Meeting Learners Where They Are

Introduction

Nolan: Welcome to the Learning and Development podcast sponsored by Infopro Learning. I’m your host, Nolan Hout. Today, we have a truly fascinating podcast in store for you. We’re going to be talking with Michelle Chipman, the Director of Restorative Initiatives at Pay Tel Communications. And we’re going to be talking about creating learner-centric strategies and specifically focusing on meeting learners where they are.

What makes this such a fascinating conversation though is that Michelle’s learners are incarcerated. And as I found out in our podcast today, there are many parallels between her world and our world that I think this podcast is going to be entertaining and educational for anybody in the L&D field. With that, let’s go ahead and meet our guest.

Hello, Michelle. Welcome to the podcast.

Michelle: Hi.

Michelle’s Career Journey

Nolan: Michelle, I appreciate you joining and sharing some of your knowledge with everybody today. Much of what we’ll discuss today revolves around meeting learners where they’re, and I’m excited to explore this topic with you. But before we do that, I’d like to open up as we start with every podcast and learn a little bit more about your role, not at Pay Tel where you are today, but what was your journey?

To get there, we recognize that many people in the learning and development field don’t necessarily follow the same path. They zig, they zag, they take different routes. How did you get to where you are today?

Michelle: Currently, I am the Director of Re-entry Initiatives at Pay Tel Communications, focused on our educational solutions for men and women who are currently incarcerated. And that’s a good question about the journey, and you’re absolutely right, a lot of zigs and zags. I was in college doing not much of anything, not invested in anything. I’m sure that’s not new to anybody. And I had a friend who became an insurance agent, and I was like, that sounds fun, I guess. I don’t know why that’d be fun to a 22-year-old, but it was. Did that, you can make some pretty decent money being an insurance agent when you’re 22 and start with a company.

I loved the statistics and customer service aspects of it, and I geeked out about insurance; ask me about Inland Marine sometime. And it was a larger corporation, and they had something called corporate training, and I was, what is that? What do you do there? What’s all that about? Tell me more. Started doing more research and education on that side, learned that it is a very interesting career, a very interesting job for people to have moved into corporate training with that company, onboarding new agents and sales training and management development. Then in 2016, I had another friend that said they work with inmate communication. I was like, what is that? What does that do? That sounds interesting, and it’s much more tech-based, software-based.

I joined Pay Tel on the other side of it. It was primarily focused on client support, including software training and onboarding for new clients. We wanted to initiate this project and conduct a deep dive into providing an educational solution for incarcerated men and women. And I was, that’s interesting. How do you plan to go about that? And shoehorned my way in. I’m overly curious and overly nosy, and that has brought me to where we’re at.

A Career Shift into Training

Nolan: That’s a great point—the idea of being curious. I believe his name is Simon Brown. He was the CLO at Novartis for some time and is now a partner at EY. He co-authored a book on curiosity and how it’s a vital strength for success in any field. I truly believe there’s a strong link between people with curious minds and those who find their way into learning and development.

I had a question for you—when you were in insurance, you started in sales and later transitioned into training, correct? Was there something specific that drew you to training? Or did someone recognize your talent, assign you that role, and you ended up enjoying it? Or was it more of an internal drive where you thought, “I want to do this”?

Michelle: Yes, I think being a bit of an insufferable know-it-all helps. I believe many learning professionals share that trait—it’s the tendency to geek out over things that others might overlook. What really drew me in wasn’t just the sales side, but the customer service aspect—the science behind customer engagement and the process of connecting with individuals.

That piqued my interest. It’s not that some people are just naturally good at selling; there are techniques and practices that can be taught and refined, which ultimately help grow the entire company.

For me, it started with asking the right people the right questions—those in the department—what do you do, how do you do it, what’s involved? Showing genuine interest, doing the background work, and being curious about all aspects of the organization and its functions—that’s what led me here.

