5 Ways to Make Claude Love Your PM Tool

Your project management tool is capable of so much more than task tracking, but most teams are using only 10% of its potential. Alane Boyd and Micah Johnson break down the harsh reality of why that remaining 90% is limiting your team, workflows, and AI automation efforts. 

If you've ever felt like your PM tool is just a fancy to-do list that doesn't really streamline anything, this conversation will change your perspective. The hosts get real about the five foundational elements that separate teams who struggle with scattered workflows from those who've built AI-powered automation hubs.

In this episode, you'll learn:

• Why standardization comes before automation and the chaos that happens when you skip this step
• How to template everything without losing your mind or creativity
• The tough love truth about where ALL work must live (hint: not in Slack)
• Why collaboration belongs in your PM tool, not scattered across platforms
• The training approach that actually gets teams using features consistently
• Real examples of how AI agents like Perry and Cleo leverage these foundations

If you're ready to transform your project management tool from a glorified to-do list into the command center for seamless workflows and AI automation, this episode shows you exactly how to build those foundations.

If this episode hits home, we have free PM basics courses for ClickUp, Asana, and monday.com at biggestgoal.ai. Share them with your team. They'll thank you.

Tools/Platforms Mentioned

• Project Management Tools: ClickUp, Asana, and monday.com
• Slack
• Microsoft Teams
• Claude Cowork
• n8n
• Perry (Podcast Agent)
• Cleo (Client Onboarding Agent)

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This episode is brought to you by Biggest Goal.

Every quarter your team spends evaluating AI is a quarter your competitors spend shipping. Most leaders feel the pressure but get stuck between ignoring AI and getting it wrong. More tools and more demos won't fix it. What actually works is hands-on training for the people doing the work.

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Transcript

Alane Boyd (00:03)
You're probably using only 10 % of your PM tool and that remaining 90 % is limiting you, your team, Cowork and AI agents. But these five things turn your PM tool from a fancy to-do list into a hub for AI automation.

Micah Johnson (00:23)
Alane, know you just did a presentation on this exact topic. So I am super, I'm flying blind on this one. I'm super interested to go through these five and hear what your perspective is on these. I have my ideas.

Alane Boyd (00:39)
Hmm, well, write down your notes on what you think I missed when we go through this. I doubt you have anything different since this is what we do. All right, so I have five and I've broken them down and they're gonna build on each other.

Micah Johnson (00:43)
Okay, I'm not sharing that afterwards.

Okay, I'm impressed already. Let's go. Let's number one.

Alane Boyd (00:57)
Okay,

so the first one is standardize before you automate. Because if you don't have everybody working the same way and you have 12 different people doing it my way, you'd have 12 different ways you'd have to automate something.

Micah Johnson (01:17)
I had, no joke, three calls today alone that centered around this topic.

Alane Boyd (01:26)
It doesn't feel like a big deal when you are talking to people initially because they have a system. They feel like, oh yeah, we've been doing We've been doing this for 14 years or 35 years. Like, yeah, we know how to do blank. But then when you get into it, it's like, well, but each one of you are doing it a different way. If we don't standardize it, we'd have that many different ways to automate it. And that's not realistic or time-saving.

Micah Johnson (01:54)
I mean, we've talked about standardization a lot on this podcast for good reason. I was on a call earlier today, like I mentioned, and one of the things that actually I realized while I was talking on this call was that a lot of times we talk about standardization at like the, outset or the automation part, right? Like if we're talking about Cowork skills, you can standardize a workflow through skills. can standardize, automation through n8n and all of this stuff, but where you get into trouble.

is the folder system. Nobody standardized where stuff is saved. Where you get in trouble is tasks. For this episode, right? Like in a project management system, nobody standardized how you name them, what information, what you put in the description, and take that across anything else. Man, I fully support this one.

Alane Boyd (02:28)
you

And this is really the foundation, these five things, even though they can be applied to anything, whenever I built this, I'm thinking of it in your PM tool. So when I say PM tool, mean, Asana, ClickUp, Monday, whatever you're using as your project management system, because it is a foundation of where work should be happening. And hopefully at the end of this episode, you're like, yes, Alane, I get what you're saying and why it's so important. But really that standardization.

even though can be applied to really anything that you're doing in your company, really important in your PM tool. When I think about some of the standardization in our company, and I start seeing this creeping up whenever we're talking with clients, is nested subtasks. When you go into four subtasks, then you go into a subtasks and you go, yeah. That is a standard thing to put in place. We only go one level down.

