I built a Claude Cowork system that does a week of PM work in a day

1. 0:00 – 3:30

   Daniel’s background and the PM overhead problem he needed to solve

   1. DBDaniel Blum0:00

      I cannot describe how powerful it is. I'm really able to do in a day now what used to take me a week. But more than that, I'll say it's a lot of deeper work. There's things that I do today that I just wasn't able to do before, whether it's more in-depth research, whether it's being more data backed. Anything you do today, you can do it almost at the top level.

   2. CVClaire Vo0:22

      One of the things, even at a company level, that I tell people is, "Look, you gotta go through the pain of switching your systems, and it's not gonna be as efficient. And yes, of course, like, the old way will be faster because it's muscle memory. But if you get to the next level, not only will you have a system that works better for you, but everybody will have more skills."

   3. DBDaniel Blum0:42

      Today, I say I manage about 70 to 80% of my time in front of the computer with Cowork alone.

   4. CVClaire Vo0:47

      We've seen a couple morning briefs, but I wanna see what you think makes yours different.

   5. DBDaniel Blum0:51

      In this daily brief, my Cowork runs through my recent Slacks, my emails, my Evernote notes, and it looks for context that it doesn't understand in these things, and it says like, "Oh, if there's a file I wasn't aware of, there's a milestone, there's a goal," it would ask me about it and say, "Hey, like, what is this? Is this important? Should I read this?" And this is, I think, where the real magic happens.

   6. CVClaire Vo1:10

      This is really genius. I'm curious how this scales beyond you. So you have your system. You're, you know, 10X PM now. Congratulations. How does this affect the team? How do they use systems like this? [upbeat music] Welcome back to How I AI. I'm Claire Vo, product leader and AI obsessive, here on a mission to help you build better with these new tools. Today, I have Daniel Blum, and he's gonna show us his Claude Cowork system to rule them all. It self-heals, it self-optimizes, and it's way better than the morning briefing you have going on. Let's get to it. Optimizely Agent Platform for Marketers is built on a bigger idea, a whole directory of agents now joined by a newly revealed squad of virtual teammates, each with a defined role and a personality of their own. This isn't about faster drafts. It's about handling the coordination, too, the research, the approvals, the handoffs, the routing, the back and forth that quietly eats your week and never makes it into anyone's highlight reel. Get the story behind it all. Hear the confessions from marketers who have handed off the busy work, meet the squad, and understand what virtual teammates can do for you at optimizely.com/howiai. Daniel, welcome to How I AI. I am so excited to have you on this episode because every week, every month, I think things get better, and I'm always impressed with how much more organized everybody but me seems to get with their, uh, AI and their personal productivity. And so tell me, like, what brought you to building this big system, and what problem were you trying to solve?

   7. DBDaniel Blum3:00

      Cool. Well, Claire, thank you so much for having me. I'm really excited to be here. As somebody who's been an early adopter of AI for quite a while, I think it took a, it-- Already like, a, a good few months ago or even a year ago, we were able to solve some of the big or at least improve some of the big jobs to be done for PMs with, uh, even with simpler tools. Like with, uh, Gems, uh, you could improve your specs, and you could improve your research. But I think, uh, as I was progressing with my AI adoption, I really felt that

2. 3:30 – 5:00

   His AI stack at Melio

   1. DBDaniel Blum3:30

      one of the biggest things that hangs over me and, and really makes my day-to-day more difficult is all this just overhead of, of being a PM, of coordinating a bunch of things, remembering endless tasks that arise on Slack and meetings and action items, and just trying to maneuver this whole, uh, this whole chaos that happens every single day, um, while at the same time wanting to do in-depth work and focus and, and really think. I felt that that was something that was really, really difficult for me, and I was getting nowhere near solving it, um, until I was able to actually build a system with Cowork that I'm actually still a little bit surprised at how powerful it is and how much it's helped transform, uh, this, this problem for me.

   2. CVClaire Vo4:14

      So tell me about your personal AI stack as a PM. How did you pick the tools that go into it? And then I wanna sh- I want you to show us how, how it all kind of works.

   3. DBDaniel Blum4:26

      Perfect. Uh, so I'll say I think most of my choices were made by my company, Melio.

   4. CVClaire Vo4:32

      [laughs]

   5. DBDaniel Blum4:33

      Um, and the tools that I'm, uh, I'm... are in our stack. Uh, but, uh, thankfully, I'm, I'm pretty satisfied with those. So for a long time, we only had, like, the Gemini Enterprise, and we were using that. And, uh, just a few months ago, we got, uh, the Claude Enterprise and Cowork, uh, and that's when things really changed for me. Uh, and besides that, I'm basically bound to whatever, whatever tools we have and use. Uh, so this is, this is what I work based off of. [chuckles]

   6. CVClaire Vo4:59

      Okay,

3. 5:00 – 6:00

   The two rules that make any AI system genuinely powerful

   1. CVClaire Vo5:00

      so this is good for everybody out there who is stuck with the tools that they're stuck with. You can still make it lurk. I-- at work. I think that Claude is obviously, like, a big part of this stack. Was Cowork just the big unlock for you? Like, where did you... When did you start building this, and what was the early tools versus what you use now?