Incarceration Demystified

Nolan: That’s great. Many of the guests I’ve had on the podcast have discussed the importance of acting as a consultant in L&D—really understanding the “why behind the why.” These ideas are deeply connected and lead us into our current conversation about meeting learners where they are.

One of the key points you raised earlier was that people often jump straight into thinking, What do I want to create? or How would I want to deliver this education on XYZ?—instead of first asking, Who is the learner? What do they need? What will they gain from this?

I’m excited to explore that further. Michelle, it might help if you could give a quick overview of your world. I remember when we started working with your team—I’m not sure how long ago that was—but it remains one of the most fascinating and fulfilling projects we’ve been part of. Could you share a bit of context about your environment, since it’s quite different from what most corporate learners experience?

Michelle: Absolutely. It can be a bit complex to explain because it’s multifaceted. As a company, we provide technology solutions for confinement facilities. More specifically, we focus on local community jails. Most people, when they think of incarceration, think of prisons or Departments of Corrections (DOCs), but our primary focus is on these smaller, community-based facilities. Every town or county typically has one.

We offer communication services—incarcerated individuals use the telephones in the facility through our system, and officers use our investigative software to monitor activity and ensure that no crimes are being facilitated from within.

What’s unique about our work is our provision of educational solutions to incarcerated individuals. This was a relatively new area with only a few players involved, and their focus was mostly on prisons and DOCs—larger state and federal institutions that receive more funding and grants, where individuals are incarcerated for longer periods.

In contrast, small community facilities often lack access to those resources. That’s where we saw an opportunity. We wanted to approach education differently. When people hear the word “education,” they often think of GED programs, college preparation, or K-12-style learning. Our model is more intervention-based.

We begin with a risk-needs assessment, developed in partnership with your team, before someone enters our platform to understand key areas of need. Do they feel safe where they live? Are they unemployed or underemployed? Are they struggling with addiction or substance use disorder? Are their relationships safe and supportive? Based on that, we offer resources tailored to those needs.

Understanding how relationships impact a person’s life is essential. Even in corporate settings, we ask: what do learners expect to gain from training? Similarly, when we talk about incarcerated individuals, it’s clear that their goal is not to remain in confinement. Our focus is on providing resources and education that empower them to make better choices after release—choices that help them build the kind of life they define as successful.

On the flip side, this is something I often emphasize: because we work with community jails, the individuals using our platform are your neighbors. Whether you’re at the grocery store, the bank, or a PTA meeting, you could be sitting next to someone who has engaged with our learning materials in a correctional facility.

This work is about more than rehabilitation—it’s about broader community engagement. It’s a holistic approach to improving our communities and neighbourhoods—making them safer and more fulfilling for everyone. When we remember that these individuals are part of our shared community, it brings a sense of realism and urgency to the work. That’s a perspective we always strive to uphold.

Parallels Between Incarcerated and Corporate Learning

Nolan: When we talk about delivering educational experiences to your learners, you mentioned some unique demographics—or rather, unique circumstances. Compared to a corporate learner, what would you say are the essential needs or table stakes for your audience? Since you previously worked in insurance training—which is likely more relatable to the typical audience listening to or watching this podcast—what are the broad similarities you see between these seemingly different groups of learners?

Michelle: That’s a great question. One thing we need to stay focused on with any learning group is how to translate a person’s lived experience—whether from incarceration, working in insurance, or at a grocery store—into the skill set we’re trying to teach.

In insurance, for example, many people reference sales techniques like the SPIN method, but at its core, it’s about risk mitigation. You’re a parent, and I’m a mom—we can talk about life insurance in terms of what it is and who it protects. That’s using someone’s personal experience to make the concept relevant.

For a younger learner, you might frame it around financial risk if something unexpected were to happen—again, it’s about risk mitigation. You’re using the learner’s background to connect with the skills you’re teaching.

