How can we best support the future workforce?

Dr. Caliento: And so it is important that we continue to think about the connections between companies, corporations, and the school systems, right? How can businesses be much more engaged in those earlier formative years to help ensure that they are preparing and exciting young people for those careers and helping those young people see people like themselves in those careers as well?

Kevin: According to the U.S. Bureau of Labor Statistics, nearly 5.9 million Americans were unemployed as of 2022. And as traditional jobs evolve, there is an increasing demand for skills training and personal development. How can we equip individuals with sustainable employment? What challenges are job seekers and employers facing today? And how can we best support the future workforce? This is “What I Want to Know.” And today I’m joined by Dr. Kathleen St. Louis Caliento to find out.

Dr. Kathleen St. Louis Caliento is the President and CEO of Cara Collective, a workforce development organization dedicated to transforming the lives of individuals affected by poverty and also promoting a more inclusive economy. She joins us today to discuss how we can best support the future workforce. Kathleen, welcome to the show.

Dr. Caliento: Thank you so much for having me, Kevin.

Kevin: You know, we’re really going to have an important conversation to talk about workforce development. I also want to get into the nexus of workforce development and education. But before we do all that and before we talk about your group, I want to talk about you and how you got into this work. When people decide that they want to get into this space of helping other folks get gainful employment and develop the skills necessary for that, that’s kind of a unique space. So talk a little bit about your journey.

Dr. Caliento: Sure, absolutely. Thank you. And, you know, when I share a little bit of my journey, I think it won’t be as surprising that I am where I am. Daughter of Haitian immigrants. So my parents immigrated from Haiti to New York City in the late ’60s as most immigrants do in search for better opportunity, American dream, and all of that. But unfortunately, as many immigrants do, they faced a lot of uphill barriers and roadblocks to their own success and economic empowerment here in the United States. They found trouble navigating the education system while they were themselves very educated. Had a hard time finding work. My father had to work as a cab driver for a long time. Eventually, finally, he became recognized through his work as a physician here in the United States. And my mother is a nurse. But it was an uphill battle for them, for sure.

And I also think about the fact that they didn’t even know necessarily how to help us navigate, their children navigate the education system, and think about necessarily where and how to achieve our highest dreams, right? They knew education was important. They said it. And so we knew that education was important when we were young.

And so when I think about my professional career, my trajectory to issues of access, equity, opportunity, they’re absolutely framed in my upbringing and the challenges to that access and to that equity and to that opportunity that my own parents faced, and as a result, my siblings and I faced as well. I think we all did pretty fairly well, but it wasn’t without its challenges. And so when I think about the opportunity to give back and help other folks who are also facing significant barriers to access, to equity, to economic empowerment, it was a no-brainer for me to pursue that line of work for my career.

Kevin: You know, it’s interesting. I was looking at your background, and we have something in common. I grew up in Indianapolis, and one of my early jobs was delivering newspapers. Now, for a lot of young people, particularly the TikTok and Instagram crowd, you won’t even know what that means. The source of information and news came through these newspapers that are completely phasing out now.

Dr. Caliento: They were tossed on your doorstep.

Kevin: They were tossed on your doorstep. And usually, some kid on a bicycle would . . .

Dr. Caliento: That’s exactly how I did it.

Kevin: . . . would have a bunch of these newspapers. I learned how to fold them the right way.

Dr. Caliento: Yes.

Kevin: And you learn how to toss them. You’ve got to be careful not to toss them too hard or fold them too tight to break a window or knock over a plant. But I did that. And at the time, you know, I was excited to do it because I knew I would get, you know, some pennies or some dollars at the end of the week. But boy, it was interesting work because it did help teach me discipline. You had to be there on time. You had to make sure you delivered those newspapers, and you had to make sure that you didn’t miss a house because people would complain.

So talk about that experience because, again, it’s kind of an old-school thing that doesn’t happen now, but it did for a lot of us, and I’m sure you, certainly me, it helped embed the seeds of what you need to do to prepare to go to work and go to work every single day.