   2. DBDaniel Blum5:20

      Yeah. So I think, first of all, in your first saying, I think it's very correct. And in general, I'll say, like, I was bound by constraints of an average PM all the time in terms of having, you know, not endless tokens and needing to, uh, work within budgets and bureaucracy, and I think it's very possible and very doable within all those constraints that, you know, real PMs face. And I think it's, it's very important to say. Um, and in terms of the tools, so Cowork was definitely the big unlock for me. But I think while I love Cowork, it's not Cowork in itself. Uh, and I think Codex could be great for this as well, or, uh, ChatGPT Work. I think the

4. 6:00 – 7:30

   The Notion board Cowork built for him (and manages on his behalf)

   1. DBDaniel Blum6:00

      real importance is for a system to, A, be able to rewrite its own, uh, core files, and that means that it keeps on improving, and B, just have connections and integrations to as much of your ecosystem. When these two rules apply, um, there is a significant, significant opportunity to really, really improve the way you work. And while I was working with, uh, Gemini Gems earlier, and there's obviously some incredible things that can be done with those- These two elements make a system really powerful and also really integrated into your daily life, but also self-improving, which is one of the biggest unlocks here.

   2. CVClaire Vo6:36

      Okay. Well, let's, let's... Show, show it to us. I wanna, I wanna see how you actually manage your life as a PM.

   3. DBDaniel Blum6:43

      Let me start with this, uh, Notion board, right? So this is, uh, nothing incredible. It's just a standard, uh, PM Notion board. It has three sections. One is top of mind, which are the large initiatives, uh, that I, I just think of, uh, you know, on a- any given, uh, time. It has my this week, which is basically the priority that I have for this week. And it has inbox, which is things that arise from Slack, email, calendar, and Cowork picks up and fills them in here. Now, the cool thing about this board is not that it exists, but the fact that not only did Cowork build this completely on its own, I was working with a very simple and messy, uh, Google Doc before, and I think Notion got... I, I think Cowork got tired of, of it and basically decided to build this for me.

5. 7:30 – 9:00

   How he contextualizes Claude with voice memos, links, and recurring updates

   1. DBDaniel Blum7:30

      But also it actually manages it on my behalf, and I think that's the pretty cool thing that I wanna show, and I'll walk you through how it does it. I'll say that, um, the most important thing about this is that it knows me really, really well, uh, because I spent a lot of time, uh, and effort contextualizing it, uh, and maintaining this context, and also centralizing all of my work in it, which took some time to get used to, but the ROI is just absolutely insane there. And I really felt how well it knows me just when prepping for this, uh, for this episode when I knew that because this is my real environment, I couldn't show, you know, names and projects and sensitive stuff. So basically, I just created this skill on Claude called Demo, and I just told it, "Replace all the terminology and, like, specifics with generic terms." Then because it knows me so well, basically in, in one prompt, I was able to replace my manager's name with Your Manager and my top initiative you can see here with Headline Feature, and that's how well it knows me. It was just able to replace all of these, and it just makes it for a really, really seamless and comfortable collaboration.

   2. CVClaire Vo8:37

      Tell me a little bit about how that context is saved. Is it just that you just put everything in Notion, so when it's searching, it kinda knows? Is there something more purposeful around your kinda personal brain? How do you, how do you inject context into the system?

   3. DBDaniel Blum8:53

      So I'll say when I built up the system, it was very important for me to build something scalable, so I did a lot of research on,

6. 9:00 – 11:00

   His weekly prep automation

   1. DBDaniel Blum9:00

      like, how to build, uh, how to set up your Claude MD and the, and the context files. Um, and basically I set it up so there's a context file around every, uh, every topic that, uh, that I have and, like, every area of my work, uh, and my goals and my, uh, and, you know, my colleagues and everything that you can imagine. I spent a lot of time manually contextualizing in the beginning, whether through, like, feeding it links and, and different decks and stuff like that, and also just a lot of, you know, whisper, just dictating endless information and blabbering endlessly about everything that I can think of, which is just incredibly powerful in how much context you can give relatively easily and quickly. Um, and then this system basically updates itself on a recurring basis. Every, uh, every few weeks, it runs and updates the, uh, knowledge files based on, you know, different things that have occurred, um, and different, uh, changes, and we will see some of that, uh, just in a minute.

   2. CVClaire Vo9:57

      I love it. Well, let's, let's switch over to Cowork and show us how kinda the system is architected and then how you maintain it and use it over time.

   3. DBDaniel Blum10:05

      Perfect. So it all starts with, um, one recurring task, uh, which is a c- composition of several skills called the weekly prep. So the weekly prep is the very basic, uh, task that helps me start my week. I'll say that I won't run this live, uh, just because, uh, I wanna be mindful of time. But generally speaking, uh, this task helps me go through all these things that you just saw in the Notion and fill them in. So we basically have the top of mind, the this week, and the inbox. And what this, uh, series of, uh, skills does, it pulls in information from my entire ecosystem, um, from my Notion, my calendar, Slack, um, from, from, uh, Granola transcripts of meetings, and basically recommends what I should be focusing on this week. If there's new top of mind items that need to be, uh, added or removed, it would recommend that. It would recommend moving, removing,

7. 11:00 – 15:00

   His morning brief

   1. DBDaniel Blum11:00

      finishing things from this week, and the same with the inbox. Um, and this basically, uh, on Sunday mornings, this is our beginning of the week, uh, it helps me start with a very, very clear and focused list of what I actually wanna do. And then finally, it helps me prep for my meetings. So it runs me through the meetings that I'm going to have and asks me how I wanna prep for them, whether it's, like, a serious preparation that requires its own task in my weekly priority, whether it's a quick reminder or just meetings that don't really need any prep. And then I confirm all of this, and I'm set to go, and this is the start. But-

   2. CVClaire Vo11:37

      And does that push all of it into Notion?

