Designing an Interview Prep Platform for Formerly Incarcerated Citizens

Product Design Intern @ FreeWorld
Fall 2023


We all know that interviewing for jobs is difficult...but, as it turns out, it's even more so impossible for those formerly incarcerated in the US prison system.

As a Product Design Consultant at FreeWorld, I worked to build the initial workings of an interview prep portal to help FreeWorld's formerly incarcerated program participants (FreeAgents) prepare for their first ever trucking job interviews.


Product Designer


5 Weeks (Oct to Nov 2023)


FreeWorld Product Design Team & Success Coaches


Cynthia Chen, Grace Roseman, Lucy Chen, Isabel Martin


Competitive Analysis, Sketching, Crazy Eights, Info Architecture, Lo-fi/Hi-Fi Prototypes, Usability Testing, Visual Design


Figma, Figjam, Zoom


FreeWorld is a mission-driven non-profit that aims to provide formerly incarcerated program participants with the resources and training needed to obtain a Commercial Drivers License (CLD-A), helping move these citizens from prison to truck driving.

FreeWorld is a tech-enabled nonprofit that aims to end generational poverty and recidivism by accelerating economic mobility for returning citizens. At it’s core, FreeWorld supports formerly incarcerated people in getting living-wage jobs in the trucking industry. Read more about FreeWorld's operations here at


But getting a CLD-A (trucking license) is just the first step of the process. After obtaining this license, program participants need to interview and land their first trucking role! 

While a majority of FreeAgents (program participants) are able to successfully obtain their CLD-A, FreeWorld identified that there room for growth when it comes to guiding these FreeAgents through the interview process to landing their first job. Success Coaches (Instructors) at FreeWorld tend to bear the brunt of questions from FreeAgents about job interviews.  

While a majority of FreeAgents (program participants) are able to successfully obtain their CLD-A, it turns out that they're stuck when it comes to interviews — especially when explaining their backgrounds.


Program participants engage with FreeWorld through a mix of self-guided learning on the mobile app as well as live Zoom sessions. Knowing this, at the core of the problem...

How might we design an additional platform on the current app to educate and prepare FreeAgents to succeed in their first-ever trucking job interviews?


An add-on to the current mobile-optimized Student Portal that helps FreeAgents learn, practice, and prepare for trucking job interviews.

*Note: This prototype is designed specifically for Android devices, taking into consideration the fact that many of our alumni prefer and commonly use Android mobile devices.

Unpacking the Problem Space

Chapter 01


FreeWorld currently has a mobile-optimized Post-Program Portal that acts as the central hub for FreeAgents managing their time after graduating from the program.

While the FreeWorld program helps FreeAgents (program participants) navigate through obtaining an CDL-A license (trucking license), the help doesn't stop there. FreeAgents also have access to a Post-Program Portal, meant to provide resources and ongoing support post obtaining their CDL-A license.


It's clear why this is necessary to solve for FreeAgents...but why is this a business problem critical for FreeWorld to solve too?

We sat down with our stakeholders to understand the problem space and see why this was critical to solve for the business. Filling in these context gaps brought us to the following key findings —


For everyone, interviewing for a new job can be hard — and this is even more difficult for FreeAgents.

FreeAgents are often unfamiliar with the job-searching process at all due to their time in the prison system, and may struggle with knowing how to present themselves.


Employers (Trucking Companies) have expressed that it sounds like FreeAgents don’t have work ethic.

There’s opportunity to increase a sense of professionalism for FreeAgents and foster a better impression that FreeAgents, and FreeWorld, have for employers.


Currently, FreeAgents ask Success Coaches (Instructors) for interview tips informally. There lacks a formal process for this to be done.

Common FAQs include:
“What am I supposed to wear?”,
‍“How can I explain my background without getting into too many details?”.


Success Coaches are getting overwhelmed with the influx of questions from FreeAgents around interviewing.

Success Coaches (FreeWorld instructors) need a way to scale this process into a more manageable way for all parties involved.


What are some unique challenges FreeAgents, being formerly incarcerated, currently face when it comes to interviewing for trucking roles?

Through discussions with Success Coaches at FreeWorld, we were able to learn about the lived experiences of FreeAgents when it comes to interviewing for trucking roles post obtaining their CLD-A. Through these stakeholder interviews we gained insights into the following challenges:


Knowing how to tackle
the 2-part interview

Trucking interviews are typically consisted of a behavioral and drive test. While FreeAgents are well prepped for the drive test, they tend to struggle with answering the behavioral Q&A portion of the interview.

