How I turned Claude into a self-improving PM assistant | Daniel Blum (PM, Melio)

Daniel Blum is a product manager at Melio, a B2B payments company, and one of the most systematic thinkers I’ve had on the show when it comes to personal AI infrastructure. He’s spent the past year building a Claude- and Cowork-based productivity system that manages his Notion board, processes his Slack and email, and runs self-improvement loops every week without needing to be prompted. Beyond his own workflow, Daniel built and scaled a “Workstation” onboarding plugin that gets any Melio employee up and running with a personalized Claude setup in about 15 minutes. What you’ll learn: Why Daniel says the two rules that make any AI system powerful aren’t about the tool you pickHow his weekly prep automation fills an entire Notion board from scratch every Sunday, without his touching itThe morning brief feature that teaches Claude new internal terms on its own, so company jargon never slows it downWhy he describes Notion as “read-only” now, and what that says about how PM workflows are changingThe self-improvement loop that watches Daniel’s edits, spots recurring friction, and suggests new skills to buildHow he uses a skill called “Improve” to filter the endless flood of AI tips without drowning in themWhat he built to scale his personal system to every PM at Melio, and the UX lesson he learned the hard wayThe capability gap that’s still keeping him from running 100% of his work through Claude— Brought to you by: Optimizely https://optimize.ly/3KD565S—Your AI agent orchestration platform for marketing and digital teams Jira AI SDLC https://ad.doubleclick.net/ddm/trackclk/N320202.6053656HOWIAI/B36397005.454541156;dc_trk_aid=648366078;dc_trk_cid=262806969;dc_lat=;dc_rdid=;tag_for_child_directed_treatment=;tfua=;gdpr=$%7BGDPR%7D;gdpr_consent=$%7BGDPR_CONSENT_755%7D;ltd=;dc_tdv=1—Get your tokens’ worth with Jira — In this episode, we cover: (00:00 https://www.youtube.com/watch?v=p2qmX6TM0kw) Daniel’s background and the PM overhead problem he needed to solve (03:30 https://www.youtube.com/watch?v=p2qmX6TM0kw&t=210s) His AI stack at Melio (05:00 https://www.youtube.com/watch?v=p2qmX6TM0kw&t=300s) The two rules that make any AI system genuinely powerful (06:00 https://www.youtube.com/watch?v=p2qmX6TM0kw&t=360s) The Notion board Cowork built for him (and manages on his behalf) (07:30 https://www.youtube.com/watch?v=p2qmX6TM0kw&t=450s) How he contextualizes Claude with voice memos, links, and recurring updates (09:00 https://www.youtube.com/watch?v=p2qmX6TM0kw&t=540s) His weekly prep automation (11:00 https://www.youtube.com/watch?v=p2qmX6TM0kw&t=660s) His morning brief (15:00 https://www.youtube.com/watch?v=p2qmX6TM0kw&t=900s) How Claude flags unknown internal terms and saves them to context (17:30 https://www.youtube.com/watch?v=p2qmX6TM0kw&t=1050s) Running 70% to 80% of his workday through Cowork (19:00 https://www.youtube.com/watch?v=p2qmX6TM0kw&t=1140s) Chrome connector vs. MCPs for tools without integrations (20:00 https://www.youtube.com/watch?v=p2qmX6TM0kw&t=1200s) The real ROI question: why the early weeks feel slow, and why you push through anyway (25:00 https://www.youtube.com/watch?v=p2qmX6TM0kw&t=1500s) Scaling the system to the team with the Workstation plugin (26:30 https://www.youtube.com/watch?v=p2qmX6TM0kw&t=1590s) The self-improvement loop (31:00 https://www.youtube.com/watch?v=p2qmX6TM0kw&t=1860s) How the Improve skill separates actually useful AI tips from the hype (32:00 https://www.youtube.com/watch?v=p2qmX6TM0kw&t=1920s) The Workstation onboarding flow, and the UX lesson from distributing “Spectacular” (38:00 https://www.youtube.com/watch?v=p2qmX6TM0kw&t=2280s) The 20% Claude still can’t do, and what changes when it can (41:00 https://www.youtube.com/watch?v=p2qmX6TM0kw&t=2460s) What Daniel spends his reclaimed time on (42:30 https://www.youtube.com/watch?v=p2qmX6TM0kw&t=2550s) Claude rage — Tools referenced: • Claude: https://claude.ai https://claude.ai/ • Notion: https://notion.so https://notion.so/ — Other references: • From a $6.90 newsletter to $3M API: How a non-coder built Memelord | Jason Levin: https://www.lennysnewsletter.com/p/from-a-690-newsletter-to-3m-api-how?utm_source=publication-search • How the founder of Morning Brew built a Claude content machine that never runs out of ideas and never sounds like slop | Alex Lieberman: https://www.lennysnewsletter.com/p/how-the-founder-of-morning-brew-built?utm_source=publication-search — Where to find Daniel Blum: LinkedIn: https://www.linkedin.com/in/blumd/ Website: https://www.imdanielblum.com https://www.imdanielblum.com/ — Where to find Claire Vo: ChatPRD: https://www.chatprd.ai/ Website: https://clairevo.com/ LinkedIn: https://www.linkedin.com/in/clairevo/ X: https://x.com/clairevo — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

