Your best reps are often "unconsciously competent" and can't explain their own success. Before an SKO, leaders must help these individuals deconstruct their process and build a prescriptive presentation, translating their individual "art" into a replicable science for the entire sales team.

Vercel COO Jean Grosser's litmus test for a great salesperson is that engineers shouldn't be able to tell they aren't a PM for at least 10 minutes. This requires deep product knowledge, enabling sales to act as an R&D function by translating customer feedback into valuable product signals.

Even a top-tier sales professional has a career pitch win rate of just 50-60%. Success isn't about an unbeatable record, but a relentless focus on analyzing failures. Remembering and learning from every lost deal is more critical for long-term improvement than celebrating wins.

Stop treating content as a purely artistic endeavor. The most successful creators apply rigorous scientific testing and investment to creative elements like thumbnails. They understand 'the science of the art,' using data to ensure creative work performs, rather than relying on trends or intuition.

Ken Griffin stresses that selling is the most fundamental, yet often overlooked, entrepreneurial skill. It extends beyond customers to constantly selling your vision to candidates, vendors, and partners. He learned this from a mentor's simple plaque: "if we're all going to eat, someone has to sell."

Instead of traditional classroom training, Stone would take new salespeople on live sales calls. They'd observe him, attempt a pitch themselves, and receive immediate feedback. This rapid, immersive cycle built competence and confidence quickly, even for those without a college degree.

A sales leader's value isn't in managing from headquarters. It's in being on the front lines, personally engaging in the most challenging deals to figure out the winning sales motion. Only after living in the field and closing landmark deals can they effectively build a playbook and teach the team.

Don't pitch features. The salesperson's role is to use questions to widen the gap between a prospect's current painful reality and their aspirational future. The tension created in this 'buying zone' is what motivates a purchase, not a list of your product's capabilities.

There's a fundamental irony in creative careers: to succeed professionally, artists must often master the very business skills they initially disdained. The passion for the art form—be it drumming or painting—is not enough. A sustainable career is built upon learning marketing, finance, and management, effectively turning the artist into an entrepreneur to support their own creative output.