Overview
This episode of How I AI features Claire Vo interviewing JJ Englert about Anthropic’s Claude CoWork and how non-technical professionals can use it as a practical “get work done” system rather than just a chat interface. The conversation reframes AI from a question-answering tool into a personal operating system that can access business tools, run recurring tasks, and coordinate multiple agents inside structured projects.
Key Takeaways
A central idea in the episode is that Claude CoWork is especially valuable for people who are not full-time developers but still want AI to take action across their daily workflow. JJ distinguishes between “chat mode,” where AI gives advice, and “CoWork mode,” where AI can actually do tasks—reading email, checking calendars, drafting documents, and interacting with connected tools like Slack, Gmail, Notion, and Google Drive.
Another important concept is the role of projects. JJ explains that a project is not just a chat thread but a persistent workspace tied to a folder on your computer, shared memory, files, instructions, and task history. This structure improves output quality because the AI is operating within focused context instead of a sprawling generic prompt. It also saves time and tokens while making results more consistent.
A standout insight is the use of skills and connectors together. Rather than asking AI to write in your style from scratch every time, JJ shows how CoWork can analyze emails you’ve already sent and generate a reusable writing skill based on your actual tone. That makes AI outputs more personalized and reduces the “AI slop” problem many users worry about.
The episode also highlights multi-agent orchestration as a powerful but accessible workflow. JJ and Claire describe using sub-agents as simulated advisors—for example, having one agent act like your boss, another like an engineering partner, and another like a customer. This creates a structured multi-perspective review system that can improve product specs, marketing materials, or strategic thinking, especially for solo founders who lack built-in feedback loops.
Finally, they stress that AI performs much better when you define success clearly. JJ recommends giving Claude examples of what “good” and “bad” outputs look like, then continuously feeding it feedback and performance data. In his newsletter workflow, this means using past issues and engagement results to teach the system what works.
Practical Steps
If you want to apply this workflow yourself, start with a small but structured setup:
- Create a dedicated project folder for one area of work, such as “Daily Operating System” or “Newsletter.”
- Add a “brain” file or instruction doc describing your preferences, collaborators, tone, and working style.
- Connect only the tools you need first—such as Gmail, Calendar, Slack, or Notion—and set permissions conservatively.
- Ask CoWork to analyze past outputs you trust, such as sent emails, and turn them into a reusable writing skill.
- Add guardrails in project instructions, such as “draft emails only; never send without my review.”
- Create one scheduled task, like a 7:30 a.m. morning briefing that reviews your calendar, email, and Slack and produces a plan for the day.
- Experiment with sub-agents for review workflows: assign one to critique from a customer lens, one from a manager lens, and one from an execution lens.
The episode’s broader advice is to build an “anti-to-do list”: identify tasks you never want to do manually again, then turn those into repeatable AI skills or scheduled automations.
Notable Quotes
“Even though you might not be a developer, you’re now an AI orchestrator.” — JJ Englert
“If you don’t tell AI what success is to you, AI doesn’t know what success is for you.” — JJ Englert
“If the internet could come to me as opposed to me having to go to the internet, what would I want the internet to come to me with?” — Claire Vo
Full Transcript
One of the things I love about having this project system, you're orchestrating now. Even though you might not be a developer, you're now an AI orchestrator. You can run many agents at once and have this top-level view to be able to just quickly see which agent needs your attention and just give them those permissions or to pop back in. I don't know, this is very sad. All my friends are agents. I'm a solo founder. It is very hard to just me, by myself, ensure that all my ideas are great. When you use sub-agents, it will spin up three different agents. And each of those agents can have their own persona with a fresh context window, meaning like fresh perspective to go and look at your work in an objective way. If you're a product manager, build it and put your boss in there, your engineering partner, and your customer and say, every PRD review from these three points of view and give me feedback. If you're in marketing, you're ICP. I think there's just a lot of places where this multi-view feedback mechanism is super useful. 100%. We could take this a step further and say, hey, create this sub-advisory skill, maybe three of the agents. Like one agent is literally your boss that you send an agent to go research who your boss is, their role, their perspective, and have them simulate the feedback that they might give you before you even go to them. The sky is the limit here. You just got to tell Claude what to do and it's going to go and do it for you. 