How AI Is Taking Over Project Management Work

00:00:06 Mark Smith
Welcome to the MVP show. My intention is that you listen to the stories of these MVP guests and are inspired to become an MVP and bring value to the world through your skills. If you have not checked it out already, I do a YouTube series called How to Become an MVP. The link is in the show notes. With that, Let's get on with the show. Welcome back to the MVP show. I'm glad you're here. Today I'm joined by Cindy from Michigan in the US. Cindy, welcome to the show.

00:00:42 Cindy Lewis
Thank you. Glad to be here.

00:00:45 Mark Smith
Good to talk to you. You're involved in an interesting product category area that I want to explore. And of course, how tech is changing the world and the customers that you work with. But before we start, food, family, and fun, what do they mean to you?

00:01:01 Cindy Lewis
Interesting. So I'm actually an audiobook fan just because I like to walk and listen and I'm really big into murder mystery type things.

00:01:11 Cindy Lewis
So, you know, somebody kills someone and I want to figure out what happens. And food, I'm actually a vegetarian, but I'm, interestingly enough, a popcorn connoisseur. So you may not know this, if you pop your own popcorn, it comes in different flavors. So right now, midnight blue is my favorite, but a lot of people don't know this. And when I was traveling recently, I said, search out like Amish popcorn, and you'll find that there's a lot of different things out there. And Yeah, I am married. My husband is retired and does his own thing. But here I am, you know, I'm pretty tech oriented. And when we met, I'm Microsoft and he's kind of anti-Microsoft, so funny.

00:01:59 Mark Smith
That is awesome. That is awesome. My wife worked for Google for 10 years. And so, and I was on the Microsoft side for, and it was always, yes. Two different sides of the tech equation.

00:02:13 Cindy Lewis
Yeah, he's Linux pretty much, so. Ah.

00:02:16 Mark Smith
You know, so interesting you say that. I used to teach Linux 20 years ago, might it be? And no, longer than that, ago, probably 25 years ago. And now I'm using it massively again for all the AI stuff I'm doing.

00:02:35 Cindy Lewis
Wow.

00:02:37 Mark Smith
So I'm using it in Azure, but I'm using it a lot. Like there would be hardly a day that I don't have a bash window open and interfacing directly with Linux just to do the AI stuff I'm doing. So that's so interesting that, yeah.

00:02:51 Cindy Lewis
Hey, the shirt you're wearing, I have it. I don't know if I'd say that. I wouldn't, was that Microsoft Certified Trainer Summit and MVP Summit, and they gave me a whole bunch of shirts 'cause they were cleaning out the closet.

00:03:04 Mark Smith
I was hoping that it would have a 15 year because I've gone 15 years, but...

00:03:09 Cindy Lewis
I got 15 too.

00:03:11 Mark Smith
Have you got one with 15 on it?

00:03:13 Cindy Lewis
I do, but I don't know how many they have. I just got it.

00:03:16 Mark Smith
I was hoping to get that, as in that program's changed a lot over time, hasn't it?

00:03:20 Cindy Lewis
Yeah. Rohan is the new person.

00:03:23 Mark Smith
Ah, interesting.

00:03:25 Cindy Lewis
I don't know. I'll have to look up. They keep changing people.

00:03:29 Mark Smith
Tell me about Planner. You're of specialty. Tell me about it, particularly why it's relevant now in the tech landscape.

00:03:42 Cindy Lewis
Yeah, so my specialty is I'm a certified project management professional. So big in the project management institute world. I know a lot of people use other methodologies. But the big question is, how do we deliver projects on time with the right people? It used to be everybody did Project Desktop because that was the, you know, and it still is a very powerful tool. But now really the future is collaboration and artificial intelligence. And most companies, at least the ones I work with here in the US, they do Teams as their communication portal. So Planner is basically become the project management tool of choice because it plugs into everything. And I do have an interesting trivia. Microsoft said it sort of came to be by accident. They started with tasks in Planner. They also started with To Do. And they figured out everybody needs task management. So there was one side working on those tools. There was another side working on another web product. And they ended up developing something similar and came together and made a planner. So I guess they had to argue over the name. But Karuna from Microsoft says, everybody starts with a plan. And if you frame that, whether or not you're trained in project management or not, everybody has a plan. So yeah, does that help?

