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The Scary Things That Can Make You a Stronger Leader

A "stretch" assignment can be stressful -- even terrifying. Here's what one government leader learned from the experience.

The research on leadership development says that the most powerful learning experiences for emerging leaders are scary, unwanted assignments -- "stretches" -- that take us out of our usual routine. However, sticking with a stretch assignment -- a daunting project that expands your definition of yourself -- is arduous work, riddled with self-doubt, ambivalence, even terror.

Here's my war story about the stretch assignment that almost got away from me, with five epiphanies.

At the time, as a new parent, I had been on a two-year hiatus from my work as a clinical social worker. A colleague told me about a start-up demonstration program: a 50-bed treatment center for addicted men in the criminal justice system. The county needed a manager to hire the staff and build the program. Was I interested?

Mostly I wasn't. Criminals scare me. They know more about guns and knives than I do. They curse. They have tattoos. At 34, I looked young, used too much hair gel, had fancy degrees (social work, the humanities) and preferred having worried people come visit me in a therapy office with a trickling desktop water feature.

But I was desperate to get into a leadership position -- to do something bigger and more stimulating; to be challenged, and my parenting ennui was hardening into something that looked like depression. This job was the one possibility in front of me. Because I was a bit depressed, I was myopic. For a stretch assignment of this proportion, that was a good thing.

My first week on the job, my corrections colleagues barely suppressed their scowls. For a director of a treatment program targeting men deemed "treatment failures," I didn't look the part. Once, after meeting some peers, someone pointed and whispered, "He applied for the job you got." Another person told me, "I think I could have done your job."

One of my biggest challenges was convincing clients to enter the program. The lures were tepid. To complete the program, an alternative to jail, could take six months, longer than most inmates' sentences. It would take them away from drug use and a lifestyle that many enjoyed. They would be in counseling sessions all day. Worst of all, the center was located in a windowless basement that had been softened with used couches, dilapidated ping-pong tables and a dozen well-meaning counselors.

One colleague invited me to come to the jail where she worked. I expected a meeting room with her and a few inmates interested in recovery.

When I got there, she announced, "We're going to have you talk to the pod."

"How many inmates in a pod?" I asked.

"Just sixty," she said.

"Are you coming with me?"

"Why would I need to?"

This moment was the pinnacle of this roller-coaster career move. Any change in my reputation -- any uptick in credibility -- hinged on how I would respond.

I took a deep breath. All that mind-static about drug-addled criminals I had to put to the side. No stereotype was going to help me now.

She led me into the pod where 60 inmates were milling. They wore fluorescent orange uniforms. Some were lying on bunks. Some were talking in huddles. Behind a console, a guard sat with a glare and a gun. When my colleague said what I would be doing, he rolled his eyes.

Then she left. The guard barked an announcement.

What else can you do when surrounded by a horde of disgruntled inmates? In the most down-to-earth manner I could muster, I talked about what I knew. I described the program. I reminded them it was voluntary. I told them treatment might be a life-changing move.

There were some mean silences. Some listeners jeered. When I mentioned the six-months-in-the-basement-with-a-bunch-of-nice-drug-counselors, they hooted with contempt. When I was done, the crowd cleared and I consoled myself. It had been a rousing failure, with a dash of humiliation. (However, on the bright side, I hadn't been stabbed with a shank.)

But then, as I gathered pamphlets about treatment to make my exit, three inmates approached me. Each said in a different way, "Sign me up. I'm tired of living this way." Those three inmates, when they finished the program, became my ambassadors. They translated my fancy talk about sobriety and pro-social living into terms meaningful to other probationers. In no time, my program filled up, with a waiting list. It stayed that way for years.

Here are the those five epiphanies that I took from my stressful stretch assignment, lessons that I still rely on when I tackle big leadership tasks:

1. Resistance, often ugly, is part of the terrain that leaders navigate. Accept it.

2. Uncertainty and not knowing is part of the landscape. Thinking on one's feet is the map.

3. When in doubt, remember who you are and that you are enough. Breathe deeply.

4. Sometimes failures are successes that aren't apparent to us yet. Be patient.

5. Help comes from unlikely places. Sometimes even in fluorescent orange. Keep your eyes open.

Wayne Scott manages learning and organizational development initiatives for Multnomah County, Ore.
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