and I mean A LOT) of losing to get there. As resilience guru Angela Duckworth captured so perfectly in Grit, “when you have setbacks and failures, you can’t overreact to them.” If you don’t learn that in sales it will simply crush you. If you can learn that, the grit and resilience you build will be unshakeable. 

   One question to ask yourself: what could transform in your work life if your failures didn’t feel so existential? 

So I’ll ask you again: are you ready to make it rain? Here are four places to start. Report back to me on how it goes in “closing the deal” in your work life and expect more in this continued series on how non-sales-practitioners can leverage sales skills to achieve their professional dreams.

Randi Braun is a coach, consultant, speaker, and the Founder of Something Major. Get in touch with Randi via email or social (below). Copyright 2020. All rights reserved.