Dr. Caliento: Absolutely. The discipline of having to do this every day, every morning, as you mentioned, was really a skill set, right, and a competency that you had to learn of how to show up every single day, even when you didn’t want to, even when the weather wasn’t cooperating. And it taught me customer service and how to approach people, right? If people were out on their stoops or on their doorsteps, rather than throwing it, I would get off my bike and hand them the newspaper, right?

Kevin: Yeah.

Dr. Caliento: Then you’d ensure you’d probably have a repeat customer. So that was always great. And on Sundays, we’d have the community rallying, right? My mother would pack us in the hatchback of her 280ZX because the papers were so heavy and would have required multiple trips. And so she drove us around to deliver those papers as well. So lots of lessons in those early employment years, I’ll say.

Kevin: You know what’s interesting, and I don’t want to spend too much time on this, but when you said customer service, I just remember for the first time that there were certain customers, folks who I delivered papers to, who periodically would have cupcakes and cookies and, you know, they would . . . And I just remember, you know, I needed to make sure I took care of those folks and make sure . . .

Dr. Caliento: Yes.

Kevin: . . . I was not going to be late because I knew at some point I was going to get some goodies.

Dr. Caliento: Exactly. That’s absolutely right.

Kevin: It’s fascinating. So let’s talk about the workforce sector today, because what’s really good about this illustration of delivering papers, which is an antiquated now job opportunity for, you know, 12, 13, 14-year-olds, things have changed so much. And the workforce sector today in America has changed so much. When I was young, many, many years ago, you know, a lot of folks worked on traditional assembly lines, or even their 9:00 to 5:00 office jobs were totally different. Reams of paper that they had when they went to store material, warehouses. Now everything is digitized. We have, you know, the virtual office meeting setting. So talk a little bit about what you are seeing and what you expect to see in terms of how young people look at this idea of day-to-day work because it’s totally different. And the thing is, Kathleen, my experience is many of the radical changes in the workforce world have really taken place in the last 10 or 15 years.

Dr. Caliento: That’s right. And I think even more so accelerated by the global pandemic over the last few years.

Kevin: Yes.

Dr. Caliento: And I couldn’t agree with you more in that the workforce landscape has changed pretty significantly. We’re looking at things like 100% remote for many jobs, right, where that was not something that was even a consideration previously. The idea of, you know, you don’t have to show up to every interview and workspace in a three-piece suit, right, the sort of business casual kind of outlook on dress, but also in terms of industries, right? And so I think in terms of the things that we’re seeing, some things will always remain, you know, manufacturing, healthcare, hospitality. But we see that those industries, to varying degrees, get impacted depending on what’s going on environmentally.

And so for us, at Cara Collective, it truly is about I would say a couple of things. One, ensuring that we’re providing enough of a diverse offering in terms of career opportunities and pathways for our participants, that we’re preparing them for those diverse settings. Right? How do you take a virtual interview? It’s very different than showing up in person, right? What does your background look like? And how are you showing up on screen? And then ensuring that they are then prepared for success.

But it’s also talking to our employers and making sure that they understand the changing workforce demographic and the desires of that work form demographic, I would say, across untapped talent and tapped talent in terms of what folks are desiring and seeking in those workforce. They’re looking for much more flexibility. I think the pandemic did have some silver lining, if it’s okay to say that, in that I think it allowed people to sort of prioritize what’s important to them. And so now it’s sort of a balance between, you know, employers and even ourselves as a nonprofit to think about what can we offer? What can we provide to our staff to ensure that they feel seen, welcomed, supported, but that we’re also able to get the job done in terms of meeting our job seekers where they’re at as well? Particularly when you’re a direct service organization, that’s what makes it tough.

Kevin: Well, and speaking of Cara Collective, you know, tell us a little bit about what Cara Collective does.

Dr. Caliento: Sure, absolutely. So we have more than 30 years in Chicago as a leader in the workforce development and economic empowerment space. We’ve worked with people experiencing poverty. And these circumstances often are associated with addiction, incarceration, homelessness, systemic inequities truly, domestic violence, and so on.

