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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Transcript

Jacki Hayes

Welcome to season 10 of Here's What I Learned. I'm Jacki Hayes, a systems and ops strategist, romantasy reader, and D&D nerd who's endlessly curious about what makes a business actually work. This season is about experiments.

Big, small, accidental, and transformative. Because every business is built on trial and error, noticing, and iteration. If you're growing a business that changes with you and you're tired of one-size-fits-all advice, you'll feel right at home.

So let's get into it. Welcome back to another episode of Here's What I Learned. Today, I have Bridget Baker once again back with me on the podcast.

For those of you who have not listened to the previous episode, I'll make sure to link to it in the short notes. Bridget is brand and website designer and strategist. And when I say that, what I really mean is that she is this person who creates a very safe space to collaborate on figuring out who it is you are, what and who your business is, and how you want to show up in the world.

So welcome back again, Bridget. Thank you. 

Bridget Baker

That's like the best description I've ever heard.

Jacki Hayes

Feel free. It's all yours. So Bridget, I asked you on here to give me an experiment. And what is it that you're assigning to me?

Bridget Baker

So the onboarding of a group, essentially. I'm great. I'm being more great about onboarding individuals, right?

That's its own thing. But onboarding a group program. So I host a virtual writing retreat four times a year.

So I think I'm doing it right. And I screwed it up twice. And I'm like, yes, learning curve.

But I'm like, that becomes no longer cute after about screwing it up twice. So just that the process of not only onboarding the tech stuff, not assuming that people understand the tech, not assuming that they're getting an email, not assuming any of these things, and still being able to give them all the same information and get them on the same page. I think as well as, I don't know if I mentioned this, but as well as adding in this component of like different learning styles.

I've got a Slack group for this community. Some people are like, cool, I don't even want to be on there. Other people, I want them that want to be on there.

I really want them to utilize that tool. So making it inclusive for different learning styles, as well as making sure everybody gets the right links, the right information, all of that kind of stuff.

Jacki Hayes

So we're going to have you do this experiment. I know that your writing community retreat is you're launching it again in the start of the new year. You've run it.

Have you run it twice now? Twice. Yeah.

Okay. Yeah. So tell me a little bit about what that experiment is going to look like.

I know that you and I had a lot of conversations, write a text message back and forth as to some of the things that you were, or maybe it was, you know, Bridget and I talk on too many platforms.

Bridget Baker

Yeah, we do.

Jacki Hayes

So like we talked a little bit about some of the struggles, like you said, like you felt like you screwed up, as you just said. I would always argue there's no screw ups. There's just experiments.

So we got results. Yeah. I say that for myself more than anybody.

But what were some of the things that you are currently defining as screw ups? And then what was some of the conversation back and forth that you and I had?

Bridget Baker

Yeah. So I think some of the scripts was around like manually having to put in emails, sort of the, oh, you can export a CSV and import that in. But then just a couple people get added.

So you don't have to do the whole CSV, Bridget. You could just manually add their email in because you're smart. Right.

And I like had a typo in one email. I think I don't even know someone else. I had used the email that they bought the course with, but that wasn't like the best email for them or something.

So there was something around just the manual doing of things and also the messiness of like, how do I know I'm going to get everybody the right email, the onboarding of the email sequence? Like if they sign up the day before, because I keep the cart open, if they sign up the day before, will I know that they get all the right emails to be prepared to show up? So I felt like it took about two weeks for people to actually really get fully into a month long retreat because they were still like figuring out, oh, what Slack?

Oh, I should, I missed that email. Oh, whatever. Just all those kinds of things.

I felt like people got onboarded well enough to be set up to start on day one, which is what I wanted. I think there was something else around calendar. So one of the benefits of the retreat is that, again, if you choose to participate in the Slack, ideally, is that people can host their own impromptu co-writing sessions in this writer's retreat.

And it's sort of been like, how do I, how do people know someone wants to host one? So we tried all these different tech things. I experimented with everybody because I was like, okay, does anybody want to experiment with me?

