The Digital Project Manager

The Retro: The AI Skills That Will Future-proof Your Career

• Galen Low and Kelsey Alpaio

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In this episode of The Digital Project Manager podcast, Kelsey Alpaio sits down with Oliver Yarbrough—founder of Not Your Father’s AI and a LinkedIn Learning instructor—to talk about the AI-driven future of project management. With automation creeping into every corner of our workflows, PMs are no longer just task managers; they're becoming AI operators, process optimizers, and digital workforce leaders.

Oliver breaks down what PMs should be doing today to stay ahead: learning to communicate effectively with AI tools, mastering process optimization, and strengthening foundational PM skills. Whether you're just starting to explore AI tools or already dabbling in automation, this episode gives you a roadmap for evolving your skill set and redefining your value as a project manager in an increasingly digital workplace.

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Kelsey Alpaio:

Hey! I'm Kelsey. And welcome back to The Retro on The Digital Project Manager podcast—where we dig into past lessons, future trends, and what they mean for your career. So today we're diving into a topic that's pretty much impossible to ignore right now, and a topic you really shouldn't be ignoring—how AI will impact the future of project management. So at this point, we've all heard about the different tools, all of the use cases for AI that can save you time and take those annoying tasks off your plate. But how much thought have you given to how AI will reshape what it actually means to be a project manager—and what skills you should be building now to make sure you have a long and successful career in this field moving forward? That's what we're getting into today, and we have a great guest here to help guide us—Oliver Yarbrough. Oliver is the founder of Not Your Father's AI, which is all about helping people apply AI in their jobs and businesses. He's also a LinkedIn Learning Instructor with a popular course on artificial intelligence for project managers, and he's a longtime project management trainer. Oliver, welcome to the show!

Oliver Yarbrough:

Thanks. I'm glad to be here.

Kelsey Alpaio:

Oliver, tell us a little bit more about yourself and the work that you do.

Oliver Yarbrough:

I'm a project management trainer first and foremost, and in the last eight years or so, I started talking about the artificial intelligence specifically as it relates to project management. As of, the last couple of years I've been doing this thing called Not Your Father's AI, helping people just understand the practical uses of artificial intelligence. Not just for project management, for other areas as well, but for purposes of our conversation, of course, project management.

Kelsey Alpaio:

Great. So let's get right into it here and talk a little bit about how AI is already starting to reshape the project management role. So what are some of the major shifts you're already seeing?

Oliver Yarbrough:

I'm seeing people take what they do on a daily basis and starting to just incorporate it at a small level. So of course there are people who are using it at a much larger level, and we'll talk about that as well. But it's basically finding out, what you're doing and figuring out how can I squeeze inefficiencies out of those by hopefully incorporating various aspects of artificial intelligence and or automation. Those are some of the basic areas I would say there. Then I'm also seeing people use it to just help them write better. A lot of people, even if we're good writers some of us want to enhance it, or at least not start with a blank page. So I don't care if it's a presentation, if it's, an email. You never have to really start with a blank page. So those are just some of the basic areas I'm seeing there.

Kelsey Alpaio:

And how do you see AI continuing to make an impact over the next five years or so? Like what is the PM role really going to look like as AI continues to make its mark on this profession?

Oliver Yarbrough:

That's a very good question. And literally this morning I had a call with another company and where I see this evolving to, it's, unlike some people who have this no, no scare tactics and stuff, it's not really gonna be the elimination of the project management role. What's going to happen is you're gonna have the people who embrace it, who really learn it. Are going to be more or less operators, they're going to be the ones directing, training and retooling. But literally, and I'm not talking about this happening like next week, but possibly over the next 2, 3, 4, 5 years, they're gonna be managing a group of digital stakeholders and or employees and or coordinators. And so a lot of these things, it's gonna be, project managers are gonna be more operators, is what I'm saying. And you're gonna have to understand project management. Then also understand how to lead, and this is gonna be a whole new field here, how to lead digital agents, just like human beings, whatever. So in some environments it's gonna be more like a hybrid environment where there are gonna be human coordinators working underneath, like a project manager or some other new title, anyway. And so also a digital agent too. And so I call that more of a hybrid environment.

Kelsey Alpaio:

Really interesting. So I wanna dig in a little bit more to what those skills are that project managers should be building right now to help prepare themselves for that. So first off, how should PMs be thinking about AI on the day-to-day? What kind of mindset should they have around using AI in their current roles that can help prepare them for that future?

