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How to Hire an Assistant

For the first time in 11 years, I needed an assistant. But was I really ready to let go?

Jason Fried is the co-founder and president of 37signals. Basecamp, Highrise, Ba

Jason Fried is the co-founder and president of 37signals.

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My desk used to have a very large pile of envelopes stacked in the corner. It included notices from various agencies in the states in which our employees live, pitches from would-be business partners, personal correspondence, and too many other things to list. Under the desk was a box, which contained all of the stuff that had been crowded off my desk. At times, there have been multiple boxes.

I didn't ignore the stacks and boxes. But I didn't exactly deal with them, either. Well, I always took the first action: I opened the letters and took care of the urgent stuff, such as paying the bills. But the bulk of these papers required some measure of detailed follow-up or further thought or action. And that's generally where I dropped the ball.

Sometimes, I would stare at that stack of envelopes or the boxes under my desk. I wouldn't actually do anything about them; I would simply stare and think that they were symbolic of just how overwhelming the administrative side of my business had become. It wasn't just paperwork. It was phone calls: getting back to the landlord about some issue with the parking garage, contacting our payroll provider to settle some tax issues, searching out new health care plan options, making sure people who helped us out got thank-you notes. The list went on and on. 37signals, the Chicago software firm I co-founded, has been growing fast, but the administrative responsibilities have seemed to grow even faster.

I've always shared these responsibilities with my partner, David Heinemeier Hansson. Though we both take pride in being efficient and getting stuff done, we found ourselves being distracted from focusing on our products because so much time was being sucked away doing—or stressing about—administrative work. We needed help. It was time for us to find an executive assistant.

It sounds duh-obvious, but this was kind of a big deal for us. In the 11 years we've been in business, 37signals has never hired someone who didn't directly affect our products. We hire designers, programmers, system administrators, customer service people, data analysts—employees who have a direct impact on how our products look and work. But we haven't much bothered with administrators or managers.

What's more, delegating isn't easy for me. Even though the paperwork and other chores were piling up, I still had a hard time letting go. I have a feeling I'm not alone in this. It's tough for the person who started the business to begin to let go. For more than a decade, I've been involved in every decision at this company, from which hosting company to use to what brand of paper towel goes in the kitchen. When you're that used to having every decision run through you, it can be a bit unnerving to surrender control. I understand that it's silly to believe that every small decision needs to run through you. But it's such a primal instinct when your business is your baby.

So we set out to find an assistant: someone to assist me, David, and anyone else at the company who needed help with administrative tasks. Since we'd never hired for this kind of position, I went online and reviewed a bunch of assistant and office manager job postings. But the listings didn't really do much for me. This is a problem with job listings in general: They don't seem to describe an actual day's work. They're heavy on skills but not actions.

We decided to go in a different direction to locate our new assistant. Instead of a boring list of skills—this software, that many years of experience, "team player," etc.—we wrote a list of 26 things that this person would have done in a week had he or she been working here.

The list included things such as "Booked two hotel rooms and two flights for out-of-towners"; "Packed up and shipped out about five copies of Rework to various people"; "Coordinated with Abt Electronics to schedule installation of four flat-panel TVs"; and "Researched and recommended local floral arrangers for weekly flowers for the office." This way, whoever was applying would know exactly the kind of work he or she would be expected to do. (You can read the job posting here).

We posted the ad on our company blog, Signal vs. Noise, thinking that the unusual approach would help narrow the field of potential candidates. It didn't quite work out like that. Instead, we were bombarded by hundreds of applications. We were a bit overwhelmed by the response.

We sorted through them and began to interview a few folks who seemed most promising. We realized pretty quickly that either we left something out of the ad or this was an especially hard position to hire for—at least according to the way we usually hire people at 37signals. In the past, we've always looked for people who are in it for the long haul, people who are truly interested in developing and growing with the company. Though we've hired a bunch of new employees recently, most of our crew has been with us for years.

We interviewed some really good people. The problem: Most of the best candidates saw the job as a steppingstone. They wanted to start out as an assistant and end up somewhere else. That's completely fair, of course, but it didn't do us much good. We needed an assistant who wanted to be an assistant—someone who actually enjoyed sweating the details at a small but growing company, someone who would excel and grow but not grow out of the job itself.

Usually, we fill job openings pretty quickly. But in this case, we wound up interviewing dozens of candidates over several months. And then, finally, we found Andrea LaRowe. She'd been doing a similar job at a nonprofit organization here in Chicago, so she was perfectly qualified. She also emphasized how much she actually enjoys her work. She started on February 28.

I have to admit that in the week or two before Andrea started, I was nervous. I looked at the pile and the box and wondered if I really would be able to let go. But my worries were unwarranted. Once I was able to get a few things off my plate, it became easier and easier to let go of nearly all the administrative chores.

And it didn't take long for Andrea to have a big impact. Suddenly, everything is taken care of. There are no lingering issues with a question about our 401(k) or health care plan. Our catered events come off without a hitch. Travel arrangements have been spot on. Research projects have been researched. Applications and forms have been filled out and submitted.

You know how you can tell when you've made a good decision? If you feel like you waited too long to make it, then it's a good decision. That's how we feel now. We should have done this a long time ago.

And here's the real bonus: David and I have clearer minds. We know the administrative details are taken care of. We've refocused on the work, the ideas, and the important decisions that need to be made about our products. And my desk, finally, is clean.

Jason Fried is co-founder of 37signals, a Chicago-based software firm, and co-author of the book Rework, which was published last March.

IMAGE: Laurent Cilluffo
From the May 2011 issue of Inc. magazine




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