I'm like, you paid for this thing and I'm not going to force you to experiment, but if you're willing, will you? So a couple of people tested some things out. We tried GoBrunch.

We tried Zoom. We tried Google Meet. We tried all the things.

Then I figured out, oh, I can pay more for Zoom, have someone just jump into this Zoom room anytime without me being there. That's great, kind of. But then it was like, as far as a calendar or someone going, oh, let me just add something to our calendar.

They were like, how do we do that? And I couldn't figure out how to make that happen either. So it was just like, I say this thing is a cool thing that can happen and then the execution doesn't really work for people.

So I want to make it a space where everything works.

Jacki Hayes

Well, and I know a couple of things that we talked about was, like you said, ideally people are in the Slack, but not everybody was. And some of that was because some people had never been in Slack before. And so therefore, and then there's other folks like myself that I know Slack, I know how to use Slack.

I just don't ever go in Slack. It's overwhelming. It's just another overwhelming thing for me.

I know my personality just can't handle. So I know that we had kind of a back and forth on that. And then kind of the conclusions you kind of came to, I'd love for you to share.

But then also you mentioned that took two weeks for people to get settled in for a month long program. And I know that you've made some decisions on that as well. Yeah.

Bridget Baker

Yeah. So part of that, I think that I decided from us chatting was starting to already onboard them to Slack two weeks before the retreat actually starts. So I think of it like it's a virtual retreat.

Part of the point is supposed to be, it's like, you're going to a retreat. So when people go to a retreat, they usually get there the day before they have time to settle in because there might be a flight delay. I was trying to think of it like that.

So I'm like, they need some time to get in and get to know each other and chat in there before we start. And even if they don't want to be in Slack, most of the people kind of come and introduce themselves at the beginning. And then you can even say, Hey, I'm not going to be on here much.

That's completely up to you to say, Hey, I still want to participate, but I find Slack overwhelming. You can text me anytime or email me or whatever. Some people have done that.

So again, there's something in that. And then I know I had said before, I was like, but Slack is where everything happens. So I would get disappointed if people weren't in there.

So number one, letting go of my own expectations about everybody needs to use this the same way. But I did have, there was the benefit of Slack was they get DM asynchronous coaching with me. So if they don't use Slack, they weren't getting the coaching.

And so it was a little, I'm like, but they're missing the thing that's in there. And I feel like I'm not giving them value. And I'm like, no, again, it's up to them.

So I added in an element in the future one that it's literally a one-on-one Zoom session at the beginning. So they could just do the Zoom session with me and do their own retreat, basically. They could do the Zoom session and show up to every scheduled session.

They could be in Slack and do Zoom. I've just tried to create multiple ways for people to do it. And I think my initial thing was like, oh, make it easier for you.

Don't do all these different ways. But honestly, I think that is easier for me is to make it more inclusive versus chasing people down. Like, are you okay?

You're not in Slack. Do you hate me? What's happening?

It's just so ridiculous.

Jacki Hayes

Yeah. I think, too, there is an argument for doing things in a very productized way of it's this container. And then there's an argument for, like you said, making it more functional and accessible for people on a multiple different ways.

And a lot of what yours came down to was your expectation of what it should be. And people were coming into it with their own expectations, which is that's how things work. And when we onboard clients, we want to make sure that we are, quote, unquote, managing their expectations.

Whether that is this is the specific timeline, you have to be in Slack to get notifications, or you can be in Slack if you want to be in Slack. But if not, that's perfectly okay. And as long as everybody's on the same page, that I think is where the simplicity lies.

Because if you have somebody like myself come in, and I'll be like, I'm introducing myself, but you're never going to see me here again, then that you don't have to go chase me down. Because I'm just not going to be on Slack, and I'll show up to the coworking calls. Because that's what I need, etc.

