Working with Individuals, Employers to Unlock Purpose, Potential, Passion, and Success

For over 30 years, Cara Collective has worked directly with individuals experiencing a number of barriers to employment work through their challenges, invest in their development, and get great jobs. They've also worked with employers to help them rethink their hiring procedures so that they don't miss hidden gems in their communities for any number of reasons. In this conversation, Kathleen St. Louis Caliento, the president and CEO of Cara Collective, shares her personal story to this role, the work of Cara Collective, and the stunning success they've had for over 8,000 individuals in helping place them not just in 13,000 jobs, but in jobs where they are more likely to persist and do work that matches their own sense of purpose. We explore what they've learned, how they've sharpened their process, their outcomes, and more. As always, subscribers can listen to the episode, watch it below, or read the transcript.

Michael Horn:

Welcome to the Future of Education, the show where we are dedicated to building a world in which all individuals can build their passions, fulfill their human potential, and live a life of purpose. And to help us advance that, today we have a great guest, Kathleen St. Louis Caliento. She's the president and CEO of Cara Collective, where she's been since 2021. She and I got to be on a panel together at the ASU-GSV Innovation Summit around the future of learning and work. And Kathleen, it is great to have you here. Great to see you.

Kathleen St. Louis Caliento:

It's so great to see you again, Michael. Thanks so much for having me.

Michael:

Yeah, you bet. So first, let's dive in. Tell me about the work that you do that CARA Collective does. How do you describe what the organization itself is?

Kathleen:

Absolutely. What I like to say is CARA Collective is an organization that helps people find themselves and then find jobs. We are a Chicago-based workforce development organization with a national footprint. And we have served over 8,000 individuals in helping to place them in 13,000 jobs. We understand the barriers, the particular barriers that many of our participants face, homelessness, poverty, health, child care, formerly incarcerated. And those are the barriers that often, unfortunately, keep them from employment. At the same time, we know that they are incredibly talented, and they have either found us because of a misstep, misfortune, or injustice, as we know prevails, unfortunately, in our society. And so the goal really is to figure out a way to help them, as I said, find themselves and find jobs. So Cara Collective is really comprised of four entities in the way that we do that. The first is Cara, which is our personal and professional training program. That's where we provide these workplace competencies to help them prepare for jobs. But also what's sometimes even harder is those social-emotional competencies, right? So we have workshops that are called Love and Forgiveness, and helping people truly understand what it means to rid themselves of some of the baggage, some of the myths, some of the narratives that they've been told their entire lives. And so those are the things that those personal and professional training workshops that truly help them get prepared for the workspace. As part of that, we provide these supportive services because, again, as we know, our folks are facing significant barriers to employment. And so connecting them to resources that help them address housing, homelessness, their health care, child care, if they have record expungements that need to take place as well. So those are the things that we're helping them with in terms of background services. Then we have two social enterprises because we recognize the need for some of our participants to truly begin to build their resumes back up. And some of them had significant gaps in their work history or facing particular records and backgrounds that were not being taken on by some employers. And so giving them those reps through some social enterprises. Our first, CleanSlate, is an external beautification company. And we work with social service districts, chambers of commerce, neighborhood organizations to help beautify the city of Chicago and its neighboring areas. In addition, Connex is our mission-driven staffing firm. That's where we work with employers who are looking for that temporary, sometimes temporary to permanent positions that we help to place our folks in. And then finally, the work of Cara Plus is our expansion. That's our expansion arm. We do a few things there. Number one, we work with other workforce development organizations like ourselves to think about best practices and how to continue to multiply their impacts, working with employers and their job seekers as well. But we also work with employers to think about what it means to truly be inclusive in their employment practices. So providing them supports as they're thinking about everything along the talent continuum from hiring, sourcing, and hiring to developing and retaining, in fact. And so that's the work of Cara Plus. The final piece that they do there is affiliation. That's where we work with local organizations who are looking to lift up workforce development programs and help them build those in their local communities. So really, really proud of the work that we're doing, the impact that we're seeing. Again, as I mentioned, the number of folks that we serve, but also retention is important for us. So a big measure of our success is that our folks are staying on the job longer than most folks. So our retention rate right now hovers between 65 and 70% for one year, same firm retention, which is really incredible, especially when you think about the national average being typically around 50 or lower percent.

