What hiring someone who spent 20 years in prison teaches you about workplace loyalty

Employers across the country are saying the same thing. It’s harder to find loyalty. Turnover seems constant. Training costs keep rising. Teams seem less stable than they used to be.

What often goes unsaid is the quieter truth behind these complaints.

Many employers are systematically excluding some of the most loyal workers available. Millions of qualified candidates are automatically eliminated because they have criminal records. At the same time, companies insist they cannot find reliable employees. Both things cannot be true at the same time.

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We came to this topic from opposite sides of the same system — and today we sit on the same side of the table.

One of us spent decades as a prison warden, responsible for keeping units safe and trying to send people back home more prepared for work and the community than when they arrived.

The other served decades in the federal prison system, sentenced to 213 years for a series of armed robberies committed in his early 20s, and is now an executive at Social Purpose Corrections, working with employers and correctional authorities on workforce development and social reintegration.

What we have learned, from very different perspectives, is that the labor shortage described by so many employers is often a problem of their own making.

Inside prison, we saw men and women show up every day for demanding jobs, complete difficult programs, earn degrees, and hold themselves to high standards in environments that would exhaust many professionals in freedom. The talent was there. The discipline was there. The loyalty was there.

What was missing was access.

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When people return home, many never make it past automated screening systems. Not because of a lack of competence or work ethic, but because of a box checked on a form. The doors close before any conversation even begins. Over time, this exclusion not only limits individual opportunities. It also limits the job market itself for employers.

This is not a “motivational” argument. It is supported by evidence.

Research cited by the Society for Human Resource Management shows that employees with criminal records perform as well as—and, in some cases, better than—their peers without criminal records. A peer-reviewed study published in IZA Journal of Labor Policyfound that, in several employment categories, workers with criminal records had longer tenure and lower voluntary turnover than those without records.

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In a job market defined by turnover, loyalty is not a sentimental concept. It is an operational factor.

Employers often justify their hesitancy in terms of risk. Risk to culture. Legal risk. Brand risk. These concerns are understandable. What is rarely recognized is the cost of constant turnover, chronically understaffed operations, and teams that never stay long enough to contribute to their full potential.

From where we are today, we see three aspects that companies miss when they automatically filter people with criminal records out of the candidate funnel.

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First, retention potential. People who finally get a real opportunity after years of closed doors don’t treat it with disregard. They fight to keep it.

Second, the sign of culture. When a company hires someone who has had to earn back trust through effort, it sends a message to the workforce that growth is possible there and that people are not disposable.

Third, problem-solving experience. People who survived and transformed inside prison spent years managing shortages, conflicts and high-stakes decisions. This is not a liability. It’s an asset.

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“Fair second chance” hiring is not about lowering standards. It’s about applying standards with intentionality. Background checks remain important. Performance remains important. Accountability remains important. What changes is the assumption that a past conviction forever defines someone’s value at work.

At Social Purpose Corrections, where we both work today, “fair chance hiring” (fair chance of hiring) is not a slogan. It is the daily management practice. People are hired with clear expectations, measurable goals, and accountability mechanisms — just like anywhere else. This approach reinforced what the data already indicates: when someone is entrusted with responsibility, many respond.

Across the country, employers are demonstrating the same principle.

Awake Window and Door Co., an Arizona manufacturer, built its business from the ground up on a foundation of employees — who were on their “second chance.” More than half of its workforce is made up of formerly incarcerated people, and the company has grown by maintaining a stable and committed team. This is not charity. It’s a retention-focused business decision.

There is also a broader impact that deserves to be recognized. Stable employment is widely recognized as one of the strongest factors in reducing criminal recidivism. When people leaving prison find meaningful work, families stabilize, communities become safer, and fewer people return to the prison system. The same decisions that improve retention can also reduce long-term social costs.

For business leaders wondering where to start, the path doesn’t require a leap of faith. It requires disciplined experimentation.

  • Review your hiring filters. Eliminate blanket exclusions that prevent qualified candidates from even reaching a human evaluator.
  • Test vacancies or “fair chance” units. Start with a function or a location. Set clear performance standards. Measure retention and turnover compared to your baseline.
  • Seek partnerships with organizations that know this audience. Don’t improvise. Work with groups that can help design policies, support employees, and prepare managers to lead with clarity and accountability.

None of this requires reducing the requirement. You’ll recognize that loyalty and potential don’t disappear because of one line on an application form.

Business leaders pride themselves on seeing opportunities where others see only risk. Hiring to give a fair “second chance” remains one of the clearest opportunities left to do just that.

Loyalty has not disappeared. The workforce is not broken. We are the ones hiring as if it didn’t exist.

2026 Fortune Media IP Limited.

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