Episode 11: Reskilling vs. Upskilling: Why It Matters in the Age of AI

In this episode of Coexistence: Humans and AI in the Workplace, Dr. Z and Latif are joined by Jennifer McCready, a tech leader, coach, and career development expert with over two decades of experience in the industry. Together, they unpack one of the most misunderstood—but critical—topics in the age of AI: the difference between reskilling and upskilling.

Jennifer explains why these terms matter, how organizations misuse them, and what’s at stake if leaders fail to design the right programs. The conversation explores:

• The disappearing entry-level jobs and what this means for early-career professionals.
• Why workers over 40 often feel overlooked—and how career ladders are becoming skill ladders.
• Jennifer’s practical tools, including the Tech Career Survival Scorecard and a Gen Z Guide for graduates.
• The importance of community-driven, cross-generational mentorship in making reskilling stick.

This episode is a reminder that in an AI-driven world, your skills are your equity—and building the right ones is essential to thrive.

Explore Jennifer’s resources here: https://stan.store/JenMcCready

Transcript

Latif: Hi everybody. welcome back to Coexistence Humans and AI in the Workspace.

Thanks for joining us for episode. Oh my goodness. Episode 11. Wow. Dr. Z, we've been busy. This episode is special because we have a special guest joining us, to discuss, , the age of AI is sort of talk about reskilling or upskilling and, how do we rethink our career growth,

the age of ai. So. We have with us today, Jennifer McCready, who is an, expert in, this field. In fact, he coaches people, on, the dynamics of, how do we, get still, sort of new age of ai.

And, Dr. Z, I'll hand over the mic to you. 

Dr. Z: Thank you Latif, and I am very excited about our conversation with, Jennifer today. We often talk about these terms, interchangeably between re-skilling and up-skilling, and I am thrilled to go deeper with Jennifer , in terms of the differences between the two and how can we start rethinking about re-skilling and up-skilling.

So with that, Jennifer, over to you. 

Jennifer: Thank you Latif and Dr. Z. I am thrilled to join you and my passion really has been around helping people, especially those over 40 who feel stuck or overlooked, find the resources and confidence to thrive in a tech-driven kind of AI economy market. Well, that's, \ really fabulous though.

Dr Z: So, Jennifer, you have spent over two decades, in technology. You have worked really hard in terms of building partner programs, and distribution channels. So if you take it from that perspective, how do you see AI intersecting with career developments today? 

Jennifer: I think career development has been flipped for the most part, for people early in their careers.

The entry level jobs that used to be a starting point are disappearing because AI has been taking on those tasks, those processes, and those functions, and for people over 40, the career ladder has shifted. Into a skill ladder, and it's not about titles anymore, it's really about re-skilling and project or gig work.

So the concern I have around roles that take years of practical experience to learn is that if we remove too many of those stepping stone jobs, we risk not having enough people ready for critical roles when today's experience professionals retire.

Dr Z: Before I, give my, I have a lot of thoughts to that Latif, is there anything that jumps out to you from those?

Latif: So I am barely over 40, right? I can totally relate, to what Jennifer, just said. And I see , my friends, their kids graduating from college, wondering. What it is that they're gonna do for their first job. Because a lot of these first jobs, whether it's a paralegal, or a programmer, , et cetera, , a lot of these are,, being replaced, by AI or, they're in the process of being replaced by ai.

So what Jennifer says resonates in terms of the younger. Generation in terms of folks my age, it's not about the title anymore, are you a VP or an SVP? No one really cares because the, organization structure is changing from a hierarchical structure to a , goal and objectives-driven organization.

Folks over 40 folks over my age., It's really down to do I have the necessary skills to survive in this new organization sector? 

Dr Z: So, Jennifer, when we are talking about this word skill, and then we, mentioned these words, upskilling and reskilling. , I personally have also seen many leaders use these words.

Sometimes it's interchangeably, sometimes it's just one or the other. You have been very outspoken about how these terms are often misused. Can you help our listeners understand the difference and really why does it matter?

Jennifer: Yeah, re-skilling is picking up completely different new skills to move into a different kind of role, like training to lead AI agents, being an AI agent boss , or focusing on AI ethics and responsibility and upskilling is building upon what you already do. Let's say somebody is a Salesforce admin, but Salesforce adds a new feature.

They learn all about that new feature and it adds to their skillset that they already had,, or adding cloud migration skills. If you already have been working with AWS, the key is that one prepares you for a brand new lane. And the other keeps you competitive in the lane you're already in. 

Dr Z: So it, seems the distinction is very important to make because if we are not able to understand and even name the difference, that could potentially be a risk around why programs don't succeed that are created for development of people because it's not targeting the correct audience in mind.

Having said that, Jennifer, what message do you think leaders need to hear most when it comes to access to re-skilling opportunities? 

