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Host
The CEO of Microsoft A trillion dollar business just give away his four most powerful prompts that he uses on a daily basis to make him an incredible AI enabled leader. Well, I have made some updates, some tweaks, some minor edits to those prompts to make sure they are usable for all of you. And we are going to go through those prompts on this show and and show you how AI enabled leaders like Satya are able to use AI to get way more done and to 10x their productivity. All of that and more on this episode of Marketing against the Grain.
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So let's get into smart medium prep. So here is the prompt. So basically it says based on my email history, let's do Kip. One thing I will just say is this may not work very well for me because I'm very much a Slack person and so I may have some email history, but all of my stuff is really on Slack. Our shared documents we should say in particular project documents and any one on one documents. What are five topics they'll likely want to discuss? So you want to make sure you have connectors. I have web search, G Drive, Gmail, calendar and Asana, which is a really great one. Right? So now I can get all my project materials and then you have these connectors that I can connect. I can connect it to HubSpot based on my email history With Kip and our shared documents, particularly project documents and any one on one documents, what are five topics I likely want to discuss? So what this is really helping you do is get ready for your one on ones. How many times do you have a one on one? There's no real clear agenda. What's the point in even doing that? This way you can actually preempt what are the most important things to talk about. You want to make sure you have some connectors here. So I have web search, G Drive, I have Gmail search, I have calendar search I have Asana HubSpot, so Claude has access to all of these things. Now we can basically say in particular any project documents or anyone on documents using my Google Drive and Asana. So you can tell it which ones you want. But this is one of the ones that Satya uses to make sure he's prepped for his one on ones. So let us run this. Okay, so it's back. Has done a really good job. So it's kind of pulled out some of the things that Kip and I might want to talk about. You know, we have our big event inbound 2025, starting this week, September 2nd. It's in San Francisco. And so there's a lot of back and forth around the kind of impact of moving it to San Francisco, budget, things like that. So there may be items that Kip wants to discuss here. It's pulled out some of the ones. We obviously want to go really big on AI. So based upon some of the board meetings we've had, strategic documents, how do we go faster with our AI strategy? How do we make sure Breeze AI, our incredible tool, is integrated into marketing initiatives. So we're using that. We have a really great surround sound AI engine optimization strategy that's working really well and we want some updates in that. And then internal AI adoption and agent vision for 2025 is a thing that we are talking about right now. So it's got a bunch of different things that it's pulled out. And that means that I am really prepared for any meeting. So anyone you have a meeting with, you can run this prompt and you can get all of the details you need to make sure you're prepped. Now let's move on to the next one. The next one is a real project status. So let's say we want to review a project, review a project communications and we should give it a project. Right? That's review all project communications for marketing against the green from the past eight weeks and draft an update with KPI's blockers and questions I should prepare for. Now. If you're going into a meeting and you have to prep for a project update, then this is another really great one, right, that you can make sure that you are prepped with everything you need to be prepped. And it's just a simplistic prompt. So let's run this one. Okay, so here it basically will pull out your goals, it can pull out your current performance indicators. So it's here. It's pulled out my episode frequency, content, focus, which is really good. Guest pipeline that we booked through. We have a great episode coming out. By the time you'll see this, we'll have released the episode with Anton. The founder of Lovable goes through the key blockers and issues. So we talk about the growth plateau concerns. YouTube is a grind. YouTube channel transition missing potential discovery subscriber growth opportunity. That is true cross promo content saturation risk. Because there's a lot of AI questions to prepare for. Again, think about this for your own project. We go in and we say, well, basically, are we on track? What's our status? How are we differentiated? So it gives you like the right questions to prepare for talks about your budget and resources. So just goes through this whole prep of all of the things you need to know to be prepped for any kind of project. And that's based upon this single prompt that we just ran. Right? All right, so that was a real project status. Let's get into deadline reality checks. So basically what you want to know for your projects are based on our project docs and recent emails. What's the probability we hit our deadline of September? Let's say. So basically what you want to do is you want to ask about the project docs, the recent email updates, you want to say, what's the probability we'll hit a certain deadline? And then you want to give it the actual project. And so we're going to run that. And what this allows you to do is see, like, are my projects actually going to hit the deadline that we set them? Okay, so what have we done now? Again, it's searched across all of the connectors and then has told me how probable this project is likely to hit. If you think about the way that I'm using AI like Satya, I basically got all the details I need for my one on ones. Then I can go in and I can get all of the project statuses. So I'm ready for any meetings that I have or comms that I need to do around these projects. Then I basically can actually go and say, well, what projects are even going to hit their deadline? And so what it does, it will come back with a probability score. Then it will say, what are the positive indicators? Like we're making positive progress towards this deadline. It talks about the risks that it's found, which are really good. Talks about some of the organizational challenges, scope concerns and then critical path what we must complete by October for this to be successful, recommendations to improve that probability. So it's figured out, like, what are the things you actually need to do to make sure you're on track to hit that. And then what is the most likely outcome? You would likely achieve a partial launch by October, but mainly November for full feature parody. Key question for leadership, would you prefer limited but functional October launch or delayed to November? So in this way I can actually make sure that we know if projects are going to hit or not. Like that's pretty cool, right? So that's three ways that Satya is using AI each and every day. Let's move on to the fourth.
Guest Speaker
Real quick. I'm giving you my ultimate four prompts that keep me organized and on top of everything as a business leader. These help me prep for meetings faster, get real project updates instead of fluff, and actually know if my deadlines are realistic. I use these every week. They're game changers for staying productive without the overwhelm. You can get it right now. Click the link in the description below. Now let's get back to the show.
