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Jeff Schmitt: From the Bottom Up

When to Give Someone a Second Chance

“Everyone deserves a second chance.” It’s a sentiment that embodies our deepest hopes: connection, achievement, and salvation.

A former employee recently reminded me how life-changing a second chance can be. I was returning home, seething over late deliveries, belligerent customers, and milk carton managers. Opening my e-mail—and expecting the usual deluge of spam—I received a surprise message from Brett, instead. His awkward opening, in which he gushed about my supposed sales prowess, raised a red flag. Just another guy fishing for a reference, I thought. Indeed, he did want a reference, but Brett did something that disarmed me: He thanked me for standing by him. He even cracked a joke about how he must taken years off my life.

Brett was an intern I hired years ago. He nearly cost me my job. Back then, he was a skinny prankster a semester shy of graduation. On paper, Brett grabbed my attention. He’d recently made the dean’s list and had already managed people. In person, I could relate to him. He was on the cusp of the real world, knotted up, craving something bigger while living in dread of finally leaving the cocoon. Sure, I sensed that he coasted and couldn’t always check his emotions. But corporate life has a way of straining these tendencies. I saw Brett as a younger version of me. The kid had potential. I was going to be Obi-Wan and Brett would be my Padawan learner. I was going to give him an advantage: the mentoring I never received.

My fantasy was quickly shattered. On Brett’s second day, I watched him arrive in a taxi and learned he’d lost his driver’s license due to a DUI conviction. Soon after, the local paper reported that Brett had been sentenced to 30 days in jail for a different incident, an assault. The details of the incident were conflicting—and both parties shared blame. Brett just took it a step too far.


Now everyone looked bad: HR didn’t perform a background check, and I hadn’t pressed his references for negatives. Naturally, Brett wasn’t going to volunteer this type of information. I felt betrayed—and stupid. People were watching and whispering, joking how I finally got what was coming to me. My boss was livid; I looked like an amateur who couldn’t even handle an intern. I knew it would be a long time before my superiors considered me a candidate for our executive team again.

When I confronted Brett, he appealed for another chance. He was afraid of losing his internship and just wanted everything to go away. The actual assault had happened months earlier, and he was trying to turn his life around. Like so many others, he wanted to escape this past and start a new life. I believed him. The authorities would allow Brett to leave jail to go to class and work during the day (maybe they figured working for me was punishment in itself). Against everyone’s wishes, I kept him around. But I wasn’t going to be lenient. Brett had skated through life on charm and talent. Without intervention, his gaps—entitlement, poor self-control, carelessness—would ultimately doom his career and relationships. Maybe he recognized that at night when he looked out from a dark cell. If he hadn’t, he’d certainly learn it in a cubicle.

I made Brett my mission. I expected A work from a B student. And I was in no mood for excuses. He was going to earn his second chance. No, he wasn’t getting a cushy desk job. Instead, I placed Brett in sales, the toughest (and most important) function of any organization. He needed to hear “no” over and over. Every day, I’d monitor and critique his performance. We’d role-play, repeating fundamentals until he could fend off objections and pivot back to the close. When he’d present opportunities, I’d interrogate him until he could deliver prospects’ motivations, expectations, and timelines. Then he’d write a plan on how he’d close those accounts. Brett learned to come prepared—and bring solutions instead of just problems. Sometimes, he’d push back. But I didn’t care if the 22-year-old Brett thought I was a tyrant. I cared how the 36-year-old Brett would look back upon his experience working with me.


Brett persevered that semester. He started asking the right questions and bringing strategies I’d never entertained. After graduation, he bounced around, struggling to find his way like many twentysomethings. Then Brett landed a position at a bank and eventually became the region’s top producer. Now, here he was, reconnecting via e-mail, reminiscing about philosophical talks we had when I’d drive him to jail after work. Those days must now seem like a lifetime ago to Brett. I’d like to believe his e-mail meant I’d made a difference. Maybe Brett would’ve found his way without me. But happy endings are so rare. We need such victories, however small, unmerited, or tenuous, to get through the day.

