Your AI Accountability Partner: Build a Daily Check-In System for Project Managers | Matt Corroboy | Skillshare

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Your AI Accountability Partner: Build a Daily Check-In System for Project Managers

teacher avatar Matt Corroboy, Projects, leadership, life and mindset.

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Taught by industry leaders & working professionals
Topics include illustration, design, photography, and more

Watch this class and thousands more

Get unlimited access to every class
Taught by industry leaders & working professionals
Topics include illustration, design, photography, and more

Lessons in This Class

    • 1.

      Lesson 1 Introduction

      2:11

    • 2.

      Lesson 2 The Framework

      1:23

    • 3.

      Lesson 3 Building the skill

      7:15

    • 4.

      Lesson 4 Watching it work

      15:14

    • 5.

      Lesson 5 Expanding further

      6:29

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About This Class

In this class, I'll show you how to build a simple AI-powered daily check-in system that keeps you on top of spinning plates and focused on what matters most.

You'll build it live in Claude — no coding, no complex setup. Just a practical system you can use from tomorrow morning.

By the end of this class you'll have:
- A morning check-in that surfaces your priorities and flags what's at risk
- An end-of-day review that closes the loop and captures what moved

This class is for project managers, programme managers, and anyone who juggles complexity and wants to think more clearly with AI — without the hype.

The full version of the PM Assistant Skill — including the complete morning and evening check-in, weekly review, risk register, and issues log — is available as a digital download to go alongside this class, click here: -> Full PM Assistant Skill

Meet Your Teacher

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Matt Corroboy

Projects, leadership, life and mindset.

Teacher

Hello, I'm Matt Corroboy.

I've spent 25 years leading software programmes in the life sciences industry -- building the teams, the tools, and the habits that keep complex projects moving when everything else wants them to stop.

These days I'm channelling that into something I genuinely care about: helping project managers, programme directors, and anyone juggling complexity to work smarter -- and increasingly, to use AI as a serious thinking partner, not just a novelty.

On Skillshare you'll find courses on the real craft of project management: managing your day, leading without authority, keeping plates spinning, and building the mindset that separates good PMs from great ones. My newest class brings AI into that mix for the first time.