Oliver Yarbrough:

I think that it really boils down to three core areas. I'm not saying that these are the only areas. We've all heard about soft skills and all these things, and those are very important. Okay. In this new era, I think it really narrows down to three core areas. Number one is project management. You need to know your field. You need to know project management. It's hard to evaluate human beings or agents if you don't understand project management. So that's number one. Number two is it's understanding artificial intelligence. I'm not saying that you have to go out and learn python and no programming, but you need to understand how these LLMs think. And that's, like that's not super, super technical. I'm not saying again, that you need to go learn how to program it, but understand how it thinks. And then number three, which is not necessarily on a lot of people's radar, but I think it's just as important, is you need to understand process optimization. How to optimize a process. And why do I say this? Because in order to get the most use out of AI, you're gonna have to figure out how to squeeze out inefficiencies in your processes. That entails at a basic level, let's just say in any given week you do a hundred tasks, is figuring out of those a hundred tasks, which ones have to be done by a human being. And then of those ones that have to be done by a human being, which ones have to be done by me, or which ones can I delegate? And then of those other ones that can't be done by a human, which ones can be done by AI? Then of course the third category in there is which ones should not be done at all. The combination of those three, eliminating ones which should not be done, outsourcing tasks to either AI or to other human beings. And then what's left for me as the project manager to ultimately do, I cannot outsource it to anybody else or anything else. I think that's where I really focus my attention going forward.

Kelsey Alpaio:

Got it. So can you talk a little bit about the process of developing those skills now for the future? So are there specific AI skills, PMs should be laser focused on building, and what are the things that are going to be deal breakers if you don't know how to do them in the near future? Is it prompt building, is it something else? Let's dig in there a little bit more.

Oliver Yarbrough:

Okay. So we're talking about what we typically call AI. Okay. What most people call AI. If we start and I have this concept that I've talked about for a long time. It's project stakeholders, AI stakeholders. If we're gonna treat AI as if it's a stakeholder, as if it's any other stakeholder, if you're talking about like a RACI diagram, right? Like basically it's a stakeholder, it's one of the stakeholders on your projects. You have to know, like any other stakeholder, you have to know how to engage it, how to interact with it. So it's really finding out what that agent or what that AI bot needs in order to give you the optimal answers. So how do we communicate with AI? The basic level is prompt engineering, so the prompt engineering title might go away, but the need to prompt or write good prompts is not going away. This is basically knowing how to engage your bot. So I would say, prompt engineering is very important, more or less knowing, how to write a good prompt and there's different levels to it, right? As I stated earlier, knowing how to optimize a process. So take you like some of Six Sigma or something. Take any classes or courses that will help you streamline a process and squeeze out any type of inefficiencies. And then as a third level, I would definitely say some type of soft skills, meaning that you know how to, negotiate, you know how to buy things and various things that compliment what your AI agent can't do or maybe can't do as well as you like. Anything that involves human engagement. Here's why. It will allow you to compliment what AI does. You'll actually add value in a different sense. You'll add value to what AI is already doing. I think that those are where I would spend more time.

Kelsey Alpaio:

That's great. I wanna do a little bit of a, like 101, 201, 301 here, for those who might be wondering, where to start and how to level up. So at the 101 level, for someone who's maybe a little newer to AI or try to, it was like, eh, what advice do you have to help them get started on building these skills?

Oliver Yarbrough:

That's a great question because so many people get overwhelmed because they come in and they, oh, I need to start to build charters and I need to start to do sprint planning and everything. Start with something simple. Start with how do I streamline and automate taking meeting minutes? How do I create a presentation that I can then deliver to my team? Why do I say this? Because even though this might not be the technical aspects of managing projects, what it is it gets you a quick win. It gets you feeling some of the time saved. Initially it's about saving time. So yes, I could sit here and take meeting minutes. I could sit here and take an hour and create a PowerPoint presentation, or I could write a prompt, load up a document or two and have a presentation done in five minutes or less. Now, maybe I do need to obviously tweak it a bit, but I don't start from scratch. For example, I can take meeting minutes. I can then load those minutes into if I don't wanna do full on automation. I can take those meeting minutes, I can then load them into a chat bot and summarize it, and then I could then send it out as a summary. That's if I use no automation. If I use automation, it gets a whole lot better.

Kelsey Alpaio:

Yeah, that's a great, I feel like first step. And so at that 201 level, once you feel like you've got a handle on it, you've been using it day to day for a bit, you're in a groove, what's the next step? What's that surprising use case you might not have thought of? How can you advance your skills from the basics and really start to do some of that future proofing of yourself?