   3. DBDaniel Blum11:40

      Yes. And that basically... This task that I ran earlier basically created this state that we have, uh, now, the, the Notion, uh, that we have right now. But I'll also show you how it updates it.

   4. CVClaire Vo11:53

      Yeah, let's look at that.

   5. DBDaniel Blum11:54

      Perfect. So the unique thing about this is that I think, and this is something I ran into, uh, after having created the first weekly prep, I think one of the things any, any PM, uh, can resonate with is the fact that there's two worlds, right? There's this beautiful, clean, organized world that's in our weekly priority or our roadmap where everything is very clear and beautiful and fits in, and then there's reality where, as we said, this chaos of Slack and meetings and pr- urgent priorities and executive asks and endless things that just flow in and out. And what I was feeling in the beginning is this real, um, this real ... gap between what I was doing and prepping and what it was happening in real life, where I was spending all this time doing all these small tasks. And I think I've built the system to really work alongside me, and part of the fact that it knows me really well is also that it knows how I work. So for example, I'm inbox zero both on Slack and on email, so it knows that if something is, was saved on Slack and is no longer, it means it's likely done. Or if something was on inbox in, in Gmail and is no longer so, then it probably means I already read it, and that really, really helps in how we collaborate smoothly. So basically, let me run to, uh, my next scheduled, uh, my next scheduled task, and this is called the morning brief. And this is, I think, where the real magic happens. So actually, we're going to run this live right now.

   6. CVClaire Vo13:21

      I have to laugh because I think folks' AI setup is a real reflection of their internal personality, and you strike me as somebody who is organized and thoughtful. You're an inbox zero person. I am sorry to anybody that tries to text or email me. I am like a chaos reigns person. I cannot put my stuff in a table. I cannot put my stuff in a Kanban board. I need just a bot, and I need when it's 2:00 in the morning or it's 6:00 in the morning or it's 2:00 in the afternoon, I just need to be like, "Dear bot, what's going on? [laughs] What's going on?" And so it's always fascinating to me to watch people who I just, uh, pre-AI have, like, a much more structured approach to their work. And then post-AI, I think it really reflects in how you build, build your system because mine looks... It probably should look like something like this, but it looks nothing like this. [laughs]

   7. DBDaniel Blum14:20

      [laughs] Well, I think, uh, I'll say first of all that, uh, y- you are correct in, in me being quite an organized person, but I will say, like, again, in reality, a lot is a mess and a lot is, like, I, I've found out how much is, like, business logic in my brain, and I've had this experience with the system where I continuously, like, do discovery on myself and how I work, and I continuously run into these places where the system is not good enough 'cause it doesn't cover this. And when it doesn't cover, like it has a blind spot, then it becomes much less powerful. So over time I've, like, covered all different angles.

   8. CVClaire Vo14:57

      [laughs]

   9. DBDaniel Blum14:57

      Um, and I think it's doable. I think it's doable,

8. 15:00 – 17:30

   How Claude flags unknown internal terms and saves them to context

   1. DBDaniel Blum15:00

      and up until recently, I would say in a way I was also operating chaotically. You know, some of the tasks were in saved on Slack. Some of them were, like, in my inbox. Others were just, like, tabs that are open in Chrome, and I've just had Claude, like, learn to work with all of these, um, and say, "All right, I'll take..." Unfortunately, it can't take an open tab as a, as a task, but, uh, everything else it just learned to look at, uh, the same way I do.

   2. CVClaire Vo15:24

      Well, let's look at this morning brief 'cause we've seen a couple morning briefs, but I wanna see what you think makes yours different.

   3. DBDaniel Blum15:29

      Okay. So I think th- there's several things, but I'll, I'll walk through this, uh, very quickly and, and show, uh, the different parts, and I'll highlight the interesting things. So the first part is that, uh, this brief basically walks me through my meetings. I think one of the biggest pains of PMs is we have a ton of meetings. Uh, we need action items. We need to act on them. Almost every meeting creates new work, but we have to run to the next meeting, and oftentimes it's back to back until the end of the day and then, you know. So this helps me kind of catch up on, on yesterday's meetings, um, and it shows all the different things, and basically you can see this takes the Granola transcripts, uh, and it gives me a one-liner about each meeting and if there's an action item. So here I can see, uh, from all of these meetings, looking through them, uh, there's one action item, uh, to share the walkthrough and recording of a, of... And, and a writeup in the feature channel, uh, with go-to-market, um, and that's it. So it's gonna offer me to, uh, expand or draft any summaries. I'm gonna say, uh, "No, let's continue for now." And we're gonna walk, walk on over to the next phase, which I think is pretty cool. One of the things that I think is super powerful with Cowork and, and with these harnesses is that you can set them up for improving themselves. And one of the things I've done is I've, over time, uh, I'm building up towards, uh, Claude being more agentic and being more able to act on itself. Um, and I'll show you this, and I think it's pretty visible in this flow. This part is pretty cool, where basically one of the difficulties in life is keeping the context clear, right? So you have, you have the system, you contextualize it, it knows things, but then how do you make sure that it keeps track? So this is one of the ways I've thought of. So basically what it does is imagine in this daily brief, my Cowork runs through my recent Slacks, my emails, my Granola notes, and it looks for context that it doesn't understand in these things and it says like, "Oh, if there's a file I wasn't aware of, there's a milestone, there's a goal," it would ask me about it and say, "Hey, like, what is this? Is this important? Should I read this?" Uh, so here it flagged something.