“Trucking interviews care about your personality, who you are, and why we should bring you on. Most of the time what matters is if you can drive, but doing well in these areas are what makes you stand out and land the role.” — Success Coach


Ensuring brevity in explaining their background

What questions are interviewers asking? A big portion are questions about the candidate’s history — which is especially challenging for FreeAgents to explain in a positive and concise way, given that their background correlates with the prison system.

“Many of our FreeAgents struggle with explaining their past in prison without getting into too many details. They don’t know how to explain it on a professional level — that’s the #1 question I get.” — Success Coach


Learning how to properly present oneself

Not only that, but FreeAgents are very new to job interviewing — they don’t know what to wear, how to talk, when to show up, and more.

“FreeAgents already have two challenges to overcome: no experience, and a criminal background. Some have never had a ‘real job’ and are unfamiliar with the interview process; they don’t have good interview skills.” — Success Coach


Overall, there’s opportunity in designing an interview prep platform that would help FreeAgents tackle the parts of the interview they’re struggling with the most: how to talk about their background, and how to properly present themselves.

Defining an "Effective" Educational Experience

Chapter 02


In order to properly design an educational platform we had to understand the learning styles of these FreeAgents. How do we make this an “effective” educational experience?

Further research brought us to two insights to drive how we should design for how FreeAgents learn:


Due to being formerly incarcerated, FreeAgents tend to have the average reading level of a 3rd grader.

HMW deliver educational content in a way that meets them where they’re at?


Additionally, FreeAgents have lower tech literacy, and primarily use older mobile devices (ex: Androids).

HMW design to best fit the technological / mobile device constraints?


What are some guiding design principles to keep in mind when designing educational content for formerly incarcerated folks?

After learning more about FreeAgents, we created a set of five principles that would define what makes the content delivered “effective” or “successful”. Aka, what principles can we design by to make sure this educational portal is one that they want to use and know how to use?


Next, I evaluated design patterns for how other platforms deliver educational content.

How do other platforms deliver content in a clear and engaging way? We looked at platforms geared towards audiences with diverse learning levels, ultimately drawing inspiration from CalFresh, Duolingo, and the Nintendo Online Shop.


Insert Gamification Concepts

Insert gameplay elements in non-gaming settings, so FreeAgents enhance user engagement with a product or service.


Leverage Visual Communication to Make a Point

Utilize illustration, images, or drawings to communicate information outside of a text-only based way.


Break Up Content into Bite-Sized Pieces

Instead of putting all content on one scrollable page, put information screen by screen to best capture short attention spans.


Give Them a Personal Coach

Using an illustrated “mascot” helps users feel like they have a coach or friend to encourage them/provide feedback in a personable way.

Design Ideations & Iterations

Chapter 03


In collaboration with Success Coaches (Instructors) at FreeWorld with knowledge of course content, we set up the information architecture of the platform.

After auditing the existing post-program portal to get familiar with the design, flow, and information architecture of the site, we sketched up some initial design iterations before moving to Figma.


As this was a short design sprint, gathering as much feedback as possible was key! We conducted three rounds of testing over the span of three weeks.

Every end of the week (Thursday & Friday), we met to test with Success Coaches and FreeAgents.

Week 1

Concept Testing with 3 FreeWorld Success Coaches (Instructors) on Lo-Fi designs

Week 2

Usability Testing with 1 FreeWorld employee and 1 FreeAgent on Mid-Fi designs

Week 3

Usability Testing with 3 FreeAgents on Hi-Fi designs


Here's a sampling of design decisions and iterations made.

After auditing the existing post-program portal to get familiar with the design, flow, and information architecture of the site, we sketched up some initial design iterations before moving to Figma. Usability Testing w/ 3 FreeAgents on Mid-Fi designs

01 — Implementing an Intro Quiz

FreeAgents are introduced to what they're about to learn with an introductory quiz.

Our research involved experimenting with different iterations of this quiz, encompassing a confidence-based format, an assessment-oriented approach, or the absence of a quiz altogether. What was decided was a confidence-style quiz modified to fit page-by-page per question for shorter attention spans.

02 — Lesson Modules Homepage

It's important that FreeAgents can see the homepage and know what to do next. Showing course progress and leveraging existing design patters (checkboxes) was key.

We experimented with differing variations of modules presented, especially when they differed in state (ex: not yet completed vs. completed).

03 — Delivering Lesson Content

Leveraging multi-modal mediums to deliver educational content is most effective.