It’s the same with incarcerated individuals. Most people might not realize it, but they are developing valuable skills in that environment—especially interpersonal skills from navigating a confined space with people from diverse backgrounds. Those can be directly translated into employability and social skills after release. On a scale we may never fully comprehend, they are placed in an environment with strangers from diverse backgrounds, living together 24 hours a day. The ability to navigate that setting builds skills that can directly translate into employability or social competencies. The key is not just focusing on the upskilling itself, but understanding how to connect their lived experience to the new skill—and helping them recognize the strengths they already bring.

Breaking the Cycle of Negative Learning

Nolan: I think a lot of that highlights the pros and cons of different learner environments. For example, in an insurance learning environment, a common challenge is that people don’t have time. In a call center, any time spent on training means being off the clock—so employees aren’t earning money.

In contrast, for someone who is incarcerated, the situation may look quite different. What stood out during our conversation was that it’s not necessarily about the learning content itself, but rather about understanding the individual circumstances each learner faces on a given day. Everyone’s situation is different, so how can we design learning programs that account for those differences?

One point you brought up, which I hadn’t considered before, was the impact of negative educational experiences and the importance of addressing them. It reminded me of a podcast I did with a woman who worked on bias reduction through simulation training. She said it’s incredibly difficult to educate people on bias because the moment you say, “This training is about removing bias,” people get defensive. They immediately respond with things like, “I’m not racist—I have friends of different races,” and so on.

That’s why their approach was so effective—they didn’t tell learners the purpose up front. Instead, they allowed them to uncover it themselves, which helped bypass those negative educational associations.

So I’m curious: what kinds of negative learning experiences are you working to overcome in your environment?

Michelle: Absolutely. That’s something we had to learn—understanding the barriers that prevent someone from engaging in self-help or education. A key factor is whether the individual is ready to receive the information.

Let me speak specifically about substance use disorder or addiction recovery. It’s one of the hardest things for a person to admit. It’s difficult to say, “I’m an addict” or “I struggle with addictive behaviors.” So we begin by asking softer, less confrontational questions.

We collaborated with a professor of criminal psychology to determine the best way to frame these questions. The goal was to help someone acknowledge an addiction issue without forcing them to state it outright if they weren’t ready.

For example, we might ask, “Do you find yourself spending more money than you’d like on drugs or alcohol?” This doesn’t directly label the individual—it instead invites them to reflect on whether substance use is impacting other areas of their life.

Nolan: In a very real sense, money is a tangible resource. When you’re asked that question, it makes you pause and think—how much am I actually spending, and how much disposable income do I have? It immediately draws me into the conversation.

Michelle: Yes, absolutely. If they answer yes to that, it’s a gentler way of acknowledging the issue.

When it comes to relationships, this is often the most difficult area. Asking someone directly, “Are you being abused by your partner?” or “Are you abusing your partner?” is incredibly hard—both to ask and to answer. A person has to be truly ready to say, “Yes, I’m in an abusive relationship.”

Instead, we ask more reflective questions, like: “Do you and your partner argue more often than you’d like?” or “Do you find yourselves having repeated conflicts throughout the week?” These softer questions still gauge the same concern but in a way that feels less confrontational and more approachable. They open the door to further conversation.

The same applies to parenting. If you ask a parent directly, “Do you have a bad relationship with your child?” the answer will almost always be no—because most parents believe they’re doing their best.

But if you ask, “Would you like to improve your relationship with your child?” you’re more likely to receive an honest and open response. From there, you can guide them to explore relevant course topics in the catalog. It allows them to make a choice and acknowledge the issue in a more comfortable way—perhaps even thinking, “I’ll read this because I know someone it might help.”

Nolan: What’s fascinating about that is it reminded me of a great sales book I read called The Jolt Effect, which is a follow-up to The Challenger Sale. I’m not sure if you’ve read it, but it came out about a decade ago, and the follow-up discusses how fear, uncertainty, and doubt are increasingly affecting how people make purchasing decisions because of the perceived risk.