9. 17:30 – 19:00

   Running 70% to 80% of his workday through Cowork

   1. DBDaniel Blum17:30

      Let's see what it is. A term I didn't know, the settlement cap. All right, this is some payments thing, and it says like, "I read the thread and understand it's a limit working through. Want me to save?" Yeah. So I'll say save, yes, save it to the context. So basically this is how Claude helps me keep it contextualized and not lose track of things.

   2. CVClaire Vo17:50

      This is really genius, and I want people to just take a pause and reflect on what this is because it looks like for your context, you are making sure that Claude understands internal definitions, terms, goals, et cetera. And so many of us work inside companies where the things that we say are not in the training data. They... Well, not yet at least. They're not in the training data, and so actually proactively prompting Claude to say like, "I don't understand what you're talking about here. Can we define it together? And then I'll save it to my context and I'll know what you're talking about moving forward," is really, really sharp and something we haven't seen on the podcast yet. I love this.

   3. DBDaniel Blum18:28

      Yeah. So it's, it's super hard to just keep track and, and the unlock is that you're able to say, "Oh, I can just ask Claude to be my partner in doing this and automatically, you know, follow up and, and insist on, on getting this knowledge," is a really, really big unlock.

   4. CVClaire Vo18:45

      Amazing.

   5. DBDaniel Blum18:46

      So let-

   6. CVClaire Vo18:47

      So you run it weekly, you run it daily. Do you actually spend time in the Notion, or are you still, like, navigating all this with Claude?

   7. DBDaniel Blum18:58

      So the main idea is that Notion

10. 19:00 – 20:00

    Chrome connector vs. MCPs for tools without integrations

    1. DBDaniel Blum19:00

       is almost a read-only for me. I, I look at the Notion to get my focus, uh, to remind me of my top of mind, to remind me of, uh, my priorities and focus this week. Um, you know, every so often I'll, I'll mark something as done if I just finished it. But generally, my goal is to have, uh, Notion as, as something I only look at and Claude manages on my behalf. And in general, I s- I'll say this is something that has happened to me naturally, but I think it's one of the core pillars of building a strong system. Today, I say I manage about 70% to 80% of my time in front of the computer with Cowork alone. Almost everything I do here is through Cowork. Um, and I try to do more and more of it, 'cause anything that I don't do in Cowork, then the context is not as well caught as if I do it through Cowork, whether it's, you know, other applications. Whether it's Jira, Slack, uh, Queries, Pro- anything generally, so.

    2. CVClaire Vo19:57

       Are you using Cowork with Chrome

11. 20:00 – 25:00

    The real ROI question: why the early weeks feel slow, and why you push through anyway

    1. CVClaire Vo20:00

       at all? Like, are you using browser use, or are you purely just using, like, connectors and MCPs for all of this?

    2. DBDaniel Blum20:09

       Yeah, so I, I would say in the beginning I was using, like, Chrome a lot. In my personal Cowork that I have, I use Chrome a lot. Um, as, as time proceeds and, and there's more and more MCPs and connectors, then obviously those are comfortable. But at, like, the Chrome connector is a critical, critical piece of, uh, you know, of the puzzle for when you don't have these connectors and integra- integrations, and you need to use the browser.

    3. CVClaire Vo20:35

       And do you feel like this is really saving you? Like, w- what's the benefit here? Is it, like, saving you time? Do you feel like you just know everything? Are you getting better work done? Like, why? 'Cause, you know, again, these systems take time to maintain, and I think we're all sort of at this point with our AI systems where we're like, "Okay, they're all super cool, but, like, why are we, why are we doing this?" And so I'm just curious, like, what is the benefit you're getting as a PM to, to running this system?

    4. DBDaniel Blum21:01

       Yeah. So it's, it's a great question, and I think [laughs] honestly, oftentimes we make systems that, uh, don't give us great benefit. I just, uh, I built a personal, uh, agent that its main work is sending memes about my wife in our s-shared panel on Telegram.

    5. CVClaire Vo21:15

       [laughs]

    6. DBDaniel Blum21:16

       Which, hey, to me is huge value, I think. [laughs] It's helping me, uh, win arguments. But, uh, jokes aside-

    7. CVClaire Vo21:24

       Uh

    8. DBDaniel Blum21:24

       ... I, I think-

    9. CVClaire Vo21:24

       Quick pause. You need to watch our episode with Jason, the CEO of Memelord, who actually has a meme API, so you can plug that into your agent. That was a, a very weird episode [laughs] that we did.

    10. DBDaniel Blum21:37

        So I, I haven't watched it yet, but I will say it's literally, like, the top to-do task in my per- in, like, the Claude session that I manage my agents. And what, what's next? The, [laughs] the meme API is, is definitely the next one.

    11. CVClaire Vo21:52

        It's really good.

    12. DBDaniel Blum21:53

        [laughs] Yeah. Um, but I'll say I think it's a really, really good question. And I will say also that probably in the beginning, um, it's not gonna... Like, the ROI is not gonna look great, especially when you set up something that's as robust and as significant. It's gonna take some time, uh, because while it doesn't know you and your personal, we can call it business logic and, like, the way you operate, it's gonna be very friction-full. And everything it does or says or thinks, it's gonna be a little bit off. And you're gonna lose trust, and you're gonna be very skeptical, and then you're gonna double-check everything. But the value tremendously compounds. It's just incredible. The more you kind of power through these first few weeks of, A, contextualizing ruthlessly and continuously sharing everything you can, and B, centralizing whatever work you can in Cowork or in your harness, even if it doesn't feel so natural, over time, it is just in... I cannot describe how powerful it is. And I'll say personally, I think, first of all, I'm really able to do in a day now what used to take me a week. And, and-

    13. CVClaire Vo23:02

        Love it

    14. DBDaniel Blum23:02

        ... I stand behind that. It's, and you know, it's something that sounds like a, like a hypey LinkedIn post headliner.