But essentially we have four entities that we operate under, under the collective to help build and strengthen inclusive employment pathways that create, as I mentioned earlier, access, equity, and opportunity for the people that we serve. So, briefly, the four entities are Cara, which is what many people know us for. That’s our signature, professional, and personal development training session. And that’s where we provide personal training, workshop training sessions, but also wraparound supports. These are the things that actually differentiate us from other job shops in that we provide opportunities and resources to help our participants stabilize before they get into the workforce. So we provide coaching, resource support, training, as I mentioned.

We then have two social enterprises. Our first, Clean slate is our flagship social enterprise that helps to transform landscapes, external beautification, exterior maintenance, and it provides, honestly, temporary jobs for folks who may not be able to land those permanent jobs quite yet, whether because of gaps in their history, recent incarceration, etc. Our second social enterprise, Cara Connects, is our mission-driven staffing firm. So there we truly work as a standard staffing firm, where we’re the employer of record, working with connecting our talent to jobs in leading Chicago companies.

And then finally, Cara Plus is our expansion arm. So that is the arm that truly works with employers to help them think about how do we progress along our inclusive employment journey? You know, I truly believe that many of the employers that we work with, and even those that we don’t, have a will and a desire to bring in more untapped talent and to work and to help develop those. There’s often not the way. There might be a will, but there’s often not the way. And so what Cara Plus does is help pave the way from helping to identify things and barriers as early as the job description phase, all the way through professional development, ongoing support, etc.

So those are the four entities that we operate under, and we’ve helped place more than 1,000 people per year into jobs annually, not only in Chicago, but beyond Chicago through our affiliations as well. And we’re also helping to shift some of the policies and perspectives that happen in hiring today. So really excited about that work.

Kevin: One of the reasons why I wanted to have you on is because we hear so much about unemployment. We also hear about the fact that the unemployment challenge or the unemployment issues in this country are in many ways based on job reports getting better. But still half the folks in this country live at or near the poverty line. And for those who don’t have the necessary skills, and we know our education system, two-thirds of America’s high school graduates are neither career nor college-ready. So we know that there is a growing number of the population out there that is not ready to enter the workforce.

And I remember years ago, when I was a public official in D.C., I worked with several members of the clergy, and we developed something similar to what you’re doing on a small scale in my councilmanic ward. And we called them grace jobs where we would work, you know, with employers on training folks to get them the skills they needed. And then, you know, at the Safeway or back here was the Giant supermarket, we had certain employers, you know, the utility companies who would volunteer or designate a handful of jobs. So every year we knew that we could place, you know, a few hundred folks into these jobs. Even though some of them may have come from the criminal justice system and may not have, you know, the certification, but we’re developing skills while at the same time, as you said, providing some many staffing support to get them placed. And we had employers who were committed to that.

Don’t you see that with technology increasing and the fact that you have to be significantly digitized to have a strong job, and don’t you see that there’s some tension there in getting people up to the skill level they need to be and having employers willing to work with you? Talk a little bit about that, because I still see that as a huge potential gap.

Dr. Caliento: Absolutely. And I couldn’t agree with you more. We are seeing many more roles that require access to an understanding of technology, digital roles, etc. And so what we’ve done even here at Cara Collective, as an example, there was a program that started off in just one of our co-location spaces, in Belmont Cragin, working with Northwest Center. And we had offered to the residents and participants that we were working with in that neighborhood and that community, digital literacy services. And what our amazing chief program officer realized is this is actually something that is needed and required by all of our participants, knowing and recognizing the role that it plays in many jobs. And so that is now a permanent piece of all of our programming that we provide to all of our participants and job seekers.

The other thing that I’ll say too is we also recognize that many of our job seekers have not traditionally or historically had access to tech careers. And so we are starting to work with organizations to think about how do we train and prepare our job seekers for positions in those careers that we know can pay upwards of six figures? And so allowing them the opportunity and the access to say, “You can do this, and here’s a pathway for you to get there,” is something that we’re deeply committed to and we’re excited about growing.