I was talking to my brother, who’s planning to implement some of these ideas at his company, and we discussed how difficult it is to get salespeople to admit they’re not the best at what they do. I’m drawing a parallel here—obviously, what you’re doing has a much greater impact on the individual—but similarly, a salesperson will rarely admit they’re not top-tier. Part of their success comes from their confidence.

The real challenge is getting people to care about the training program. I was thinking—what kind of questions could lead them there? Something like, “Are you earning as much commission as you expected when you joined?” or “Are you closing as many deals as you thought you would?” These are questions that can guide them toward recognizing the need for support, without forcing them into it. As you mentioned, it’s about making it easier to say yes. That was such a powerful insight you shared.

Michelle: There are things we’ve had to focus on that, in hindsight, I probably should have prioritized 15 years ago in my career. This audience forces you to think more deeply about those situations—and those insights can be translated elsewhere. We still conduct corporate training at Pay Tel, and although I’m not directly involved in that, we’ve applied many of the techniques we’ve developed on this side.

As you mentioned, incorporating simpler ways for learners to say “yes,” offering more choice, and using a more flexible, open-catalog approach to training—these are universal concepts that work across contexts.

Trauma-Informed Learning and Its Importance

Nolan: There’s another topic we wanted to explore—trauma-informed learning and how to design content with that in mind. I’m not very familiar with the term. What does trauma-informed learning mean?

Michelle: Yes, and I want to clarify that I’m not an expert in this area. I can share some sources, but there are true experts in the field. That said, as I mentioned earlier, a key part of our approach is translating individuals’ lived experiences into opportunities for upskilling.

This also means being mindful that certain topics, which may not seem sensitive to us, could be deeply triggering for others. When designing anything related to relationships, for example, we need to avoid making assumptions. Not everyone has a foundation of positive relationship experiences.

It’s important to recognize that certain behaviors, even seemingly positive ones, can stem from trauma. When we present content, we take a highly analytical approach to consider how it might be perceived by someone in active addiction, someone with a history of difficult relationships, or someone who has experienced educational trauma—such as being placed in alternative schools or facing repeated failures.

We have to remember that behaviors labeled as “negative” may, in fact, be signs of past trauma. So how can we be sensitive to that? How do we address it?

Take, for instance, someone who is slow to trust. This may be due to a history of incarceration or other difficult experiences. If we’re trying to upskill them in a customer service or sales environment, we need to understand that hesitation might stem from deeper issues.

It may not be appropriate to confront that directly, but as we write content and design programs, we must acknowledge that some behaviors could be trauma-related. Doing some research in advance helps ensure we create content that is both effective and informed.

Challenges in Correctional Education 

Nolan: I’ll draw a few parallels here. I was speaking with someone from Deloitte yesterday, and he mentioned that we need to improve how we structure smaller learning cohorts to better segment and target audiences. That thought came back to me as you were explaining trauma-informed learning.

It reminded me of sales training—an example I often reference. In a typical sales team, depending on the sales type, about 50% of people might not be hitting their targets. That becomes part of the culture: large goals, with maybe 80% achieving them, or sometimes only 70%. When you ask people what they want to improve, they might respond, “I can’t pay my bills,” or “I’m struggling.” You’ve now created stress. Instead of empowering them, your program may have triggered anxiety by highlighting areas where they already feel inadequate.

That’s a perspective I hadn’t considered before—how a training program might negatively impact someone who’s already struggling. You might be unintentionally deepening their challenges.

Now shifting gears, Michelle, since you lead many of these programs—what are the main challenges you face in the correctional setting? Do you deal with budget constraints? We do. Do you struggle with finding subject matter experts? Because we certainly do. What about learner engagement? From an organizational standpoint, what are the key obstacles in your environment?

Michelle: Absolutely—budget issues, subject matter expertise challenges, engagement concerns—we face all of it. Let me walk you through the SME journey, which has been especially interesting.