    15. CVClaire Vo23:09

        [laughs]

    16. DBDaniel Blum23:09

        But it's, it's, it's true. You know? It's, it's insane. I, I look at, um, I look at my, the way I work through these, like, this week, and oftentimes I can get through this week in a good day, uh, which is just mind-blowing. But more than that, I'll say it's a lot of deeper work. Um, there's things that I do today that I just wasn't able to do before, whether it's more in-depth research, whether it's better, uh, being more data-backed when checking things, working less off of hunches and more off of, like, facts and researches, whether it's competitive researches. Like, anything you do today, you can do it almost at the top level. Um, as opposed to back in the day, moving, moving fast meant you need to, you know, operate on a lot of hunches, um, not work off of data, um, not be as robust in terms of your documentation. And today it really, really changes.

    17. CVClaire Vo24:07

        I, I love it. I love it. You- you've sold me. Um, I don't know if I'm gonna get as organized as you, but I... And I think that's absolutely right. I... One of the things, even at a company level, that I tell people is, look, you gotta go through the pain of switching your systems. And it's not gonna be as efficient. And yes, of course, like, the old way will be faster because it's muscle memory. But if you get to the next level, not only will you have a system that works better for you, but everybody will have more skills, and I think that's almost The more important part where this is a personal productivity system that works for you, that's great. Um, but I'd say probably the, the bigger benefit is it forced you to learn how to use Cowork and l- use these AI tools in a different way. And as a product builder, you have to know that stuff. You have to think about, well, what if my product's being used only through Claude? What, what do

12. 25:00 – 26:30

    Scaling the system to the team with the Workstation plugin

    1. CVClaire Vo25:00

       I want that to look like? And I think it's just, if you are in product, it is just one of the most important things that, that you could, you could do. This episode is brought to you by Jira by Atlassian. The teamwork graph in Jira delivers 44% more accurate agent results with 48% less token usage. That's a huge difference when working with AI coding agents like Claude, Cursor, Codex, or Copilot. The hardest part of shipping with AI isn't the code, it's the context. What's the right ticket? What did the spec say? What got decided in Slack? The teamwork graph pulls all of that from across your entire stack, from Jira and Confluence to GitHub, and feeds it directly to your agents before they write a single line. You assign the work, the agent gets everything it needs, and a PR surfaces when it's ready. No digging, no context switching, no broken flow. Same team, smarter agents. Try them free at jira.dev. That's J-I-R-A dot D-E-V. I'm curious how this scales beyond you. So you have your system, your, you know, 10X PM now, congratulations. How does this affect the team? How do they use systems like this? How do you share? Kind of how does that all, does that work?

    2. DBDaniel Blum26:19

       A lot of what you brought up is, is super relevant in that sense. Um, and I think one of the things that have made me, you know, in a sense, uh, wait for, uh,

13. 26:30 – 31:00

    The self-improvement loop

    1. DBDaniel Blum26:30

       for Cowork, for example, when a few months ago there was this endless hype about Cursor and about Claude Code, and, you know, I was kind of sitting on the sidelines, um, a- and, and waiting, like, "Should I adopt these, like, tools that are not meant for me and are super, super technical, can be scary?" Um, and I'm glad I waited for, for Cowork because it's a lot about, like, you know, just UX and, and experience and simplicity, and a lot of the tools that we've built for, for the team and whether it's the gem that helps the team write, uh, specs, product specs that we did almost a year ago, or, uh, what we call the workstation that we have that I'll show a little bit later. At the end of the day, if you make something accessible and simple and the value is clear, um, then it, then it gets adopted much better.

    2. CVClaire Vo27:16

       All right, before we get to the workstation flow, which is gonna be how you get this across the company, across the team, you also have some self-improving loops that I think are really interesting. So how do you improve this over time? How does it get better? What have you figured out there?

