Job Interviewing Strategies for Individuals After Experiencing Incarceration

Job interviews can be humbling, exciting, nerve-wracking or any combination of those emotions. But for people who have been incarcerated and are preparing for a job interview as part of their reentry process, this anxiety-inducing experience can be even more stressful. 

Many people in this situation don’t necessarily have the skills to help them get their foot in the door and obtain a good job, explained Emily Kleeman, MSW, LCSW, executive director of The Reentry Initiative (TRI) in Longmont, Colorado. At TRI, Kleeman helps people who have been incarcerated overcome that obstacle, which can be challenging if employers have intrinsic biases about people who have been involved with the justice system.  

“How do you persuade someone on the outside who’s never experienced prison not to get scared or judge?” she said.  

Emphasizing how they have grown from their experience and what they would like to achieve in this new phase of their life can be an important part of that answer. 

Every person who has been involved with the justice system has a unique experience. Reflecting on that experience can help people who have been incarcerated identify what they have learned and how those lessons can be applied to a specific job. Preparation is key to acing a job interview. Applicants need to know their strengths and weaknesses, either through honest self-assessments or with the help of groups like TRI, and they need to be able to make a compelling case for why they are right for the job.  

People who have been incarcerated may underestimate what they have to offer an employer. A good place to start when thinking about skills that they bring to the workplace is reviewing their previous work experience before entering the justice system. While there may be a gap, if they have held previous jobs, the skills and knowledge that they retained could still prove useful in a workplace setting. 

This is also an opportunity to consider what tasks they enjoy and believe that they can perform well. Not every opening will be their desired position, but having a career goal to work toward can encourage individuals to make incremental steps in a direction that can lead to a fulfilling career.

And individuals who have been incarcerated shouldn’t discount what they have experienced as irrelevant to the workplace. Those who are in the reentry process and searching for work can reframe their experience to emphasize the positive outcomes.

Attributes to highlight:

• A willingness to acknowledge and fix mistakes
• The ability to persevere and remain resilient under difficult conditions  
• The desire to learn and take on new opportunities and challenges 
• A proven capacity to follow directions and maintain focus on achieving goals 
• The ability to follow routines and procedures while respecting authority 

Employers want to trust employees. Be honest about a criminal record because employers will do background checks. Candidates should balance transparency with humility when talking about why they were incarcerated, Kleeman said. Again, framing the experience can be critical when trying to convey a sense of accountability. When talking about incarceration, emphasize that the experience was a wake-up call, a life-changing event or a blessing, and be prepared to explain why you feel that way.

Approaches to Owning Your Story 

“I served time for [_____]. I’ve changed. I am more mature now and will give the job 100% .”

“I was incarcerated for [_____]. I have learned from my mistakes, and I want to prove that I am a good worker.”

“While serving time, I learned the value of following a routine and keeping a schedule. I am dependable and reliable.”

Even if they are nervous, a candidate who shows accountability illustrates to a potential employer the significance of this opportunity for them and their willingness to put themselves in a vulnerable position in order to achieve a goal. That said, applicants should also remember to feel confident in themselves and their abilities. Every person who makes it to the interview process is worthy of the job and has been deemed qualified in some way for the position. 

Talking about the experience of being incarcerated can lead to a host of emotions for individuals. Past trauma may affect how people who were involved with the justice system communicate with others, sometimes resulting in the development of a protective demeanor when asked to broach the topic. Others may feel empowered and divulge too much.

Practicing social skills is important, Kleeman said. She encourages the people she works with to slow down, think through what they want to share and consider their audience before sharing.

Communication Tactics for an Interview

Use short sentences to deliver information efficiently without getting lost in details.
One-word answers can make it appear like you don’t care about the question or don’t want to answer it. Long-winded answers can lose the attention of the interviewer. 

Use a conversational tone without becoming too casual. Remember that you are interviewing for a job. Maintaining a polite and friendly tone will convey a sense of comfort with the topic of incarceration, which may also be new to the interviewer. 

