The 5 Individual Milestones of AI Fluency

Most business leaders talk about AI adoption. But Alane and Micah are asking the real question. How do you actually measure it?

In this episode, they introduce a five-milestone framework for tracking individual AI fluency on your team. This framework was built from a real gap Micah observed at a recent COO conference where everyone agreed the topic mattered but nobody had answers.

If AI adoption at your company feels more like chaos than progress, there's a good chance your team has no shared baseline and no way to know who's moving forward and who's stuck. Alane and Micah make the case that undefined fluency goals are a business problem, and that the fix is easier than most leaders think.

In this episode, you'll learn:

• How to define milestone one so every team member has a clear, achievable starting point with Cowork
• Why Skills, Folders, and Connectors are the baseline every team member should hit, and why that alone drives major efficiency gains
• How one team member spent 5 minutes on something that now saves 45 minutes every single day
• The two-track model (individual vs. organizational) and why measuring only one of them leaves half the picture missing

If you're ready to stop guessing about where your team stands with AI and start building a measurable path forward, this episode gives you the exact framework to do it.

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🛠️ Tools & Platforms Mentioned

• Cowork
• Claude
• n8n
• Python
• APIs & Webhooks
• ChatGPT

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This episode is brought to you by Biggest Goal.

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Transcript

Micah (00:00)
So what does AI progress really look like? Well, we actually see there's two separate tracks, an individual track and an organizational track. So keep listening to learn about both tracks and see if you can identify how many milestones you've actually achieved.

Alane Boyd (00:19)
Micah, this is an interesting concept because it's something that we're really starting to see itself is a good way to say it, because each person's technical aptitude or what they're willing to try out, their confidence, all these things play into where they are personally with trying AI, different AI applications, and then where a company is as a whole.

and how many things they've accomplished to bring AI to the forefront of the company.

Micah (00:49)
Yeah, I think, you know, it all boils down to AI fluency. Alane, I don't remember if we've talked about this on a podcast episode in particular, but at that COO conference that I went to recently, this was a huge topic. What is AI fluency? How do you measure it? But what really stuck out and why I think this is such a fun topic to talk about today is that nobody had answers. It was

yeah, AI fluency. We need to measure it. But how?

Alane Boyd (01:16)
Mm-hmm.

Even though that's what you mean by fluency, when I first hear about this, it's also are we speaking the same language? And I see so much confusion around concepts like agents and what an agent is. And it's kind of getting really blurry now, but I even see that as part of the fluency in the organization. Are we all able to talk about AI and have the same understanding of what we're talking about?

Micah (01:44)
Yeah. I totally agree with you on that. if we were to frame all of this fluency into milestones, there's certain milestones you hit. And in the intro, that's what we were talking about from the two tracks. So what you're referring to is there's this individual track, even base level is terminology. What the hell is an agent?

Alane Boyd (01:57)
Mm-hmm.

Mm,

mm.

Micah (02:05)
You

know, when you understand what an agent is, you're getting closer or you've achieved a milestone, right? Like you now can articulate the difference between what is an agent and what is not an agent, what makes an agent. And when you achieve that milestone, you're able to look at how things work and what's happening and what people are saying differently than going, all right, everything's an agent, right? Everything's agentic. I don't know.

Alane Boyd (02:35)
Yeah, and why we saw these two things kind of happen simultaneously is there is a difference on where even if everything feels like apples to apples for an organization, we're providing the same training, we're providing the same opportunities. Let's just say across the board, you're gonna have certain team members that just jump in completely, not scared. They're just gonna try things out, and then we're gonna see others that really want to just

Try it on for a minute. Or, you know, learn, learn everything they can. And that's okay. And you really have to understand where each person is. And I and I like where we've really started to look at this is like, okay, your path might take you three months. These are the milestones you're aiming for. But others might do it in a month because they are just quicker to jump in and try.

Micah (03:06)
Try it on, yeah.

