“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.
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