So it's in that communication back and forth, which is such a big part of onboarding people. Because I know that you said you wanted to be almost like this concierge experience, this high end, they're not going to like the YMCA, you have to retreat, they are going to like a spa retreat, yoga retreat at a high end hotel. And so if I'm going to a high end hotel, I kind of want to be able to say, I want to skip that thing, because I want to go read my book at this time.

Yeah, but I will be there for my massage, you can guarantee it type of a thing.

Bridget Baker

Yep, that's a very good way to put that now. Now that you mentioned it, I'm even thinking of it in different, I have a client that does solo led travel retreats. So it's like she, they, everybody does their own travel, they stay in their own place, and then they meet up, and she like basically talks to them about how to like calm your nervous system when you're solo travel, or how to like navigate traveling alone as a woman, like all these different things.

But they mostly get to go do their own thing, right? And so they know they have the option, here's when we all meet up, and they still don't have to do that, right? And so I think it is, it's using the language of the onboarding, that's like, instead of them being overwhelmed, like, oh my god, there's so many things I have to do.

It's like, here are your choices, here's what you can do. And then continually kind of reminding them, like a reminder that we have this chat. So like, if you like, even if you hate Slack, if you want to go connect with someone, that's probably the best place to do it.

And then you can go connect with them and go have a chat outside of there. But like, that's where you're gonna meet them. Like, still got to put on the message board, so to speak, right?

At the retreat or something. So, which gives me an idea. Ultimately, I would love some kind of like software that creates these different like retreat rooms that are sort of like, now you can go in the social room.

Now you can go in the co-working room. Now you can go in the, there's going to be workshops in this room. So that it like actually looks like different rooms of a lodge or something.

Like, that's my ultimate visual goal.

Jacki Hayes

And that can happen, that can happen. And I find that, you know, you and I have talked about onboarding and lead management and stuff for your website design portion of your business. Because one of the things you struggled with there was, I need to do it a certain way, but my clients don't want me to do it a certain way.

Where is that line where I am providing a good client experience for them and also not making it harder for myself. And this is, it's the same thing because you want to accommodate folks and also you don't want to make it harder for yourself. So giving yourself that lead way before the retreat starts, where you can upload an entire CSV file instead of being like, somebody's showing up two hours before the whole thing.

I have to input their email. Oops, I put a period in their own spot. There's ways of accommodating both.

And again, it's just being upfront with everybody from the very start of what expectations they can have. Yeah.

Bridget Baker

Yeah. Because you have to just assume, you have to go, oh, well, I assume they got the email or didn't you see the email? Why aren't you on here?

Or something like that. So that's what starts to happen. And I found myself like before the first session, I'm like, okay, everybody's not in the first session.

What went wrong? And one person didn't get the email, one person, the link couldn't figure out the link. I don't know what the story was, but it was like, okay, do I need someone?

Do I need an actual concierge? Like, am I the concierge? Maybe I'm not the concierge.

Like, that's the other thing is ultimately as I grow this and I really want to craft that experience, maybe there is someone that's like the onboarding specialist that tells them where their towels are, where the spa is and where whatever, like, maybe that's not my job in this. I don't know. I don't know that I'm gonna have to play with that idea.

I don't know that that would fix the problem though. I don't think it, I think it would just be adding another person to the mix.

Jacki Hayes

There's always little things. And I love what this whole conversation does is that your business is a continual experiment. And you try one thing and you find where it didn't work.

And even if the whole container itself worked, there's little pieces and parts that you're always going to want to improve. So you'll make these changes with the next one in the spring of the new year. And you're still going to be like, well, I could do this a little bit differently.

Or if I had not this piece of software, it would, we'll do this. And there's always something that you're going to learn from. There's something you're always going to tweak.

And that's just kind of the approach to running your own business.

Bridget Baker

Yeah, that's a really, really good point. And I think the other thing is you can't, in my, I keep trying to please everyone. And so I keep like moving the needle.

Like, oh, let me make sure it's accommodated for that person and that person and that person. And I'm like, wait a minute, maybe this just isn't for everybody. That's the other thing is, because I know I've signed up for things and gone, oh, other people are getting a lot of value out of this.