Oliver Yarbrough:

So at the 201 level, I'm taking it from the basics, I just talked about. Now we're gonna do something like build our own custom GPT. This would require a paid account, and every type of LLM has like their own version of it. Gyms and Google, other ones have other ones, right? So what I wanna do now is in a paid account, either in a, for example, ChatGPT teams account. It comes native, right? It comes where you don't have to worry about your data being shared with the outside world. But if we use a regular $20 a month account, you do need to designate, don't share. So I'm saying this so that you feel comfortable now uploading your personal information to it. We can train a GPT on our specific information. And here's where I think a lot of people are challenged. They try to have one GPT do everything. Like they load it with 50. Documents and just have it do everything. No. What I wanna encourage people to do is to train a GPT to do one specific task and do it very well. So for example, I want you to create project charters. All this does is it creates project charters. It doesn't do every single bank. All it does is I load it with examples of great project charters and other information I want. I then put instructions in it, which for example, you are a project manager working for X, Y, Z company with 15 years experience and other details. So now the reason I do that in the instructions is now I don't have to type that every single time. So now when I come in and write a prompt for this new charter, all I have to do is say, write me a charter for X, Y, Z. It gets pretty good if it's fine tuned. The train rate. So that would, I would say, would be the easiest and probably best way to go in at a 201 level.

Kelsey Alpaio:

That's great. Yeah. So at the 301 level, like we're talking basically expert users here, what are some of the skills and tools to be focused on at that level? What does the ultimate project manager, AI user look like?

Oliver Yarbrough:

I would say where we are now, you're getting into automation. At this level, you're getting into intelligent automation. This is where you're not just using a chat bot, but you're connecting them and you're using software such as a make.com. Make.com, Zapier, and what these do is these integrate these allow you to pull in information from one piece of software and bringing it to like another one. So for example, here, let's just say like you're using a software like your project management software. Something like Clickup or whatever, right? You can, for example, use an Airtable or a Google Sheet as a database of sorts. You can pull information from Clickup into an Airtable. You can then, for example, take that information from the Airtable and run it through, say like a ChatGPT, bring it back into the Airtable, and then spin it out into a dashboard or something. This is also, of course, assuming you're not using the AI that's already built into various pieces of software, which may already do a lot of these things anyway. But one of the reasons you may wanna have your own database is in case you want to have a record of it in your own environment, and you may want to do other things with it outside of just managing like one or two projects for example. So I would say, to answer your question, in a nutshell, it's intelligent automation.

Kelsey Alpaio:

Great. You mentioned this a little bit with a couple of those stages there, but one challenge I hear about often is PM saying I'm really excited about using AI and I really wanna be using it more regularly for my work, but my organization's just not there yet. They're wary of it. They're not sure of the security implications. So what advice do you have for someone in that position who wants to be building these skills but is limited by their organization or access to the tools?

Oliver Yarbrough:

I would encourage people, whenever I'm faced with pushback or a challenge, and I've had this back when I worked in corporate America, doesn't matter what job you're in, you're gonna face pushback. The first thing I ask myself is, why am I getting pushback? What's the root cause? What's driving this? What's the fear factor here? Because without understanding what's the fear factor or what's driving it, it's really hard to come back and offer like a reason. For example, if the question they're just asking, we find out it's a privacy issue I can address that. I can let them know that, for example, if you are using the Microsoft Suite, they have privacy built in. It's not gonna be used to train the larger data set. If we're already using Microsoft products already, then it's gonna be less of a less of a hard sell. If we're using ChatGPT, we can have a paid account or a teams account. For example, if we're using a teams account in ChatGPT, it comes natively. It does not share information with the larger dataset. So if privacy is the main driver for not using it, then that sort of lets some of that fear go away. If it's just the fear that if AI is going to just take our jobs, then there's other ways in which you can address that as well. By, again, as I stated earlier, showing them how they can save time. Showing them how it's not necessarily going to take their jobs as much as it's going to enhance what they're already doing. And so over time we can hopefully start to chip away at that fear, that hesitancy and get people to ultimately move forward.

Kelsey Alpaio:

Yeah, that's great advice. I do feel like that aspect of fear, kind of a fear that AI is going take your job is one of the challenges that I think some people run into. And I'm wondering if there are other, common traps that you see PMs falling into when they start building these skills. Are there misuses, overuses just bad habits, mindsets that they need to overcome? Can we talk a little bit about that?

