Cowork Can Create Silos and This Is How to Solve It

What happens when someone goes on vacation and all their AI work becomes inaccessible? Alane Boyd and Micah Johnson tackle the collaboration crisis emerging as teams adopt Claude for real work.

This isn't really about vacations. It's about work getting siloed in individual AI sessions where no one else can access the research, problem-solving, and progress being made. When AI tools actually do the work instead of just providing suggestions, everything changes.

In this episode, you'll learn:

• Why AI work gets trapped in individual sessions and how to prevent it
• The paradigm shift from sharing AI chats to sharing AI outputs
• How to use Connectors and Skills to automatically save progress to shared systems
• Real examples of ClickUp integration that keeps work flowing
• Why this collaboration problem affects daily teamwork, not just vacations
• Practical systems for making AI enhance collaboration instead of breaking it

If you're ready to stop treating Claude like a personal diary and start using it as the collaborative tool it's meant to be, this episode shows you exactly how.

Tools/Platforms Mentioned

• Claude
• Project Management Tools: ClickUp, Asana, Monday.com
• Help Scout
• Pipedrive
• Salesforce
• Front
• Slack
• Teams
• Dropbox
• Google Drive
• SharePoint

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This episode is brought to you by Biggest Goal.

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Transcript

Micah Johnson (00:01)
What happens when somebody goes on vacation? The work doesn't stop, but if everything they're working on is in AI and lives in those sessions, then nobody else can pick it up and build from it. And that's not a vacation problem.

And that's a training problem you need to address.

Alane Boyd (00:19)
You know, Micah, thinking about this subject for us was something years ago that we solved when people would go on vacation and we wanted to make sure that we could handle their client work. We put in Help Scout back then. So we had a ticketing system. We used Asana so that we were always keeping client work updated. But because of Cowork, and Cowork's only been around since February, we're diagnosing these new

ways that people are working and that we've got to pull information out. And, you know, we're definitely huge advocates of using Cowork and AI, but work can get siloed in those sessions for individual people. And we have to account for getting that work that they're doing amazing stuff with, getting it out of there. So when they go on vacation or they're out of office, that we can still access the work that they've done. So other team members can keep it moving forward.

Micah Johnson (01:15)
Yeah, I think you know, this is really starting to be prolific. And we're seeing this across the board as more and more companies adopt Cowork and start using it. It is that paradigm shift from chat. I could share my chats and you could collaborate and do stuff. But even to that, it it wasn't like the work was necessarily getting done. That was like a quick chat and then I'd copy and paste, and the work lived somewhere else. In Cowork, the work can live.

Alane Boyd (01:41)
Hmm.

Micah Johnson (01:44)
It's getting the work done. And if you're not sharing the outputs, if you're not, you know, putting those somewhere, and you just drop it all in your Cowork and leave it and go off to the Bahamas, then nobody else, unless you know, have administrative rights and get into your user and log into your like that's ridiculous. It's just not accessible. And all of that is hidden and siloed.

Alane Boyd (02:13)
Oh my gosh, it's so stressful being on the side where you're still in the office and you're assisting with client work, but you can't get the information out. And I know there's some people listening and they're like, well, we would just text or message the person and ask them to get on and do it. That's what we're trying to avoid.

As a company culture, we do not want to bother people that much. Like the whole idea of getting time away from work is to get time away from work and it's healthy for our mental health, or get that time back for ourselves. But also, if we don't have a system for it, then every single thing that is needed outside of that is making you mandate that you have to bother them to get it out if you need it.

Micah Johnson (02:56)
Well, I think you just hit the nail on the head, Alane you need a system for it. And it's not a tech problem. Don't stop using Cowork because of this. You just have to provide the resources and train your team on what like a acknowledge that this is a problem and why it's a problem, and help them understand hey, if you're in this situation.

Alane Boyd (03:04)
Yeah.

Micah Johnson (03:20)
You know, somebody goes on vacation and you need information from them, you need information from us, you would very much like the work that we've already progressed on the project or the initiative to be accessible to you without having to ring us up on vacation. Help them see what is actually going on when they don't share that work.

Alane Boyd (03:43)
And this really, I mean, we're we're really pointing this out around vacation because that's when people are away from the office. But this is still an issue when people are in the office because you're not the a lot of times you're not the only person working on a project. It's across departments or across teams, or you know, multiple people are involved. And so when you are the single source of truth working with just Cowork and you.

Micah Johnson (03:54)
absolutely.

Alane Boyd (04:11)
Then no one else gets that valuable information.

