Question
I have a client who has a stained record, both in regard to work experience and some run-ins with the law. She keeps getting fired when employers eventually find out. What do you suggest?
Nick’s Reply
It seems you are a career counselor or a lawyer or a recruiter. Some might think your question is a joke, but I’ve encountered a number of people who can’t get or keep jobs due to serious problems in their history.
What you must ascertain is whether your client is truly ready to straighten out her life. When a person is serious about cleaning up their act, they can help themselves by taking a few common sense steps. If they expect they can keep playing games with their reputations, then neither you nor I can help them.
You don’t say what, exactly, this stained record is, so I’m going to assume it doesn’t involve violent behavior or anything that could put an employer or other employees at bodily risk. (Of course, there may be other risks.) But you will have to judge whether this person is redeemable and safe to work around.
I’ll offer some tough-love advice I’ve given to ex-convicts, alcoholics and addicts, people who’ve been fired for cause, and worse. It’s painful, and it’s not easy, but it can work if a person is diligent and sincere. Here’s what I’d tell her.
1. Fess up.
If you have a stained record, you must disclose to the employer your past problems, though you need not do it until you have a job offer. But under no circumstances should you accept a job without coming clean. Failure to disclose is what gets you fired, and every time you’re fired you go deeper into the abyss. The law may not require disclosure, but you asked my advice — this is what I would do to demonstrate I have integrity.
2. Get recommended.
Face it: An employer is right to be worried your problem will become their problem. It takes a powerful personal recommendation to help an employer get over that fear. This means you must cultivate good recommendations — people who will put their names on the line to endorse you.
I said this wasn’t easy. But you must find one or two people whose word the employer will trust. Then have them call the employer to recommend you — don’t wait for the employer to make that call. If you don’t have such references, take a low-level job and perform well, until you’ve made your boss and your co-workers believers who will speak up for you. Then, don’t make your references regret sticking their necks out to help you overcome your stained record.
3. Ask for guidance.
When you disclose your problem to the employer, you must also ask them to tell you what you must do to help them trust you. As long as it’s not illegal, unethical, or injurious to you or others, do it. Your mistakes are costing you. Pay the price and move on. Taking such guidance from the employer makes you partners. Be ready to be judged. Don’t let the employer down.
4. Make a commitment.
Once it’s clear what the job is and what the employer expects of you, look them in the eye and say, “I will make a commitment to you to do X, Y, Z [whatever the job and the employer require], and I will not fail you. If you’re not happy with me or my performance at any time, I will leave without you needing to fire me. But that will not happen. I will make sure you are happy with me and my work. That’s my promise.” Again, the law may not require such a commitment, but it’s what I’d do.
Since your client will also have to explain why she got fired, I suggest she read this article: How much should I say about getting fired? The comments from my readers are even better than the article.
Break with your stained record
There’s nothing magic, fun, or easy about cleaning up a stained record. Your client must take her lumps, be honest, cooperate with an employer, and then deliver on her promises. I wish her the best. My compliments to you for trying to help her.
Some may take issue with the “take your lumps” suggestions I offer. Some might view this as too risky for the employer, or unfair to the job seeker. I believe it’s worth considering helping anyone willing to try to fix their lives, but no one should do anything they think they shouldn’t, even if I suggest it. Use your best judgment.
Have you ever had to recover from a bad reputation, whether you earned it or not? What did it take? Ever take a chance on a person with a troubled past? What did they say or do that convinced you? How did it turn out? What further advice would you offer in this case?
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Good advice. Two things to note:
1) Some employers are very proactive and embrace hiring people in recovery. They tend to be community service nonprofits or companies with that kind of culture — yeah, the same folks who support DEI. So do some research to find out who they are and use Nick’s methods to introduce yourself to them.
2) Employment law protecting people in recovery varies from state to state. For example, no surprise, but CA has some of the most progressive laws in that regard.
This is a challenging but not impossible road. Everyone deserves a second chance, but the key lies in ownership, transparency, and action.
Let me offer some humble advice to your client from an HR perspective:
Your past does not define your future, but how you handle it will. Instead of running from your history, take control of your narrative. Employers respect honesty and accountability. Address your past head-on—not as an excuse but as proof of your growth.