I’ve always believed people deserve one redo, a second chance when life goes back to how it was before you said or did something in haste. We want to give our superiors, reports, and peers the benefit of the doubt. But we can’t kid ourselves. People stray, lie, connive, disappoint, cheat, omit, and betray. They’ll embarrass you and slip into old habits—living in denial and justifying it with a straight face. No amount of time, sweat, or compassion will change that. So where do you draw the line? How do you know if someone has turned the corner—or is just conning you? Here are some criteria I’ve used:

Severity: We all want to believe in sin and deliverance, repentance and redemption, frailty and forgiveness. But those yearnings aren’t always possible at work. Look at the offense. Was it bad judgment or a quasi-criminal act? Was the act premeditated or a moment of weakness? Was the intent to harm or help? Was the damage directed toward others or ultimately just himself? Regardless, your second chance must be based on one expectation: The offense can never happen again.

History: Author James Baldwin once wrote, “People are trapped in history and history is trapped in them.” Think about your time with the other party. Was the offense an isolated incident or does it represent a larger pattern? Does it reflect underlying tendencies like self-centeredness that must be curbed? Sometimes, people cannot escape from the experiences, motivations, and inclinations driving them. Listen to your gut as you look back. If something doesn’t feel right, there’s a good chance that person will be asking for third and fourth chances soon enough.

Actions Since: Flash forward to the present. Your bad apple claims to have seen the light and changed his ways. Amen. You want to believe his sentiments are sincere. Chances are, they are when he utters them. But we often get in the way of what we want to do and be. So give it a little time to see if he has really changed. Talk to your peers and monitor his actions. Has he swallowed his pride and apologized to those hurt? What has he done to make amends to them? How has he treated everyone since his transgression? Has he taken ownership or is he still relying on caveats and excuses? Like any sinner, he’ll need to pay his dues, perform penance, and rehabilitate his image before he is again accepted. Question is, is he willing to prove he deserves another chance?

Potential: Fair or not, some employees are perceived to have more worth than others. So how do you identify who brings more harm than good? If she works for you, ask yourself: Does she really want to be working here? Does her quality and output show she cares about what she does? Does she fit our culture and values? Do her failings pose a threat to your organization and customers? Is she open to suggestions and flexible in her approach? Fact is, there is no substitute for talent. Weigh whether that special something she brings offsets the occasional misstep. If the other party is a superior, you’ll probably have to give her a pass, publicly at least. Behind the façade, ask yourself how badly you need this person. In other words, what are you prepared to live with by forgiving … or severing?

Environment: He’ll claim he wants a fresh start. But then he’ll go back to his old surroundings, friends, and routines—the negative influences that shaped the mindset that got him in trouble. There, the voices will tempt when the silence isn’t hardening. It is only a matter of time before it happens. Fact is, success is about more than good intentions. It also requires a support system. With whom does he spend time both inside and outside work? Are they the same people who led him down the wrong path? It’s easy to apologize. It’s much harder to change. Despite what many believe, forgiveness isn’t an act; it’s a commitment. Do you have eyes and ears around to support him when you aren’t there?

Of course, second chances aren’t always about another’s crime, punishment, and deliverance. They’re also reflections of ourselves. Before you forgive, consider your status. Giving a second chance is a crapshoot. Sure, it could pay off big. You could mold a wayward soul into a responsible adult who’ll someday pay it forward. Or your empathy could blow up in your face. If you fail, your peers will question your judgment in other areas, calling you naïve; soft, even. No, your reputation is on the line. Is it worth your while to be be dragged down with this person? Whatever the situation, don’t ignore the political calculus. Have you built the goodwill and respect to weather the storm? Or are you down to your last chance, too?

Finally, consider whether you’re forgiving for the right reasons. We all have an innate desire to help. We believe we have others’ best interests at heart. But why are we forgiving, really? Maybe it fulfills some Messianic streak, the hubris that we alone can save someone. Maybe we’re repenting for a long-ago sin ourselves. Step back and think about why. Be realistic about what you expect to accomplish by extending a second chance to others. As I learned from Brett, your efforts often bear fruit on their timeline, not your own.

Jeff Schmitt is an online columnist for Bloomberg Businessweek. He has spent 17 years in sales, marketing, project management, training, legal compliance, and recruiting. You can reach him via e-mail or follow him on Twitter.

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