Micah Johnson (03:33)
four layers deep, you're in the subtask catacombs.

Alane Boyd (03:42)
That is a standardized way that we operate at Biggest Goal and what we advocate for other companies because you can't get any visualization of what's going on when you are nested that far down. It's so hard to dig.

Micah Johnson (03:54)
Yep.

And we standardized, we don't even comment in the subtasks. We keep all of our conversations for that whole task and the parent task.

Alane Boyd (04:05)
And that was one of the pieces of standardization. And then we can move on to the next one. Is your common language at your company around these things? So the language would be, don't comment. Most of the time, there's very few times where we comment on the subtasks, we comment on the main task. That way your comments about the work being done aren't being nested and you're not digging around. We have a common language in the company, a standardization that we say.

this is how we operate. And so working on what that looks like at your company, because if you have that, then if you wanna have an AI agent or call Claude Cowork to go do something for you, it has a standard way that it can go and find what you need or use a template or something along those lines where it can apply that.

Micah Johnson (04:54)
I'm so glad you mentioned that because I wanted to go on a quick tangent before we get to number two on the fact that we've been, you I wanted to talk about consumption because what we have to design systems for now is not just human consumption. It is AI consumption. And so you have to think about, well, what do the people teams need? But then what does a tool like Claude Cowork need?

Alane Boyd (05:13)
Mm-hmm.

Micah Johnson (05:22)
We talked about this in a very recent episode, very similar things, but I just want to make sure that everybody that's listening to this is thinking that this isn't, we're not saying go in here and do all this stuff manually. Hell no. Get Claude Cowork, get an AI tool to help you do all this stuff. These are just the things I'm assuming, correct me if I'm wrong, Alane, that will help both the people and the AI succeed in the project management tools.

Alane Boyd (05:49)
That, yeah, I mean, absolutely. Because at the end of the day, we're really helping people. Because we don't want to work all the time. So how do we make these systems easier? All right, are you ready for number two? All right, number two is templatize everything you can.

Micah Johnson (06:00)
I'm ready.

Yes.

Alane Boyd (06:06)
And

this one gives people a mental breakdown at first, I will say, because they freak out like, well, everything we do is custom. No, it is not. You have similarities and repeatable pieces of everything you do, or you would be using 52 different invoicing softwares. There is consistency there. You send a client an invoice.

When does that happen? That is something repeatable in your process. So instead of looking at everything from a negative perspective and saying, well, everything we do is custom, flip that mindset and find what is repeatable in the things that you do and start there.

Micah Johnson (06:50)
Yeah, yeah. Again, oddly enough, had a call that touched on this point today as well. You know, when you think about generating assets and outputs and reports and spreadsheets or whatever, at first glance, a team could go, well, everything we output is custom, like you said. But the reality is, all the formatting's the same. The structure's the same. What it really comes down to is,

Maybe the tone is different. Maybe it's looking at a different data source for one thing or the other, but 89, 95% of the rest is all the same, and it can be processed the same.

Alane Boyd (07:35)
And for this, people always wonder, well, where do I start? Because they go, okay, template everything. Of course, that feels extremely overwhelming because you've got a lot of well, first, start with the next thing you have on your plate. Are you building a website? Are you onboarding a new client? Start documenting the steps there. And I've got a new term that I started using. It's called a Template WIP It's a Template WIP W-I-P.

Micah Johnson (08:01)
A what?

Alane Boyd (08:05)
A work in progress. It's a. ⁓ my gosh. It's G rated here so it's a Template WIP. It's a work in progress because what I started thinking about how I work with my team is that's what we do. I've I've got one right now that is a template work in progress and we start with a task for whatever the item is. So let's just say.

Micah Johnson (08:07)
Okay, not what I was picturing. I'm really glad you spelled that out. Other people probably was thinking, you know.