• 0:00Speaker 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.

• 0:22Speaker 01

  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 going to 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.

• 0:42Speaker 00

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

• 0:47Speaker 01

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

• 0:50Speaker 00

  In this daily brief, my cowork runs through my recent slacks, my emails, my internal 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.

• 1:10Speaker 01

  This is really genius. 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?

• 1:26Speaker 01

  Welcome back to How I AI. I'm Claire Vau, product leader and AI obsessive here on a mission to help you build better with these new tools. Today I have Daniel Bloom and he's going to 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,

• 2:10Speaker 01

  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 AI and their personal productivity.

• 2:53Speaker 01

  And so tell me, like, what brought you to building this big system? And what problem were you trying to solve?

• 3:00Speaker 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 already like 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, even with simpler tools like with gems, you could improve your specs and you could improve your research. But I think as I was progressing with my AI adoption, I really felt that one of the biggest things that hangs over me and really makes my day to day more difficult is all this just overhead of being a PM, of coordinating a bunch of things, remembering endless tasks that arise on Slack and meetings and action items

• 3:45Speaker 00

  and just trying to maneuver this whole, this whole chaos that happens every single day, while at the same time wanting to do in-depth work and focus and really think. I felt that that was something that was really, really difficult for me. And I was getting nowhere near solving it 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 this problem for me.

• 4:14Speaker 01

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

• 4:25Speaker 00

  Perfect. So I'll say I think most of my choices were made by my company, Melio, and the tools that are in our stack. But thankfully, I'm pretty satisfied with those. So for a long time, we only had like the Gemini Enterprise and we were using that. And just a few months ago, we got the Claude Enterprise and cowork. And that's when things really changed for me. And besides that, I'm basically bound to whatever tools we have and use. So this is what I work based off of.

• 4:59Speaker 01

  Okay, so this is good for everybody out there who is stuck with the tools that they're stuck with. You can still make it 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?

• 5:20Speaker 00

  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 BM all the time in terms of having, you know, not endless tokens and needing to 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 very important to say. 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. And I think Codex could be great for this as well, or ChatGPT work. I think the real importance is for a system to, A, be able to rewrite its own core files.

• 6:05Speaker 00

  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, there is a significant, significant opportunity to really, really improve the way you work. And while I was working with Gemini gems earlier and there is 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.

• 6:36Speaker 01

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

• 6:43Speaker 00

  Let me start with this Notion board, right? So this is nothing incredible, it's just a standard PM Notion board. It has three sections. One is top of mind, which are the large initiatives that I just think of, you know, on any given 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 Google Doc before. And I think Notion got, I think cowork got tired of it

• 7:27Speaker 00

  and basically decided to build this for me. But also it actually manages it on my behalf. And I think that's the pretty cool thing that I want to show. And I'll walk you through how it does it. I'll say that the most important thing about this is that it knows me really, really well because I spent a lot of time and effort contextualizing it 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, 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.

• 8:11Speaker 00

  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. But because it knows me so well, basically 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.

• 8:37Speaker 01

  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 kind of knows. Is there something more purposeful around your kind of personal brain? How do you inject context into the system?

• 8:53Speaker 00

  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 like how to build, how to set up your Claude MD and the, and the context files. And basically I set it up so there's a context file around every, every topic that, that I have and like every area of my work and my goals and my, 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,

• 9:35Speaker 00

  which is just incredibly powerful and how much context you can give relatively easily and quickly. And then this system basically updates itself on a recurring basis. Every, every few weeks it runs and updates the knowledge files based on, you know, different things that have occurred and different changes. And we will see some of that just in a minute.