Michael:

Wow. That's a huge number, just to say it, especially for these people facing these barriers in their lives that have held them back historically. I'll also say, wow, I love the integrated nature of what you all have built, not just the support in terms of skills or social emotional, but then we're going to help you with that first job in effect. We're going to help work with the employers to change policies that maybe have held back people like you that they didn't even realize that they were missing this talent historically and so forth. I want to get into more of that in a moment, but I want to actually just stay on you for a moment, your own path into this role, because you've had a really interesting career path as well. And I think people would benefit from hearing some of that conviction as well.

Kathleen:

Sure. Sure. And I think people who sort of know my background at first are sometimes surprised or interested that I've landed in the role that I am. But once you actually stop and think about the trajectory, it makes a ton of sense. So humble beginnings and roots, you know, daughter of Haitian immigrants who came classic American dream story to find a better life for their for their children. And and and unfortunately, often face the kinds of lack of access, lack of opportunity and inequity that many immigrants face in this country. And so, you know, they struggled themselves in terms of making sure that we had the right educational opportunities and in their own and being recognized for their own professional assets and what they could do. And so that's always been a driver for me thinking about the road, the tough road that my parents had. But even where I've faced some of that, some of that myself. And so the majority of my career, because my father was always about education, truly pushing education. And he would say something to me that was actually a little harsh that I've mentioned before, which is, you know, you're black and you're a woman. Unfortunately, you're not going to be taken seriously by anyone unless you have an education. And so that was really kind of like you got these two strikes against you. This is what's going to be the great equalizer for you. So do what you need to do to sort of get yourself where you need to be. And for him, that was truly education, which then doesn't surprise anybody that I ended up getting my doctorate from Columbia University in science education. But that truly led me down a road of education reform. And so it's really around thinking about education reform and educational equity. And the work that I did was various types of equity. How do we provide folks who didn't have access to data about their own children's performance, helping them understand what that what those data meant? Right. How do we work in Chicago to make sure that this every school has highly qualified teachers and principals leading in those schools? And so that kind of work, when you think about it, there are themes of access, equity, opportunity that continue to sort of run through those themes and through those through those experiences. And as I continue to move on through that educational equity work, I thought myself doing more education to career. So helping companies recognize the talent that was coming up through education that may not know that their job was an opportunity. So when I was working with a young boy, you know, from the south side of Chicago, who's interested in math, knowing that he could do work at a company like KPMG exists, right. And that's an opportunity for him. And so really helping them build bridge those mentorships and helping the young folks understand the power of their own possibility. And so that was truly those those last couple of roles were really around that kind of education to career space. And so that now we find myself I find myself squarely in that in that career workforce development space, which, again, when you think about the social determinants, education, health, employment, these are inextricably linked. And so it's really not much of a stretch. It's really more about the what I was trying to do. It didn't really matter how I was doing it.

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Michael:

No, it makes a ton of sense. And it's inspiring to hear the story and then how that's translated to the here and now. And I want to dig in because you talked about, you know, your first answer, the full integrated nature of all that you're doing. But as you said, you know, that starts with a lot of deep work, right, with each individual, each job seeker. And so I'd love to know, you know, the skilling and so forth like that's part of it. But I'd also love you to talk about, like, what are the conversations and interactions look like at the individual level? Like what's that process? You talked about the best practices and so forth. What's that process that you've developed to take them through on their own journey?

Kathleen:

Yeah, absolutely. And so, as I've mentioned, you know, we've had we've had more than 30 years in Chicago leading this work in workforce development, working with folks that have experienced a number of barriers to employment. And so when I think about the impact that we've been able to have, it truly is meeting people where they are, right. And so the way we know that no one's journey out of poverty is the same, which is why from day one of working with us, they meet with our admissions team. We begin to understand who are they? What are the challenges that they're trying to overcome? Where have they been? What are the stories that they've told themselves, right? What are the what are the what are the untruths that they believe about who they are and what their what their possibilities and limitations are? And start to think about what role that we can play in helping them achieve and realize their dreams. You know, community is such a core value in terms of who we are. And we were founded on that belief of it takes a community to lift someone up and out of poverty when they're experiencing particularly such a low point, which, by the way, is often an unknown piece. But that's the origin of our name. Right. So many folks often think that Cara means is an acronym. And it's a fact, in fact, an old Gaelic word, old Irish word for friend, because we know that everyone needs a friend when they are at their lowest point. And at Cara, we we we talk about community and how important that is. And so our job really is to walk alongside each individual. So, again, from the beginning of our recruitment team, we're talking to them about what their needs are. And from that, from the beginning, we're connecting them to those resources that I mentioned earlier in terms of housing, child care, health, et cetera. They move on that into the training program that I mentioned, that personal and professional development training is a foundation series where they're truly just understanding some of the workplace competencies, but also understanding who they are as a person. And then once they've gone through that, which is about a four week program, they then move into what we call our leadership program. And they're really starting to think about more and then they become what we call send out eligible. So they are ready to be put in front of a an employer. They've demonstrated those the five competencies, training, excuse me, teamwork, timeliness, professionalism, conflict resolution and communication. So those are the five that we work with companies that say these are the skills that we want folks coming in with other things that we can teach. But these are the skills that are going to be important to us. So once they've demonstrated that, we then work with the over 70 employee employment partners that we have to find that right person. And it really does help when we understand who our participants are from the individual perspective, because then we can put them in that right spot. And so that's that's that's their journey with us. And in fact, you know, many folks think that once we place them, their work with us is in our work with them is over. But in fact, you don't graduate graduate from Kara once you get the job. We actually stay with you for another year. So we provide individual coaches to each of our job seekers for up to for a year into that that first job, because we know that once they get that first job, their problems don't suddenly disappear. So how do we ensure that they have someone, they have a network and a community that they can fall back on when we need them, when they are needed the most?