Alane Boyd (08:33)
a website and we start adding subtasks. We start thinking about everything we have to do and whenever we need to do the next website. Okay, let's use that template and let's use it and see how it goes because we were going to miss things when we're just trying to think about things on the fly. You know, we're not in it. So we're of course, we're going to miss things humans are very inconsistent. We're very forgetful. We're not going to remember everything and then work from that template.

That's a work in progress and see what you missed and keep evolving it. Then once you feel like, hey, I've got this in a really good place, turn that into a template in your project management system, so in ClickUp, there's a way to save things as a template. So it can always evolve, you can always adjust it, but that's gonna be our best version that we've determined at that moment.

Micah Johnson (09:22)
Yeah, and all three platforms, Asana, ClickUp, and Monday, they all have template features.

Alane Boyd (09:29)
I love a template. So when we have a template and why this is a foundational piece that you need to be doing in your project management system is because automation can call on a template. So we've talked about Perry, our Podcast Agent. So we give our agents real human names. So Perry, whenever we feed it a transcript from our new podcast, the AI agent is going to create the podcast task in ClickUp for us from the podcast template.

It's gonna have everything a human needs to do that the agent can't do. So in our ClickUp template for the podcast, it has the main task and then all the subtasks that a human needs to do, and it automatically assigns to the human that's responsible for doing it.

Micah Johnson (10:15)
Love it. What's number three?

Alane Boyd (10:16)
Same thing for, okay,

we'll move on. I just wanted to give another example, but.

Micah Johnson (10:22)
⁓

yeah, I mean you can you can I just I like the this like I'm like alright standardizing cool. I like that you have this building upon each other because the template is a way of standardizing, but it's a very specific way of standardizing multiple things at once and getting huge gains like love that we've been doing it for years. I'm terrible at it. You're way better at it.

Alane Boyd (10:46)
I love a template. All right, so the third thing, and I will say people, this is tough. This is tough for people. All work lives in the project management tool.

Micah Johnson (10:59)
yeah, this one is tough. This one is tough.

Alane Boyd (11:01)
So

not in sticky notes, not in your head, not an email, like the stuff that you need to get done for a client gets actually put in the project management tool in the correct client project task. All of that needs to be in the right place, not in Alane's personal tasks for the day. I don't just keep it and horde it there that it actually gets put in the right place for that client or

that to do goes in the right project.

Micah Johnson (11:30)
But to your point on the stacking, Alane, I could see why, you know, we've been preaching this a long time. We had to live this ourselves and experience what it looks like and what it feels like more than anything to be able to say, ⁓ hell no, we are not putting anything anywhere unless it lives in our project management system. That is the source of truth. Once you break that vow, that source of truth, the whole thing falls apart.

If you don't have standardization, if you don't have templates, it's really hard to then see the benefit of doing this. It just feels like you're being asked to do something without knowing why you're doing it. The purpose of it kind of just floats away and you go back to your notebooks and your Post-it notes.

Alane Boyd (12:14)
Well, and it becomes where you're recreating the wheel for everything. So if all the work lives in the tool and you've standardized your language with the company and the number one, but you skip templates, then every single thing now becomes dependent on that human to add everything in there. So if you miss that, then it's a lot of extra work every time you do something to get that into the project management system.

Micah Johnson (12:41)
You know, talking about this, I will say this got a hell of a lot easier with tools like Cowork because you can build Skills and you can just ask Cowork and you can connect it up to your project management system. And it already has all the information to create a task for you in the way that it should be standardized and potentially use the right templates that you've already created that you probably already got done by the time you've listened to that segment on this podcast episode. I'm sure everybody got that done already. And so.

Alane Boyd (13:09)
So,

Micah, that's exactly the example that I have in here about, okay, well, I get it. I got off this client call. I've got a million things on my plate. I have another call in 15 minutes. How do I get all the stuff done so I actually get it into my project management tool? And so if we already have the mindset that this stuff is gonna happen, this is our foundation. We believe in this as a company. We are going to get all work that we're doing from a client.

Micah Johnson (13:14)
There you go.

Alane Boyd (13:38)
into the project management system. Then you can use Skills and Cowork. So you have a call debrief, it goes through the call, it finds the things that need to get updated, and then adds it to that specific client in the project management tool.