Yes, we face real budgetary constraints. Our education program is entirely non-revenue generating. It’s not paid for by the learners, facilities, or through taxpayer funding. Instead, it’s fully supported by the revenue-generating side of the company.

As for subject matter experts, they’re scarce in this industry. Unlike the corporate world, where there’s an abundance of literature on sales and business, this space doesn’t have that depth of resources. However, we’ve discovered a powerful resource: formerly incarcerated individuals. Many don’t even realize they’re subject matter experts, but they are.

Thanks to our partners and networks, we’ve been able to connect with these individuals—people who have reentered society and built successful careers across industries, including higher education. We rely on their perspectives, especially in areas where our internal team may lack experience.

I have two instructional designers who create courses and work closely with these contributors. Together, they form the core of our learning content team. We focus on amplifying the voices of those with lived experience. Not everyone becomes a lawyer, professor, or entrepreneur, but every story holds value. We actively seek their input and collaborate with organizations that support reentry.

Their voices bring instant credibility. When someone talks about reentry or starting over, it resonates more deeply if they’ve actually lived that experience—sat on that cot, eaten that food, and endured that reality.

One of our biggest challenges, though, is that we have no direct communication with our learners. That was something I had to figure out early on, and it’s not a common situation in the learning field. It forces us to be creative about how we collect feedback.

There’s a saying that we have a “captive audience,” and it’s true—they’re not going anywhere. But at the same time, it’s hard because there’s no two-way dialogue. We can run basic surveys, but they’re limited—simple agree/disagree questions, typically on a 1-to-5 scale.

That said, the response rate is incredible. At any given time, we serve about 20,000 individuals. When we send out a survey, we often receive around 10,000 responses in just a couple of weeks. They genuinely want to share their feedback, which is great and helps us learn a lot.

Still, survey data is arm’s-length. It’s not a conversation. You don’t get the nuance, the back-and-forth exchange that helps you adjust in real time. Coming from a corporate background where I was used to direct interaction—whether in sales, training, or software onboarding—it’s a big shift. I could once read the room, sense when someone was confused or disengaged, and pivot on the spot.

Now, we release self-paced learning programs—and we hope.

Redefining Incarceration with Technological Innovation

Nolan: Great. We launch the content, hope for the best, and wait for feedback through a survey later. These are very familiar challenges. It’s difficult for us to secure budget because, in many organizations, learning isn’t well-funded—or it isn’t seen as something that drives direct revenue.

I understand that Pay Tel does have some revenue generation through other areas of the business. So the question becomes: how do we justify the cost of providing a service that doesn’t have an obvious link to revenue?

We face similar challenges. How do you demonstrate that a learner who’s more engaged ultimately brings more value back to the company? Most organizations struggle with this too.

Capturing the learner’s voice is also challenging. And while we’re not working with incarcerated individuals, the issue still exists. Our learners are not incarcerated, but we still face obstacles in engagement and feedback.

Honestly, it makes me think—next time I hear someone say it’s too difficult, I’ll say, “No excuses. Michelle’s working under far tougher conditions, and she’s finding a way.”

One final parallel I want to explore is related to technology. You mentioned the tools you’re using, and I was thinking about the scale—20,000 people. In your case, most of the learning is delivered through tablets, right? These 20,000 learners are actively engaged.

From what I’ve seen, your utilization is something most corporate clients never reach. If you compare it—20,000 learners on your platform versus 20,000 learners on a corporate platform—the difference is dramatic. You’re seeing 90% engagement, while corporate averages are closer to 10%.

So how are you using technology to create such a high-impact, engaging learning experience in your environment?

Michelle: Great question. There are others in this space doing impressive work in self-paced learning, and there are plenty of strong resources available for working with larger data sets. One principle we’ve consistently followed is balancing content with infotainment.