I'm also the a... See full profile

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Transcripts

1. Lesson 1 Introduction: Hi, I'm Moy, and I'm a software projects director in the life sciences Industry. And for the last four or five years, I've been teaching on a Skillshare about what it takes to be a great project manager. If you see my other classes, then you'll know I'm not one that's just about theory and for the practical stuff, the things that you can use every single day to make a difference. And today's class, it's exactly that, but actually a little bit different because today, I'm going to show you something that I've actually built for myself, something that I use every single day. And honestly, when I first started to put this together, I wasn't actually sure it was really going to give me the value I was looking for, but it did, and I think it might change the way you think about AI tools moving forward forever. So let me start with a question. How many of you tried using AI tools, for example, HachiPTs, cord Geminis, et cetera, and found it genuinely useful, but also at the same time, a little bit frustrating. You ask it something, it gives you answers. You ask it again, it gives you answers again, but every single time, it's started from scratch from a blank sheet of paper. It doesn't know you. It doesn't know your project. It doesn't know your ways of working. Every conversation is a blank page. Now, what if it didn't have to be? What I'm going to show you today is the difference between a prompt and a skill prompt is a question. You type something in, I responds and gives you an answer, and that's that. A skill is different. A skill is a set of instructions that you give to the AI that defines who it is, what it thinks, and how it responds to you in the context of how you set it. You build it once, and then every time you open it, it's already briefed. It knows your project and knows your framework. It already knows how to help you and what your concerns might be. For project managers, I think this is genuinely exciting because we're not just building a tool that asks questions. We're building a thinking partner. And that's what this class is about. By the end of it, you'll build your own PM Assistant tool that you can start using every single day to start your mornings with clarity and end them with a sense of control. 2. Lesson 2 The Framework: Before we build anything, we need to give the skill a framework to work from because this is really important. The AI is only as good as the tools that you give it. If you've seen my spinning place classes, then you'll know what's coming up. For those that haven't, then here is a quick prilot. The spinning plate model says that being a great project manager isn't about going specifically deep on individual topics. It's about being able to manage multiple aspects of the project all at the same time, whether that's risk, change, budgets, leadership, project tracking, the lot. The analogy is quite simple. You're the project manager. Try to keep all those plates spinning. And not necessarily spinning all of them yourself, but you need to know every single day that those plates are spinning because the plate that wobbles that you don't notice is the one that's going to end up on the floor. Now, I've been using this model for years, and when I started to think about using an AI tool to help me in my day to day, it was the obvious foundation to start from. The AI would hold the framework, and I just have the conversation. Now, there are 12 plates in total as part of the model, and we'll take a look at each one of them as we build out the skill. But if you want a particularly deep dive in any of them, then check out the spinning plates class, which is one of the first ones that I did. For now, though, let's start building. 3. Lesson 3 Building the skill: Right, I'm going to switch to my screen now and we're going to focus on building this skill together. So I'm using claude.ai for this. You can find a link in the class resources for the actual tool that I'm using. It's free to get started, and you don't actually need any technical setup. Now, if you use any other AI tool, and the same approach applies, you're just looking for somewhere to put your instructions before the conversation starts. And this is the same whether you're using Chachi PT, Gemini, or any other kind of AI tooling. So here in Claude, we're in the co working section, and we're in the projects area. And what I'm going to do is open a new project here on the right hand side. Now projects let you set instructions that run in every conversation you have within that project. That's where the skill actually lives. Think of it as a briefing document for the AI that it reads before they walk into the room for every conversation you're having. And for the purpose of this, we're going to create a brand new project that we're going to start from scratch, and we're going to give it a name. So our brand new PM Assistant and in this, we've got the instructions piece. So you could create projects and the instructions build over time. But what we're actually going to do is give it more detailed specific expectations of how I want it to operate, and we're going to talk through that together. So I've got my skill section actually here open in obsidian, and I'm actually going to walk through each area of this before I paste it into our instruction set, because understanding what each piece does with the AI is actually the whole point of this class. Let's start with identity. Now, this is the most important piece, and it's the one that often people skip. We're not asking Claude remember a question here. We're telling you who it actually is. So let's read through some of this with me for a second. You are a senior project management accountability partner. You know the spinning plates model, the idea that a great PM must keep all key areas of project moving simultaneously, not just the loudest one. You are not a cheerleader. You are not a task list. You are the trusted