Micah Johnson (13:55)
Only do it if you have things standardized.

Alane Boyd (13:58)
That's right, and the client is in there with all the information.

Micah Johnson (14:01)
I'm loving this. I just like that we're on the same page through this whole episode so far. Almost stole your thunder.

Alane Boyd (14:05)
So far, anything could happen.

No, no, no, not at all. All right, are you ready for number four? Okay, so if all the work is going into the project management tool, all the communication has to also go in there and not in Slack, not in Teams, not in text messages, you are collaborating and communicating on the specific task or project in your PM tool.

Micah Johnson (14:13)
Kind of, yeah.

I was wondering if you were going to use the word collaboration for this, because it's such a key term, I think, to really paint the visual image of what are we doing in the work. The collaboration, the I'm going to message Alane, Alane's going to message me, we're going to work on this task or this body of work together in the project management tool. That's the collaboration piece, not.

Email, not Slack, not Teams.

Alane Boyd (15:07)
You could dig for days trying to find something in one of those and in seconds you could just go to your PM tool, pull up the task and see what the status is.  I do and you can share it, go ahead. So the client summary Skill can be used and when you set up these Skills and you have this data and information already living in your PM tool,

Micah Johnson (15:16)
Do you have the Cowork example on this one too? Okay, I'm not gonna steal your thunder this time.

Alane Boyd (15:34)
then when you use the Skill, you say /clientsummary, tell it the client, and it just go, it already knows what to do. You don't have any other words you need to say, because the Skill itself knows to go look at your PM tool, look at the tasks and the projects that have been worked on, and looks at the comments and the conversation that are happening. Checks the previous week's summary, so you're not just regurgitating information.

and puts together a summary for you that you could send to the client because all the information was there. That's a lot of manual work.

Micah Johnson (16:09)
That's a lot of time that it's. Yeah, absolutely. You just go in and wing it. Never done that. All right. So anyway, the other thing that I was kind of thinking about this that I find myself doing on this one, Alane is if there is stuff in email, even if it came in from a client or if it was discussed in a internal meeting and we have the transcript, well,

Alane Boyd (16:11)
And a lot of times it just doesn't happen.

Micah Johnson (16:33)
I'm not gonna go in anymore and leave a comment. I could, but it actually works better if you use Cowork to have the context. Am I stealing another example? Okay. All right. And then so it already has all the context and then you take the transcript or the email. And of course it already has the instructions on how to write the comment.

Alane Boyd (16:46)
No, no, think this is great. Go ahead.

Micah Johnson (16:59)
And now you have a perfectly formed comment with cross-referencing of other assets and other information, other emails, what meeting it was on, way better than I could write a comment. And every once in a while, what I will say is I still go to the comment that it created and read it and do any minor edits. I don't just leave it. That's a really important piece that I want to add to this.

But that cross-referencing and the formatting and the structure, it allows me to keep that standardization that we like to make it easy, the cross-referencing, even I might consider this a comment template, just saying.

Alane Boyd (17:39)
There you go. Man, I didn't even think about a comment template. Okay, so are you ready for the last one? Okay, this one, when I presented everybody moaned like, yeah. So it is, you have to train your team on the project management tool functionality, number one.

Micah Johnson (17:46)
Yes.

Like a bad moan. Okay.

Hahaha

Alane Boyd (18:07)
Number two, how your company uses it. Those are two very distinct things. They are not the same and you cannot rely on that PM tool support center to know how to actually put in a workflow. Like they can tell you.

Micah Johnson (18:22)
Yeah, describe

these for the listener, Alane, because I think the delineation between these it can sound abstract, it can sound confusing. If it's train your team how to use it, train your team how we want to use it. What?

Alane Boyd (18:34)
Okay, good point. All right, so when you, I remember when we first used ClickUp and we had been using Asana for a decade. And so we had been using a project management system very, very like thoroughly, I would say for years. Yeah, but when we switched, I was so overwhelmed and I was so frustrated because the functionality and features of ClickUp

Micah Johnson (18:43)
Mm-hmm.

to these five points.

Alane Boyd (19:04)
and how you do things in ClickUp was very different than Asana. How you create spaces, you can create folders, you could, just change things so much differently. Even how you use slash commands back then. Like it was just everything was very, very different in structure and how you did things. I needed to learn how to work in ClickUp. And that for you could mean, well, what's the hierarchy?