Own Your Story – Acknowledge mistakes, but emphasize the lessons learned and how you’ve changed. Integrity builds trust.
Build Credibility – Find people who believe in you and will vouch for your character and work ethic. A firm reference can open doors.
Seek the Right Fit – Some companies value resilience and redemption. Look for mission-driven employers, second-chance hiring programs, or roles where your unique perspective can be an asset.
Prove Yourself Daily – Every job is an opportunity to rebuild trust. Show up, work hard, and let your actions speak louder than your past.
Your reputation isn’t just what you’ve done—it’s what you do next. The road to redemption isn’t easy, but it is possible. Every day is a new chance to prove who you are. Rise to it. Believe in your ability to change. Never let your past overshadow the greatness you can achieve.
Best of luck to your client. They’ve got this!
Just to expand on Demina’s great advice…In many communities, there are volunteer groups that specialize in working with the formally incarcerated to help with their transition back to work.
Services often include coaching what Demina referred to as “Own Your Story”, helping job applicants clearly articulate what happened, what they learned, and their intentions going forward. That’s not a conversation you want go into unprepared.
They will also have a network of local companies that are committed to hiring workers transitioning from incarceration, in recovery, etc. Many will even have relationships with specific hiring managers, and as Nick always says, there is no substitute for a personal connection.
Well, I went down this path as a sponsor and later manager who had a stained employee. It did not end well for me, the company, and the stainee. Proceed cautiously.
@Bob: Been there, done that. It hurts but you can learn a lot. Sorry to hear you had to deal with a bad outcome. Don’t let it make you cynical.
I knew a guy that got in to trouble with drugs. He caught a break, the judge basically said “If you get in to *any* trouble…jaywalking, spitting on the sidewalk…”
He got the message. And cleaned up.
He also did not not have many work prospects.
His probation officer needed some handyman stuff done around his house. They went to the hardware store and bought some tools and materials (the tools were an advance on the job). The work was good. Good enough that his probation officer recommended him to others (“No job too small”).
I have also known people that employed hard crews for hard work (think “hot asphalt roofing on a Texas summer day). Some mornings he would swing by the jail to take someone on his crew to the job site.
My point being that sometimes the way back from our mistakes is hard. Especially in the workplace.
But showing a willingness to work hard, stay out of trouble, and abide by whatever restrictions the employer puts on us can be a way out of the mess.
@Gregory: Amen to that, Brother.
Nick, thanks for taking this question. I had not realized how significant an issue this was.
https://bjs.ojp.gov/library/publications/prevalence-imprisonment-us-population-1974-2001?iid=836&ty=pbdetail
“If incarceration rates remain unchanged, 6.6% of U.S. residents born in 2001 will go to prison at some time during their lifetime.”
And while, depending on the job, someone might be able to deal with a short time in jail as a temporary interruption, a year or more in prison seems like needing a hard reset to recover from. How to find a place to live? How to get a job? (There are places where someone on probation cannot enter an establishment with a liquor license, putting many restaurant jobs out of reach.) How to make friends who are not criminals? How to avoid joining a gang, if they offer a living?
@ Nick Not cynical, but much more probing and careful. In this case the stainee duped over 4 other managers at 3 different companies.
Hi Nick and thanks for this question and the great responses from your readers.
Other suggestions for her are
1. if she served her sentence with no problems and was a “model prisoner,” see if she can get the warden or lead prison guards to write a reference letter on her behalf, especially if she did exceptional work while in jail serving her time. THEN
2. Strive to get her prison/jail records expunged and still be honest about the incarceration when she “discloses”. THEN
3. Google “Companies that hire ex-offenders”, choose the companies that she prefers, where she knows she will do an excellent job. THEN
4. Do the job in the interview, preferably before she “discloses”
Other suggestions for offenders still incarcerated and who may be in “pre-release”:
1) Always, stay out of trouble and do good work while incarcerated (groundskeeping, construction, firefighting crew, laundry, cooking, data entry, etc.) to build a reputation of responsibility, discipline, trust, commitment
2) Connect with prison ministries and other nonprofit organizations that help prisoners while incarcerated and help with people/life skills, work skills, education//training, housing, wellness, family relationships, etc.
3) be willing to help others turn their lives around