Sunday Morning Coffee
I’ve seen a lot of résumés in my career.
Good ones. Bad ones. Résumés with six different fonts. Résumés that somehow manage to be four pages long despite the applicant having one job. Résumés with objectives so vague that I'm still not entirely sure what the person wants to do.
So yes, I believe in teaching people how to write a good résumé.
But I also think we've spent far too much time acting as though the résumé is the thing standing between people returning from incarceration and meaningful employment.
Most of the time, it isn't.
A beautifully formatted résumé can’t remove a hiring restriction. It can't create reliable transportation. It can't explain a ten-year employment gap without revealing something an employer may immediately judge. It can't make a professional license available to someone who's prohibited from obtaining one. It can't turn an entry-level wage into enough money to support a family.
And it definitely can't make an employer call you back.
Yet much of what we call "job readiness" continues to focus on preparing the individual to become more employable.
Maybe we need to spend more time preparing the system to employ them.
We've Gotten Pretty Good at Job Readiness
Most workforce and reentry programs offer some version of the same preparation: résumé writing, interviewing, job searching, workplace communication, appropriate attire, soft skills, and perhaps a credential or occupational training.
Those things are valuable. I teach them. I've built programs around them. People need to understand how hiring works and how to present their skills effectively.
But there's a problem when we assume that completing those activities means someone is now "job ready."
Imagine someone does everything we've asked. They earn the credential. They build the résumé. They practice interviewing until they can answer "Tell me about yourself" without breaking into a cold sweat. They're motivated and ready to work.
Then they start applying.
The application asks about criminal history. The employer has restrictions based on offense type. The job requires a driver's license they don't have. The shift ends after public transportation stops running. Their occupational training led to a field where licensing restrictions create another hurdle. They don't have reliable internet access to complete onboarding. Their supervision requirements conflict with the work schedule. Or the employer simply chooses another qualified candidate without a record.
At what point do we stop calling that person "not job ready" and acknowledge that perhaps the job isn't ready for them?
Barriers Travel in Packs
One of the things I've learned through correctional education, reentry, and workforce development is that employment barriers rarely arrive one at a time.
Transportation affects which jobs someone can accept. Housing instability affects whether they can consistently show up. Lack of identification can delay employment altogether. Limited digital skills can prevent someone from completing an application that never existed on paper in the first place.
Then add criminal-record restrictions, gaps in work history, limited professional networks, family responsibilities, supervision requirements, substance use recovery needs, and the reality that many people return to communities where good jobs aren't exactly waiting on every corner.
Now imagine we're standing in front of that person saying, “Have you thought about making your résumé one page?"
The résumé may need work, but the résumé is not the problem.
A Job Isn't Necessarily a Successful Outcome
We also need to be more thoughtful about what we mean by employment success.
I've seen programs celebrate job placement as though the story ends the moment someone receives a paycheck.
Employed? Check.
But what kind of job?
Does it pay enough to meet basic needs? Does the person have a predictable schedule? Is there a realistic way to get there every day? Are there benefits? Is there an opportunity to advance? Does the job connect to the training the person completed? Can they keep it while meeting supervision and treatment requirements?
Most importantly, what happens three months later?
Getting a job matters.
Keeping one matters more.
And being able to move from a job toward greater economic stability and mobility matters even more.
If our workforce programs only measure placement, we may be congratulating ourselves at precisely the point where the hardest part begins.
We Need to Stop Fixing Only One Side of the Equation
Traditional workforce programming tends to focus heavily on the job seeker.
We coach them.
Train them.
Assess them.
Credential them.
Correct them.
Prepare them.
Meanwhile, the employer side of the equation often receives considerably less attention.
That's beginning to change, and it needs to.
If we're serious about employment for people with criminal records, workforce development has to include employer development.
That means helping employers examine hiring policies rather than simply asking whether they're "second-chance friendly." It means understanding which convictions actually create legal restrictions and which exclusions are simply organizational habits. It means preparing supervisors to support employees who may be returning to the workforce after years away. It means creating advancement pathways instead of permanently concentrating people with records in the lowest-paid positions.
And it means building real relationships between employers and workforce organizations.
Sending employers a stack of résumés isn't a partnership.
The Goal Should Be Mobility
This is one of the reasons I've become increasingly interested in the idea of workforce mobility rather than simply workforce readiness.
Readiness asks: Can this person get a job?
Mobility asks bigger questions.
Can this person enter the workforce, remain employed, build skills, increase earnings, navigate workplace expectations, develop professional relationships, and move toward greater economic stability over time?
That changes what we teach.
Yes, we still teach résumés and interviewing skills, but we also teach digital literacy, executive functioning, financial capability, self-advocacy, communication, problem-solving, workplace navigation, and how to keep learning after formal training ends.
We help people understand not just how to get the first job, but how to use that job as a step toward the next opportunity.
And on the other side, we work with employers to make sure there actually is a next opportunity.
That's a much more ambitious goal than placement.
It should be.
Sometimes the Program Needs a Different Question
When someone completes a workforce program and still struggles to find employment, our instinct is often to look at the participant.
What else do they need?
More interview practice?
Another certification?
Better soft skills?
Maybe.
But before assigning another workshop, I'd like us to ask a few different questions.
Are we training people for jobs that actually exist in their communities? Are the employers hiring for those jobs willing and able to hire people with their records? Do the wages make those jobs sustainable? Can participants realistically get to them? Are our employer partners actually hiring our graduates, or are they simply attending our events and appearing on our partner lists?
And when someone isn't getting hired, are we studying why?
Those questions may be less comfortable.
They're also much more useful.
The Person Is Not Always the Problem to Be Solved
There’s something deeper underneath all of this that I think matters.
For years, many reentry and workforce systems have operated from a deficit model. The person comes to us with barriers, and our job is to fix those barriers until the person becomes employable.
Sometimes people absolutely do need skills, education, coaching, treatment, support, and opportunities to develop new habits, but we should be careful about sending the message that if someone cannot find work, they simply haven't improved themselves enough.
People can do everything right and still encounter systems that make success unnecessarily difficult.
Our responsibility is to prepare people for the realities of the labor market.
It's also to work on those realities.
Yes, Fix the Résumé
So please, keep teaching résumé writing.
Remove the six fonts.
Practice the interview.
Help people translate skills they've developed inside correctional facilities into language employers understand.
Teach them how to navigate online applications and talk about gaps in employment. Help them earn credentials that have genuine labor-market value.
Do all of that.
Then keep going.
Build relationships with employers. Examine hiring policies. Address transportation. Teach digital skills. Create career pathways. Follow people after placement. Measure retention and advancement. Find out why people are leaving jobs and why employers are rejecting candidates.
Because if someone has completed our program, earned the credential, practiced the interview, built the skills, and sent application after application without getting a meaningful opportunity, handing them another résumé template isn't enough.
At some point, we have to be willing to look across the table instead of across the desk.
Maybe the person doesn't need more fixing.
Maybe the system does.