    3. DBDaniel Blum27:31

       Yeah. So I think this is one of the coolest unlocks that have helped me continuously improve the setup while not dedicating too much time to it. And basically, it's almost not self-improvement, but it's Claude helping me improve it. So I'll walk you through something called the self-improvement, uh, loop. It's a scheduled task that runs weekly, and it has several skills attached to it, and, and I'll walk through them. So again, it, it works in parts. Uh, a trick I've found really helpful when, when I have a bunch of information that Claude feeds me. So I'm gonna walk through this, uh, in retroactive. Uh, so first of all, the first part is how my drafts landed. So what I've found over time is that when I write with Claude, it'll give me a draft, and then I'll change it, and I'll just send it. But the thing there is that Claude doesn't learn what the gap is between, uh, the draft that it wrote and what I actually sent. So I have Claude, uh, when running this task, looking for drafts that it, it's shared with me, and I didn't respond, and then looking to see if I sent them in a different way, and learning from those drafts and saying, "Oh, so we actually ended up writing this," and doing the learning on, on its own. So in this specific, uh, in this specific week, I see that there was nothing learned and insignificant, but this is very helpful in continuing improving and, you know, uh, polishing Claude on, on how I write. Now, this is a cool one. The second one, and this is skills that are worth building. So basically, Claude, on an ongoing basis, looks for things that I do, uh, on a recurring, uh, basis and suggests turning them into skills. Many of my skills actually ended up being, uh, from this flow. Uh, so you could see it, uh, I've been prototyping a bunch lately, so it's, uh, helping me. Uh, it's suggesting I create a Claude design handoff, uh, skill between Cowork and where I do the research, and design where I actually build the prototype, um, and a bunch of other interesting skills, uh, that I've built. I have a skill like this, by the way, that's handoff between Cowork and code, uh, which I use kind of as the exec- executing arm of Cowork. This is the second part. The third part is fixes to my existing setup. So basically, all of my skills and recurring tasks have, uh, lines in their, in their files to collect feedback and friction from my interaction with them. So over time, they gather this. I don't need to do this proactively. Whenever I ask for a fix or something, they gather and track this information, and every week, it surfaces the top frictions from my interaction with Claude and suggests to improve them. Um, so these are also super helpful, as you can see. And then finally, this is, uh, a really cool one. This is actually the, uh, the Improve skill. So basically, uh, we're all dealing with an endless flood, I think this resonates with anybody, endless flood of tips, uh, hyping up from X and LinkedIn and, and, and newsletters and blogs about setups and how to improve your AI usage, and you must have this, and you must build that. And, uh- I found this incredibly overwhelming. On one hand, I don't wanna drown in it. At the same time, I wanna be able to actually implement what's relevant. So I've built a skill called Improve, which is basically like a very critical, um, auditor for these. Uh, and I share them, uh, usually through my phone, through a Slack channel with Claude, and I ask them like, "Is this real? Is this powerful? How, how does this adapt to what we have now? Is this needed?" And then it helps me review it, and together we basically decide whether we wanna build it or not. Uh, so here I ran it against, uh, Claire, your,

14. 31:00 – 32:00

    How the Improve skill separates actually useful AI tips from the hype

    1. DBDaniel Blum31:00

       uh, How I AI episode on designing loops. Um, and it basically gave me like a, a criticism of the episode. It said it's like a good vid- uh, video, and it says like, listen, loops at the end of the day are essentially like scheduled tasks, so you're running loops in many ways, but I don't have goal loops that are, uh, the, the way you suggested. So this is something I can adapt. Um, uh, there's some things I can adopt, and basically this is... helps me, you know, keep track of all the things that I run into and all these like tips and tricks, and at the same time not drown in them and also not, um, you know, give into the hype too much. So these are all the different things I do to, you know, Claude helps me continuously improve it over time with as little, you know, dedicated effort as possible.

    2. CVClaire Vo31:43

       Love the-- We could've done the entire episode on the last three minutes. So good. You know, I, the first one where it's like take everything that you wrote for me that I hated and did it, did it separately or dropped or rewrote and then just learn from that, that's genius. We saw

15. 32:00 – 38:00

    The Workstation onboarding flow, and the UX lesson from distributing “Spectacular”

    1. CVClaire Vo32:00

       Alex Lieberman had like a write like me self-learning loop, but this one is really interesting because it takes the indirect signals of rewriting and builds it. I also, in the loops episode, have a skill writing loop. So I think that's a good one. Look at our work over the last couple week or last week and, and write loops. And then what was the... Let me look at the third one real quick.

    2. DBDaniel Blum32:22

       So the third one is just taking interactions with Claude over the week. It's similar to building new skills, but just fixing existing ones.

    3. CVClaire Vo32:30

       Yeah. And then, um, and then the third one, which is so genius and I wish more people did this, is build in feedback or telemetry into your skills and then review that over time and improvement. I've seen a couple folks, like I think Intercom does this a little bit with some of their skills that they share across the org, but I haven't seen anybody for themselves say, "Anytime that you gather feedback from me, positive, negative, on a skill, or you hear feedback from me that's indirect, put it somewhere that we can review on a weekly basis." Super, super, super smart, and then of course, ingest all this great content, especially from How I AI, and improve your systems. I love it. What I also love that you've told us you do is you take this mega system that you've built across Notion, across Claude, this improving loops, and you figured out a way to scale this to the org in, is it called Workstation? Workstation. Okay. Let's, let's see that.

    4. DBDaniel Blum33:33

       For sure. So basically, um, I'll say that one of the, one of the main things that were important for us, and we were debating whether to do this w- with Claude Code, which was much more powerful, or with, uh, Cowork, and we decided on doing it with Cowork. Uh, we have this, what we call the workstation, which is essentially this, uh, I would say operating system. It started out for PMs in Melio, um, but it actually expanded to all Melio workers. And basically, uh, what it does is, you know, it, it, it creates an ecosystem, uh, and an operating system for you. But I think the cool thing here is this onboarding, and it's important to say I built this with some very, very talented and, uh, smart, uh, colleagues of mine. Um, we really insisted in the beginning on, on a good UX. And after having, you know, a, a few PMs try to do it with Claude, uh, Code through the terminal and taking three days, you know, to install everything and run all the dependencies, we understood that we need to do something that's simple. So basically, one of the key elements of this workstation is that it basically does everything for you. So it's a UX built into the flow, into the chat. Um, so basically what it does is walks you through everything you need to do. So besides just, you know, clicking on a few confirms and maybe, uh, addressing a few questions, it basically gets you up to speed on everything. It gets all your tools connected, confirms your roles, maps your colleagues, your management, where you sit, um, looks at your calendar and what that looks like in your Slack, helps you create your own voice so that you basically, from day zero, you're writing in a way that sounds like you and just doesn't sound like a stranger, um, captures your goals and basically helps you, um, get moving really, really fast. I, I couldn't do the full flow here because I, I have it set up already, so, uh, but you could see it's very, very simple. It takes you hand in hand, uh, and guides you to this like very, very robust, uh, system that helps you, you know, work in Cowork fully and become native.