• 9:57Speaker 01

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

• 10:05Speaker 00

  Perfect. So it all starts with one recurring task, which is a composition of several skills called the weekly prep. So the weekly prep is the very basic task that helps me start my week. I'll say that I won't run this live just because I want to be mindful of time. But generally speaking, 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 series of skills does, it pulls in information from my entire ecosystem, from my notion, my calendar, Slack, from, from granola transcripts of meetings and basically recommends

• 10:50Speaker 00

  what I should be focusing on this week. If there's new top of mind items that need to be added or removed, it would recommend that. It would recommend moving, removing, finishing things from this week. And the same with the inbox. And this basically on Sunday mornings, this is our beginning of the week. It helps me start with a very, very clear and focused list of what I actually want to 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 want to 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.

• 11:34Speaker 00

  And this is the start.

• 11:36Speaker 01

  And does that push all of it into Notion?

• 11:40Speaker 00

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

• 11:53Speaker 01

  Yeah, let's look at that.

• 11:54Speaker 00

  Perfect. So the unique thing about this is that I think, and this is something I ran into after having created the first weekly prep. I think one of the things any, any PM 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 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, this real gap between what I was doing and prepping and what was happening in real life.

• 12:37Speaker 00

  Or 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 my next scheduled, 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.

• 13:21Speaker 01

  I had 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 two in the morning or it's six in the morning or it's two in the afternoon, I just need to be like, dear bot, what's going on? What's going on? And so it's always fascinating to me to watch people who I just, hey,

• 14:05Speaker 01

  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.

• 14:22Speaker 00

  Well, I think, I'll say first of all that 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 this places where the system is not good enough because 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. And I think it's doable. I think it's doable. 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.

• 15:07Speaker 00

  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 and say, all right, I'll take. Unfortunately, it can't take an open tab as, as a task, but everything else it just learned to look at the same way I do.

• 15:24Speaker 01

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

• 15:29Speaker 00

  Okay. So I think that there's several things, but I'll walk through this very quickly and, and show the different parts. And I'll highlight the interesting things. So the first part is that this brief basically walks me through my meetings. I think one of the biggest pains of PMs is we have a ton of meetings. 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. And it shows all the different things. And basically you can see this takes the granola transcripts and it gives me a one liner about each meeting and if there's an action item. So here I can see from all of these meetings, looking through them,

• 16:11Speaker 00

  there is one action item to share the walkthrough and recording of a, of, and a write up in the feature channel with go to market. And that's it. So it's going to offer me to expand or draft any summaries. I'm going to say, no, let's continue for now. And we're going to 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 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, I'm building up towards Claude being more agentic and being more able to act on itself. And I'll show you this and I think it's pretty visible in this flow.

• 16:54Speaker 00

  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 and those 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? So here it flagged something. 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.

• 17:40Speaker 00

  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.

• 17:50Speaker 01

  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.

• 18:28Speaker 00

  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.

• 18:45Speaker 01

  Amazing. 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?

• 18:57Speaker 00

  So the main idea is that Notion is almost a read only for me. I, I look at the Notion to get my focus, to remind me of my top of mind, to remind me of my priorities and focus this week. 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 a Notion as something I only look at and Claude manages on my behalf. And in general, 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.

• 19:40Speaker 00

  And I try to do more and more of it because 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, queries, anything generally, so.

• 19:57Speaker 01

  Are you using cowork with Chrome at all? Like, are you using browser use? Or are you purely just using connectors and MCPs for all of this?

• 20:09Speaker 00

  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. As, as time proceeds and there's more and more MCPs and connectors, then obviously those are comfortable. But like the Chrome connector is a critical, critical piece of, you know, of the puzzle for when you don't have these connectors and integrations and you need to use the browser.

• 20:35Speaker 01

  And do you feel like this is really saving you? Like, 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? Because you know, again, these systems take time to maintain. And I think we're all sort of at this point with our AI systems. 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?

• 21:00Speaker 00

  Yeah, so it's, it's a great question. And I think honestly, oftentimes we make systems that don't give us great benefit. I just, I built a personal agent that its main work is sending memes about my wife in our shared channel on Telegram, which hey, to me is huge value, I think. It's helping me win arguments, but jokes aside.

• 21:23Speaker 01

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

• 21:37Speaker 00

  So I, I haven't watched it yet, but I will say it's literally like the top to do task in my, in like a Claude session that I manage in my agents and what, what's next? The meme API is, is definitely the next one. Yeah. But I'll say, I think it's a really, really good question. And I will say also that probably in the beginning, 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 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 frictionful.

• 22:18Speaker 00

  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, 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 I stand behind that.

