Job Retention Challenges

Getting the job is only the beginning. Keeping it can be the greater challenge.

Employment is often considered one of the major milestones of successful reentry. A steady paycheck can provide independence, help someone secure housing, meet financial obligations, rebuild credit, support family, and begin planning for the future.

For someone returning from incarceration, receiving that first job offer can feel like an enormous victory—and it is.

But successful reentry cannot be measured only by whether someone gets hired.

We also need to ask:

What will help that person still be employed 30, 90, or 180 days from now?

Job retention is where many of the other challenges of reentry come together.

Getting Hired Does Not Make Reentry Barriers Disappear

A person may find employment and still be dealing with unstable housing, limited transportation, family responsibilities, supervision requirements, financial pressure, health concerns, treatment appointments, lack of appropriate work clothing, or difficulty adjusting to a completely different daily routine.

Employment can actually expose problems that were less noticeable before someone started working.

Transportation is a good example.

Getting to an interview once may be manageable. Getting to work at 6:00 every morning, five days a week, is different.

One missed bus connection, a vehicle breakdown, a schedule change, or an unexpected transportation expense can suddenly threaten someone’s employment.

The same is true with housing.

A worker who does not know where they will sleep next week may find it difficult to arrive rested, clean, prepared, and on time every morning.

Employment provides stability, but people often need some stability in order to maintain employment.

That is one of the complicated realities of reentry.

Small Problems Can Become Job-Loss Problems

Many people returning from incarceration have very little financial cushion.

Someone who has been working for several months may eventually be able to absorb an unexpected $50 or $100 expense.

Someone who has been working for three days may not.

A pair of required work boots can become a crisis.

A broken phone can mean missing a call from a supervisor.

A lost transit card can mean not getting to work.

A schedule change can create a transportation problem.

An unexpected supervision appointment can conflict with a work shift.

A sick child can create a childcare emergency.

A paycheck that arrives later than expected can mean not having enough money for transportation or lunch.

From the outside, these may appear to be small problems.

For someone rebuilding with almost no savings or backup resources, they can become employment-ending problems very quickly.

The First Paycheck Doesn’t Solve Everything

There can also be a dangerous assumption that once someone starts working, support is no longer necessary.

The thinking sometimes becomes:

“They have a job now. They’re doing fine.”

But the first weeks and months of employment may actually be one of the most important periods for continued support.

The employee may not receive a paycheck for two or three weeks.

Even after the first paycheck arrives, there may be rent, transportation, food, clothing, phone service, legal financial obligations, child support, supervision costs, debts, and other immediate expenses competing for that income.

Financial stability takes time.

Getting a job changes the direction of someone’s life, but it does not instantly repair everything that happened before the first day of work.

Adjusting to Workplace Culture Can Be Difficult

Job retention is not only about practical barriers.

There is also a social adjustment.

Someone who has spent many years incarcerated may be entering a workplace culture that feels unfamiliar.

Communication styles may be different.

Technology may be different.

Workplace expectations may have changed.

Supervisors may communicate through text messages, scheduling apps, email, or online employee portals.

Coworkers may come from backgrounds and generations the returning individual has had little experience interacting with.

Receiving criticism from a supervisor can also be difficult for someone who has spent years responding to authority in a correctional environment.

A simple workplace correction can sometimes feel more personal or threatening than it was intended.

These are skills that can be learned.

That is where mentoring and employment coaching can make a significant difference.

Workplace Problems Should Be Addressed Early

One of the most important job-retention skills is learning to address problems before they become crises.

If transportation is becoming unreliable, talk about it before repeatedly arriving late.

If there is confusion about a schedule, ask questions.

If a supervisor gives corrective feedback, try to understand what needs to change rather than immediately assuming the job is lost.

If a coworker creates frustration, avoid allowing one conflict to turn into a resignation or termination.

If supervision or treatment appointments conflict with work, communicate as early as possible with the appropriate people.

Many employment problems can be resolved when they are addressed early.

The difficulty is that people navigating reentry may not always know whom to ask, what to say, or how to approach the situation.

Having someone available to talk through the problem can help.

The First 90 Days Matter

The beginning of a job is often the period when new habits are being established.

Showing up every day.