And I find it totally overwhelming. Okay. What's up with that?

Like, maybe this is not because of the platform they choose, chose to host it on. I didn't like, and it was like, oh, okay, cool. I don't have to be a part of this anymore because I don't like the platform and they're married to it and like, bye.

Yeah. So you're not going to please everyone. Just keep learning, keep fine tuning, all of that.

But yeah, just to, to, to onboard a group, I just learned was so different than onboarding one person.

Jacki Hayes

Yeah. A lot of folks think, oh, I'm going to do what I do if I want to learn. I'm just going to do it with more people.

And there are so many more elements to that. And so many more moving parts that you really have to take your time to stop and be like, okay, if I am onboarding 20 people, what's that going to be like versus onboarding one person?

Bridget Baker

Yeah. And some people have, or when the last one I had that did two of them kind of in a row, I did one in August, one October, some people had already been to the first one. So they were already like familiar with each other.

They already knew each other. And I'm like, that's a good thing, right? Like they're going to help orient the other people, right?

And it didn't totally work out like that. So I want to make sure new people coming in don't feel like outsiders. So I try to create ways to not to, to make those people feel included.

I'm always kind of looking every group I'm in, I'm always looking to like include people. Like, don't assume that these people know this private conversation over there, like fill them in. And that's always important to me.

So it's not, yeah, it's the tech parts, the inclusive parts, and you just kind of want everybody to be on the same page when you start and to know what the expectations are. And even it comes even I think, from the selling, because I think you had managed something like, oh, God, if I had to be on Slack the whole time, forget it, I wouldn't do it. I'm like, oh, God, does it sound like that?

Okay, let me change the wording.

Jacki Hayes

That's part of the conversation we have back and forth. It was like, do you expect them to be on Slack? And does it say that on your sales page?

And then that's where you were like, okay, going for a walk, I need to think through.

Bridget Baker

Yeah, because I was like, oh, I'm thinking, well, because again, because it was set up for the coaching to be in there. And like, okay, it's like, they're not getting the coaching part, but they paid for the coaching part. So but that's on them.

Like, I have to remember, that is on them.

Jacki Hayes

And after I keep reminding them, it's still here. It's here for you if you want it. Bridget, I can't wait to talk to you again, when you've onboarded your next group in the New Year, it's currently December of 2025.

So you'll be hosting again here shortly. And we'll have you back on to talk about how that went and what lessons you learned with that new experiment.

Bridget Baker

Yeah.

Jacki Hayes

And folks, I will also be having Bridget back on in the future, because she's going to give me an experiment to try based on the work that she does. So keep listening. And you will be able to hear the results of this experiment as Bridget gives to me.

Bridget, where can people find you and learn more about your writing?

Bridget Baker

Really at Bridget Baker Branding, but on Instagram at Bridget Baker Branding, I talk about it a lot. So that's really the biggest place.

Jacki Hayes

And all those links will be in the show notes. So for those of you who are driving or walking right now, you can just click on the back and take a look. I highly recommend she also hosts Write Shit Mondays, a working time every Monday.

So make sure you check that out. It's a lot of fun. It's a great space to get some stuff done, as well as meet some interesting and awful.

That's not what I meant to say. Awesome people. It's been a long day.

I bring you all the awful people, right? So go check that out as well. Thank you so much for being here today.

Awesome. Thank you. Thanks again for spending time with me on Here's What I Learned.

If this episode gave you something useful to try, rethink, or explore, the best way to support the show is to follow and lead a review. That helps more curious business owners find their way here. And if you want more real talk about the experiments that shape our businesses, plus practical doable system ideas, join my email list.

I send one to two emails each week with stories, insights, and strategies that help you build a business that supports your life, not the other way around. You'll also get updates on workshops, new offerings, and the things I'm learning as I experiment alongside you. Until next time, keep experimenting, keep paying attention to what those experiments tell you, and keep building a business that fits you.

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