Jennifer: One thing that I have witnessed , are the enablement platforms within an organization that have been set up and it's,, go and get what you need. There are little guidelines around the use of AI within the corporation or organization.

There are a lack of use cases and where they may be applicable to someone's role or within a team or the scope of the work that they're doing. The message leaders most need to hear is everyone learns differently, but there needs to be some consistency across the entire organization for how everybody is going to be aligned to learn AI and over what period of time. And that may differ by role, by group, within an organization, but there needs to be sort of a one-stop shop as to, here are the guidelines, here's how it's being rolled out, here's how it impacts your role, and here are all of the resources that we are going to provide.

Unfortunately when I'm brought in from a, consulting angle into a company, what I've noticed lately is that, there's a lack of investment being made in re-skilling folks that don't already have AI skillset and there's a lack of upskilling existing the existing workforce., Whether they're software developers, engineers, admins for all of these platforms that are being managed,, 'cause we've got marketing tech stacks, we've got it tech stacks,, new technology that's really cool, like Zapier Automation that has.

A lot of APIs connecting in and out and running co-pilots now, and there really needs to be a central home from an enablement standpoint, almost like a mini PMO for re-skilling and up-skilling the workforce. It not only serves the company, but it gives equity to everybody that's working there to give everybody.

Equal advantage in learning that not only benefits that company, it the employees, the partners, and the end customers. 

Dr. Z: So Jennifer, you've mentioned a few times how organizations need to invest correctly when it comes to resources. You, have developed. Practical tools and resources.

And an example of that is the Tech Career Survival Scorecard, and a Gen Z guide, for graduates. Would love to get your thoughts around how the resources that you have has helped people and continue to help people navigate these career transitions in the AI economy particularly.

Jennifer: So there's been so much noise out there that it's hard to know where to start, especially if you are a new grad coming out of college with all of these promises of it being easy to land a job, easy to land a high paying job in the tech sector because the computer science graduates have been mostly impacted, in it being difficult to find these entry level roles that were there several months ago and now all of a sudden, overnight they're gone.

And I built this tech career survival scorecard to give direction., And it lays out skill categories, low cost ways to build them, and how to prove the skills, whether you're going through an interview or you are at work. I have these four skills. A lot of them are general in nature and you can niche down where you need or dependent upon what your.

Most interested in, but we need financial acumen. We need to know what's happening in marketing. We need a little bit of information across an entire organization to be successful now, and aside from that, which helps people,, prepare for interviews or for work and promotions. I also created a Gen Z specific guide.

To help early career recent grads., And it's a simple playbook that helps 'em get hired, get paid, and get ahead. And the reason that I did that is because I had so many parents calling me. And being only one person, I am not able to scale to more hours than there are in the day for phone calls.

And I also had a lot of students calling me , that were very nervous with very large , student loan bills coming due. Somebody just invested four years of their time , based on the Occupational Outlook handbook, it said, this is what you should go to school for.

You will get a job. It's guaranteed, and they come out of school and that's not the case. And they're unable to repay their student loans and. A lot of these Gen Z kids are so smart and they're digitally savvy, and I knew that if they had some sort of a playbook, they could utilize that playbook and self-serve.

And so it was my way to scale the conversations I had been having. 'cause at the point that I created the Gen Z guide, I had spoken to over 50 , recent grads. And kind of consolidated all of that information, all of their questions that they wanted to ask, really in particular Gen X, like, how did you do this?

How does this work? What do I do in an interview when the pay topic comes up? How do I know what the red flags are when I'm applying for jobs? Is it a real job because I've been scammed? Things like that. So I put it all into, it's about a 40 page. PDF, and it's done in a visually appealing way for the Gen Z and millennial audience, and I've had a lot of good feedback, from it.

And it's very low cost so that people have practical tools that they can use. Parents can go grab it, give it to their kids. Kids can grab it. And, it's something I'm really proud of. But also I am just trying to help as many people as possible. That's great. That's just fantastic. What you've invested so much of your time and energy, and leverage your experience to come up with these, I guess, pay books, for the lack of a better word,

Latif: For, the different generations, Gen Z and then, the older generation like me . so I'm really curious. You've got, these playbooks but you know, the workforce, you've got the younger generation obviously interacting , with the older generation.

How these two generations come together, in the sense that the needs, as you just pointed out, for the Gen Z are very different, to the needs, for folks like me, in terms of the steps they need to take, to really embrace the new technologies.

How do you see that interplay from your experience, between these two generations in the workforce? 

Jennifer: I think the future of re-skilling is. Community, and I've seen this firsthand when I run a workshop. It's very interesting these days running a workshop where we're running through., Typically if I come in and there's a group of people, there are people from marketing and sales and operations and legal and, and product and engineering. and what I've noticed is this shift, everybody's in a room together, but there are generational gaps.