Be mindful of body language. Slouching can read as disinterested. Crossing arms can appear defensive. Sit up and make eye contact with the interviewer to convey confidence, care and attentiveness. 

Every interview is a learning opportunity. Applicants show interest by asking questions that can help them get a better sense of what will be expected of them on the job and a better sense of who their potential employer is. 

“You’re interviewing them as much as they’re interviewing you,” Kleeman said.

Questions To Ask in an Interview

• What do you consider the qualities of a good worker? 
• If teamwork is critical, how does collaboration work?
• What does a typical workday look like? 
• What is your management style?
• What opportunities exist for career growth?

The job application process takes time, regardless of a person’s background. And job applicants often experience a significant amount of rejection and disappointment. But that shouldn’t dissuade applicants from continuing their search. Rather than allowing rejection to damage their psyche, applicants should take the extra time to develop their job-interviewing skills. 

Kleeman uses three hours a week of situational role-play lessons with the people she works with to help prepare them for their job interviews. Role-play provides job applicants opportunities to practice being candid, honest and thoughtful about responses and questions while highlighting transferable skills.

Role-Playing as a Tool for Job Applicants 

Step 1:

Applicant should visualize the situation.

Employer: How did you end up in prison?

Step 2:

Discuss: How would the applicant instinctively react?

[Shrugs shoulders.] “It wasn’t my fault. I was young and did everything that my cousin told me to do so I just followed along. I should have known better than to listen to him. I didn’t know what I was doing. I got caught in the wrong place at the wrong time.”

Step 3:

Discuss: How should the applicant react in a job interview?

[Sits up.] “I understand that I made a mistake that changed people’s lives. I should have known better than to [_____]. Because I never want to serve time again, I will continue to make better choices and will work hard as an employee.”

Organizations and Websites

CareerOneStop: Department of Labor hub for job seekers with a criminal record to explore careers, get training and find a job.

Center for Employment Opportunities: Organization that offers assistance, from job-readiness training to retention services.

Goodwill Industries: National organization with local branches that provide services including GED classes, job-skills training and help with placement.

Jails to Jobs: Northern California-based nonprofit that offers formerly incarcerated men and women tools to help them find employment.

The National Reentry Resource Center Reentry Services Directory: Database of local reentry services organizations and agencies.

Open Doors: Rhode Island-based organization that helps formerly incarcerated individuals and their families.

Operation New Hope: Pre-release and reentry work programs assist individuals in Northeast Florida.

Prison Entrepreneurship Program: Texas-based organization that offers entrepreneurship boot camps and reentry programs.

Prison Fellowship: National faith-based organization that provides help for incarcerated men and women, including assistance with reentry.

Prison to Employment Connection: California-based program that offers a rigorous employment preparation program to inmates at San Quentin State Prison.

Project Return: Nashville-based organization providing tools and assistance needed for successful reentry and employment of the formerly incarcerated.

The Reentry Initiative: Colorado-based program that provides support to women and men returning to the community after incarceration.

ReEntryWorks.com: Directory of felony-friendly employers and reentry tools.

Successful Release: Organization that helps people who were formerly incarcerated find employment. 

Volunteers of America Correctional Re-Entry Services: National organization with local offices that provide reentry services that may include employment placement and skills training.

Resume Help

“How To Write a Resume When You Have a Criminal Record”: Prison Fellowship offers advice for filling out job applications and a downloadable example.

“The Complete Guide to Making an Incredible Resume (for Former Felons)”: Successful Release’s step-by-step video series provides easy-to-understand tips.

Tattoo Removal

Directory of U.S. Free or Low-Cost Tattoo Removal Programs:  This database from Jails to Jobs offers a searchable list of programs available to people who want to get rid of unwanted tattoos.

Wardrobe Help

Career Gear: Not-for-profit social enterprise that provides clothing to improve employment outcomes for men reentering the workforce.

Dress for Success: Global organization that works to improve women’s employment opportunities by offering clothing and other support.