Well, there's spaces, there's folders, there's tasks, and there's lists that are all a part of that. I did not put that in the correct order, but those are all parts of the hierarchy. Well, then what's the status? What's a custom field? That's functionality in there that's available. How to save things in the Template Center, that's functionality. What your template is, is how your company works. When to use that template is how your company works.

Micah Johnson (19:54)
Yeah, so let me say it back to you, see if I got it right. What you're saying is it's one thing to know about the features of the software. That's only a percentage of what you need to train on. Then you need to take those features and answer questions like, well, when do we use a space? When do we use a folder? When do we make it a list? When do we use a subtask? When do we not use

eight levels of nested subtasks to get down to the earth and molten core of subtask world?

Alane Boyd (20:27)
Mm-hmm.

Or how to archive something in your inbox.

Micah Johnson (20:34)
Yeah, when to archive it. How do you manage your inbox? How do you manage your own damn tasks?

Alane Boyd (20:35)
How many times do we have somebody share, how do you manage your inbox?

I mean, one of my things that I always laugh at it is every single time it's so rare that I see for somebody that we're seeing their PM tool inbox for the first time, they're scared to death to archive something. They just leave everything in there instead of just hit archive. Just let's just get it out of here or snooze. If you do really wanna see it again, snooze it to pop up when you wanna look at it.

But actually learning how to manage that inbox. So all of these things are the training on how you use the tool and the tools themselves have so many different settings, so many different things. For us, day one, somebody coming to work for us, part of the training is go and fix your settings. Don't get an email notification and a notification in ClickUp. Go turn off the email notification. We don't have to do double work for something pointless.

So those are things that are unique to how we operate.

Micah Johnson (21:39)
Yeah, and bringing this kind of back to the AI perspective, if you don't know how you want to use the features of your project management platform in the same way, so everybody's speaking the same language, that everybody now includes AI. If you can already delineate how and when to use specific features and when things should be archived in your inbox and what different priority values mean,

and how you leverage due dates and what this custom field is and what these statuses mean, if you can't articulate that, you can't articulate that to an AI. An AI cannot help you. It will guess every damn time. If you can articulate it, you can very much add that to the AI's instructions, the skills, and in minutes, you can have AI doing things that you used to have to do manually.

Alane Boyd (22:36)
Yeah, because without that consistency of your team using the tool the same way that whether you use Cowork or an AI agent and you're asking to go do something, it's going to get confused or it's going to be inconsistent on itself because it doesn't have what it needs to be there. It doesn't have that foundation.

Micah Johnson (22:54)
Yeah. I love this list. And I definitely agree that each one built upon Maybe this sounds like a lot of work, but they all support each other. And I don't know the best way to say this, Alane, but what I'm trying to get at is when you start doing one and then the next one, the first one got a little bit easier. And because the first one got a little bit easier, the second one got easier.

And when you implement the third one, it's a little bit, everything just gets easier and easier and easier.

Alane Boyd (23:24)
It does. I think from conversations that I've had and the experience of putting these things in place when we weren't doing it, you know, 10 years ago, is it's actually a harder culture shift than it is the work to do these things. Because if the culture of your company is used to slacking everything, to get them to stop doing that and communicate in the system, put the work that they're doing in the system,

That is a culture change. That isn't that the work is hard to do.

Micah Johnson (23:53)
This reminds me of something else that I see a lot too in the culture change side. Maybe you know where I'm going with this Alane, which is if you're a decision maker, if you're a leader, if you're a founder, co-founder, getting to a point where it's like, well, we don't want to upset anybody. We don't want to do this or do that. We're just going to let people kind of learn on their own way. Please don't do that. It makes it harder for everybody.

Just say, hey, we're gonna try doing it this way. Give me, we're gonna try, just, you know, stick with me here. We're gonna try it. You might love it. You might hate it. We're gonna give it four weeks. Then let's talk about it. But nobody's gonna always be happy. And if everybody's wishy washy on everything, your culture never changes. You get stuck in the mud and it will feel like implementing anything in your company is walking through molasses.