Kevin: One exciting thing also is the fact that schools are slowly but surely recognizing that skill development should be an essential part of their offerings. Many schools are putting together career academies, you know, school-to-career relationships with various employers. Talk a little bit about the role of schools because, you know, not only are far too many kids graduating without the requisite academic proficiency that they should have received, but they also don’t have the corresponding skills. And while we need to make sure that we continue to press to make sure kids can read, write, and count, and that they have those skills when they graduate, this idea of introducing young people as early as middle school to career pathways where they can get their certifications and use the virtual learning experience to help them, you know, accelerate their skill development even before they graduate, it’s a huge piece of that. And with the clientele you work with, you sometimes see the backend of that. But talk about why it’s so important for us to change our approach to even how we view the education system as it relates to workforce development.

Dr. Caliento: You’re speaking to my heart here just in terms of that connection, as we talked about earlier, between all of these social issues, right, societal issues, the education, healthcare, employment, and they’re all inextricably linked. And, you know, one of the organizations that I worked for prior to Cara did exactly what you’re describing, Kevin. We helped place middle school students in companies in downtown Chicago for a year, having a mentorship with someone, right? So if there was a kid on the south side of Chicago who loved math, he should know that KPMG exists and is a company that he could hone those skills at as an adult.

And so the sort of value proposition to companies was really this is the pipeline that’s coming up. And unless we help them understand the possibilities and the opportunities that are available and open to them out there, they’re not going to see that as an option, right? And so that young kid then might not major in math or econ or finance, or become an actuary, and know that he could work at, you know, KPMG.

And so that is just one example. And so I agree with you that that sort of we’re not seeing that interest be built and those connections be made. And so it is important that we continue to think about the connections between companies, corporations, and the school systems, right? How can businesses be much more engaged in those earlier formative years to help ensure that they are preparing and exciting young people for those careers and helping those young people see people like themselves in those careers as well? I think that’s a critical piece as well.

Kevin: So, Kathleen, this is my last question. This is what I really want to know. There are going to be a number of school administrators, superintendents, school leaders that listen. What advice would you give them if they’ve wanted to get involved in the career development space or at least expose their students to more of those opportunities, but they may not be sure how to do that? They may come from a rural or a small community where even the job market isn’t huge. What kind of advice would you give them in terms of providing more of these opportunities and options for their students?

Dr. Caliento: Yeah. I think that there’s a couple of things, right? So one, you know, particularly in maybe smaller areas that might not have opportunities, are there some local businesses where you might be able to form a partnership and have folks come in and share about the myriad number of roles that exist in their organization, right? And so I think that’s an opportunity. I think in larger school districts, there are, you know, career technical education departments and programs, and there are these formative relationships that can be formed between schools and companies. I’ve seen companies adopt schools and become sort of the school mascot in terms of a career choice and an opportunity.

But as we talked about, we live in a very digital world, right? And so if there’s a way to sort of bring on a panel of experts, even over a Zoom kind of a scenario to allow folks to see beyond their potentially rural, small-town environment and see what’s possible even beyond those virtual walls, if you will. And so I think there are lots of ways that schools and companies can work together to help excite young people for the possibilities that lie ahead.

Kevin: Kathleen St. Louis Caliento, I really do appreciate you joining us. And more than anything, I appreciate the work you’re doing for your clientele and the folks in Chicago. Thank you for joining us on “What I Want to Know.”

Dr. Caliento: Thank you so much for having me, Kevin. Appreciated being here.

Kevin: Thanks for listening to “What I Want to Know.” Be sure to follow and subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app so you can explore other episodes and dive into our discussions on the future of education. And write a review of the show. I also encourage you to join the conversation and let me know what you want to know using #WIWTK on social media. That’s #WIWTK.

For more information on Stride and online education, visit stridelearning.com. I’m your host, Kevin P. Chavous. Thank you for joining “What I Want to Know.”