colleague who always has the PM's back. That last line matters. You're not just a cheerleader, not a task list, the trusted colleague. That's the tone I want. That's the one I want in the room with me every single day. Then there's two triggers, two things I can say to activate it. There's the morning check in, which is something they'll want to start every day with. And then there's also the end of day to close it. That's it. Just two words each for the skill. Remember, this is just a simple thing we're building, and the skill then does the rest. So let's move on to Section two, which is the spinning plates model. Here's the framework, all 12 plates each with a daily question attached. So let's just step briefly through each of these. So the skill has risk where the daily question is, Am I ahead of risks or am I reacting to them? Is going to ask me about change. Is there any change happening that needs managing at that point in time? It's going to ask me about roles and accountability within the project. Are we sure that everyone knows what they're doing? Is there something to address there? It's going to ask me about tracking. Do I know where we are against the plan? It's going to ask me if there are any escalations on the project. Are there any flags in the projects that I need to raise or chase? It's going to ask me about stakeholders. Really important category, I everyone who matters informed and engaged? It's going to ask me about things like process and documentation. Are there any documentation gaps building up, anything I need to focus on there? He's going to ask me about my own leadership. Am I serving the team today or am I creating friction? And then it's going to move on to some of the fundamentals like budget and finance. Is there spending control? Is there things that I need to be thinking about there? Really really important success in KPI measures. Do I know how we're measuring success on the project and what do those KPIs currently look like? It's going to ask me about reporting. Are my reports up to date and clear? Do they need addressing? Then finally, for those that are doing slightly bigger projects with extended life cycles, are there any post delivery obligations that need to keep moving forward? Now your project may have more plates that need to go in here or less, and you can add them, obviously to the skill as you built it. So what I'm doing here is giving the AI a complete picture of what PM needs to be thinking about every single day. It knows the model as well as you do. So again, we'll paste this section in to the instruction set. What built into the skill here are two sections talking about the morning check in and the end of the day. So morning check in, fairly straightforward. The trigger is going to be morning check in or start my day, and it's going to have multiple steps to it. Five steps structured takes about 5 minutes. Sprint focus. What is the one outcome you're driving towards this week? The Domino question. What's the single task they've done today unblocks the most? We're then going to do a spinning plates scan. Remember, the AIA is going to have a memory here and be able to remember the status of each one. So it's going to ask you a quick green, yellow red on each of the 12. We're then going to talk about LMD, leverage, manage, do. What should I be doing myself, managing that other people are doing or just completely handing off and delegating to others? It's going to ask me specifically about the critical path. Is anyone or anything at risk today? And then it's going to close with one clear sentence. It's going to tell me today what my focus is, what my lead domino area is, and it's going to tell me what to watch. This is how I want to start each day. Then at the end of the day, we've got another part of the instruction set here where there's three simple questions. What's move today? What's at risk for tomorrow, and if tomorrow goes sideways, then what's the one thing that still has to happen? Now that last question is the one I want to come back to most because on a busy project, tomorrow, we'll go sideways sometimes, and knowing you answer that question before it does, then that's control that you're looking for. And then we end with the tag line in here. Remember, you don't have to spin them all yourself, but you do have to know that they're spinning. That's the important part. And that's it. That's the instruction set that I'm going to paste into the clawed instructions as part of the project that we're building. So let me copy these now. I now I'm switching back to this starting a new project in Claude, and I'm going to paste in that whole instruction set. Now the problem with this screen, which is why I was showing you in obsidian, is quite a small screen. But this is now everything we've just talked through pasted in to the instruction set. So that's it. Everything pasted in to the instruction set. I'm not going to tell you where I want things to be saved. That can be done separately. I'm not going to drop any files in at this point on. I do have a memory on. That's really important because I want it to remember the conversations, and we're going to create this project. So now we've got our brand new PM assistant here at the top. So that's the skill built. Now let me show you what it actually does. 4. Lesson 4 Watching it work: Okay, so this is now a fresh conversation within this project, our brand new PM Assistant. And as you can see here on the right, here's the instruction set, which I can see. I remember I can edit this at any point in time, if I wanted to add or remove various different elements, and you can see the full kind of breakdown here of what we pasted in previously, which is good. So fresh conversation in flight instructions are all set. The skill is ready. I'm not going to explain anything in particular to the PM assistant at this point in time. I'm just going to type in two words and get things moving. So let's go with morning, check in and it's gone off. It's having it first think about what this project