Send a textOnboarding one client is one thing. Onboarding a group is an entirely different experiment. In this episode, I’m joined again by Bridget Baker to unpack what really happens when you try to onboard a group program in a way that feels inclusive, clear, and genuinely supportive without turning yourself into a full-time concierge. Bridget shares what she learned from running her virtual writing retreat, including where things broke down, what surprised her, and how her expectations shifted around tools, timelines, and participant behavior. We talk honestly about Slack resistance, missed emails, manual workarounds, and why “just doing what works for you” often falls apart at scale. This conversation is about letting go of perfection, designing for real humans with different preferences, and treating your business like a series of experiments instead of a fixed system you have to get right the first time.Topics covered:Why group onboarding requires a fundamentally different approach than 1:1 onboardingThe hidden risks of manual processes when managing multiple participantsDesigning onboarding that works across different tools, learning styles, and comfort levelsManaging expectations without forcing everyone into the same containerHow small onboarding gaps compound in short-term programsTreating every launch as an experiment you can learn from and refine You can find Bridget at:Website: bridgetbakerbrandingInstagram: @bridgetbakerbranding Mentioned in the episode:Running a Location Independent Business with Bridget Baker  What next?Follow Here's What I Learned on your favorite podcast playerLeave a review so the podcast is seen by more people like youShare this episode with a friendThis podcast is powered by curiosity—and by listeners like you. Support future episodes at ko-fi.com/jackihayesFollow me on Instagram at @jackihayes_obm Proud member of the Feminist Podcasters Collective, a community of indie creators amplifying each other’s work through collaboration and care. Credits:Intro and Outro Music: Atomic by Alex-Productions |https://onsound.eu/Music promoted byhttps://www.free-stock-music.comCreative Commons / Attribution 3.0 Unported License (CC BY 3.0)https://creativecommons.org/licenses/by/3.0/deed.en_US