In search of the perfect assistant
When seeking a new secretary, I made a big mistake. I hired one who didn't understand my business--or me.
By Kevin Kelly, FSB Magazine

(FSB Magazine) -- Last year I finally broke down and hired an executive assistant. I had avoided the move for several years, despite hounding from my wife and managers that I needed one desperately. My stubborn refusal flowed from the embarrassment I felt at having someone totally dedicated to serving my needs. How egotistical, it seemed to me. My mind also reeled at the overhead I'd be adding--a good assistant in the San Francisco area goes for more than $55,000--and I couldn't quite stomach giving scheduling and filing over to someone other than me. Control freak, indeed.

So what finally changed my mind? Back in the middle of 2005 I had some health issues. I couldn't keep logging 50-or 60-hour weeks, and as a result I began to fall behind. Files piled up next to my desk, I failed to return phone calls, and I made no progress on projects I wanted to tackle, including the development of a new product that I hoped would drive our sales in 2006. Finally my wife prevailed upon me to hire someone. She became so insistent I asked her to vet the candidates for me. In fact, I felt so run down from my illness that I didn't feel I could adequately tackle the search myself, and I barely paid attention to my wife's efforts.

She presented me with two candidates to interview, and one of them had no personality. The one I ended up hiring had an upbeat manner, and I bonded with her thanks to her love of the San Francisco 49ers, my favorite football team. But my limp, one-hour interview really didn't tell me much about how she'd help me manage my day or, rather, how she'd manage me. Talk about a recipe for failure.

Given the landscape, it should be no surprise that the person I hired didn't work out. Certainly she was pleasant and hardworking. But I never learned to trust her, and as a result I never felt comfortable turning tasks over to her. Though my controlling nature played a role, part of my skepticism was reality-based. Most of her working career had been as an assistant to lawyers. She understood nothing about manufacturing and considered our process of making plastic bags a mystery. Her lack of knowledge meant I had to take the time to train her, time I didn't have. By the end, I simply ignored her for the most part, which was unfair to her and to me.

Still, it took about a year for me to let her go. I blamed myself for the failed relationship, and the guilt immobilized me. This was hardly an example to my managers, to whom I preach that if employees aren't working out, let them go. I felt so bad when I dropped the hammer that I gave her several weeks' pay and promised her health care until she found a new job.

But her departure put me back in the hole I had found myself in earlier in the year. While my health was back to normal, I was busy as ever, and it still made no sense for me to do clerical work. So I made a quick decision. I shifted an employee who'd been in customer service for more than 25 years, who knew me and understood our business, and whom I trusted implicitly. And bingo, like magic, I suddenly found myself loading my assistant with work. In fact, she's tackling a project I'd never laid on my previous assistant: a five-page vendor-qualification form from a national grocery chain that demands intimate knowledge of our business to complete. Handing over that task has saved about 20 hours of my time.

Most of all, though, I love it that my new assistant knows me. She understands that I often don't put meetings in my Outlook calendar, which leads me to forget them, so she harasses me every now and then to make sure I have my appointments up to date. She reminds me when I have early-morning meetings--also something I tend to forget--and when I'm busy she offers to fetch lunch, a meal I often skip. She has the intuitive understanding of me that my first assistant lacked. And my wife? Since the first month with the old assistant, she'd been begging me to move this employee into the job. As usual, I should have taken her advice a lot earlier.

Kevin Kelly, once a journalist, now runs plastic-bag maker Emerald Packaging.

9.5% Average increase in administrative assistants' salaries between 2005 and 2006

Source: International Association for Administrative Professionals Top of page

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