is. So it's gone away, round the instruction set, and it's ready to work. So look what it's doing. It's not just answering a simple question. It's now running the structured process with our sprint focus first. So let me start giving it some real answers here. What's the one outcome you're driving towards this week? Uh need to clarify the scope requires requirements for this project. So let's say we're doing that. That's the one outcome that we're going to try and drive to this week. So he's got it. It's clarifying the scope. He knows that and it's got a tone to this. That's a foundational piece that unblocks everything else. Yes, absolutely, really, really good. And then he asked me at Lee Domino. So what is the single task they've completed just today unblocks most of the rest for this week. So let's carry on this theme of scope requirements. So need to agree with senior product manager what the scope, what the scope is, and when the documents will be complete. So that's today's task, let's say, as a project manager, got that work to be done. So again, given the instructions there. So now it knows that. It's got that logged in its memory. And now this is the spinning plates question. So now it's going to go through each of the spinning plates. Now obviously, this is just a demo project that we're going to kind of step our way through. But this could be a huge project with lots and lots of tasks, lots of things happening, and it's really important to go back through the spinning plates scan with the AI on a regular basis. So let's walk through these pretty fast. We'll start with risk. I'll just go risk dash low risks at the moment, the scope. Mainly green. We're going to go for change. Is anything changing? It's change happening that needs managing. I'm going to go with scope is reduced. Then we'll impact choice of manufacturer. So again, I'm just putting that in there. We've got roles and accountability. What I'm going to say here is that need to bring in a new product owner. Amber will need work next week. Again, just giving it a bit of context. Tracking will go all on track. All good. Escalations not today, but if scope reduction, actually, no, let me do something. So escalations, what I'm going to say here is a budget cut budget cut from last week needs escalating in my weekly report. So I'm going to put that in the stakeholders. Is everyone who matters informed and engaged? Yes, everyone engaged or good. So we're going to do that, processing docs. Amber as a I got processing docs, Amber as requirements document due this week. Leadership. Now, leadership is really important to me. This is, Am I serving the team today or crating friction? Doing well, but product manager conversation is key. Is key. Also want to then lead with a clear message for the project team. Based on the outcome, we'll need it to be positive irrespective of scope change. And then we've got budget. This is red, budget cut from last week. So flagging that in there, and then success and KBIs all good. Reporting report due tomorrow, an extended life cycle. Nothing due. What to do say early stages of projects. Nothing to focus on. Okay. So, that's it. I've done a quick answer to all 12. Remember, this is the first time I'm doing this. So it's building up a memory that it'll use moving forward as it has those conversations moving forward. So here here's Good scan. Here's what I'm seeing. And it's giving me basically interpreting my language with that green, Amber and red. Obviously, it said the budget was the problem cut last week, N active management. And, you know, some of those Ambers is saying where there's things that needs to be done. Scope decision will cascade to manufacture a new PO needed plan for next week. It knows that. So three plates need your attention today, budget, escalations and docs, and they're all connected to that PM conversation and tomorrow's report. Then asking me that step four that we've got in the morning check in. Let's divide and conquer. Look at leverage, manage, do. What should you be doing yourself only you can own it. So I'm going to say, I need to I need to speak with the product manager today. Has to be done. First thing, get the hard conversation. Conversation out of the way. I need the finance business partner to, uh, clarify any other budget impacts. Chase this today, and then leverage. I'm going to get quality rep to stay on top of the requirements, Doc, after my meeting with the product manager. So these are things that are currently in my mind on the project. There's things I can do. There's things that I need to make sure I'm moving forward. And then some things like the last one where on is in place. I just want the quality rep to make sure that drives forward. I don't need to do that myself. So again, just telling this project within the skill where things are. So yeah, clean LMD, that sequencing is right, the PM conversation unlocks, everything else. So it's interpreting kind of my concerns which I've talked about and saying, so do PM conversation, first thing, hard conversation, get it done, manage chase the finance business part with full budget impact picture, and then that quality rep owns the requirements document. Step five, this is, again, the last part of the morning check in. One last check. Is anyone or anything on the critical path at risk today? Specifically, and again, it's interpreted what I've already put in. Is the product manager available and confirmed for this morning? And is there any chance the scope conversation gets kicked till later this week? Yes, it is. It is a risk E the product manager. They have a busy schedule. I need to get on I call with them within the hour. It is my soul my sole focus. So again, just re emphasizing. And what's happening here with this dialogue is it's compounding in me as a project manager, the area that I need to focus on. I'm not going to get distracted now. So understood that's the one thing right now. Today's focus, get the Pm on a call within the hour and land the scope conversation. So your lead Domino is