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. When Claude CoWork first came out, I was pretty much a skeptic, but I have been hearing more and more that CoWork is the way that everybody I know, especially those who are a little less technical than us engineers, get their daily work done. Which is why I'm so excited to have JJ Engler here from 10X, who is a CoWork power user, but is going to take a step back and show us how to zero to one on Anthropic's new get work done tool. Let's get to it. This episode is brought to you by Tines, the intelligent workflow platform powering the world's most important work. Business moves faster than the systems meant to support it. Teams are stuck with repetitive tasks, scattered tools, and hard to reach data. AI has huge promise, but struggles when everything underneath is fragmented. Tines fixes that. It unifies your tools, data, and processes in one secure, flexible platform, blending agentic AI, automation, and human led intervention. Teams get their time back, workflows run smarter, and AI actually delivers real value. Customers now automate over 1.5 billion actions every week. Tines is trusted by companies like Canva, Coinbase, Databricks, GitLab, Mars, and Reddit. Try Tines at Tines.com slash How I AI. JJ, welcome to How I AI. It is a pleasure to be here. Thank you for having me. I'm excited about what you're going to show us because when Claude CoWork, which is what we're going to talk about, first came out, I wrote this article that kind of blew up on Twitter and a bunch of podcasts talked about it, which was, Who is CoWork for anyway? Because when I first tried it, it seemed like a UI that had just been slapped on top of Claude Code. And I looked at it and I said, okay, if you're not, you know, in Claude code all day, writing in the terminal, but you're not super technical, like, what is this product that's in the middle? And, you know, shame on me, because as it happens, product continues to progress week over week. The Anthropic team, the Claude team is cooking nonstop. And I just kept hearing more and more from my non-technical friends. Oh, my God, CoWork is amazing. Or, oh, my God, I use CoWork to do everything in my job now. And then, you know, I've given it a spin in the past couple of weeks and the UI has really gotten there. What it can do really has gotten there. And so I'm so excited for you to show us the zero to one for CoWork. And I just have to ask you, what got you hooked on this particular tool? Yeah, I think, like many, we were just experimenting with it. And then quickly I saw that how easy it was to connect your business tooling to it. Whereas, like, you know, I built a lot in Claude code, but if I wanted to just connect my Slack, my Gmail, my Notion, CoWork is just one click. And then all of a sudden you have an AI processing all of that information, helping you do your job better. And it's just so easy. And so, like, that's where it started. But then I started to like, really like, go deep on it. I'm like, oh, my God, this is really helping me my day-to-day. So I use CoWork for all of like my productivity stuff of like emailing, slacks, building projects and documents. And then Claude code, I still build with. I love that because everybody is saying, oh, everything's going to be a CLI or an API or a TUI, all this stuff. And I'm like, people just love clicking a button. I don't know. They're just people want a button. So, part of what I hear for you is like, it gave you a button to click to get connected to all your business data. And then when you're working in CoWork, you're in sort of like business mindset, personal productivity mindset. And then when you're in Claude code, you're in builder mindset. Yeah, exactly. And, you know, I'll pull up my screen in a second here, but, you know, the Anthropic desktop app has three different modes, chat, CoWork and Claude. We've been in chat for a while now with ChatGPT, et cetera. Like, I think most of the knowledge workers are like in chat mode too. But the CoWork switch over to that tab is like the first kind of switch where these knowledge workers, even if they're not technical, can start doing more with AI. And it enables you to just do so much with AI in a very similar chat interface, but where, like, it's actually doing stuff for you, where, like, in chat, it's like, cool, you told me what to do, but now I got to go do it. CoWork is literally doing it for you. Why don't you get your screen started and you're going to show us if you were completely brand new to CoWork, if you had spent all your time in that chat tab and you were ready to click that middle tab CoWork in the Claude desktop app, what you would do? And I just want to call out for folks, CoWork is available in the Claude desktop app. So I think you have to be on desktop, not web, and it shows up, again, as one of these three tabs across the top. The middle one says CoWork and you have to click that and then you're going to show us what to do once we're there. So I have CoWork pulled up here. This is on the desktop app and they also have a mobile app as well. Mobile app does not work as well with CoWork. That's where kind of Claude code continues to be really powerful. But CoWork, let me give you the lowdown here. So CoWork can actually access