Whatever You Do, Don’t Screw Up

I was about to step into a cavernous meeting room packed with mostly male executives, the crème de la crème at the top of the company. I had the results of a readership survey to share with them, along with recommendations to revamp the employee communications program. As I was beckoned inside the open door, my extremely nervous boss leaned in closely and whispered, “Whatever you do, don’t screw up.”

I remember getting through the presentation calmly and receiving insightful questions and positive feedback, plus a decision to proceed with my recommendations. But the impact of that little whisper from my insecure boss became a tiny seed of doubt that rooted itself in my psyche, growing and blooming and becoming as real to me as my youthful rock-solid confidence once was.

Many years later, and several years into being a boss myself, the outgrowth of that experience often manifested itself as a hypersensitivity to bad bosses, and a strong desire to never become one. I had learned by then that good bosses compartmentalize whatever else is going on around them —or within them — so they can focus, listen, guide, advise, encourage, praise, course-correct, and thereby build trust, with everyone on their teams.

“Being a good boss is extraordinarily simple: Be human. Be real.“

I had wonderful bosses in my corporate career. But I had a few who challenged my patience, my sanity, my core values, and even my overall health. One deserted her post, leaving a leaderless team to fly by instinct during an unprecedented crisis; another worked odd hours behind closed doors and sent rambling emails on imaginary grievances. I had more than one boss who successfully stepped over legal and ethical lines. And finally, almost laughingly, a boss who would inexplicably burst into arias in the middle of staff meetings.

Even with the irritations, frustrations, agonizing disappointments and occasional damage stirred up by not-so-great bosses, the truth is that I learned something from every single one of them. I learned what not to do, of course. I learned as well that there is a broad spectrum of grays between the black and white of bad and good bosses.

On the very dark side of that spectrum, I learned that some people are adept at rationalizing their behavior, even when that behavior causes harm to others, and even when confronted with facts that prove wrongdoing. I learned there are sociopaths among us, leading teams, making all the right motions of management yet leaving psychological casualties in their wake, all the while twisting situations to their own self-protective advantage and dodging repercussions like slippery eels. I know from experience that the damage done by the worst of the worst bosses travels with us, sometimes taking years to resolve.

Perhaps the most valuable lesson overall was the realization that bosses can move along that spectrum from dark to light or bad to good as circumstances change, as time goes on, or with the impact of one earth-shattering epiphany. One such transformation involved a boss I judged initially as superficial, flighty and indecisive. I could not have been more wrong. It was a style difference (my issue), not a leadership deficit on her part. I came within a hair’s breadth of missing the gift of her vastly different, yet highly effective, approach to leading and teaching people.

“If you want the people on your team to believe in you, to trust you and come together despite their differences and individual agendas, you must suspend what you know, lean in with what you feel, and balance that with what you must do, as a leader.”

I learned the secret to writing like an experienced journalist (as opposed to an English major) early in my career from a boss I saw initially as moody and difficult to read. He walked into my office out of the blue one day, dropped a copy of The Wall Street Journal on my desk, tapped his index finger like a hammer on one specific column, looked me in the eyes and said, “Write. Like. This.” And then he turned on his heel and walked out. At first, I was intimidated and a bit insulted. But I picked up the newspaper and scanned the column, then read it word for word several times. Suddenly it all became clear, along with all the other times he had tried to turn me into a reporter. He needed to get my attention, and it worked. I never forgot that lesson, or the lesson that not all good bosses come with happy smiles and heaps of praise.

I did not fully embrace the good boss side of me until somewhat late in my career, once I’d had time to absorb all the lessons from the bosses I’d had and figure out how to bring to life the very best of the gifts I had received. In the end, I learned the secret to being a great boss is not a secret at all.

Being a good boss is extraordinarily simple: Be human. Be real.

The most stressful time in my career was when I suddenly found myself leading a team of people virtually — people I did not know, did not select, and would rarely see in person. I led this team from Houston, while most of them were in London. The expectations on all of us were weighty, fraught with criticism, surrounded by pitfalls and potholes. I was lodged between a rock and a hard place with only scattered bits of advice or guidance that I could understand, much less trust.

Early one morning I sat in a tiny fishbowl meeting room in London, horribly jet-lagged, with one after another of my team members pouring out their obstacles and challenges, occasionally with tears. After several hours of this, I had a moment — a freezing, frightening, paralyzing moment — when I thought, I have absolutely no idea what I am doing. So, I led with my heart – I just kept listening, as hard and long as I could, trip after trip after trip.

A few years later, I realized my instincts had been spot on all along. It was not charisma, brilliance or a shining personality that labeled me a “good boss” by this team. It was my human, honest and transparent self — the caring, sharing, listening, reinforcing, reassuring, I believe in you approach that made all the difference for these people, and brought us together like no team I had ever experienced. It was the best of the best — and I grieved when it was gone.

That little seed of doubt planted in my psyche decades before had finally dried up and blown away. I was proud of the boss I had become.

There are times when corporate rules and policies are in order, along with academic management-speak that offers instruction and methods on leading others. But there are many more times when none of that matters. If you want the people on your team to believe in you, to trust you and come together despite their differences and individual agendas, you must suspend what you know, lean in with what you feel, and balance that with what you must do, as a leader. Authenticity, vulnerability and compassion, along with integrity, are the keys to building connections that can move mountains.

Be human. Be real.