that conversation. Scope clarity unlocks the manufacturer decision, gives the quality rep what they need for the requirements doc and shapes the message that you take to the team. Everything else waits until you have that outcome. The watch for today, the budget needs to be in tomorrow's report with the escalation clearly framed and the requirements doc deadline this week. So after the PM call, brief the quality rep, chase the finance BP, then you'll have everything you need to write strong report tomorrow. Go make that call now. Good luck. You've got this. So again, if you think about that instruction set that we had at the very, very beginning where we wanted to make sure they're not a cheerleader, they're not after just the task list. They're a trusted colleague who always has the PMs bank. Grounding them, fusing them, calling out those wobby plates early, and helping them start on end each day with clarity. So it's the end of the day now. We're just going to say wrap up. And again, we gave it a few bits of language that we can use, but this is the end of the day call that I'm making. So end of day three quick questions that the AI now project accountability partner is actually asking me. So the first one is what move today? Any wins, progress or completions big or small? So let's tell it ly though. So let's go finally agreed. With the with the PM, PM very happy, only one minor change that needs communicating. So that was really good. So that was massive. Scope fanny read. Brilliant. So what's a risk for tomorrow? Any plate showing yellow or red as you head into the evening. Still the budget to be resolved. Finance business partner is chasing and will update me first thing so that I can get it into my report. So again, it's come back. That's in motion. It's not stalled. There's action in place, and you'll have numbers runber the leverage, manage do we want it. It's there. So then it's asking me as I think about how I'm going to approach my next few days, is if tomorrow goes sideways, so if all things collapse, what's the one thing that still has to happen? I have to get my report out irrespective of anything. Okay. So putting that in even with a spin mistake, all good, and that's non negotiable, the report goes out. And then what happens here is there's a bit of a summary of the day that the AI says. So today, we've landed the scope agreement with the PM. The key outcome was for the week one minor change to communicate, but the hard conversation is done. Watch for tomorrow, budget figures from the finance BP first thing. They feed straight into the report, get those numbers, frame the escalation early, and the report goes out. So first thing tomorrow, finance BP update, then write and send the report. Good day, Matt, the lead domino fell. Again, this is its own context that it's building. It's all memory, and it's got a personality to it, which is really important. Now, the good thing with this is that I can free start a little bit and go, remind me of where we are against the spinning plates. And again, because it's got the memory, because I've given it the instructions, it's telling me, Hey, remember, here's the snapshots from this morning's update. So reminding me again, budget is the only red plate, and it's got a clear path finds BP tomorrow, good position heading in to tomorrow. And again, I can rinse and repeat and go through this every single day, and it will capture a building picture in its memory that you can call upon at any point in time. So remember, because this project isn't just completely fixed on those two prompts that we asked it to do around the morning check in and the end of the day run, similar to the spinning plates question, we can ask it more generic things like, can you summarize the state of the project and key progress? So just giving it a general statement, again, it's going to harvest from its own memory where things currently stand. So here we are. Here's where things stand based on today's checking. Big win today was agreeing the scope for the Senior PM. That was the week's critical outcome, and it's done. It's talking about project Health's broadly being solid, tracking is unplanned, stakehers engaged, et cetera. The leadership priority now is translating today's scope agreement into clear, positive message. Talks about the open issues all known and owned. Talks about the fans business partner working on the full impact of the picture from a budget cuts. Talks about roles and new product only needs to be brought in. It's Amber item planned for next week. Talks about tomorrow's priority straightforward. Get the fans BP update right and send that report. One hard conversation done, one report to go. The project is in good shape. So, see that? It pulls it all together because everything I've told it this morning, whether it's the plates, the focus, the risks, it's held all of that in its memory and will continue to do so through the course of the project. And that's the fundamental difference between a prompt and the skill that we've been built, which makes it infinitely more useful as that PM assistant as we move forward. And this will really make a difference in your day to day because it's not going to allow you to forget things, and it's going to remind you what you've agreed to focus on for the day ahead. And that's really where the value is in utilizing these AI tools to really make a difference and continue to make you a great PM. And and, 5. Lesson 5 Expanding further: So that's the version that we've just built together, and I want to be honest with you, that's really valuable. You can start using that straightaway. Some of you will take it, run with it, and get genuine value instantly straight out the game, which is fantastic. And you can continue to edit that as you see fit. But what I want to show you now is something that I genuinely use. It's a little bit richer and contains a lot more project elements in it, so I'll give you a brief demonstration of what's in that skill file. Right, so here it is. Here's what I actually use. This