your desktop. And a lot of people in the beginning days of like, hey, CoWork, go and like organize folders for me or go and like organize these receipts for me. And yes, CoWork can do that. But CoWork can do so much more as well. CoWork accesses your computer. It can access your browser. It can perform actions on your behalf. If you need to order or, you know, book reservations for dinner, it will go find, you know, restaurants looking for you on your browser, you know, contact them, et cetera. Right. Now, when you get started with CoWork, you'll go to a new task and it's going to ask you to open up a project. OK, now this is a very important concept that a lot of people kind of get stumbled down. It's like, what is a project? Well, in the simplest form, a project is a folder on your computer. This is where we are going to work out of and store our files for this project within that area. So if I look at my computer, I have a location called JJ. And within location JJ, I have projects and this is where I build all of my projects. Now, some of these are Claude code projects and some of these are CoWork projects. CoWork is a really great like on-ramp to Claude code, teaching you some of the basic skills of like how to operate in Claude code without going full terminal mode, all that kind of stuff. So within this, I have a popular workspace that I use called Claude CoWork Workspace. That is like a generic high level workspace. And I start off this workspace with what I call is my brain. OK, so my brain goes into very detail of like, what are my working preferences? Who are the team members that I work with? And if I were actually to open this up, I'm just gonna hit spacebar. It's just an MD file, which is essentially like a doc file, a text file. This is a very specific series of instructions that, you know, also known as a prompt that Claude can read to get up to speed very quickly of who you are, how you like to work, who you work with and all of your different preferences. This way, once I trigger project. Okay. Now this project, this chat right here, and any other chat that I have, they all share the same context and they all, and Claude knows what you're working on and can bring that with all the new stuff together. Okay? So if you do anything new, and it's very specifically knowing like what other chats you've had about this and picking up where you left off. Yeah, so there are two things that people need to know about from an organization perspective, which is one, we're going to pick a folder on your computer that contains all the files and context and all that stuff for a specific area you're working on. And then two, you're going to attach that folder to something called projects, which is available in the left-hand nav to make sure that every time you're working in that folder or in that topic, you're not only working with those files, but you're working with the memory of all the other things that you're either actively working on or have worked on in the past. And then you can give it, if you see in the top right, you can give it just general instructions, which is helpful for guiding any work you do in that in that specific. And this is specific project instructions. And so each project can vary for different kinds of instructions, right? Which is also really good context to have. Yeah, and speaking of context, if you look along the right-hand side, there is a section that says context. And there's exactly what we talked about, which is the context of the folder and then the context of the memory that's been generated about this project. Right. And so this is like the HQ for each project that you work on, right? And it's really become so helpful for me because as you start to have more tasks, all of the different agents for that project are listed here and you could see like a high level orchestrator view of like which agent is working, which agent needs your help. And all of those tasks and conversations are like shared together for that shared memory. Again, we want co-work to do stuff for us. And we want it to do it well and give us good consistent results. Sometimes when we operate at this high level, it's getting so much information about all the different things we're doing and the results can get confusing or fuzzy. But if you're operating within a project, it's very specific context about the specific project and your requirements for it, and it helps you get results faster. Like the prompts are literally faster because you're sending less context, you're saving tokens because you're more focused and organized and you just get better results in a more consistent way. All right. So let me continue to build on this so we can eventually have something that you can download at the end of this show to start using for your own daily operating system. Sound cool? Yeah, let's do it. Cool. So with a couple of things that I want to call out here, connectors. So important. So to add a connector, I'm going to right click here and I'm going to go into connectors and I could see that I've already enabled some of my connectors, but I'm just going to click here so you can see this view. So connectors allow you to connect your systems to co-work. Okay. So right now I have connected Gmail, Google Calendar, Google Drive, Notion, and Slack. And if I wanted to add more