We ask ourselves: how can we make a traditional self-paced course feel more like watching a YouTube video or listening to a podcast? One way is by breaking the content into smaller, digestible chunks. For example, we have a parenting course that totals about 12 hours. Seeing a 12-hour course can be overwhelming, so instead, we offer it as a parenting series—divided into 20-minute segments.

And we don’t force learners to go through them in a set order. Each session is self-contained, allowing learners to pick and choose what’s most relevant. This approach leads to significantly higher engagement. If we can turn a four-hour topic into a five-minute session—even if that means creating 20 short courses—that’s a worthwhile trade-off for us.

Our learning design also includes video and audio, which is essential in our environment. We face several literacy challenges, so every piece of text includes an audio component. Additionally, many learners don’t have access to glasses in some facilities, which affects their ability to read. To address this, we ensure all written content has a text-to-speech or audio narration option.

This flexibility helps more learners engage deeply with the material. Some topics are especially popular—videos, interviews, and courses created by formerly incarcerated individuals see the highest engagement. Often, learners start with an introductory course. Take addiction recovery, for example: the first course might simply ask, “Do you spend more money than you’d like on drugs or alcohol?”—a soft entry point. It offers high-level insights without diving too deep.

From there, learners can explore more advanced options. They might choose a 10-hour course on harm reduction or an in-depth opioid education course developed in partnership with Harvard Medical. Having these accessible, low-barrier entry points encourages learners to gradually explore deeper content at their own pace.

Nolan: And it’s about personalizing that experience. If I remember correctly, Michelle, when individuals enter the facility, they receive a tablet that serves multiple purposes—one of which is educational. They can take surveys, and based on how they engage with introductory or teaser courses, the system builds a personalized learning profile that’s highly relevant to them.

That’s a powerful application of technology—ensuring learners don’t have to dig deep or be treated as if they’re all the same. For instance, someone might enter the system on a drug-related charge, but that doesn’t automatically mean they’re struggling with addiction. It’s important to let them chart their own learning path in a way that works for them.

I think we face a similar challenge, albeit in a different context. People say, “Well, you’ve got a captive audience.” Maybe so, but that doesn’t mean they want to spend 12 hours on a program. It’s not engaging. Similarly, a call center agent might have to ask themselves, “Do I want to spend an hour—maybe even in my own time—on training?” They’ll only do it if they believe the return is worth the investment.

It comes down to what’s in it for them. If someone believes that stopping a certain behavior could result in saving money, that might be enough of a motivator. In my experience, if you want to drive behavior change, tie it back to helping that person make more money—it’s often the most compelling motivator.

Technology plays a huge role here. It allows us to break learning into smaller, manageable chunks and makes it easier for learners to say yes to investing time in their own development. That was a major lesson during COVID. Everyone suddenly had to move to digital learning. We bought platforms like LinkedIn Learning and OpenSesame, but people still didn’t engage. They kept saying they wanted access to better training—and yet, those platforms alone weren’t the answer.

LinkedIn Learning isn’t a training strategy. You still need to design meaningful learning experiences that connect with your audience. Technology helps, especially in collecting data and creating personalized experiences.

Closing Thoughts

Nolan: Michelle, I have to say—knowing a bit about your world, I didn’t expect to see as many parallels as I do now. But this conversation has really changed my perspective. It’s helped me rethink challenges our learners face by looking at them through a completely different lens. You’ve reminded me how critical it is to understand who the learner is—often more deeply than we assume we do.

And honestly, the challenges you’re addressing are so immense, they make mine seem minor by comparison. You’ve not only shared your insights but also inspired a new level of appreciation for the work you’re doing. Thank you so much for being here. It’s been an absolute pleasure.

Michelle: Not at all. Thank you for having me and allowing me to share a bit of my experience. Before I entered this world, I didn’t even know it existed. It has truly been eye-opening in many positive ways.

Nolan: Wonderful, thank you, and I’m sure we’ll catch up again soon. Bye.

Michelle: Bye.