The Myth of Average

Michael:

Something you just said sparked something for me, which is that, you know, there's this aspect of your program, you've been working with individuals at the individual level, right, for decades now as an organization. So you've been able to do a lot of continuous improvement. But you also said no individual, right, is in the exact same circumstances, like there's some tailoring to that individual's needs. So you've been literally working at the level of what I would call N of 1, as opposed to like average effects, right? You see the average, but you're actually able to identify the individual circumstances and so forth. And so my instinct is that you're sort of able to get below the best practices or average effects right at a population level and say, like, actually, you know, we've seen this individual, like we understand their circumstance. And we can have a deep sense of what causes them to maybe struggle in their workplace or conversely, sort of how do we help them thrive to be able to live a life of purpose and fulfill their potential? And so I guess my hypothesis is that you've been able to change how you approach people based on identifying these individual circumstances and patterns over time that maybe wouldn't be apparent at a macro level if I'm an economist, you know, collecting a big data set and sort of looking across the population, maybe that's wrong. But that's sort of the instinct I have. And so you can correct me if I'm wrong, number one. But if I'm right, I'm just sort of curious how the organization use this end of one data and specific circumstances to really improve the individual interactions and success rates over time.

Kathleen:

Absolutely. You know, and I love the way that you're thinking about that and framing that question, because, you know, it's sort of two sides of the same of the same point in that, yes, there's this idea of this end of one and we know that everyone has their own individual story. And I think understanding and hearing multiple stories over time, you also you also generate some themes and some trends. Right. And so and so I think that I'll say a couple of things. One, ensuring that we have the ongoing individualized feedback from our participants is key so that we provide opportunities for them to provide us feedback at multiple steps throughout the process from that, you know, from our from the intake perspective, intake point right at the beginning to, you know, a week or so into a few weeks after they've completed the program to a couple of months after they've gotten their first job and so on and so forth. And so having a better understanding of are we actually, in fact, meeting the needs of our participants is critical. Another example is what something that we talk often about at CareCollective is this idea of transformation, helping really our our jobseekers transform their lives. And you can't do that top down and you can't do that outside in. Right. That's got to be coming from the people who know themselves the best that say these are my goals and dreams. These are the things that I'm trying to achieve. And so one of the things that we work hard at is helping our jobseekers develop and define goals that they want to achieve for themselves. Right. So so this idea of, you know, and of what it might be that, you know, one person says they want to finish that they want to open a bank account and one person might say that if they want to have their first apartment, both of those are financially driven. Right. And so we might bucket those to say that we have folks who are interested in thinking about their financial a financial goal that they want to achieve. But that looks different depending on the person that you're talking to. Right. You might have somebody who says, you know, I want to go for a different job in my in my current career or I want to, you know, finish my my degree so I can have different skills that are opening up for something else. That's kind of thinking about career advancement in some way, shape or form, perhaps coming at it different ways, but really thinking about it in different ways. And so having folks drive that is important, is important for us. So so those are those are the few things that I would say we think about as we think about, you know, so how do we use this and want to actually help us do our work much more impactfully?