We've got Gen X next to Gen Z, we've got millennials, we've got everybody in between and varying degrees of experience and backgrounds, and skill sets. And what I noticed is that mentorship isn't top-down anymore. , It goes both ways and it's kind of exciting. So I'm Gen X and I've learned a lot from Gen Z and millennials about the different way that they think, what their thought process is, what they see in the market that maybe I would've missed.

As a Gen X, they're so digitally savvy and I've grown up with these mobile platforms. So the way that they think about a product launch is different, and everyone learns differently. They ask me questions like, how do they succeed, at the company? How do they succeed in different teams?

How do they navigate through an organization to move from say, marketing and sales so they can get this breadth of experience that a lot of Gen Xers have? And at the same point I saw a comfortability with. A lot of the Gen X folks that were in the room in the workshop having conversations with Gen Z, whereas before, I would say maybe a year ago it was Gen Z on one side of the room, gen X on the other side of the room.

And there wasn't a lot of meshing from a collaboration standpoint. And now I do see that there's a lot more collaboration happening, which is great to see. So that back and forth I think can be really powerful. Where everybody is collaborating, everybody is aligned to the same mission. And that kind of brings me to this enablement within a corporation as well and that being really flexible.

We have multi-generational, ways of learning, in an organization now. It will be like that for some time. And learning needs to be flexible so that if people learn best on a mobile app, we are supporting that. If they learn better in an online course, in a self-serve fashion, we should be supporting that.

Or if they learn best in person, there should be some sort of accommodating that. And because everyone learns differently when the platforms don't reflect that people get left out and then that reskilling and or upskilling. Approach and adoption that we expected to have, isn't realized. And the real opportunity for companies right now is combining inclusive learning with cross generational mentorship.

And that's when this reskilling is really going to stick. 

Latif: Yeah, it's interesting 'cause as you know, Jennifer, I run a startup and then we're building, tools for businesses, for technology companies, help themselves, through the channel.

And I know that they have a lot of experience in. And I, really feel for this audience because these technologies are changing every day, I mean, there was the time, I remember when I entered the workforce, you had a handful of technologies. You all used the same word processor and all used the same, tools to communicate.

And you all used, the same back office tools to do your accounting. And that wouldn't change for years. So you could learn a tool and that experience or that knowledge and that skill. Would be relevant for the following five or 10 years. That's not the case. So the point that you're making about, how do you get these generations?

One generation is used to a much slower pace of technological advance and, the Gen Z that's quite used to switching apps every three to six months. 

But, Dr. Z love for you to chime in and, give us your thoughts. 

Dr. Z: Yeah, I would probably say that listening to both you and Jennifer speak it reaffirm.

Reskilling and or upskilling. These aren't buzzwords anymore, and leaders need to start sharpening their understanding about these words before they design anything around career development and growth for their people. And they definitely need to bring in people like Jennifer to the table, as a consultant, as a coach, so that, they are able to understand, number one, the differences and then also see how can programs , either fit into re-skilling or up-skilling., Having said that, I would also like to add that, it continues to , reaffirm that it is leader's responsibility to make sure that anything that is being created, whether it is to reskill the talent or if it is to upskill. These things need to be accessible.

They need to be relevant across generations, and most importantly, they need to be human-centered. I did have a, chance to look at the guide that you have created , for Gen Z. And I will say that it's very relevant. I have done a lot of fields, work with Gen Z, so I could see how, things like what you have created could be beneficial.

Jennifer: Thank you. . 

Latif: It's really, just great to see all the structure. that you're helping build., Because to be quite honest, , I speak to friends and colleagues and people are confused. They don't know where to start. There's this avalanche of information.

Online tools, learning this and learning that, and AI, and it's just very confusing. And I think what you've done is, tremendous in. Basically, think, Hey, you know, if you're in this specific part of your career, then here are some steps that you can follow, in a very structured way, to advance your skills.

The reskilling that people thought can be upskilling as well. 

In closing, the one thing that I would love for you to answer is if someone listening to this is, stuck in their career, regardless of what generation they've fallen in, what would be that one, or, two pieces of advice you would get them?

Jennifer: I would say these days. In 2025 and beyond, because I don't see this changing. Your skills are your equity. Your profile, your public persona, whether you have one today or not, your resume, your portfolio, that is your equity. And the more you grow your skills, the more leverage you are going to have in the AI economy.

And so I think that's really where people should focus. 

Latif: That makes a lot of sense. Hey Jennifer, thank you for joining us. Hopefully we'll get a chance, Jennifer, for you to share the links to some of the material that you've, you've created so our audience can.

Take a look at this, material. But, you know, thank you again for joining us and for all those that are listening, stay curious, stay adaptive, and most of all, stay human. Ciao.