Employment after Incarceration: How We Help Participants Master the Job Search

Employment after Incarceration: How We Help Participants Master the Job Search


“How do I explain my gaps in employment to an interviewer?

“Is it legal for potential employers to ask about my conviction history?”

“If I’ve spent the past three decades incarcerated, what career paths are still open for me?”

Finding a new job can be a daunting process for anyone—but for those reentering the community after incarceration, the prospect of obtaining employment comes with additional questions and anxieties. Still, although individuals with justice involvement face a number of legal and societal barriers to employment, having a stable job is vital to their successful reentry.

Luckily, The Fortune Society is there for them. Our Employment Services program offers an intensive, two-week Job Readiness Workshop with a curriculum designed specifically for the issues our participants might face during the job search process.

An Employment Services instructor at The Fortune Society teaching participants

Workshop Facilitator Moses McBride, who teaches the workshop, imparts a positive outlook:

“The world is an opportunity, rather than a barrier. The world is there for you to mold and shape so that it helps you.”


He encourages job seekers–regardless of their background, work history, or age–to find and embrace possibilities. “[Many individuals with justice involvement] can still go to college. There is still a very large span of space in front of them to excel. Individuals can also find a path for employment. [Even without higher education or work training,] there are still things that fit the mold for [them, such as] counseling and mentor positions,” McBride says. Participants are taught to look at their lived experience as an asset and determine ways to turn their personal qualities into job opportunities. “If you can get somebody to believe that they have value, that they have something to contribute, interviewing is easy,” he says.

Getting to that point, however, takes time. While incarcerated, many individuals “are taught to defer and not show assertiveness or confidence. [In interviews,] they don’t make eye contact, they talk really low, they avoid being confident in expressing themselves,” McBride explains. Often, people are unsure how to explain their justice involvement or discuss their employment histories. Additionally, participants that have not spent much time in the workforce may have little knowledge of professional practices and etiquette.

Through lectures, videos, and other resources, our Job Readiness Workshop coaches students on the steps necessary to reframe their past and aspire to new careers. Course materials explain pertinent topics like how to explain one’s justice involvement in an interview, how to dress in professional attire, and best handshake practices.

Individuals are also taught about the laws regarding what New York City employers can ask during the interview process about one’s justice involvement, as well as tactful methods to respond when these rules are breached.

A participant in The Fortune's Society's Employment Services program completing our mock interview process

Mock interview sessions allow students to put this knowledge into action. Our team of volunteers, consisting of professionals with industry experience, conduct a number of short interview sessions with participants. The process allows them to test their skills and receive feedback in a low-stakes situation.

McBride stresses the ability to calmly deal with the pressure of different personalities and interview styles:

“No matter what an interviewer says, what he does, you stick to your plan. If they say something aggressive to you, you stay in your method.”


Individuals that complete the orientation course often move on to great opportunities at Fortune and in the greater community —our Career Advisors work to ensure that participants receive jobs, internships, or specialized vocational training.

For more inspiration, learn about our Employment Services offerings in detail or read personal stories about our participants’ successes.

Don’t miss stories like this—Subscribe to the Fortune Weekly today.

*Written by Carmen Rojas, Development and Communication Associate at The Fortune Society

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