Michael:

I love that answer. And it's actually interesting. I didn't expect it to go this direction, but it's mirroring the book that I'm working on right now about how to help people switch jobs. And one of the things we constantly hear, right, is they'll say, oh, I want more money in my next role. And we unpack that with them. Like, what does that actually mean? Is it about because, like, you want to be better respected? Is it because you have to afford child care and like child care is expensive? Is it because you're trying to save for your retirement and like be able to step back at some point? Right. And the answer to each of those questions, that why underneath money actually points you in very different solutions once you understand sort of that deeper why. So I love that you're sort of able right to go down that journey with the individual and really help understand what is what is best for you, which might be different from best from someone else that you're working with, if I'm understanding correctly.

Kathleen:

Absolutely. Absolutely right. That's absolutely right. And I love that you're you know, I think that we often talk about also just you're making me think about this idea. And I think we've already been brought it up in the panel that we're in. But this idea of dignity of choice. Right. And so it's something that we think about often at Care Collective, because one of the things that we don't ever want to appear to be doing is forcing people to be thankful for any job. Right. And so this idea of what are your dreams? What are your aspirations? Right. So that that question of you kind of double clicking and saying, why is it that you actually want more money? What is it that you're actually trying to achieve? Going double clicking is so important for someone to be seen and to feel as if they do have dignity in terms of charting their future.

Michael:

I want to geek out on this one more bit with you, because I'm curious, like how you help people to even articulate those dreams sometimes? Because sometimes like people, you know, you mentioned about the individual doesn't know what KPMG is. I always say you've heard me say it. I grew up in Washington, D.C. I didn't know that engineering was like a possible pathway in the world. Right. I thought that was like a train conductor or something. So, like, how do you help them articulate a dream that they may not fully understand themselves or have the social capital to be able to articulate?

Kathleen:

That's such a great question. And it's a balance, right, because we could be so excited and say, no, you really want this job. And it's like, is that really their dream? Right. I have a colleague who talks often about how to ensure that we are offering opportunities to our participants that that stand beyond food, files and floors. Right. And that's sort of a gross oversimplification of these entry level roles that we know exist and that many of our job seekers go into. And to me, probably the biggest way to do that is to offer them exposure and opportunity. Right. And so you didn't know what an engineer was until you knew what an engineer was. Right. And when they see the diversity. So for us, it's our responsibility to ensure that we have the diversity of industry in terms of the employers that we're working with, but also in terms of pathways that we provide, skilling or training and that we're in preparation for in terms of our job seekers. And so it truly is that exposure. It's the knowledge, it's the awareness and that that leads to equity, because if someone knows that this is an opportunity and a possibility, they might go for it. Right. And so it's helping them understand and see something that they might not have seen.

Flipping Supply and Demand in the Labor Market

Michael:

Fascinating. So let's flip to the other side of the equation now, because as you mentioned up front, you're not just working with the individual job seekers. You're also connecting their demand to the supply. And I know I'm talking about this differently from for most, I suspect, when you talk to labor economists, they're like, no, the, you know, the employers of the demand side and the people or the supply, the human capital, from my lens, like I think of it like no individuals are demanding progress in their lives. They get to hire that next job. It's that element of choice that you just talked about. So I suspect it matches a little bit of what you're talking about. But when you talk to those suppliers of jobs, otherwise known as employers, how do you help them move beyond, you know, those applicant tracking systems and the filters and the biases, right, that are sprinkled throughout their processes that would, you know, that otherwise they'll miss the hidden talent that's right in their communities.

Kathleen:

Yeah, absolutely. And that bears repeating. Right. Each year we know companies miss out on thousands of motivated job seekers and employees due to just their own internal processes. And these processes are ones that prevent folks from joining and at the bar and staying at particular firms. Right. So losing this kind of talent, we know, costs companies millions of dollars annually. But it can be these are fixable problems. These are fixable problems. And so this is truly a big focus of the work that we do with our Care Plus arm that I mentioned earlier and through specifically through our Inclusion Action Lab one is one specific way there. We've worked with more than 30 companies to date nationally and really helping them rethink everything from how they recruit, what's on their job descriptions, what might even be the platform those job descriptions are placed on to hiring policies and how they're retaining to thinking about how whether or not managers who are supervising untapped talent are well are trained adequately to be able to provide the kinds of support and guidance and development that untapped talent who might find themselves in environments that are new for them, making sure that they have the resources and tools necessary as well. Otherwise, we know that they're, again, missing out on a big piece of the population. So, you know, what we have found, which is which is really wonderful, is that more than 90 percent of the folks who've attended our Inclusion Action Labs have actually identified shifts to their job requirements or hiring processes or other practices that they engage in to either attract or retain untapped talent. One global firm, in fact, reported that they were able to hire more than 100 additional people annually because of shifts that they made in their job requirements. So, again, we know that these are fixable problems. And I often say that it's not I don't I don't find that it is a matter of will. I think it's often a matter of way. Right. And so where do I start? Where do I begin? How do I even start to think about this? Right. And if you're not used to going to diverse places to find that talent, you know, how do we help you get there? And so that's really the work that we do in helping to shift some of the mindsets.