Arriving on time.

Learning the job.

Understanding workplace expectations.

Getting along with coworkers.

Responding appropriately to supervision.

Managing money.

Planning transportation.

Getting enough sleep.

Balancing work with appointments and family responsibilities.

These things may sound basic, but together they create the foundation for long-term employment.

This is why reentry employment support should not end when someone receives a job offer.

A simple check-in can make a difference:

How is the job going?

Are you getting to work okay?

Is anything happening that might put the job at risk?

How are things going with your supervisor?

Do you have what you need for work?

Sometimes those conversations identify a problem while it is still small enough to solve.

Job Retention Is Also Career Development

Keeping a job is important, but long-term employment success should eventually become about more than simply avoiding termination.

Once someone becomes stable, the conversation can begin changing.

What skills are you learning?

Is there an opportunity for advancement?

Can you earn a certification?

Could you move into a higher-paying position?

What does your supervisor say you need to improve?

Is this job helping you move toward the life you want?

A first job after incarceration does not necessarily need to become a lifetime job.

Sometimes it is the first step.

The goal should be to help people move from getting employed, to staying employed, to eventually building a career and greater independence.

Employers Can Be Part of the Solution

Second-chance employment works best when employers understand that hiring someone is only the beginning of the opportunity.

This does not mean lowering workplace standards.

Employees returning from incarceration should still be expected to arrive on time, perform their jobs, follow policies, communicate appropriately, and meet the same reasonable expectations as other workers.

Support and accountability can exist together.

What helps is having an employer willing to communicate when a problem develops rather than immediately assuming the employee cannot succeed.

A supervisor who says, “You’re doing good work, but your attendance is becoming a problem. What’s happening?” may discover a transportation issue that can be corrected.

That conversation could preserve a good employee.

Reentry Organizations Have a Role After Hiring

Reentry organizations should also resist the temptation to count a job placement as the final outcome.

A placement is an important output.

Job retention is an outcome.

The difference matters.

If someone starts five jobs in six months but cannot maintain any of them, the underlying barriers have not necessarily been resolved.

Employment support should include reasonable follow-up after placement.

That may involve coaching, transportation planning, workplace communication, budgeting assistance, problem solving, encouragement, referrals, or simply having someone available when a difficult day occurs.

Sometimes the best intervention is not doing something for the individual.

It is helping them think through the situation so they can handle it themselves the next time.

That builds independence.

Successful Employment Strengthens More Than the Individual

Job retention benefits everyone.

The employee gains income, experience, confidence, skills, and greater independence.

The employer retains a trained worker and reduces the cost of turnover.

Families benefit from increased stability.

Communities benefit when individuals returning from incarceration have meaningful opportunities to build productive lives.

And successful employment can become another protective factor against returning to old behaviors.

That is why job retention should be viewed as more than an employment issue.

It is a reentry stability issue.

The Solution: Support Beyond the Job Offer

At Compass Reentry Peer Support, we believe employment support should not necessarily end when someone gets hired.

The job offer is worth celebrating.

Then the next conversation begins:

What do you need to keep this job?

The answer may be transportation planning.

It may be appropriate work clothing.

It may be learning how to communicate with a supervisor.

It may be encouragement after a difficult shift.

It may be helping someone understand that one bad day does not mean they should quit.

And eventually, it may be helping that person identify the next opportunity for advancement.

Reentry is not simply about helping someone survive the first days after release.

It is about helping people build the skills, relationships, confidence, and stability that allow them to become increasingly independent.

Employment is a major part of that journey.

But getting the job opens the door. Keeping the job helps build the future.

Join the Solution. Join the Conversation.

If you are an employer, consider becoming a second-chance employer—and think beyond hiring to retention.

If you work in reentry, continue checking in after the job placement.

If you mentor someone returning from incarceration, ask how work is going and listen for small problems before they become large ones.

And if you are rebuilding your own life, remember that asking for guidance when a problem develops is not failure. Learning how to solve problems before they cost you an opportunity is part of becoming stronger and more independent.

One successful hire can become one stable employee, one stronger family, and one stronger community.

Learn More

Compass Reentry Peer Support

www.compassreentrypeersupport.org

We walk with people until they can walk with confidence.

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