00:05:25 Mark Smith
Yeah, that does help. And you know, I've seen this whole, you know, maybe when I was like 18 years old, even the desktop downloadable version of, what was it called? Or was it a project, right? Microsoft Project.

00:05:41 Cindy Lewis
Microsoft Project, and it's still around. You still can get it.

00:05:46 Mark Smith
And so there's those iterations and then in the business application team, they started to create a whole project management, like more tailored towards service management, like, or particularly software IT project builds. And then as you say, then out came Planner. And is everything now under one product team that own that kind of story now? Or is it still... multi-product team from Microsoft's perspective.

00:06:16 Cindy Lewis
I think they're trying to put everything together because that's what all of us want. We want one place for all our to-do items, whether we flag an e-mail, put it on this app. I don't think it's all there. A lot of conferences, they say, we're putting it all together, but you know, real life, it's not there yet.

00:06:34 Mark Smith
Interesting, after all this time, right? It's not like that blows my mind. So you mentioned to-do. And Microsoft acquired a product called, started with W, out of Germany, I think, Wunderlist or something like that. And I had that before Microsoft acquired it, and it was amazing for task management. And then Microsoft took it and destroyed it, in my opinion. They took so many features out of it that were just amazing that just worked.

00:07:06 Cindy Lewis
I think you're right. Yeah, I agree.

00:07:09 Mark Smith
Do people use To Do now with Planner, like for their own individual task piece out of that Planner session?

00:07:14 Cindy Lewis
They do. So there's a couple ways to go and I really support, you know, hey, if To Do is what you like, keep using it. I personally keep my own Planner plan organized by my own categories. But that's because, you know, I'm in a meeting and people want to say, Hey, you know, you're a Planner MVP, you better demo Planner. But I think the mobile app for Planner needs a little bit of help compared to what Todo can give us. That's my personal opinion.

00:07:45 Mark Smith
You know, I've heard a complaint recently by another former MVP, actually, that's been in the space for about 10, 15 years. And they said with AI coming along and Microsoft's, all their product teams just hard pivoted to everything had to be AI. And really there are so many things on the product roadmap for various products that just, they took all the backseat to what's the AI, what's the AI? And so three years later, Microsoft is facing global adoption of Copilot at 3.3% was the latest data that's come out. They've just done a whole IT reshuffle of the entire senior leadership because it's not, product market fit is not happening in the market. If people have the choice of a different AI tool, maybe Anthropic or ChatGPT on the desktop and Copilot, they will use one of the other products every time as opposed to Copilot. And so Microsoft has a massive issue, but I want to talk about the issue with roadmap development of the product. And let's take Planner as an example. Have you seen in the last three years a continue iteration of things that you're asking for. You know, as often as MVPs, we at the coalface, when we see what the customer wants and we'll ask for that to be put in. Have you seen that iterative or is it like so many Microsoft products, you get V1, maybe V2, but never a V3 that is really moving the dial on feature parity and stuff with other tools in the market?

00:09:25 Cindy Lewis
Yeah, they are innovating and I will say they are really listening to customers. So something I learned recently, and then I've tried to educate customers on is, hey, you really need to reply on those thumbs up, thumbs down, give them feedback. And luckily, when I have meetings with people at the product team, I'm able to tell them, hey, you know, this is what people are asking for, but they hear the same things over and over again. I'm happy that corporate templates are coming out. That's a new one. Another thing they've announced is they're merging the basic and the premium plan because everyone was confused. Why does this feature work here?

00:10:03 Mark Smith
I didn't realize there were two plans.

00:10:05 Cindy Lewis
Well, they're merging it because it's so confusing. Because this one has this feature, this one has this feature, you can upgrade it, or why do I need to upgrade it? And it was just too confusing.

00:10:17 Mark Smith
One of the features that I have heard a lot about requested, and I don't know if you've seen the same thing, is that A sub-task in Planner, you can't assign it to an individual. So you can have the entire area, but the sub-tasks, activities that needed to be done, couldn't be assigned to individuals. Has that been improved or replaced?