Michael:

Yeah. So that seems like such an interesting point, right? It's not will, it's way. And because and you just have the data to back it up. But it seems like so many employers right now are dropping degree requirements. Several years ago, it was, you know, banning the box around marking if you'd been incarcerated. Right. And things of that nature. And yet, like the needle hadn't fully moved. And I think what you're saying is like, well, that's because, like, yeah, the intentions are great, but they have to do more in the process. Like there's more work to be done that we know can be done to actually change those outcomes.

Kathleen:

Absolutely. And it's absolutely right. That's absolutely right. I was at an event recently where the chief human resources officer talked about a couple of things that they did. One was right. They wrote a little disclaimer at the end of each of their job descriptions that said something along the lines, slightly paraphrasing, but it was something along the lines of, you know, research shows us that women and people of color often are unlike or least likely to apply for a job where they don't feel like they check all of the boxes. If you don't feel like you check all the boxes, but this is something that interests you, we encourage you to apply for this role anyway. And just like that is just so powerful to read. Right. And to think about that, you're saying I don't have to check all the boxes, whereas this was my thought going into this of like, I can't do this. I don't have all these requirements. And to provide that kind of push and nudge to somebody who might have been on the fence anyway to apply for something to say, OK, maybe I'll go for it is incredible. So it's just thinking about, you know, small shifts, again, that are so possible that would open up the aperture in ways that we that we haven't seen.

Fulfilling Purpose

Michael:

Terrific stuff. Last question, as we start to wrap up here, which is, you know, from my perspective, you're not just in the job placement business. Right. And you've said it yourself, like that may be the product, but it's much larger than that by placing these individuals in a job. And as you said, you're not just placing them like you're putting them in a place where they're going to succeed. They're going to retain. Right. Crazy, you know, much higher rates than we otherwise would see. It seems to me you're really helping them make progress, meaningful progress in their lives, you know, claim their dignity, helping them fulfill purpose. Can you just speak to what that looks like and how perhaps job placement becomes an entryway into something larger, both for the job seekers and employers themselves?

Kathleen:

Absolutely. You know, and that's the exact right phrase is to help folks claim their dignity. You know, I think I described it earlier as helping them find themselves and then find jobs because that's just as critical and just as important. And we often, as I mentioned, think about that dignity of choice in a job and what that does to someone's confidence in their ability to say, maybe I can go for that next thing now and that they do have the right to choose their own career. And so that pride in creating your own path and creating your career creates that ripple effect in your family, in your community. And you inspire others. I'm thinking of a young woman, Bridget, who is just an incredible force. She's quite the firecracker if you meet her. She's been a member of our community for more than a decade. She's worked in Cara, worked in her Cara place for seven years, but she ended up leaving it in 2020. We all know what happened in the world then. But she returned to us back in about two years later, ready to work, ready to do her next opportunity. Her personality, her determination, her skills honestly would have made her best fit for any job. But she wasn't getting those opportunities on her own, which is what brought her back to us. She was persistent in truly looking for the job that she wanted. And I remember her saying to me, you know, I hope my coaches don't get mad at me because I know they're wanting me to go to some of these interviews, but that's not what I want. I know what I want, Ms. Kathleen, is what she would tell me. And today she is in that role. She's in that role that she wants. It's actually at Deloitte and she is thriving. We've received such positive feedback from her supervisors. I get notes about what she's doing there every day. And she's celebrated actually her year, what we call the Great Wall. So once you've made your year, you get on a plaque. We invite supervisors back, the participants and the job seekers back to celebrate that they've lasted in this role for a year. So, you know, her story really shows us there's true power in that dignity and being able to choose your own career path. And we know that when you focus on transforming individuals, you transform their families. You, in turn, help transform those communities that have been historically disinvested in. So this is a ripple effect that we're that we're continuing to see and one that we're we're incredibly proud of.

Michael:

Very cool. Transforming individuals, family trees, communities, employers. Very cool work, Kathleen. I'm very thankful that Stand Together brought us together for this conversation a couple times now. Thanks so much for the work that you all are doing.

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