    5. CVClaire Vo35:34

       I love this. I have seen so many people try to train this into their team, like sit and say, "Okay, step one, step two, step three, step four," et cetera. Just making a skill to say, "Okay, do you have all your connectors set up? Great. Have we pulled your voice? Great. Have you told me about you? Great." Like, tell me, you know, so let me set all this up, and then from day zero, someone on your team-- Look, they're gonna customize it, maybe. Some people won't though.

    6. DBDaniel Blum36:06

       Yeah.

    7. CVClaire Vo36:06

       And so if everybody's starting from this, it takes what? 15 minutes, something like that?

    8. DBDaniel Blum36:11

       Yeah.

    9. CVClaire Vo36:12

       Ugh.

    10. DBDaniel Blum36:12

        Give or take.

    11. CVClaire Vo36:12

        I love it. And then do you just do this as like a shared skill in Cowork?

    12. DBDaniel Blum36:15

        This is a plugin.

    13. CVClaire Vo36:16

        Plugin, great.

    14. DBDaniel Blum36:17

        So everybody in Melio has it in our library, and anybody can access it. And you know, now it's already like it, it's become quite a big thing. Like, my colleagues have taken it to, to the next level, and it's really, really impressive. Uh, but yeah, I, I couldn't agree with you more. I think for me this, this landed when- About a year ago, I built, uh, uh, our spec writing gem. Call it, call it, uh, Spectacular. And-

    15. CVClaire Vo36:40

        [laughs]

    16. DBDaniel Blum36:41

        ... I, I was using it for my own, and I built it to be really, you know, back, back in the day, a year ago, you know, getting, you know, holding up the template was something really hard to achieve, and making it not hallucinate in a long spec was, like, something that's hard. And after I built something that was really powerful and good for, for the way I was working, and I was exciting to... I, I was excited to distribute it. I had, like, uh, live demos with several PMs that I watched them operate it from zero, and I saw how different... Like, I thought it was already this complete, uh, fully, like, baked, uh, tool, and I saw them using it and struggling because it was completely adjusted to how I work.

    17. CVClaire Vo37:16

        Yeah.

    18. DBDaniel Blum37:16

        And that's when it started, when into this gem, I built this UX that guides you hand-in-hand. It tells you, like, "All right. I'm your, I'm your spec writing, uh, assistant. Here's how you can work with me. Here's what I recommend you to do. Here's how you can start," and basically guiding them hand-in-hand, making it simple and accessible. Um, so yeah, good UX and simplicity is critical even for, you know, internal teams, and PMs, and technical people.

    19. CVClaire Vo37:41

        I, I love this so much. This is br- I mean, this is something, if you haven't taken it away as somebody watching this podcast, go... Every company should go do this and build, like, your sort of, like, bootstrap my personal AI skill or plugin inside Claude or inside Codex. Everybody starts, um, from the same

16. 38:00 – 41:00

    The 20% Claude still can’t do, and what changes when it can

    1. CVClaire Vo38:00

       page, and you can just get your most, like, AI-pilled people on the team to build it for you and share, and then everybody can have shared ownership over it over time. Daniel, this has been awesome. Just to recap for folks, you have Notion as sort of like a read-only database source of truth for all your context and priorities for a week. You run two anchoring automations in Cowork, which is your weekly setup, which sets up this whole Notion thing, preps you for meetings, priorities, and then your, um, daily briefing that, um, kind of cycles through the next day, takes care of stuff. And then you've been able to scale this in the org through kind of a, a workstation plugin that anybody can use and kind of set up this thing for themselves. And now you're living your best life. And again, um, you know, bosses, don't listen to this, but the man says that he can do in one day what he used to do in a week. So, you're getting real, just, like, real productivity gains from this. Um, and you have learned maybe to be more organized, and Claude, uh, plus Notion have made you more, more organized as a PM. So everybody's, everybody's benefiting here. Um, this has been awesome. I wanna do, like, a couple quick lightning round questions, and then we will get you back to all your highly productive work. You know, I wanna go back to you saying that you operate almost 70, 80% through Claude and through Cowork. What do you think is missing? What, what, what is that remaining 20, 30%? And do you think it's gonna be 100% at some point? Or kinda what's that gap and what's missing in, in terms of you being able to use AI or use Claude for everything?

    2. DBDaniel Blum39:52

       So it's a really, really good question. I think the missing piece, and I, I'm... my, my personal sense is that it's very close, is A, the ability to operate in a, i- in the cloud essentially in a way that's, uh, unrelated to when my computer is open and running. I think that's critical, and I think that was also created with the, uh, with the Claude tag, which we don't yet have in our company, but I've heard good things. Also, that it's expensive. I don't know.