• 23:03Speaker 00

  It's, and you know, it's something that sounds like a, like a hypey LinkedIn post headliner, but it's, it's, it's true, you know, it's, it's insane. I, I look at, 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, which is just mind blowing. 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 better, 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,

• 23:46Speaker 00

  like anything you do today, you can do it almost at the top level. As opposed to back in the day, moving, moving fast meant you need to, you know, operate on a lot of hunches, not work off of data, not be as robust in terms of your documentation. And today it really, really changes.

• 24:07Speaker 01

  I, I love it. I love it. You, you've sold me. 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. But I'd say probably the, the bigger benefit is it forced you to learn how to use cowork and use these AI tools in a different way.

• 24:52Speaker 01

  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 I want that to look like? And I think it's just, if you are a 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?

• 25:34Speaker 01

  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 it 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, you're, 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 work?

• 26:19Speaker 00

  A lot of what you brought up is, is super relevant in that sense. And I think one of the things that have made me, you know, in a sense, wait for, for cowork. For example, when a few months ago, there was this endless hype about Cursor and about Claude code. And I was kind of sitting on the sidelines and, and waiting, like, should I adopt these like tools that are not meant for me and are super, super technical, can be scary? 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 specs, product specs that we did almost a year ago,

• 27:03Speaker 00

  or 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, then, then it gets adopted much better.

• 27:16Speaker 01

  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?

• 27:31Speaker 00

  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 loop. It's a scheduled task that runs weekly and it has several skills attached to it and I'll walk through them. So again, it, it works in parts. 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 in retroactive. So first of all, the first part is how my drafts landed. So what I 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.

• 28:15Speaker 00

  But the thing there is that Claude doesn't learn what the gap is between the draft that it wrote and what I actually sent. So I have Claude, 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, in this specific week, I see that there was nothing learned and insignificant, but this is very helpful in continuing, improving and, you know, 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 on a recurring basis

• 28:59Speaker 00

  and suggests turning them into skills. Many of my skills actually ended up being from this flow. So you could see it, I've been prototyping a bunch lately, so it's helping me. It's suggesting I create a Claude design handoff skill between cowork and where I do the research and design where I actually build a prototype and a bunch of other interesting skills that I've built. I have a skill like this, by the way, that's handoff between cowork and code, which I use kind of as the 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 lines in their, in their files to collect feedback and friction from my interaction with them.

• 29:44Speaker 00

  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. So these are also super helpful, as you can see. And then finally, this is a really cool one. This is actually the the improved skill. So basically, we're all dealing with an endless flood. I think this resonates with anybody. Endless flood of tips, hyping up from X and LinkedIn and newsletters and blogs about setups and how to improve your AI usage and you must have this and you must build that. And I found this incredibly overwhelming.

• 30:29Speaker 00

  On one hand, I don't want to drown in it. At the same time, I want to be able to actually implement what's relevant. So I've built a skill called Improve, which is basically like a very critical auditor for these. And I share them usually through my phone, through a Slack channel with Claude. And I asked him, like, is this real? Is this powerful? How does this adapt to what we have now? Is this needed? And then it helped me review it. And together, we basically decide whether we want to build it or not. So here I ran it against Claire, your How I AI episode on designing loops. And it basically gave me like a criticism of the episode. It said it's like a good video. And it says, like, listen, loops at the end of the day are essentially like scheduled tasks.

• 31:12Speaker 00

  So you're running loops in many ways, but I don't have goal loops that are the way you suggested. So this is something I can adapt. There are 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, 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.

• 31:43Speaker 01

  Love it. We could have done the entire episode on the last three minutes. So good. You know, the first one where it's like, take everything that you wrote for me that I hated and did it separately or dropped or rewrote and then just learn from that. That's genius. We saw 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 built it. I also, in the loops episode, have a skill writing loops. So I think that's a good one. Look at our work over the last couple week or last week and write loops. And then what was it? Let me look at the third one real quick.

• 32:22Speaker 00

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

• 32:30Speaker 01

  Yeah. And then, 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.

• 33:14Speaker 01

  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've figured out a way to scale this to the org in, is it called workstation? Workstation. Okay, let's, let's see that.

• 33:33Speaker 00

  For sure. So basically, 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 with Claude code, which was much more powerful, or with cowork. And we decided on doing it with cowork. We have this, what we call the workstation, which is essentially this, I would say, operating system. It started out for PMs in Melio, but it actually expanded to all Emilio workers. And basically, what it does is, you know, it creates an ecosystem, 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 smart colleagues of mine. We really insisted in the beginning on a good UX.