connectors, I can go to browse connectors and I could see a ton of connectors that I could do. It's normally like a one-click, you authenticate, and it comes in and you're connected. That essentially means co-work has access to that application and a lot of those actions within that application. If I wanted to go into like my Gmail connection here, I could see that co-work now has access to all of these tools and can actually do these for me. And if I wanted to get very specific about the permissions, I can go in here and say, hey, co-work, I'm not going to allow you to create any email draft or to do something, but I am going to allow you to do this. Or sometimes I want you to do this, but always ask me for permission. So with each connector, you can go in and modify those permissions, but generally this gives you a connection to your tools that you can use. Now I can go back into co-work here and I'm going to go back into my projects, daily operating system. And the first thing I'm going to do is say, hey, analyze my Gmail, specifically the emails that I have sent in the last 30 days and use this to create a writing skill, specifically for emails that I write using my emails as an example of my writing structure. So whenever I want you to write an email in the future, you know exactly how I write my emails and you'll use this skill. So this is going to start building an email skill for me and it's going to do it by connecting to my Gmail, looking at my outbox of all the emails that I've sent in the last 30 days, analyzing that writing skill, and just perfectly matching the tone that I use in my writing. You know, AI is used for writing in a lot of different ways. And of course there's a lot of AI slop, but when you can feed AI, like a series of like a hundred messages, it can really get close to your exact writing style. And that's what this is doing here. So just to kind of take a step back, connectors are really important because this is not only the tools that are going to do work on your behalf, right? I think this is something that people might miss, which is, yes, we can do connectors so you can draft emails to Gmail or write docs in Notion. But there's also this ingest path that can make your use of these AI tools a lot better. And I haven't seen this use case before, so I want to call it out for people, which is have AI go read your emails and come back and build a skill, which I think is really important. And skills, remember for folks, are just these like containerized little sets of instructions that can be called at any time. Go build a skill that writes emails in my tone. And, you know, I think as somebody who's developing a daily operating system, I call this your like anti-to-do list, is you come up with these lists of things that you just like never want to do again. Like, I never wanna have to first draft my emails again. I never wanna have to like show up to a meeting late because there's a conflict on my calendar or they've been set back to back. I just want these things that I never have to worry about. And I think as somebody who's coming in and trying to think about how could I use co-work or something for my daily operating system, this idea of like burning down your anti-to-do list and then building skills on all those is really sharp. And what I think you're showing is you can use connectors plus the brains of co-work to kind of come together and not only functionally achieve that, but achieve that in a way that's high quality for you personally. Yeah, and the results have been really good with it too. Yeah, you have, I mean, are you really getting emails that like sounds like, sounds like you? Exactly, exactly. And normally what I'll do is I'll go into my instructions here and I haven't done this step yet, but I'll say never send emails on my behalf, only write them as drafts for me to review, right? And now this is a very clear instructions of like, hey, it's actually never gonna send anything for me because I don't trust that yet. But everything that I ask it to send, it's going to write that draft and just prepare it on my outbox or my drafts so I can approve it and then send it as well. By the way, you're being very chill about all your voice entry stuff. What is your voice tool of choice? Whisperflow. Whisperflow. It's just, it's captured my heart. I'm a monologue girl, so you know, we all, we all pick our favorites. You know what? It all works. It all works. It all works. This episode is brought to you by Cursor. If you all have been watching How I AI, you already know this. Cursor is my favorite way to code with AI. Whether I'm using plan mode to build out an ambitious feature, reviewing AI generated diffs right in my editor or kicking off cloud agents to multi-thread our roadmap, I reach for Cursor as my favorite multi-model coding platform. Even better than building myself in Cursor, I love collaborating with Bugbot to fix PRs for code security and quality and have begun relying on Cursor's automated agents to keep our codebase clean. It's not just me. The most ambitious teams love Cursor too, including engineers at Stripe, OpenAI and Figma. Ready to build more? We're giving $50 in Cursor credit to How I AI listeners. Claim your credits at chatprd.ai/howiai That's $50 in Cursor credits by going to chatprd.ai/howiai Okay, so you've