    3. CVClaire Vo40:18

       [laughs]

    4. DBDaniel Blum40:19

       But I think the ability to run, uh, Claude away from your computer or have it run on its own, something like OpenClau or like a Hermes, uh, is really, really critical to do more of these things and to achieve more. I've found some ways to work around this. Like, I have a cha- a Slack channel that Claude pul- pulls, and when I'm away from the computer, I can send him some things, uh, and then he could read them later. But it's, it's still something that has to happen online. Um, and this is, I think, the, the real missing piece. Once I have something that's able to operate, uh, in the cloud when I'm away from my computer, when it's off, and, you know, uh, coordi- like, act on things, uh, that, that will be huge. And also

17. 41:00 – 42:30

    What Daniel spends his reclaimed time on

    1. DBDaniel Blum41:00

       closely related is just the ability to actually, like, you know, do, do things. So I've been building up the system in order to enable to, to basically prepare for it. Um, I've been having Claude not only capture my tasks and when they're done, but basically it looks at my tasks. It assigns, like, what it looks, what it would imagine is a closed scenario. So let's say something, somebody asked a question and I saved it on Slack. So it would say, "Okay, if there's a reply and it's unsaved, it means it's done." And then it looks at how I resolve these things, and that's building up towards the, the time where I hope that for the simplest tasks that may take up time and be annoying, you know, when people... somebody asks you for something or somebody asks about a file that you need or, or know, or to a- or to schedule a meeting, then it would just know to do that on its own and it wouldn't need me. And, and that's what I'm building up towards, and that will be really powerful.

    2. CVClaire Vo41:53

       That's, that's the dream. But we're not at the dream yet. And so I'm curious, you know, we... our audience is a lot of PMs, and I'm just curious, now that you have this extra capacity and time, what are the, the product tasks that you're doubling down on, that you're doing even more, you're spending even more time on? Where do you think the effort should go?

    3. DBDaniel Blum42:15

       I'm not gonna say anything surprising, but just purely in-depth work. That's one. Um, so talking to customers, talking to users, and a lot of research. I think those two are, uh, really, really important and given, and also just

18. 42:30 – 46:06

    Claude rage

    1. DBDaniel Blum42:30

       the standard things that any PM aims to get more time for. But I think that in today's world, something that really, really is important and interesting, um, and that is new is A, um, improving the system. So I think the beauty about this is that if a system is built correctly and on the right pillars, it can grow and improve over time, and I've improved my system basically week over week. Uh, and this is done through, you know, dedicating time to research and learn about AI, catching up to speed on how things are progressing, and implementing them. Um, I have a skill that's called Improve, uh, which I send, uh, posts and tweets and articles to with, like, recommendations and tips about, uh, AI setup. And together we review it and see if it fits for me or if it's just, like, LinkedIn hype, and how it can collaborate with what my system is today. And we continuously improve the system together with, you know, tips from, uh, from a bunch of resources. This is a skill that I think is critical today in order to be able to keep up and, and become better. Um, yeah.

    2. CVClaire Vo43:35

       I, I, I love it. And then finally, my favorite question I ask everybody. You're organized, so maybe, maybe you're nicer than me. When Claude is not doing what you want, when AI is not giving you the response that you want, what do you do? Do you yell? Are you nice? Are you polite?

    3. DBDaniel Blum43:53

       [laughs] So I think after having watched quite a few of your episodes, I think my response is pretty similar to everybody. Um, if I'm using Whisper, I may yell. I don't get road rage, but I get Claude rage. So I think-

    4. CVClaire Vo44:06

       [laughs]

    5. DBDaniel Blum44:06

       ... like, I can... I don't, I don't know if I've cursed, but I, I've definitely, like, raised my voice, and I'm also frustrated at the fact that that doesn't go through Whisper well enough. Like, I'm like, you know, exclaiming passionately, and then I just see the transcript and it's like, "Why isn't this working?" So Wh- Whisper folks, if you're out there, this is a feature request. Make, make my exclamations be more felt. [laughs]

    6. CVClaire Vo44:32

       I love it. Yeah. I have this... Like, speaking of Claude rage, I have this hypothesis. I have this Aura on. I have this hypothesis that you can tell what model I'm working with with, like, how agitated and stressed [laughs] I am. So maybe, maybe that will be a future How I AI benchmark. I'm, I'm, I'm baking a noi bench, which is, like, how-

    7. DBDaniel Blum44:52

       [laughs]

    8. CVClaire Vo44:53

       ... furious-

    9. DBDaniel Blum44:54

       That would be amazing

    10. CVClaire Vo44:55

        ... an agent, uh, an agent or an AI makes me.

    11. DBDaniel Blum44:57

        It's-

    12. CVClaire Vo44:57

        This has been so much fun. Thank you for showing us your full system. I think it's totally accessible. Um, I think a lot of people are gonna put this in their own Improve skill. And I love how you're figuring out ways to share this with the rest of your team. Where can we find you, and how can we be helpful to you?

    13. DBDaniel Blum45:14

        Awesome. So this has been super fun, Claire. Thank you so much. Um, people can find me on LinkedIn, Daniel Blum, um, and also on my website, imdanielblum.com. Uh, I can share some of these resources. Um, this, this, a big part of this, uh, system is available, uh, for download, so check out the website, and yeah.

    14. CVClaire Vo45:35

        Awesome. Well, thank you for joining How I AI.

    15. DBDaniel Blum45:38

        Thank you, Claire.

    16. CVClaire Vo45:39

        [upbeat music] Thanks so much for watching. If you enjoyed the show, please like and subscribe here on YouTube, or even better, leave us a comment with your thoughts. You can also find this podcast on Apple Podcasts, Spotify, or your favorite podcast app. Please consider leaving us a rating and review, which will help others find the show. You can see all our episodes and learn more about the show at howiaipod.com. See you next time.

Episode duration: 46:07