Micah Johnson (04:15)
What's interesting and what's changed with Cowork, is that you aren't sharing, you know, in Cowork it's called creating tasks. So you're not sharing tasks. That doesn't even make sense when I say that out loud. But you used to be able to share, you can still share chats when you're chatting with AI. It doesn't really transfer over to when Cowork is helping you do the work. And so the thinking and the paradigm shift is it's the output

from the work that you're doing that you need to share, not the work to get to the output like it used to be with the chats. And I yeah, I don't think a lot of people are all the way making that jump. And then it becomes a little bit more obvious when you think about it like that. Because if the output is a word doc, well, I know how to share a damn word doc and I know how to collaborate

Alane Boyd (04:50)
That's a really good point.

Micah Johnson (05:09)
on a Word doc or a Google Doc or a Sheet or a Slide Deck. The output is the result, and that's what needs to be shared. But if you have a bunch of outputs and say it's not even a document style output, say it's a course of knowledge or it's a summary of something, you gotta put that somewhere. You've got to be able to share that, you've got to be able to collaborate on that.

Alane Boyd (05:31)
Yeah. And if if you're listening to our episodes out of order and you didn't listen to our previous episode on a single source of truth, put this episode on pause and go back and listen to that one first because it it this one piggybacks to this one. This one really is a part two to the single source of truth. And so that that is so important to have that first because that's going to be the reference material that our team is using. But then when we're we're talking about sessions a lot here, Micah, like because it's a session that we're

a task that we're working in Cowork with. And then when we're done, is where does that output go? Well, hopefully some of that is going to go into that single source of truth, but there could be other places. And and this is where we can start talking about too like the resolution to like what are some options to make this happen with individuals? Well, we have Connectors. You know, I'm thinking Micah, just on how we operate

we have Connectors that hook up to our CRM, Pipedrive, to our project management system, ClickUp, to our Google Drive, to our Dropbox. And we can have a Skill that says, hey, when this runs, go and save this in here.

Micah Johnson (06:40)
Yeah. I've got a great example for this, Alane. I'm glad you brought the Connectors up. This actually was something that happened to me earlier today that I was working on. I was trying to solve a problem. You know, our team's busy. I'm a problem solver by heart. Alane, you know this more than anybody. And I'm like, I can figure this out. So I'm working with Claude Code. I'm puzzling through different options. we're working through it. I got the idea as I was working through it. I'm like, I'm connecting Claude Code

up to the specific task that this is already created for in ClickUp. And as I'm puzzling through it, instead of Claude just telling me what it thinks, every quote unquote milestone that I'm hitting in that path, I'd validate stuff, I'd look at stuff, I'd test it, I'd have Claude do some research, you know, working together like that. I'm also having Claude document as ClickUp comments in this task.

Alane Boyd (07:34)
Mm.

Micah Johnson (07:35)
So when we hit a milestone, like, ⁓ this is the problem. Cool. We validated, we know that's the issue. That now goes in as a comment. Then we make it a little bit further together. 30 minutes later, another comment. Here are three options that we can legitimately use that have been validated that we could go down this route. And then all the way through to like, let's prototype some stuff. What is everything? And then at the end, before I handed this off to my team.

I had Claude summarize everything in the quote unquote, the fewest bullets possible, and put that as a final comment. And now, like I could have stopped halfway through that, and anybody could have gone to the ClickUp task, reviewed the thread, started using Claude in their session, picked right up, had all the information that they needed, no knowledge transfer, no meetings, nothing. And all for the simple sake that

Alane Boyd (08:27)
Mm-hmm.

Micah Johnson (08:29)
I'm getting that stuff out of Claude. If I would have just operated in Claude and not done anything with it, then what are my options? I would have had to jump on a huddle or a Zoom and say, like, here's what I figured out, and we spend an hour talking about it. Nah, that's ridiculous.

Alane Boyd (08:46)
I mean, the easiest thing, and that was such a good example too. But the easiest thing that I'm seeing as a user of this to make sure that I don't forget to do things is to have it a part of the Skill. And Micah, we just went through and dissected Anthropic, they just released, their sales process with the four main Skills that their sales team uses now on a daily.

Micah Johnson (09:06)
Yeah.

Alane Boyd (09:11)
weekly and quarterly basis. And the manager of the sales team in the US, he's like, I don't have to spend any time now managing Salesforce because the team is using Skills and Salesforce is being updated because of the Skill and it's making everyone's life easier. Well, that's a single source of truth for that sales team. Where are we at on this pipeline or this deal?

That's getting updated automatically by a Skill. So that's one of the easiest ways is to write it into the Skill, and Claude Cowork will help you do that.

Micah Johnson (09:43)
Totally,

totally. And it yeah, it goes back. If an Account Executive is out on vacation or sick or whatever, then another Account Executive or the Sales Manager can immediately know where they were at across all their deals because that's a shared source of knowledge, but a single source of truth.

