THE BLOG
04/25/2013 04:29 pm ET | Updated Jun 25, 2013

How to Hire the Perfect Assistant, Using the Rules of Online Dating

Listen, we all online date. There is no shame here. For my girlfriends and me, sitting around swapping war stories of online dating has become our favorite pastime. From the OCD creep to the rude asshole to the way-too-sensitive guy, we have dated them all. And just like trust falls and company picnics, I like to think of our dates as character-building exercises until the right one (the right guy - not the right company picnic) comes along.

But interestingly enough, I've also learned that online dating can be an excellent training tool for choosing your assistant.

As I interviewed assistant candidates this past week, it dawned on me that finding not just a good one, but a perfect one, is a little bit like finding your soulmate. Because you're not simply looking for a polished resume. You're looking for a long-term match. A partner. Somebody who "gets" you.

So little did I know that all those dates were actually just career training in disguise. Here now, five ways online dating helps you find your perfect professional assistant:

1) It is a numbers game. While I don't always go a million dates, I always keep my Ok Cupid profile active - just in case. It's not rocket science. The more people you meet, the more likely you are the find "the one." Finding the right employee operates on the exact same principle. The more effort you put in to getting out there and finding someone, the higher the likelihood you will find the perfect match.

2) Asking innocent-sounding (but very loaded) questions. Come again? What does that mean? I have a few questions in my arsenal of dating tools that I ask as a character assessment. For example, "how was your weekend?" or "what do you normally do on weekends?" They seem like innocent niceties, but I am really gauging to see how social they are, because hermit behavior is a deal-breaker for me.

The same goes for interviewing possible employees. Your candidate will come armed with the same canned, BS answers. Are you good at time management? Yes. What is one challenge in the workplace you had to overcome? Blah, blah, blah. Those questions/answers will not give you real insight. Sprinkle in questions about weekend plans, hobbies, dating, school work. I promise you will learn a lot more about whom you are going to hire.

3) Keep your search targeted. It's not just about Monster.com, folks (or, to continue our analogy, Match.com). Just like online dating, you have to hit up niche sites to find what you want: JDate to find somebody Jewish, Meet A Cowboy to find a cowbody, Purrsonals to, no joke, find a fellow cat lover. This same tactic can be helpful when looking for employees: searching in niche markets will narrow the playing field. Post the opening in an industry specific group on LinkedIn. Or, send a job notice to target students at your local college or university studying the appropriate majors.

4) Knows your non-negotiables. You have to set surface-level criteria to help narrow down the applicant pool. For me, when it comes to dating, height is a big thing. Since I am tall, I won't date anyone that is under 5'10. Even if he is the greatest dude of all time, I am sorry; I still refuse.

The same method is true for finding an assistant. When I was going through my search last week, I decided that follow-ups and confirmations were going to be my big thing: If the candidate didn't e-mail me the day before our interview to re-confirm time and place, then I was automatically done with them. What if they forget to follow up with a Good Morning America producer the day before a client goes on?

5) Have an escape route. Bad interviews can be just as awkward as bad first dates, and they tend to be a major time suck. Most likely, you know if the person is a good fit within the first few minutes. If they aren't, you always need an exit plan. For dating, I like to meet for coffee or drinks because I "have dinner plans," even if those dinner plans involve me, a frozen pizza, and my good friends, The Real Housewives.

When you are meeting people for interviews, you also need to have a way to get out. There is no use wasting time if the person isn't a good fit. I usually rely on this one: "I have a very important client phone call in 10 minutes." Sometimes, it's true.

As I learned last week, finding a personal assistant is no easy task. But it can be easier if you apply the rapid-fire character assessment tricks we online daters know already. With enough time, you'll find the perfect match.

Rebekah Epstein is the founder of fifteen media, an agency that works exclusively with PR firms to streamline media relations in a digital era. She specializes in business, lifestyle, fashion and beauty PR. Rebekah also [amateurly] blogs about the ups and downs of Gen Y entrepreneurship at fifteenminutesblog.