The Personal Touch: Confessions of a Loser

My former boss called me a loser.

Not to my face, of course. No, he probably said it to my successor…no different than he did with my predecessor. Like him, I was another cautionary tale.

I can picture it like it just happened. Somewhere between Topeka and Salina, he’d share my story with the new hire. Regardless of protagonist, his tale contained the same lesson: The gap between success and failure was measured in inches. It only took one misstep—a puzzled expression, clumsy response or creased suit—for prospects to doubt you.

In his world, your persona was everything. From your car to your shoe shine, you were selling an image and lifestyle that made people want to be you.

I’d nicknamed my boss Yoda. He was squat and bald, with thick shoulders and cauliflower ears that gave away his prowess on the wrestling mat. While he lost interest in school early, he retained a love of competition—for quickly sizing up the other guy and using technique, leverage, and determination to subtly wear him down.

In public, Yoda’s soaring rhetoric was culled from years of digesting motivational tapes in transit. Privately, his language was sprinkled with the cocksure lingo from Wall Street and Boiler Room (oblivious to their pesky moral subtext). To Yoda, people—customers and employees alike—were walking, talking dollar signs.

Yoda was the head recruiter for an insurer. In his world, there were only haves and have-nots. Most often, we interviewed the have-nots. They were reeling from divorces, layoffs, and health problems.

When they read our ad, they saw a second chance. They envisioned a better house, car, and vacation, or giving their children those luxuries their friends enjoyed. For confused veterans, aging corporate castoffs, and tired truckers, we were the ticket to reclaiming their pride…and their lives.

I remember my first road trip with Yoda, where I learned the craft. His presentation was a clinic. He’d cover all the bases: our product, selling process, and training. In between, he’d profile our top producers: the fast managers and police officers who made it big by following “the plan.”

Of course, he’d share horror stories of families losing farms and businesses because they lacked coverage. Then, he’d close with the American dream: a six figure income and four-day work week (replete with an income safety net). The 35-minute pitch was devastating in Master Yoda’s hands: He sold purpose and lifestyle as much as a paycheck.

In the subsequent interview, candidates would ask Yoda if they could succeed. And he always gave the same stock answer: “That depends on you.” To his recruiters, Yoda’s mantra was simple: “Don’t say too much.” Behind the glossy brochure, we were really a meat market. We hired everyone.

Our hires sold door-to-door in the scorching or frigid countryside. They spent weekdays away from their families, paying for their own meals and lodging. Most washed out quickly. It was all a numbers game. Our job was to keep the pipeline filled, hiring, motivating, and babysitting our people until they earned a license. We washed our hands after that. Natural selection took care of the rest.

None of that mattered to me at first. I’d seen the spacious McMansions the top performers owned. They lounged at the country club on weekends and ordered from the wine list. And I was hungry for the same.

So I braved blizzards and ice storms to recruit jewelers in Joplin and salonists in Sioux Falls. I delivered Yoda’s presentation over and over, driving hundreds of miles a day with messianic zeal. I would shape-shift from Bubba to cosmopolitan depending on the recruit. I was chasing the dream, always seeking Yoda’s stamp of approval.

Every day, Yoda and I spoke from the road. He understood the disorientation, loneliness, and exhaustion from living in cars and hotels. So he’d always build me up, reminding me of my importance and sharing his nuggets of wisdom. Yoda was a management genius, too. He knew the secret was making people feel special, and how doubt was the greatest threat to success.

Still, Yoda never made it easy. He’d answer every question with a question, forcing us to evaluate our assumptions and think everything through. No, every interaction with Yoda was a test, and he was always two steps ahead.

Still, Yoda would inevitably drop his guard. Between the pep talks, his real feelings would slip out. Sometimes, a new hire would back out (costing Yoda a commission). Or a former rep would badmouth him for creating pie-in-the-sky expectations. It didn’t matter. Yoda always dismissed them with the same word: loser.

In Yoda’s world, failure was always one’s own fault. Everyone controlled their destiny and success, just as his precious tapes had reinforced. He would tell people what they wanted to hear. Behind the sweet talk, Yoda saw them as a means to an end. He was a salesman from a bygone era, where delivery outshined substance.

Perhaps this was Yoda’s armor to protect against the harsh truths of a sales career, where everyone is expected to produce immediately…no excuses. If they can’t, the higher-ups can quickly find someone else who can.

And that’s what happened to me. The reports would show me a shade below the veterans each week. And over the course of months, numbers snowball. Gradually, Yoda’s pep talks were replaced by questions and inferences. The pressure was building.

Despite absorbing Yoda’s tapes and attending his voluntary weekend trainings, there was one obstacle I couldn’t overcome. I had doubt.

Inside, I knew I wasn’t the smooth, dapper insider pulling six figures. I felt like a coward for skirting the unpleasant aspects of the job with recruits. And I started questioning whether my prospects were better off in their current jobs, rather than taking a leap where most fall short. I had reached a point—feeling phony, shady, and uncertain—where I knew I needed to start over.

I’ve heard two sales occur simultaneously in every interaction. The seller attempts to convince someone change is helpful, painless, and urgent. The other person reciprocates with skepticism and excuses, hoping to sell the seller to move on. Yoda would call it a test of wills.

We had ours over lunch one day. In the end, I won that test. So we parted—and I joined the ranks of the losers in Yoda’s eyes.

In subsequent years, I’d scan the classifieds, watching recruiters assigned to my cell number come-and-go. I wondered if we shared similar stories. I even Googled Yoda once, finding a disenchanted recruit had blasted him by name on a message board. Yoda probably dismissed him as a loser, too. But word was getting out for all to see.

Recently, I reflected on Yoda, as I rehearsed a possible acceptance speech at an awards banquet. I’m still amazed at how much I learned from him. He taught me to be “on” at all times, with no wasted motion…or fear. He reminded me to take nothing for granted, knowing everyone’s performance is judged day-to-day. And he reinforced that sales, like any endeavor, requires you to constantly strive for perfection.

Still, I pity Yoda. He is my cautionary tale. Steeped in polish, Yoda never understood there can be no split between who you are in pubic and private. He lived for the short-term, chasing the quick commission. And he forgot the key to sales: being straight with people and respecting them enough to do what’s best for them.

SMM columnist Jeff Schmitt works in publishing in Dubuque, IA. He can be contacted at jschmittdbq@mchsi.com, and you can follow him on Twitter at jefflschmitt.