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    3. My 3 Most Embarrassing Small-Business Moments»

    My 3 Most Embarrassing Small-Business Moments

    Ivan Schneider
    Getting Started

    It occurs to me that I've already written two columns here at AllBusiness, but most of you haven't the slightest idea who I am. What does this "Ivan Schneider" character know about running a small business?

    Good question.

    To break the ice, I thought I'd share a few personal small business anecdotes, and to keep your attention, they're some of the most embarrassing moments of my career to date.

    I hope you find these recollections of my past discomfort a refreshing change of pace. Plus, if just one person learns something from the mistakes of my past about HR policy, project management, and the importance of daily backups, then these are worthwhile revelations.

    Herewith, my top three most embarrassing small business moments:

    #3. The Nanny

    After college, I did some work as a computer consultant for a Newark, New Jersey-based nanny service. My job was to write software to match young women from the Midwest to well-off suburban families with children. During one of our meetings, I asked the "mother hen" if she could set me up on a date with one of the nannies. At first, she balked, but the next time I saw her, she had a phone number for me. I called, we went to the movies, and that was about it. My sweaty-palmed awkwardness with the pretty Iowa farm girl made, I fear, the wrong impression. In those years, I was much smoother with computers than with women.

    In retrospect, it wasn't very professional of me to have asked the proprietor for the phone number of one of her charges. Plus, if I had just waited until after the go-live, I would have had the entire database.

    Takeaway: Be careful before you trust the IT help with the contact details of your other human resources.

    #2. The Time Sheet

    My first real job: I worked in New York as a programmer for a small, closely held family business that tracks television and print advertising. When I joined, there were about 30 people crammed into the basement of an Upper West Side brownstone that had been converted from a laundry room into a workspace. One group of employees, the "television coders," would fast-forward through taped television shows to note the airing time of any commercial from a list of specified advertisers, and the aggregated information would be sold to ad agencies. As the business expanded, the company had to add a second shift of coders.

    I was attracted to one of the girls working on the late shift, and we would have nice, flirty conversations whenever we'd see each other. Sometimes, I would stay late at work just in the hope that she would work that evening. I didn't want to start the office gossip mill by asking the department manager about her schedule. Similarly, leaving her a note would have been a ridiculous idea. And so I came up with a brilliant plan.

    One of my first development projects had been to write custom time sheet software. Employees checked in and out several times a day by entering their initials into the dedicated time sheet Mac. It would have been trivial to add a line of code to display a message to my would-be girlfriend: "Hi, it's Ivan, call me tonight at 212-555-1212."

    Way too easy. I unilaterally increased the scope of the project into a full-fledged messaging system. Instead of relying on a hard-coded message, I would develop a useful new feature whereby a manager could leave a message for any hourly employee checking in or out. I'm not sure how long I actually spent on this sideline, but needless to say, it went over the time I had been budgeted to work on the project by a factor of infinity. In the end, the feature worked, but there were too many bugs for production, and so I killed it.

    Postscript: I asked her out on a date. We went to dinner, and then we took a taxi downtown to continue the evening. Then, she heard something playing on the radio and asked the driver to turn it up to an uncomfortably high volume. It was a preacher delivering a sermon. For 50 blocks she listened in rapture, me in absolute befuddlement. Her religious awakening was the sudden end of the date. I got a peck on the cheek -- and a few days later at my desk, one of her poems printed in ornate Gothic type and replete with graphic religious imagery.

    Takeaway: The day shift shouldn't date the night shift.

    #1. The Bed-and-Breakfast

    After getting a business degree, when I was no longer a programmer but not yet a writer, I landed a unique career opportunity. The owner of a prestigious bed-and-breakfast in Washington, D.C. (who, incidentally, started her career as a nanny) thought she might be able to employ the talents of a technically-minded recent MBA. I was invited to spend some time as a guest at the luxuriously appointed mansion with the task of finding ways to make myself useful, and the owner gave me free rein to access all of the company's records and systems.

    I wasn't really that familiar with the company's ACT! contact manager, but I was a database programmer in my prior life, so how difficult could it be? Maybe the database was running slowly, maybe I thought it was a different command . . . . Who knows why I did it. What I know now is that the "Rebuild Database . . . " command should only be undertaken after you have made multiple copies of the data file onto reliable backup media. The system hung, I had to reboot, and the data file was torched. What's more, I had to inform the owner that I might have destroyed the personal contact details of an extensive list of VIP guests who are not listed in the phone book. Fortunately, they had made a backup a couple of days earlier and only needed to re-enter a few records.

    I was told that, given my abilities, I should consider a livelihood teaching at a university.

    Several years later, I took an evening course in Oracle database administration. The instructor pointed out: "You're not a true database professional until you've accidentally destroyed a database." The implication being, once you've been scarred for life with the memory of a colossal fiasco of your own making, you'll be scrupulous in your data hygiene and backup protocols. And so it has been.

    Takeaway: Only hire people who admit that they've made mistakes.

    What's your most embarrassing small business moment? Write to ivan@ivantohelpyou.com with the incriminating details, and include your name if you dare (or an alias if you daren't).

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    Profile: Ivan Schneider

    Ivan Schneider is a writer, analyst, business technologist, and a keen observer of what makes a winning small-business concept -- and what doesn't.

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