Yeah. So you know, I think the the key around this is what all the COO's at that event that I went to were talking about is that you need to be able to measure this. You need to be able to understand exactly what you're saying, right? You have individuals on your team. Some are gonna rip through these milestones really quickly. And they might even get to the point where they can start troubleshooting or start training other people. Whereas there's gonna be other people on the team that

Are it's not worse or better. They're just going to be slower going through the milestones. It may be that they just don't even have enough time. It may be that their fluency just takes longer to get through or whatever it might be. But being able to set these milestones to understand what they are and to know that, what we've talked about so far are really on the individual side. And there's this whole other track of milestones that's on the

organization or the company side. And that's like setting up your systems. And we're going to get into to each of these tracks, but being able to set up the foundation and set up the systems to help the individuals through their milestones is where you're going to see the success happen when you're following and measuring both tracks.

Alane Boyd (04:48)
So why don't we go from here to talking about what we see as some of these milestones for the individual and for the company? So yeah, okay. So one of them I I think one thing that we've really noticed and that we we talk about is we don't use chat hardly ever, any type of AI chat. If I go look at my Claude chat.

Micah (04:56)
Okay, I'm good with that.

Alane Boyd (05:14)
There's five in there and it's like the most silly things like, hey, can you give me five made up business names? Like it's all just stuff for like a demo or something that I wanted to do and I didn't want to have to think about the names. So it's all like such basic stuff. Like if you're really thinking of AI chat and prompting as a milestone that news alert, that's not even a milestone.

Micah (05:38)
Yeah, I wouldn't

I would totally agree with that. I wouldn't even put that on the list. If chat I use chat now, and if you've listened to previous episodes, I think each time I say this, what I'm about to say, the number keeps going down. I'm at zero percent. I just don't use chat.

Alane Boyd (05:44)
Yeah.

Yeah, I don't either. but we do have a new milestone, which would be learning Cowork, or if you're in the ChatGPT world learning Codex, or I should say OpenAI world, then it'd be Codex. But it's really if you're trying to be competitive and thinking that AI chat is that first milestone, no way. Like you gotta get in deeper and training people

on how to use Cowork.

Micah (06:21)
And and I would say milestone one is the very basics of Cowork. Can you get into Cowork? Can you ask it to help you build a spreadsheet, help you build a document? Like nothing advanced in Cowork, just help you do some of your work that you would manually have to do otherwise. No, Skills, no Connectors, anything. That's a future milestone. So milestone one is stop using chat and start using Cowork.

That baseline is already gonna show efficiency on the individual level.

Alane Boyd (06:49)
Yeah. And then the next thing would be building on top of that, like you're saying, get in and start using Cowork. And then the next thing is getting your folders and your Skills and your Connectors. Start using those and becoming more familiar with not just that they're there, but those use cases of how they apply.

Micah (07:08)
Yeah. I completely agree. That's a perfect second milestone. You can go from using the basics of Cowork to do I know what Skills are? Can I use Skills available to me? Do I know what Connectors are? Do I know what's happening when I'm asking it to do that? And can I start a task in a folder?

Alane Boyd (07:27)
Mm-hmm.

Micah (07:29)
That's milestone two.

Alane Boyd (07:30)
Ooh, that folder thing, that one's hard, Micah. That one is really, really tough.

Micah (07:33)
That it you know, we're

the difficulty level of achieving these milestones is exponential. So yeah, that is a tough one.

Alane Boyd (07:41)
Yes. And then then the next one would be really understanding context, working out of a folder, closing a session so that it updates the file in that folder, and really becoming a skilled user, not just building Skills, but a a skilled user of when these things apply, becoming a thought leader on, hey, I've done this multiple times, let me create a Skill for this.

Micah (08:07)
Yeah. So identifying how to create basic Skills, identifying how to leverage the folder, like you're saying, the folder system and saying things like, can you summarize this and save it to the folder system so that we can restart this at another time and understanding how to create a memory functionality or just saving your progress for lack of a better term.

Alane Boyd (08:11)
Mm-hmm.

Micah (08:32)
Like that does get into kind of milestone three.

Alane Boyd (08:36)
And the expectations that you have for your team. So if you're an individual going through this, we have teams that have multiple team members going through this process together. And it doesn't mean every single person has to hit this milestone. It might be certain it might be certain people on your team may only want or need to be in milestone one and two. But really thinking through, okay, well, who could we have as these

Micah (08:51)
⁓ that's a good point.