is piano Assistant Skill version one. This was built only earlier this month, but has been used quite a lot now on the current project. So same model, same framework, but look how much more is actually in here. Context has been set similar to one we've just been through, but as well as those morning check ins, we now have a midday check. We've got an end of day check. We have a weekly review, which is really important. I've got change logs, risk logs. I can add risks, I can add issues, various different things that have been built in to that. Again, identity is there probably a little bit richer than what we built out. The spinning plates model is in there, same model, same framework. Again, a lot more in there. The morning check in slightly larger. A few other bits and pieces come into this as well at the same time. Midday triage. So again, maybe I need to just pause and recap on how the days going. Is that lead Domino still moving? Has anything come up this morning that's changed those priorities get really, really important? We've got the end of day piece in there, as we've talked to Pat before. Again, a little bit of thinking about what's changed on the project really important. A big, big one. I'm a massive believer in this. We've got a weekly review element or Friday wrap up. About 15 minutes long, five phases in there, it's all about those project highlights, and the skill will read back to me what's happening in that highlights, honest reflection. We've got a change log review in there, a motivational wrap up and look ahead to the week ahead. And that's the kind of structured Friday session that really means that Monday will feel manageable. You going into the weekend with a clear mind, nothing on your shoulders, and you know what's coming in the week ahead, really, really important. And again, we've got frameworks in here. We've got things like the wrist log frameworks or the low mediums, high, issue logs, what I expect it to keep, change logs, and again, talking specifically about its memory, its tone, all baked into this much richer skill. So if I switch back to the project itself, and this is called project manager Assistant, again, just so you can see this is the fuller skill file that I've just gone through just there now in obsiviian. But this is where I can ask basic questions like, show the change log from the last week. And again, it's a question. It's got a memory. It's going to go and look at where things are up to from what I've told it in the past. And again, now it's got a whole bunch of change log items in here. It's giving me a list of scope reduction proposed, Junior PO joined engineering confirmations. It's talking about what's come today, it's like changing the commercialization template that needs to be adopted, seven entries, mostly positive signals. All good. And it's asking me, then, anything here that needs updating or changing in there. I think that's important. And also, I can say, show me the current risk log. And again, this is me wanting to have that recap. You'll obviously be asking me this in the morning reviews. But again, I'm going to ask it to look in its memory, look at those conversations, and it's now representing how this is looking at a simple table, but low mediums highs, probability, impact, and telling me where I need to focus, which is really, really important. So every time I've told it something has changed during the day, a decisions made, there's been a scope shift, a delay, it's logged, those things. Without me doing anything extra. It's got my project accountability audit trail all baked in. That's my weekly review starting point irrespective. And I didn't build that separately. The skill has helped me build it for me, which is really, really useful. So whether it's the risk log, the change log, the issue log, these are things that are massively important. Sometimes we forget what happened on projects, but it's going to maintain that memory through the course of it. As long as you do those morning check ins and evening wrap ups and weekly reviews, it's going to be a rich resource of information that's going to help you stay on top of the project, not forget anything, and keep you being a great project manager moving forward. So the full skill file, the version I use every day is actually available as a download in the class resources below, and you can open it, paste it in into your own Claude project or whatever AI tool you're using in that project, and you're up and running just in a couple of minutes, I can start populating it with your project information and getting that value every single day. Want to build your own version, everything you need is obviously in this class, the instructions and how to modify those things to make them richer. You can start from your own identity, don't have to use the one that I've created. You can add your own framework. You can build your own modes. You can make it yours. And that's actually the point of all of this that we've been doing today. Is not to hand you a template, per se, but to show you how to think about building these things moving forward, which is really important because once you build one skill, you'll start seeing other areas where you're able to apply the same logic, a weekly planning skill, a stakeholder communication skill, maybe, a risk review skill, as we talked about there. The model is going to be the same. You're just giving the AI a new set of instructions of what you're expected to be reviewing and remembering moving forward and expanding this out into multiple skills or even multiple personas is where this gets really, really interesting. And I'll be doing a future class on that at later date. For now, I want you to go and build. I want you to paste in the instructions, try the morning check in on a real project of your own, and see how it feels and adjust from there. And that's it. Thanks so much for watching this class. As always, share your projects in the gallery and questions, drop them in the discussion board, and I'll see you in the next class.