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

46 min episode · 2 min read
·
Daniel Blum

Episode

46 min

Read time

2 min

Topics

Remote Work, Software Development, Crypto & Web3

AI-Generated Summary

Key Takeaways

  • Self-Improving Context Files: Structure Claude around dedicated context files for every work area — colleagues, goals, initiatives — then schedule a recurring task every few weeks to auto-update those files based on new information. The system also flags unknown terms during daily briefings and asks permission to save definitions, keeping internal company language current without manual effort.
  • Two-Layer Automation Architecture: Run two anchor automations weekly and daily. The Sunday weekly prep pulls from Notion, calendar, Slack, and Granola meeting transcripts to populate three Notion sections — top of mind, this week, and inbox — then recommends meeting prep levels. The daily morning brief processes yesterday's meetings, surfaces one-liner action items, and identifies context gaps for Claude to learn from.
  • Draft-Gap Learning Loop: Build a weekly self-improvement skill that compares Claude's original drafts against what was actually sent. When Claude detects a rewritten or discarded draft, it analyzes the difference and updates its writing model accordingly — capturing indirect feedback signals without requiring the user to manually critique outputs or run explicit correction sessions.
  • Friction Telemetry Inside Skills: Embed feedback-collection lines directly into every skill and recurring task file. These lines passively log friction points from each interaction throughout the week. A weekly self-improvement loop then surfaces the top friction patterns and proposes targeted fixes — eliminating the need to proactively remember or document what is not working in the system.
  • Team Onboarding via Workstation Skill: Deploy a shared CoWork plug-in called Workstation that guides new users through connector setup, role mapping, colleague identification, calendar review, and personal voice creation — all inside the chat interface. This replaces multi-day terminal-based setup and gets any team member, technical or not, fully operational within approximately fifteen minutes from zero.

What It Covers

Daniel Blum, PM at Melio, demonstrates his Claude CoWork system that self-improves over time through automated weekly and daily briefings, context-updating loops, and a company-wide onboarding workstation — enabling him to complete in one day what previously required a full week.

Key Questions Answered

  • Self-Improving Context Files: Structure Claude around dedicated context files for every work area — colleagues, goals, initiatives — then schedule a recurring task every few weeks to auto-update those files based on new information. The system also flags unknown terms during daily briefings and asks permission to save definitions, keeping internal company language current without manual effort.
  • Two-Layer Automation Architecture: Run two anchor automations weekly and daily. The Sunday weekly prep pulls from Notion, calendar, Slack, and Granola meeting transcripts to populate three Notion sections — top of mind, this week, and inbox — then recommends meeting prep levels. The daily morning brief processes yesterday's meetings, surfaces one-liner action items, and identifies context gaps for Claude to learn from.
  • Draft-Gap Learning Loop: Build a weekly self-improvement skill that compares Claude's original drafts against what was actually sent. When Claude detects a rewritten or discarded draft, it analyzes the difference and updates its writing model accordingly — capturing indirect feedback signals without requiring the user to manually critique outputs or run explicit correction sessions.
  • Friction Telemetry Inside Skills: Embed feedback-collection lines directly into every skill and recurring task file. These lines passively log friction points from each interaction throughout the week. A weekly self-improvement loop then surfaces the top friction patterns and proposes targeted fixes — eliminating the need to proactively remember or document what is not working in the system.
  • Team Onboarding via Workstation Skill: Deploy a shared CoWork plug-in called Workstation that guides new users through connector setup, role mapping, colleague identification, calendar review, and personal voice creation — all inside the chat interface. This replaces multi-day terminal-based setup and gets any team member, technical or not, fully operational within approximately fifteen minutes from zero.

Notable Moment

During the live morning brief demo, Claude flagged an unfamiliar internal payments term — settlement cap — mid-session, explained its likely meaning from surrounding thread context, and asked whether to save it permanently. This real-time self-contextualization loop had not previously appeared on the podcast.

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Episode Transcript

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. 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. Today, I say I manage about 70 to 80% of my time in front of the computer with co work alone. We've seen a couple morning briefs, but I wanna see what you think makes yours different. In this daily brief, my co work runs through my recent Slacks, my emails, my 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. This is really genius. I'm curious how this scales beyond you. So you have your system. You're, you know, 10 x p m now. Congratulations. How does this affect the team? How do they use systems like this? Welcome back to How I AI. I'm Claire Vaux, 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 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 optimisely.com/ How I AI. 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 …

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