00:10:40 Cindy Lewis
Sub-tasks you can. The heading you cannot. The summary, you cannot, and that's by design. So one thing that they did, and I give them credit, is there was a lot of mistakes people would make in like traditional project that would mess up reporting, that would mess up allocation views. So they basically hidden or made it so you can't make the most common mistakes. But on the flip side, nobody could understand the scheduling engine in desktop. So they made it so you don't have to know it in planner. You decide, do I do duration based planning? Type here. Do I do effort based planning? Type here so you can do whatever you want.

00:11:22 Mark Smith
Nice. And tell me about the AI story with it. What have they done in that respect and how much is, I notice it. One of the things when doing some research about what you did, you talked about where AI comes into the mix around project management even.

00:11:41 Cindy Lewis
Yeah, so here's a couple of hot things. They keep renaming the AI thing in Planner. So as of right now, it is the Planner agent. But I noticed with a client today and even myself, the icon has changed a couple of times. Used to be a rocket. Now it's back to the traditional Copilot icon, and it's in the lower right is the current location. I've seen it move around a little bit. But the real idea is we need to be able to ask a question of my plan, even if I don't look at it and look at the updates and have it spit out the answer. And they already have AI doing a really nice status report that used to take all of those hours. Now it's quick answers, and it can help build your plan. It can do risk assessment. It can build tasks. It can do research. It can do a whole lot more. And the average person that uses it doesn't even You can barely try or know enough to know what it could do.

00:12:50 Mark Smith
Does it feed into the Microsoft Graph as well? So therefore, Copilot broadly can go, Hey, you've got to plan an item. Do you know whether it does that?

00:13:00 Cindy Lewis
That's under NDA. So let's see here. Basic plans do. And premium plans are in the Dataverse. So that's all I can say.

00:13:13 Mark Smith
Wow, so that's interesting that you mentioned Dataverse because, you know, that was my bread and butter for years. And that must be the pieces that have come over from the Dataverse side of the health center, which is BizApps.

00:13:27 Cindy Lewis
Yeah, most of the clients I work with use Dataverse, use Power BI reports and get the story they want. So, you know, if you want resource, capacity across all your plans, across all your portfolios, Power BI is the winner. And there are still templates in GitHub that still work if you want. I mean, they're not currently up to date, but they're still out there.

00:13:51 Mark Smith
That's cool. That's cool. That's really good to know. And that there is a solid AI story there with it. I've just, as we're talking, brought it up on screen and can see the last time I used it was April, 2025 was the last time I've used Planner in my work. So it's been a while.

00:14:09 Cindy Lewis
It's a good way to data dump and be organized in different ways. And one of the things that I used to do really poorly was organize in some sections of my to-do items. Now I can use buckets if that's what I want to look at. I can use color-coded labels that I can rename. That's kind of the power. You know, it's the little annoying things that Microsoft is fixing. They don't put it all on the roadmap. Roadmap is something big. But little things like being able to click here or drag buckets around, it's that kind of stuff that they are fixing that not everybody notices. So I give them credit. They're really evolving this tool. The one thing I will say is for anybody that watches Ignite or some other big event, you're going to see these big announcements. that the average person won't see for quite a while because companies don't roll out the M365 updates every month. They might be three months, six months down the road.

00:15:13 Mark Smith
You've definitely sparked my interest. Even after this call today, I'll be going and actually cleaning house and going, okay, let's revisit this because I've got it on my subscription and see what I can do with it. You're also an M365 copilot MVP. What, what's, what's been your focus around that area?

00:15:32 Cindy Lewis
Um, mostly just trying to help people get to be a little more productive with what they do. And it's this really simple things like look through my e-mail last week and what are any hot items I should have paid attention to, or I've done stuff. I haven't met with this person in a year. Review my meeting minutes. What did I discuss? What should I be thinking about? And then random brainstorm. and Copilot is really funny. So I was doing a live demo with a customer and I'm like, okay, let's search out this topic and it put at the bottom, and this really fits you, Cindy, because you're in the planner project space. So it like is learning me and it will even know, like I was making a graphic for a customer and it says, oh, you're traveling to this customer next week. Is that the graphic you're trying to make? So it is, really helping or really involving. And what I like is customers now get prompted, what can they do? So instead of staring at a blank box, they get advice, which is really nice for the evolution.