started, I see a pop-up here, so tell me what's going on. So this is one of the things I love about having this project system. You're orchestrating now. Even though you might not be a developer, you're now an AI orchestrator. You can run many agents at once and have this top level view to be able to just quickly see which agent needs your attention and just give them those permissions or to pop back in. So right now we do see that, hey, this agent needs our attention. We can go in and review that. And it's actually just asking us if we want to allow this, okay? So without even having to go in there, I can just allow that. I could go into that connector and change those privileges just to say always allow so I don't have to do that. But in this case, that was set to a, ask for my permission, okay? This is one of It is like very hard to just, me by myself, ensure that all my ideas are great. And so, I haven't heard of anybody giving this advice of like very specific use of sub-agents, which, as you said, is just imagine like there's a chat that's chatting with other chats that have some but not all the context and their own point of view. Maybe that's how you think about sub-agents for folks that aren't super technical. And then aggregate that back up and give you some feedback. I think is a really useful just hack that everybody should have for their work. So if you're a product manager, build it and like put your boss in there, your engineering partner, and your customer and say, every PRD, review from these three points of view and give me feedback. If you're in marketing, again, like your ICP, give feedback. I think there's just a lot of places where this sort of multi-view feedback mechanism is super useful. 100%. We could take this a step further and say, hey, create this sub-advisory skill and each maybe three of the agents, like one agent is literally your boss that you send an agent to go research who your boss is, the role, their perspective, and like really define like the people that you work with and have like them simulate the feedback that they might give you before you even go to them. Like the sky's the limit here. And you just got to tell Claude what to do and it's going to go do it for you. So there's a lot of tools that you have at your disposal now to, you know, automate a lot of this. Like one example with this is I also run a newsletter. And so the skill that we have for the newsletter is a almost like a 10-step skill of like, before we even start writing this newsletter, I want you to interview me what this newsletter should be written about. Then once you're interviewing me, I also want you to run a sub-agent to do internet research on what is good in the AI world this week. What should we talk about in this? And once my interview is complete and once the research is complete, we now have an idea of like the content that we can do. And then it's going to start working through a series of sub-skills, which are like, what should our subject line be and what are really good subject lines? And it's going to have one set of instructions for that. And then my newsletter has like very specific body segments. And each body segment has a specific skill within it saying, like, here's what makes a really good AI native section or what makes a really good AI future section, right? And at the end of all those steps, it has an evaluation part of the skill where it's going to go through a series of checklists and also launch that sub-advisory board. And so it's going to go through all of this. And all I need to do is say, ultra-think skill, and then it's going to start this series that it works through and just helps me. And by the end of it, it's done so much work for me and I've just had to answer some questions and then it's outputted a draft that I think is really good. And I also feed it my past results of my newsletter. Of like, hey, we've written this together. This performed okay. And I give it the results. And it has a series of feedback and like, you know, review of like how these things are performing to see what's working and what's not, which is a very important step because like, if you don't tell AI what success is to you, AI doesn't know what success is for you. So I always love including good examples and bad examples. This is very clear for like writing. If you're writing and you really like something, include it in a good example. But if it comes back with something that you don't like, put it in a bad example. Like, hey, don't do that again. That doesn't look good. And this way you're showing Claude what is good for you and what is bad for you because that's subjective and different for everyone. And Claude needs to know it. All right. So we have this multi-agent perspective here. And we can see that we've done a couple of things. This one, the thinking partner skill needs my review. So I'm going to go in there and I'm just going to review it. And it's looking for some information here. And it looks like it had opened up. So they have this new interface here, which allows you to review your thinking skill or whatever skill you created, and see, like, and then test it in real time to see how it would come back and evaluate it like that, right? So that's very helpful if you want to use that. But what I want to do is I want to go back to my project