Alane Boyd (09:50)
Mm-hmm.

And the other way that we are using it too is if it's not written into a Skill, because not everything is a Skill yet. We've got to figure out what we want as the Skill. And we might be just kind of working through a brainstorm or working through some new ideas and we get to the end point and we're like, hey, this is something that we want to save. And we are adding it to our Vault, which saves in Dropbox.

Micah Johnson (10:24)
Mm-hmm.

Yeah. And then that way anybody that has access to those files can pick it back up. Or I mean, I love doing that because it'll be beginning of week one, I'll work on something and I might not pick that up for another week and a half. And there is no way in hell my brain is gonna remember every detail. But because Claude helped me save it to the Vault and write out all the details and summarize and put it in bullets and reference with links.

Alane Boyd (10:43)
Mm-hmm.

Micah Johnson (10:50)
The whole nine right? Now, I can pick up at any time and just simply ask, hey Claude, where did we leave off with that?

Alane Boyd (10:58)
Well, and this one's a harder piece, which is why I didn't want to start off with this one, because I'm bad at this. This is a training thing and a getting used to thing, is where you have to tell it to end the session. And when you do that, it'll update the Vault. Otherwise, before you do that, it's just using the content in the Vault to help you do whatever you're doing. And but if you want the end outcome, you have to let it know to end the session. And Micah, this was a learning experience.

Micah Johnson (11:23)
And I'm so

I wanna just interrupt for a second, Alane. The caveat is that we put in our Claude.md file and listen to our previous episodes before this if all of this sounds confusing. ⁓ they're all pretty short, but it'll get you caught up. Or check out our Cowork Masterclass on your.biggestgoal.ai. Also a perfect resource that'll fill you in for all of this. ⁓ and it's totally free.

Alane Boyd (11:34)
Yes.

Mm-hmm.

Micah Johnson (11:49)
We did in our Claude.md file give it instructions that when we say end the session, it knows what to do, it knows where to save it, it knows how to save it. So when Alane is saying we have to tell it to end the session, we're giving ourselves a shortcut, but we are instructing Claude on where to save it in the Vault, how to save it, how to structure it, how to write it, all of that good stuff.

Alane Boyd (12:11)
I'm glad you jumped in and interrupted me because that is an important piece. And it is so nice when your stuff is being saved and you have a place to go back to. I mean, the way that you set this up, Micah, is wonderful. And the part that is a training piece that Micah, you had to repeatedly train me on this is to tell it to end the session and

Why I wanted to start with talking about Skills first before we talked about this, because what I didn't realize was happening at first when we were using Skills and it was automatically adding back to the Vault, we had that written into the Skill. Well, not every Skill has been developed, so we have to tell it to end the session if it's not already written into the Skill.

Micah Johnson (12:46)
Uh-huh.

Yep. Yep. And if you don't, it doesn't do anything. It just stays in there and then you're not sharing that knowledge. And nobody can pick it up, including yourself.

Alane Boyd (13:08)
So the the nice piece about that is that we have ours syncing to Dropbox. And so anybody that has that user connected to that same folder system can go in and access that information. Or if they don't, they can't access it.

Micah Johnson (13:24)
All right, so I think bring this all together, Alane. The the big thing that we want to convey and just really get everybody to start thinking about is, you know, before this, we did an episode on the source of truth. That is super important. This is all about if everybody is working in their own Cowork and they're not saving or sharing what they're producing as they're producing it, then everything is siloed and nobody can pick up. So we've got to.

really enforce that collaboration piece. And you started out at the beginning of the episode where we talked about tools like ticketing platforms and we didn't mention it, but tools like Front for email where you can collaborate on shared inboxes. Tools like Asana, ClickUp and Monday. These are all collaboration tools that allow a team to work together on an initiative and push forward. And we have a whole episode on this as well, which is

Why your PM tool is so important to work with AI. And this is piggybacking on that really, which is as you're doing your work, like I said with ClickUp, we use ClickUp. So as I'm doing work and Cowork or Code, it's actually updating my progress in ClickUp. I'm not writing that. Hell no, that would be annoying. I'm getting the work done. I'm solving problems. I'm doing the fun stuff. Claude is doing the monotonous, let me leave comments and keep things organized and updated.

But that stuff needs to happen. So wherever you collaborate, and hopefully you're not thinking, Slack or Teams, because please listen to our earlier, earlier episodes. You know, get stuff out of Cowork, get stuff out of Code, save your progress, collaborate as a team, then send us a comment and tell us how much we've changed your lives.

Alane Boyd (15:09)
And check out the free Claude Cowork Masterclass that we have on your.biggestgoal.ai.