00:16:46 Mark Smith
Yeah, much more collaborative. I like that. When you look at 2026 and the opportunities ahead, What's your outlook?

00:16:56 Cindy Lewis
It's pretty positive. The biggest thing for me running projects or anybody working at a company delivering value is you waste time on meetings. That should be, hey, let's make that better. Well, we can now with Copilot, facilitator agent, and so on. Well, now, why can't we have an AI agent Follow us around. And that is the future. You've seen that with Planner. We're going to have this agent keep track of all our tasks, hound our coworkers that aren't doing stuff, do work itself, go to meetings, update plans, go back in Teams. I mean, the future is, it's really here, but most companies are not ready. I hate to say it. even me, I'm stuck in my old ways. Why do I keep using e-mail? We should be in the Teams channel sharing this information. I don't know. What do you think?

00:17:57 Mark Smith
Yeah, I'm definitely using e-mail less and less and less. I've operated for over 10 years on a zero inbox policy. So And it's just, it's habitual to me now. I, it's actioned, it's gone. And I used to be zero inbox daily. I've now kind of, in fact, just in the last six months, gone to zero inbox weekly, just because I was spending too much time on processing emails. And I've now fully given over my calendar to AI. So just my calendar, so it handles scheduling. It recategorizes things, puts the categories on it, makes sure time's blocked out. It does sweeps for conflicts, gives me like 48-hour notice of any conflicts. So I'm using AI to do that type of thing. And Calendar was my first touch because I feel that Outlook is really for products now, right? It's not really the outlook of the past. It is Calendar, it is People, it is e-mail. And then there's, of course, Copilot is a major feature in it now. So Calendar was my first one to really... My instruction set to the AI that runs it was over 50 questions that went through with me to really understand how I worked with Calendar. And then I put some hard rules in, like you can never delete something out of my Outlook system at all, ever, in any situation. The best you can do is archive something. So really put some really firm parameters in place. And then of course, it's never allowed to communicate with anybody other than me with anything in my calendar. So if it's, it will draft something for me to do, but it's, man, it's just made calendar management so much easier. And it's always looking ahead, like it's looking, hey, your school holidays are coming up. Do you want to block your schedule out so you can have time, more time with your kids? It's like, it's proactively doing that. It's, yeah, so it's my first piece that I feel like it's now, really my agent is an executive assistant and managing that. And that's the kind of, I really define the job description for my AI as a job role, not a automation.And so I train it on executive assistant and personal assistant type training material so that it has that kind of, dare I say it, mindset in how it interacts rather than... I feel like so many people in the space are doing AI, but they're really doing automation. They're calling it AI, but it's automation.

00:20:43 Cindy Lewis
You're right. And that is a form of AI. Yeah. You got to get a Peter Taylor's book. Now it's a little bit out of date, but AI and the Project Manager. It talks about what is AI and automation is, you know, that is one of them. And something that you brought to mind while you were chatting is I know clients are real concerned about, hey, is Copilot secure? So I've done tests real time, send this confidential document to Cindy's personal e-mail and it won't go through. So that is, you know, certainly the customer and the company has to set it up properly or with one of our MVPs. but security is tight. Even with sensitivity labels, they've got that down. And I know something coming to Planner is information barrier support. So I know GCC and GCC High, they're really strict on that. And I've been at companies where we've tested it, and it is pretty good.

00:21:46 Mark Smith 
Cindy, it's been awesome talking to you. Thank you so much for coming on the show.

00:21:50 Cindy Lewis
Yeah, thanks, Mark. This has been fun. I could talk to you for another hour.

00:21:59 Mark Smith
Hey, thanks for listening. I'm your host, Business Application MVP Mark Smith, otherwise known as the nz365guy. If you like the show and want to be a supporter, check out buymeacoffee.com forward slash nz365guy. Thanks again and see you next time.