Alane Boyd (09:03)
more skilled users of AI or leaders in the company that can take this a little bit further. And so you might have different team members hitting more of these milestones.

Micah (09:14)
I used the term baseline earlier, Alane. I think every company might be slightly different. So you'd individually, as a decision maker or as a team leader, need to identify what is the baseline that makes sense for the people on your team. And then your job is to help people work to that baseline. And you know, I it sounds like we're trying to tow this line of you have to use AI. But here's

Alane Boyd (09:35)
Mm-hmm.

Micah (09:41)
Here's where, I like from a business owner and from a leadership position, this is the way that I look at it is if half my team is using Cowork and doing things in five minutes, and then we have half our team doing things without Cowork, and it takes them hours to do the same things, and it's worse, why the hell

would I be paying people to do the same stuff worse for hours? I need to build an operation that hums.

Alane Boyd (10:08)
Yes.

Mm-hmm. It's interesting for the ones that are really jumping in and using this on our team or even other teams, like at the end of their day, they do feel better because they had some assistance to get the things done that they wanted to. It's less jumping around for them. And a lot of times, not that they did bad work before, but that they see an elevated level. I even think, Micah, even for some of our stuff internal, where we have

Cowork take our really awesome outline because we're amazing people and so smart, but it takes our our outline and creates such a badass PowerPoint for us to do executive presentations to the rest of the team. It is so nice and the quality of our work gets a better presentation to the rest of our team because we use that as an asset.

Micah (10:51)
Yeah. Yeah.

I agree. I got us off on a tangent. So we are we're off on yeah. So we need milestone number four, which is going beyond just creating basic Skills, but actually understanding how to build micro apps with Skills and how to design these Skills so that the human is in the loop. And what I mean by that is you have a systems type thinker that's looking at a workflow and going, not only can I build a Skill out of this.

Alane Boyd (11:03)
I know, Micah. People are waiting for number four.

Micah (11:28)
But I understand enough to say, I'm gonna work with Claude, it's gonna help me build this Skill. It's gonna start with AI, then it's going to go to Python code, it's gonna get out of the LLM, it's gonna save tokens, it's gonna run the same way every time. We're gonna have templates, we're gonna have essentially approval check-ins. So the AI is gonna come back with some of the output and say, hey, person, user, how's this sound?

And the human in the loop is gonna say, nah we need to change this or we need to do this. And then the human approves that. And then AI executes the rest of the Skill to go, all right, cool. Now that I have everything approved, I can do all of this other work. And the heavy lifting is on the front and the end, and the human is approving the work in the middle, much like a normal human team would work, or you know, a person based team would work. So that's milestone four.

Alane Boyd (12:24)
So this doesn't sound like a big deal that it needed to be at milestone four at face value. And I'm gonna

Micah (12:31)
really? I

thought I presented it and say like this is a powerful

Alane Boyd (12:34)
No, because in theory,

that's what everybody thinks. Where this really takes a more skilled or sophisticated person is somebody that is not task oriented. Because somebody that is task oriented doesn't want to do this. They just want to be the human in the loop only. They can't let go.

Micah (12:53)
God dang, Alane. You can't

this I but I like I say that because you're absolutely right. The earlier milestones could be all like a task centric kind of person, but you need a strategic thinker as you get into these higher milestones for sure. Yeah. Yeah.

Alane Boyd (13:09)
This is an outcome thinker. Somebody that says,

this is the outcome we need. I want the easiest, most efficient path that we can get there that makes us look like rock stars. And that's where I'm gonna use this. And I'm gonna lead the outcome and the approval and be the human with the strategic mind. Somebody that's task oriented, they can't let go. They want to be in it every single time and they immediately will lose trust instead of updating the Skill.

Of the agent or the Skill in Cowork, they just say, I'm just gonna do it myself.

Micah (13:43)
Yeah, absolutely. All right. So we're to our fifth and final milestone on the individual track.

Alane Boyd (13:45)
They just failed milestone four.