Alane Boyd (24:33)
Yeah.

A lot of friction happens because some team members are on board and doing it, but it's going to be the team members who don't that you're going to be at the lowest common denominator. The rest of your team has to go meet those people because the work isn't happening the way that you said it would be. But one thing that I do want to say on like, OK, what does this look like to start rolling out? Micah and I are big and I'm putting words in your mouth. We are big advocates for

Micah Johnson (25:03)
Yep.

Alane Boyd (25:14)
finding a small group of champions to make these changes, to put these things in place, iron out those rough edges. And then once you're like, hey, we've got some legs here, we're ready to start running, then bring the rest of the team on. But it really does help if you have, if you're really small, two to three people in your champion group, if you're a little bigger, maybe five to six people, but having different departments being represented in that champion group.

different people that are part of different parts of the process is really helpful, and then getting it in play with the rest of the people in your organization.

Micah Johnson (25:50)
Yeah, totally. You can put all those words in my mouth. I completely agree with all of that, Alane.

Alane Boyd (25:57)
I figured because that's the way that we've learned to operate because we haven't done it like that in the past.

Micah Johnson (26:02)
Yeah. And you know, I know I kind of touched on this a second ago. You're never going to make everybody happy. If you have a three person team, maybe you can make everybody happy. You have a 10 person, a 15 person, a hundred person. You're not making everybody happy. Even us, right? Like there are things that we do in our project management system that drive me effing crazy, but it works for the teams that need to run it. And I know

Alane Boyd (26:28)
Mm-hmm.

Micah Johnson (26:30)
There are things that we do on our project management system that drive you crazy, Alane, but we're not going back and forth trying to fix it for Micah and then fix it for Alane. And then that broke something else. So then we fix it for Micah and fix it for Alane. Meanwhile, our team's getting yo-yo'd everywhere going, what the hell is going on? We don't do that. We say, all right, there is no perfect. We just got to get it good enough. But if we follow these five things that you outlined,

Alane Boyd (26:54)
Mm-hmm.

Mm-hmm.

Micah Johnson (27:00)
That's where the gains are. That's the efficiency. That's the streamlining. And God dang it, is it important with AI now?

Alane Boyd (27:07)
Oh my gosh, when I show, you know, what Perry really looks like and what Cleo really looks like for our automated agents, podcast agent and our new client onboarding, people are like, my gosh, this blew my mind. Well, it is because we have this foundation. Every single time it can pull from a template, it knows where to go in the client hub and what information to happen because these five things are here.

For people that are like, oh my gosh, Alane and Micah, I really like what y'all are saying. I really wanna do this, but I'm really having a hard time understanding like, how do I hear this and how do I start? So some things to start is, start documenting what one template could look like in your organization. Number two is pick a few people in your organization to start being your champions. And the three of you go through this process of change and start communicating the tool. Start getting work in there.

that you're working on for, it doesn't even have to be client work. It's anything that you're working on in the company. And then start communicating the tool. And really it is like you're a broken record and you have to treat each other like this. You have to say, great, go put it in the PM tool. Great, let's take this out of Slack. Go put it in the PM tool. It is, you are saying this repeatedly. And I remember, Micah, like we have shared this story so many times. Like that is exactly what we had to do. And this week I was talking to a lady.

and they were, they had put Asana in and she's like, I cannot tell you how many times that I had to say, go put it in Asana over and over again. I was like, oh my gosh, I feel so heard and seen right now because that's what it's like. You have to retrain how people think and operate and you have to keep repeating yourself. So that's where you.

Micah Johnson (28:51)
Well, the funny

part with that now is, Alane, it's not go put it in Asana. It's go tell Cowork. Go tell Claude to put it in Asana.

Alane Boyd (29:00)
Yes, absolutely. So thank you all for listening to my five things. We'd love to hear from you if you have thoughts or if you have anything that you run into on trying to implement these ideas. We do have three basics courses for putting in PM tools. So if you use Asana, if you use ClickUp or if you use monday.com, we have a free basics course that we'll link to so that you can share with anybody in your team.

Micah Johnson (29:26)
Yeah, or go directly to it at your your.biggestgoal.ai.

Alane Boyd (29:33)
Good one.