Oliver Yarbrough:

Yeah, I could talk about this for like days, right? But some of the ones that come to mind are relying too heavily on the output that you get. AI is not perfect. Humans are not perfect. If humans aren't perfect, the things we program won't be perfect. And why do I say this? Because you may have heard this term, hallucinations. AI has a tendency at times to hallucinate, to make up stuff, to make you feel good. It doesn't wanna make you feel bad. If it doesn't have an answer, sometimes it will just give you what it thinks you want to hear. So there is some precedence in prompting to give your AI permission to not get everything right. Literally prompt it, give me an answer, X, Y, Z. But if you don't know the answer, tell me you don't know it. Do not hallucinate. Do not give me, do not make stuff up. Tell it that. So that's one thing I would say is something that I would definitely not overlook also. You have to continue to improve your project management skills. I cannot stress this enough, whether it be a traditional, hybrid, agile, whatever the methodology is, you have to be well versed to that because, and this is especially important, I'm really saying this not for the more seasoned people, but for the people who are maybe transitioning into the field from other areas or coming out of college. You need to really get certified, really learn the various aspects of project management because that will ultimately make you a better operator down the road when it comes to building and managing your digital workforce.

Kelsey Alpaio:

Absolutely. I think another thing too is that I get tripped up on is this fear of can I keep up? AI changes so fast and there are new tools popping up every week, new versions of things getting released like every day. And with so much changing so fast, how should we be thinking about staying current with AI and with these skills without it becoming like your full-time job, basically or should it be your full-time job?

Oliver Yarbrough:

I love this question. I'm gonna give you like a 101 answer and like a 201 answer. Okay? The 101 answer is listen to podcasts like yours, watch YouTube videos like yours. Read blogs and newsletters. I have an email account set up just to get newsletters and blog posts and stuff come in and I have filters in it, which I mean like all kind of o other stuff there, but literally. Okay, so that's 101. It's like just go out, read, listen, digest as much stuff as possible, take courses, everything else. The 201 level is automated. For example, have sign up for these newsletters, these blog posts, have them come into a dedicated email. Say for example, like a Gmail, have filters in there, and then you can have a bot go in there, pull those out, summarize them, find the key points, put them in a daily reminder that summarizes it in bullet points every single day from multiple emails and newsletters and even YouTube videos. You can get this summarized. So it's basically like having your own personal assistant summarize it and give it to you in bullet points like once a day. It's almost like having your own daily AI standup that's been summarized in advance.

Kelsey Alpaio:

Yeah, I love that. A way to make the learning a part of your day, but even just using AI to make that process easier is great. I love that.

Oliver Yarbrough:

Yeah. And the beautiful thing is if you're already in Gmail, a Gemini is built into it. Mm-hmm. So the, the beautiful thing about having AI built into something is you don't have to use automation anymore, really. It's already there. So it can summarize it instantly.

Kelsey Alpaio:

That's great. So we're just about out of time here, but to wrap things up for us, can you leave us with one thing every listener can do today to improve their AI skills and start to future proof their PM career?

Oliver Yarbrough:

One thing that you can do to future proof your career, I would say is even though it's getting to be old school now, it's been, it's been out two or three years, good old prompt engineering. Okay. And not just like your standard one. Okay. I would say that even if you're a newbie. You should probably, honestly speaking, start to learn custom GPTs, even though it's a 201 level, the basic level is gonna be, it's gonna become so basic. It's gonna be like talking about the internet like in 2025, like who talks about how to get online in 2025. So I'm gonna encourage you to advance from the 101 level to the 201 level as quickly as possible. Start learning custom GPTs and more specifically how to prompt for them. When I say this, specifically how to write instructions. Instructions, meaning that you're telling it you are X, Y, Z, working in this size company that becomes basically your avatar. You're basically, you're creating a digital avatar that you don't have to then prompt it every single time. That's the first level there, and then learning how to write the prompt after that. That's more of a workshop there, but if you just spend a little bit of time, take a couple of courses, a couple of videos, learn that it will do you wonders. It will be a tool in your tool belt that will give you a superpower for the next 18 months until everyone else jumps on board and then it becomes like a common knowledge.

Kelsey Alpaio:

Yeah. I love that. Oliver, thank you so much for spending time with me today. This has been so helpful.

Oliver Yarbrough:

Thank you. I appreciate it.

Kelsey Alpaio:

That's it for today's Retro. Be sure to follow the show so you never miss an episode. And if you wanna keep the conversation going with a crew of 1,000+ project management pros who get it, come join us at thedpm.com/membership. Thanks for listening!