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The System Reset Toolkit

A Step-By-Step Toolkit

This initiative is tough to embark on alone. That's why we're giving you a step-by-step guide to set you and your hiring team up for success. Britannia Bloom shares how the toolkit helped her establish a returning apprenticeship at Square.

Step-By-Step Guide to Hire Returning Workers

Tech companies that invest in implementing an intentional and well-planned hiring strategy will reap the most reward from hiring formerly incarcerated people.

If your HR professionals are looking for a sustainable, effective strategy to recruiting and keeping returning people at your company, look no further. Here are the five steps for System Reset at your workplace:

Opening the workplace to returning people is a bold action to promote diversity in the workplace and equity in communities. It’s important to support that action with context and educational conversations about mass incarceration and the importance of hiring formerly incarcerated people as a part of your DE&I strategy. This will create buy-in among employees and executive leadership and can help dispel stigma in the workplace once returning people have been hired. By working with your DE&I team on this, your HR directors can develop an approach that is tailored to the unique culture of your company.

Think about your future workforce needs and where returning people can fit best, according to your needs and their skills. You can do this in two ways: 1) filling technical roles with apprenticeship programs and internal reskilling of non-technical employees, and 2) filling non-technical positions as an entry-point for returning people.

Recruitment of returning people will be mostly geared towards people applying to non-technical positions; due in large part to many of the technical positions being sourced through apprenticeship programs or the development of internal employees. A key best practice is to craft your job descriptions from a strengths-based perspective; work to identify the core competencies required to perform in the position as opposed to emphasizing prior experience and the unnecessary use of technical language.

Once the job description has been written, recruiters can widen their scope of practice by attending job fairs that promote inclusionary practices or partnering with organizations specializing in preparing formerly incarcerated people for positions in the technology space. Companies can also encourage formerly incarcerated people to apply by using inclusionary language on their careers page.


While the business case for hiring returning people is compelling, it is important to acknowledge that employers are subject to negligent hiring liability. The best way to mitigate risk due to negligent hiring liability is to apply established best practices specific to the hiring of returning people. You can find the best practices in the full guide.

This is the most important step of your process. Once formerly incarcerated employees have been successfully hired, their managers should work to understand and support their experience as they transition to the new environment. Some formerly incarcerated employees may have limited work experience in an office setting and may lack important soft skills such as communicating with supervisors and colleagues. They may also require flexibility with scheduling to attend required appointments with probation or parole officers, and may face challenges with housing or transportation. Finally, they may struggle with self-doubt or low self-esteem. 

Research has identified four areas that may help address these challenges:

  1. Cultivate an environment of stability and structure
  2. Build a culture of understanding and teamwork
  3. Offer support and compassion balanced with safety and accountability
  4. Make resources readily available
  5. Require managers and mentors to complete training on how to best support returning people in the workplace.

While these steps may provide a first start in hiring formerly incarcerated people, for lasting change in an organization, a change management plan should be implemented that includes employee ambassadors, team engagement, and ongoing metrics to ensure success.

Learn More From The Full Guide

Hear Shelley Winner's story

Our advisor Shelley Winner shares her path and her top tips for companies to launch their hiring programs.

When rehabilitated people are given the opportunity to successfully re-enter our community, our society wins too.

Shelley Winner, Restorative Justice Activist and Product Specialist at International Tech Firm
Download the Full Report

Take the System Reset pledge

  • I’m committed to recruiting, hiring, and retaining people returning from incarceration at my workplace. I want to disrupt the racist cycle between incarceration and employment and want tech to set an example for companies across industries.
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