The Group Onboarding Experiment: What Happens When You Scale Past 1:1
Onboarding 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 onboarding
The hidden risks of manual processes when managing multiple participants
Designing onboarding that works across different tools, learning styles, and comfort levels
Managing expectations without forcing everyone into the same container
How small onboarding gaps compound in short-term programs
Treating every launch as an experiment you can learn from and refine
You can find Bridget at:
Website: bridgetbakerbranding
Instagram: @bridgetbakerbranding
Mentioned in the episode:
Running a Location Independent Business with Bridget Baker
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