here and I want to create something called a scheduled task with you. A scheduled task allows you to create something that runs on a frequency. So it could run every hour, day, weekdays, weekly, whatever. And this scheduled task is going to be a morning debrief. I want you every single morning to look at my email, my Slack, and my calendar and check it to help organize a plan of action for the day. So that way, when I get into the office, I am aware of any kind of messages that need my attention. And you can start preparing me for my day by looking through my calendar and looking through my events. And if I need any kind of meeting prep, helping me do that. But generally, the output is going to be like a plan for the day, helping me get started on the best foot every single day. So that's going to be the prompt. And I'm going to run that daily. And I want it to run at like 7:30 a.m. And I could choose what model I want this to run with or where these outputs should go. In this sense, it's going to be, you know, the daily operations. That's going to be good. And I'm going to just be able to save that. Ah, there it is. Thank you. I was like, why is it? Morning Debrief. I want to call out for folks. We've seen a couple of these like morning debrief examples on HowAI. We've seen Hillary has shown us she uses Obsidian hooked up to her Claude code, hooked up to her calendar. She writes plan my day. We've seen a couple of these scheduled sort of like news I need to know tasks in ChatGPT. I think what I want to call out for folks, especially those who are again, new to using AI beyond asking a question in ChatGPT, which I know honestly, many of you are, which is I've used ChatGPT or Claude to ask a one-off question, get some info, you know, like write a song for my grandchild or answer a question about my medical health or write a document to my HOA, whatever. You know, people have used that use case. But what I think you're showing here is something that wasn't accessible to folks, which is you can actually build a little software-powered system for yourself to make your day go easier. And it could be writing emails for you. It could be, you know, every morning send you a message about what your schedule looks like. Let's say you're not even, you don't even have a busy schedule. Like I'm thinking about, you know, my dad's retired. Like news that you're, you might be interested in for the day. I have a daily, you know, in the, in the technical world, we call it a cron. And when you're on the, when you're on the open clause side, but I have a daily schedule and in the morning I get pushed something kind of fun and interesting in the AI space. And at night I get pushed an article that will like make me feel good, you know? And so you just think about if the internet could come to me as opposed to me having to go to the internet, what would I want the internet to come, to come to me with? And that's what I think you focus your, your morning debrief on. So it could be like highly functional from a productivity perspective. It could be, you know, go fill your water glass. Don't drink coffee on an empty stomach, go for a walk and say hello to the sun. Give me any of those things, but it can be scheduled and it can be pushed to you. Right. And right now, since we've scheduled this within a project, it has all the context of your project as well. Meaning the skills, your connectors, and everything. And that's why having it scheduled within a project, like building up that context, it gets very powerful over time and you're going to get better results. So this could be a project debrief where like, if you're a project manager, every single day, it's going to look at this project and just help write a plan of action for all of your team members to, and send as a Slack message. So like once they enter that project plan for the day is done. Very specific to each project, right? So there's just so many ways you can use it. And this also connects to all of my tools. So it's going to read my email and my calendar and my Slack and just prepare a daily plan with all that context in mind in a safe way. That's like the unlock for me is like just being able to read all these tools and using AI on top of that to like help me do my job better. Yeah. And I'll just call out for folks because again, I think this is sort of like a cloud cowork 101 folks that are maybe newer to using AI in this particular way. And the things that you're going to hear is like, do I want AI reading my email? Do I want AI reading, you know, my calendar? And the recommendation that I give to everybody is again, just I do sometimes all caps. I've had myself being like, this is truly insane. What you just did is cuckoo. Fix it. Not not super polite, but but effective. Okay, JJ, where can we find you and how can we be helpful? I think I'm pretty much everywhere. I run a YouTube channel called 10x Builder. I'm on X for at JJ Inglert, LinkedIn at JJ Inglert as well. I work at 10x and I lead our community enablement here. We're doing a ton of stuff. So if you need help bringing AI transformation and enablement to your org, let us know. But otherwise, it is a pleasure being here. We love your work. I love your work. Thank you for inviting me. It's been a joy. Thanks for joining us. 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.