User testing reinforced the idea of leveraging images, videos, and emojis to convey learning content. We had to think lots about accessibility here: needing to accommodate for differing (especially lower) reading comprehensions and learning styles was key.

04 — Practice Quizzes (Part 1)

FreeAgents can leverage spaced repetition to reinforce the material they've just learned with practice quizzes.

We knew we wanted to incorporate quiz questions to help reinforce the learning material for FreeAgents. First, we needed to understand where to place the practice quiz — would this quiz question be on a separate page to prevent information overwhelm, or should this be at the bottom of the page?

05 — Practice Quizzes (Part 2)

But what are some engaging ways to present practice questions?

Secondly, we saw that outside of the regular MC-type question, there were other practice question types we could employ. This was especially important when it came to helping FreeAgents practice interview questions out-loud — the best way to prep for an interview is by practicing questions! Here are some design variations we tested out when it came to practice interview prep questions.

05 — Employing “E’Neal” as a Personal Coach

“E-Neal” is based off of a Success Coach at FreeWorld that all FreeAgents know and work closely with. He was also a key stakeholder for this project — he’s the one FreeAgents tend to call with interview prep questions.

We thought about leveraging a “mascot” to help provide motivation and reinforce this coach as a point-of-contact for questions. Thus, “E-Neal” was born! We tested this concept to overwhelmingly positive results, and saw efficacy in using E-Neal to reinforce learning concepts and provide encouragement.

Final Design

Chapter 04

Final Designs for the Interview Prep Portal

Note: Keeping in account with the mobile devices FreeAgents tend to use,
these designs are fit for an Android mobile screen.


Lesson Modules Homepage (Landing Page)

FreeAgents land here as their first step from the Post-Program Portal. Here, FreeAgents can start their journeys into completing lesson modules. Some design decisions…

✅  Use a green checkbox to communicate completion
✅  Utilize action terms in CTA for clarity (ex: “Start Lesson”)
✅  Communicate how far they’re at with a progress bar


Leveraging E-Neal

We wanted a “coach” and “cheerleader” figure to help support FreeAgents as they learned material. E’Neal is a cartoonized version of a Success Coach at FreeWorld (who FreeAgents are familiar with)! PS: we had his blessing, of course.

✅  E’Neal was positively received from all participants
✅  Effectively use E’Neal as a means to reinforce concepts


Introductory Pre-Lessons Quiz

Utilizing a quiz before starting lessons can help FreeAgents feel personal agency in completing lesson content, as well as know what to expect within the lesson modules.

✅  Utilize both confidence and assessment questions
✅  Clearly explain WHY they’re taking this quiz


Designing Lesson Content

Leveraging illustrations (visual images, emojis) and color helps FreeAgents learn in an clear and engaging way — especially compared to text-only content.

✅  Emojis are familiar for users and easy to implement
✅  Limiting content on a screen reduces overwhelm


Review Quiz after Lesson Content

It's key to ensure content understanding and practice reinforcement with a practice question. After testing designs with a review question on a separate page or on the bottom of the screen, the later proved to be more effective - FreeAgents can self-lear by scrolling back to lesson content on the same screen.

✅  Have review questions to help reinforce material
✅  Allow FreeAgents to review by scrolling back to lesson content


Post-Lesson Completion Screen

It’s important to celebrate FreeAgents on their progress.  Having a brightly colored celebration screen helped recognize FreeAgents on their work so far, and encourages them to continue on with the following lessons.

✅  Brightly colored and illustrative items communicated well
✅  Celebrate and acknowledge their accomplishments


Chapter 05


A Few Things I Learned…

#1: Communication is Key to Staying Aligned

Limited time to devote to the project (schoolwork + 5 week sprint) meant that we needed to work quickly and efficiently. Collaboration and communication was key – weekly check ins with the stakeholders and within our team allowed us to stay on track and keep aligned through the process.

#2: Document, Document, Document!

As we were working on delivering one design output between the four of us, there was potential for things to get messy quickly (within the Figma file, etc.). I took the lead on organizing/managing the Figma file, leveraging pages and organizing screens to maintain clarity and consistency, and learned about the importance of documentation for team alignment as well as engineering/stakeholder handoff.

#3: Talk to Your Users to Understand the Impact of Your Work

Getting to talk to FreeAgents was an incredibly rewarding experience — I learned more about what life is like for those formerly incarcerated, and got to understand their point-of-views. Being able to empathize with these FreeAgents allowed me to tangibly understand the wider impact of my design work.