• 34:18Speaker 00

  And after having, you know, a few PMs try to do it with Claude 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. 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 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, looks at your calendar and what that looks like.

• 35:03Speaker 00

  And 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, captures your goals and basically helps you get moving really, really fast. I couldn't do the full flow here because I have it set up already. So, but you could see it's very, very simple. It takes you hand in hand and guides you to this like very, very robust system that helps you, you know, work in cowork fully and become native.

• 35:34Speaker 01

  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, let me set all this up. And then from day zero, someone on your team, look, they're going to customize it, maybe. Some people won't, though. And so if everybody's starting from this, it takes what 15 minutes, something like that?

• 36:11Speaker 00

  Yeah.

• 36:12Speaker 01

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

• 36:15Speaker 00

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

• 36:56Speaker 00

  working and I was exciting to, I was excited to distribute it, I had like live demos with several PMs that I watched them operated from zero. And I saw how different, like I thought it was already this complete, fully like baked tool. And I saw them using it and struggling because it was completely adjusted to how I work. 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 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. So yeah, good UX and simplicity is critical even for, you know, internal teams and PMs and technical people.

• 37:41Speaker 01

  I, I love this so much. This is, 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 from the same page and you could just get your most like AI pill 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

• 38:26Speaker 01

  this whole Notion thing, props you for meetings, priorities, and then your daily briefing.

• 38:34Speaker 01

  That 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 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, 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. And you have learned maybe to be more organized and Claude plus Notion have made you more more organized as a PM. So everybody's, everybody's benefiting here. This has been awesome.

• 39:18Speaker 01

  I want to do like a couple of quick lightning round questions and then we will get you back to all your highly productive work. You know, I want to 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 going to be a hundred percent at some point? Or kind of what's that gap and what's missing in, in terms of you being able to use AI or use Claude for everything?

• 39:51Speaker 00

  So it's a really, really good question. I think the missing piece, and I'm, my, my personal sense is that it's very close is A, the ability to operate in a, in the cloud essentially in a way that's unrelated to when my computer is open and running. I think that's critical. And I think that was also created with a, with a 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, but the ability to run Claude away from your computer or have it run on its own, something like Open Claw or like a Hermes is really, really critical to do more of these things and to achieve more. I've found some ways to work around this.

• 40:33Speaker 00

  Like I have a Slack channel that Claude polls. And when I'm away from the computer, I can send him some things and then he could read them later, but it's, it's still something that has to happen online. And this is, I think, the, the real missing piece. Once I have something that's able to operate in the cloud, when I'm away from my computer, when it's off and, you know, coordinate like act on things, that, that will be huge. And also 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. I've been having Claude not only capture my tasks and when they're done, but basically

• 41:15Speaker 00

  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 save 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 add, 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.

• 41:53Speaker 01

  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?

• 42:15Speaker 00

  I'm not going to say anything surprising, but just purely in-depth work, that's one. So talking to customers, talking to users and a lot of research. I think those two are really, really important and given. And also just 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 and that is new is A, 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. And this is done through, you know, dedicating time to research and learn about AI, catching

• 43:00Speaker 00

  up to speed on how things are progressing and implementing them. I have a skill that's called improve, which I send posts and tweets and articles to with like recommendations and tips about 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, 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. Yeah.

• 43:34Speaker 01

  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?

• 43:53Speaker 00

  So I think after having watched quite a few of your episodes, I think my response is pretty similar to everybody. If I'm using Whisper, I may yell. I don't get road rage, but I get Claude rage. So I think 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 Whisper folks, if you're out there, this is a feature request. Make, make my exclamations be more felt.

• 44:32Speaker 01

  I love it. Yeah, I have this, 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. So maybe, maybe that will be a future how I AI benchmark. I'm, I'm baking a noy bench, which is like how furious.

• 44:53Speaker 00

  That will be amazing.

• 44:55Speaker 01

  An agent or an AI makes me. This has been so much fun. Thank you for showing us your full system. I think it's totally accessible. I think a lot of people are going to put this in their own improved 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?

• 45:14Speaker 00

  Awesome. So this has been super fun, Claire. Thank you so much. People can find me on LinkedIn, Daniel Bloom, and also on my website, I'm danielbloom.com. I can share some of these resources. This, this, a big part of this system is available for download. So check out the website and yeah.

• 45:35Speaker 01

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

• 45:38Speaker 00

  Thank you, Claire.

• 45:40Speaker 01

  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.