Building Cultures of Candor: B2B Leadership Courses with Sharon Richmond

Sharon Richmond spent decades working as an executive coach with C-level leaders at companies ranging from venture-backed startups to Fortune 50 corporations. About six or seven years ago, she noticed a pattern: even the most talented executives she coached would arrive at sessions and say they had a conversation they knew they should have — and were avoiding it. "I would find that through our coaching, we would work through the process of what was getting in their way, what were the barriers, we would practice the conversations, we would refine them, and they would then be able to go out and have these different conversations," she recalls. When several clients raised the same issue within two weeks, she realized this could become a course. Her first instinct — sending an offer to individual executives to join an open enrollment group — failed. Nobody wanted to be in a group where they didn't know the other participants. But when a current client asked her to run a pilot with an intact leadership team, everything changed. The in-person pilot with a dozen people generated uniformly positive feedback, and when COVID hit, the course transitioned to online seamlessly.

The course makes a deliberately narrow promise: have one hard conversation successfully within four weeks, and build the confidence to do it again and again. Three 90-minute synchronous sessions structure the experience. In session one, participants learn four "keys" to candid conversations, do breakout exercises, surface fears and myths, and receive worksheets. In session two, they arrive with a draft script for their real conversation and practice it using a specific peer-to-peer format: one person plays the recipient, another coaches, and the practitioner runs through their actual words. Between sessions two and three, each participant rewrites their script and has a private one-on-one coaching session. "That one-on-one coaching session is the thing that helps build their confidence so that they move into the conversation," Sharon explains. Then they actually have the real conversation before session three, where the group debriefs what worked, what went off the rails, and problem-solves together. The most common feedback: "I was really nervous about it. I didn't think it would work. But the conversation went so much better than I thought."

Sharon sells exclusively to intact leadership teams within client companies at $1,500 per participant. Her cohorts have grown from initial pilots of 10 to groups of up to 32, with two coach-facilitators joining her to handle breakout rooms and divide up one-on-one coaching sessions. The result: approximately 40% margins after paying the coaches. She researched competing offerings to position her pricing competitively, and because the course is fully online with synchronous sessions, she keeps costs low while delivering the one-on-one coaching that she considers "mission critical." When clients ask whether they can skip the one-on-one coaching to save money, Sharon says no. "I don't want to say yes to something that I don't think will give them adequate lasting value for the price they're paying." She's also introduced a free "feedback dojo" — a twice-monthly drop-in session for graduates to practice and refresh. Companies see the course as a stepping stone to a broader culture of candor, which has become a selling point. As Sharon notes, "Many organizations are thinking about how to create better inclusivity and get people to be more candid. This provides a first stepping stone into building cultures of candor."