Mm-hmm.

this one would be a really tech oriented person because they understand how to build automated workflows. Something like an n8n AI agent build that's more complex than using just Claude Cowork Skills or something like that

Micah (14:06)
Yeah, absolutely. They're looking at all the building block tools. They're going, what could be Skills? What could be n8n workflows? How do we get them to work together? Do we need n8n to start pulling from these APIs? Do we need it to save in a database? And all of this with the help of AI, because AI can help you build all of this. So the technical acumen previous knowledge doesn't have to be as high. Honestly, any

Alane Boyd (14:30)
I'm happy.

Micah (14:33)
person can learn this. It'll just take some people longer to learn it. And some people will love to do it and some people won't. And that kind of gets back to the, you know, are they a task doer or are they a strategic thinker? But, you know, again, not everybody is going to hit this milestone. And very much not everybody should hit this milestone on the team.

Alane Boyd (14:53)
Yeah. I mean, I love looking up an MCP server, but I don't want to go and build an n8n workflow. So I think that there's definitely some, you know, like I said, we don't need to hit every milestone, but these are the milestones that we're looking to build upon. So those are our five main individual milestones. I think for every company or individual, like completing the first two are is a minimum at this point. Getting

Micah (15:01)
Yeah.

At this

point yeah, at this point I agree.

Alane Boyd (15:21)
Trained on using Cowork

and using Skills, Connectors, and starting to understand what working out of a folder is.

Micah (15:29)
and honestly, even just looking at that, if every person like we've forced, forced is a strong word, we've encouraged, and I guess we've forced, like the we are, this is what we're doing. We're saying you need to know Cowork, you need to know how to use it at a bare minimum, and you absolutely need to know how to run it in a folder, you need to know how to use Skills, you need to know how to use Connectors, you need to know how all of these things combined.

Alane Boyd (15:44)
Mm-hmm.

Micah (15:58)
Can really strengthen your work. Not everybody needs to know how to write Skills. Not everybody needs to know how to build systems. But by enforcing that that's the bare minimum of AI fluency and that's how we're working, our efficiency has gone through the roof. And we see this time and time again. People like, hell, I think we even heard this earlier today. People will say things like, I just spent five minutes building a Skill.

Alane Boyd (16:05)
Mm-hmm.

Micah (16:26)
That has saved me 45 minutes for a task that I do every day. Like it's happening over and over and over again. And if you just imagine every person on your team getting through at least these first two milestones, that is an amazing goal to shoot for.

Alane Boyd (16:31)
Mm-hmm. Mm-hmm.

Yeah. Some of its habit too, like working out of a folder is a new habit that I've that I've had to work on. It's not something that I'm used to doing. So I gotta remember to attach to a folder.

Micah (16:58)
That's a it's true. That's a good point. This is a paradigm shift from chat to Cowork to thinking about this. And now it's like, all right, how do we identify this? Let's go through the five one more time, just really quickly. We've got you've just the first milestone is you can use basic Cowork. It's saving you time just on basic tasks. The second milestone is you're able to use folders, Skills, and Connectors into other platforms. The third one is you can actually build Skills.

understand how to write and read from the folders that you're opening the task in. The fifth milestone is building advanced Skills and almost like micro apps and tying into Python scripts and other things like that. And the fifth milestone is being able to build complete systems across Cowork, across n8n, across APIs and webhooks, and merge all these building blocks together to achieve big systems. And I do

As we get into that, right? There's you and I talk about starting small a lot. This is a perfect way to think about starting small. It forces you to start small. Where we see so many people make mistakes is they go to milestone five and they're like, hell yeah, let's solve this giant ass problem. Let's solve all these big things that are happening. We're gonna get these huge returns. I can guarantee you don't have enough people at milestone five yet.

To do all of this. And if you get people at milestone one and two, your returns are gonna be so much quicker and so much bigger by just focusing on those two things. And then the big problems that you want to solve are going to start to identify themselves even a lot easier and be clearer to figure out. So, Alane, unfortunately, we're gonna have to leave this episode off on a cliffhanger.

Alane Boyd (18:47)
Mm-hmm.

Micah (18:53)
Because we are out of time for the operational Skills. So tune in to our next week's episode where we're gonna dive into all the same kind of things, but thinking about on the organization track.