In the Trenches: Learning How to Use an Assistant

BrettSnyder by Brett Snyder on July 13, 2011
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I keep waffling on whether or not I need to get an assistant. Part of the concern is, of course, money out of pocket. But the other concern is… what would this person even do for me?

I know it sounds funny, but I’ve never had an assistant of my own. Sure, I’ve worked with group assistants at a variety of jobs, but I’ve never had someone that reported to me directly and had me as the primary “client,” if you will. Why haven’t I had an assistant? Probably because I’m stubborn and like to do everything myself. I know that’s not feasible in the long run as we keep growing. But I really don’t think I know what to do with an assistant.

I’ll never forget when my old boss at a previous employer was promoted and was given an assistant. The assistant was very experienced and told me how she had to train her new boss on how to actually use an assistant properly. I feel like I would be in the same place. I simply wouldn’t know where to start.

Even now with an intern, I feel the same kind of stress. I almost feel like I have to spend more time creating work for him so he’s not bored. Other times, I completely fail to even think about some things he could be doing, because it simply doesn’t dawn on me that others instead of myself could be doing it. I just assume it would be the same way with an assistant. I’m just not good at taking myself out of the work. That may sound funny, but it’s a real problem.

At some point, I’m convinced that I’ll just need to dive in and bring someone on with the hope that I can figure out exactly what he or she should be doing. The temptation is there to get someone who could “train” me, as the assistant did for my old employer, but I imagine getting someone seasoned like that would be more costly than I could afford.

I’m sure that some day I’ll look back and think how silly it was that I had no clue what to do with an assistant, but right now, that’s exactly how I feel.

BrettSnyder

Brett Snyder is President and Chief Airline Dork of Cranky Concierge air travel assistance. Snyder previously worked for several airlines, including America West and United, before leaving to create a travel search site for PriceGrabber.com. Snyder did his undergrad at George Washington and earned his MBA from Stanford.

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