1. Early Lessons in Leadership

You’ve Got Mail (You Don’t Know it)

Early lessons in leadership – #7.

Early in my career, circa 1990, my work in the nascent tech-media industry forced me to raise my game in computer literacy.  It was a humbling experience — but a great learning opportunity.

I was hired by Seybold Seminars, and when asked about my computer experience, I felt pretty confident.  After all, I had a rudimentary understanding of DOS — I knew how to enter a password to access a central inventory database — what else could there be?

So, there I was, the new guy, when my new boss asked me to cover for her while she went to Australia on holiday. She explained that she’d sent all of her contracts and follow-up information to my in-box. I assured her I was on it. After she left the country, I couldn’t find anything I needed, so I went down to the mailroom and explained that I was looking for some missing files. What I discovered was that she’d sent everything to my email box. I didn’t even know I had one — or how to use it. Epic fail.

For a few days, my work life felt like a bad sit-com. To get it back on track, I had to swallow my pride, make myself vulnerable, and ask for help with email procedures that now seem rudimentary. I had to learn an all-new way of working, and it was pretty intimidating.

Fortunately, I had an awesome, generous boss who saw beyond my shortcomings to the core competencies she knew I brought to the table.  That helped my bruised ego, because I shared her office, and had to learn a suite of new technology tools right in front of her. Every time I fat-fingered something and my Mac computer blasted  a “FAIL” noise, she just shouted out the command sequences I needed.

I never forgot the two lessons I learned from this humiliating experience. First – if you don’t know, don’t fake it. It’s better to be vulnerable and ask for help than to exacerbate the problem. Second – be patient with people who need help learning the ropes. True leaders, like my boss at Seybold, understand the importance of hiring for essential abilities and culture fit. Skills can be taught, but values define us. And empathy is a two-way street.