Host
The fourth is a pretty great one actually. The fourth is are you doing work or just in meetings? So analyze my calendar in email for the past month, tell me how I'm actually spending my time and how I could be more productive. Again, I would love it if this was Slack was included, but it's not at the moment. And so let's run this for me and see what it actually says. And so again, what we're doing here as an AI enabled leader is we're having AI try to help us be more productive and show us how we can be more productive. Okay, so now it's analyzed how my week has gone. This is actually pretty incredible. So let me talk a little bit about how I would use this prompt. So again, this is a very simplistic prompt. I think one of the things you want to do is be really rigorous about how you use your Google Calendar. I am, but I looking at this, I know I can be much better. So when I run this prompt I can get real analysis. And so what I mean by that is the average time in meetings. I use my calendar for everything, right? So if I have an hour that I'm doing work, it will be a block in my calendar. So it's counting all of that as meeting times. But I don't if it's like in the evening time, right? So I work quite late at night as well for two to three hours. But because it's quite late at night, I don't tend to put that block in my calendar and I should because I want to get that picked up because that is actually core work time. And I don't always actually put the blocks where I'm working on something in my Google calendar. And so I want to make sure I do because it's not picking up all of the work I do. And so that's actually lesson number one is put everything in your calendar. That's my big initial takeaway here is I want to make sure everything is in the Google Calendar even when it's just work blocks. Like I do really put work blocks in there, but usually only time when I think someone might try to book over it with a meeting. Now I'm realizing no matter what time of the morning, what time of the evening or whenever I should put that work block in the meeting. Peak meeting day is Friday. It's not true. Again, it's just because of the way I do the blocks of work. Lightest meeting day is Monday. Say so anyway, that's my learning there. This is really good. This is why I want to make sure that I'm actually marking all of this out correctly because it does show you work in time. Meetings and collaboration, leadership activities, strategic initiative. This is actually really useful for me. I definitely try to cut down on one on ones. I'm very different from most people where I for the most part want all meetings to be action based and everything else to be async. And so what I try to always do is in meetings is actually be working on something with someone like solving problems, going through something. Now we do do one on ones and I think one on ones are important. But for the most part my model is quite simplistic. If that's like updates, I try to get async via loom and then everything else we do together is kind of actually doing work. But it gives you pretty good categorization here. Email management again, my email is going to be quirky for me because I do really lean heavily into Slack and so it has like a monthly email volume. This is quite low actually. I think there's many more emails it has not picked up on. Total inbox size. There's a significant backlog. Quarter of a million emails goes through some email types. It hasn't really picked up everything, but it's picked up some. But this is only a single thread so that's really not a key email type Meeting coordination. That's just me sending people looping in my ea. But this is cool. You show your strengths. I protected focus time. I actually have even better focus time because I again work very late evenings, usually 9 till half 11, which is not for the faint hearted but that's just the way I do it. And so it hasn't really included that strategic balance and then external engagement. So has like talks about the strengths and then what are my challenges. Meet an overload I would say that this is like some days but not all days. I think one of the things I could do better here in the prompt is is ask it to delineate between blocks where I actually use the title focus work time because these meeting days a lot of it is because I've big blocks of focus work time. This one is really good. I actually agree with this many 30 minute blocks may not allow for deep thinking. I really struggle with meeting 30 minutes meeting 30 minutes and that 30 minutes. I just find I'm totally unproductive. I don't really know what I can do in 30 minutes time and so I just do comms and catch up on slack. It's not good time. So I think that fragmented schedule is like pretty Good. Email backlog 214,000 emails suggest attention Context switching this is a big thing for me. I am across a lot of different things. It's funny that it's picked up on this actually it's picked up on the wrong things. I'm usually switching between AI go to market and core marketing activities. So I don't know why it's done. Partnerships and content I do create a lot of content but it still is correct in that there's a lot of context switching going on and then it basically tells me how I can be much much more productive and it's given me some really good advice. So we're going to stop there. These are the four AI enabled prompts that allow you to be a really great AI enabled leader like Satya, who's one of the best CEOs in the world. CEO of Microsoft trillion dollar company and so they're the prompts you can use it in Claude, Gemini or ChatGPT. They'll all work work as long as you have the connectors and they can access that information. Hopefully this was useful for you.
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Episode: I Stole Microsoft CEO’s 4 Most Powerful AI Prompts
Date: September 9, 2025
Hosts: Kipp Bodnar (CMO of HubSpot) & Kieran Flanagan (SVP of Marketing at HubSpot)
Theme: Unpacking and personalizing Satya Nadella’s (Microsoft CEO) top 4 AI productivity prompts—with actionable tweaks and hands-on discussion for marketing leaders.
In this episode, Kipp and Kieran dive into four of the most effective AI prompts reportedly used by Microsoft CEO Satya Nadella to drive productivity and leadership effectiveness. They not only break down each prompt, but personalize and test them within their own workflows, providing listeners with practical takeaways for maximizing output and clarity as an AI-enabled leader. The tone is candid, practical, and hands-on—delivering actionable advice for anyone managing projects, prepping for meetings, or juggling multiple initiatives.
This episode offers an unfiltered look at AI-enhanced leadership, illustrating that with the right prompts and a willingness to tweak your habits, you can dramatically improve your effectiveness as a marketing leader—or any ambitious professional in the digital age.