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The Business of Personal Assisting

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    We're running out of ways of creatively telling you the economy has been suffering, but trust us: it's bad.

    On the upside, it's had a two-prong effect: It's forced a great number of people to reconsider their career arc, and an even greater number of people still to go into business for themselves. In short, if you're a new entrepreneur, you might be thinking of hiring a personal assistant to help get a sense of balance back in your life. (Or alternatively, you might be thinking of becoming someone else's personal assistant.)

    But decades of glamorizing the Hollywood elite and their lifestyles have led to a lot of misconceptions about what exactly it is a personal assistant does, or what's sensible to expect of them. To get a clearer idea and help ground your expectations, I gave Caitlin Hofherr, the founder of Alter Ego Concierge, a call. She started her local agency in 2010 after previously serving as the director of a lifestyle management and staffing firm in New York, and has paired assistants with Fortune 500 CEOs and celebrities and to work as to doulas and personal shoppers.

    What advice do you find yourself giving again and again to people who are interested in pursuing this field?

    Caitlin Hofherr: I think one of the biggest things that we get asked is, "How do you become a personal assistant?" It is one of those things that people just assume you can't go to school for; that it's one of those jobs that you fall into. The thing really is that there's a big misconception on what a personal assistant is and how to really get into it. There are actually schools that teach courses on it. One of them being the Bespoke Institute in New York.

    I think that a lot of people just lose sight of the fact that it is definitely a skill that you cannot always learn. There has to be some basic structure in place before. And basic skills that you can learn, but that you can't learn. You obviously have to have great people skills. You have to be able to effectively manage a calendar and understand time management. Knowing that no two days are the same.

    We always say you have to be able to take initiative and work well with, at times, big egos in very stressful, high-pressure environments. You have to be okay being the First Lady. Essentially, the No. 1 question that we ask is, "Why do you want to do this? Why do you want to be someone's right hand versus the person who's front and center?" I think that a lot of people enjoy that. They enjoy organizing people's lives.

    As the grounds for starting out, if you have no experience? Network with other business-savvy people who are in a similar industry. Even if it is a newer entrepreneur who has just started a business. Maybe they're looking for some part-time help. Your first job, unfortunately, most likely will not be working for George Clooney as a personal assistant. [Laughs.] You have to start from somewhere and build your resume to be more personal-assitant geared. That being said, you also have to be able to manage not only the social demands of the employer on the personal side, but oftentimes you double as an executive assistant, even if there is one in the office. You're often juggling those duties or at the very least maintaining both calendars so there's no double-bookings.

    If there are classes and people who become personal assistants are able to educate themselves, it occurs to me that employers likely haven't been disavowed of those same misconceptions. Are there boundaries personal assistants should set in the working relationship, in terms of tasks that might be unreasonable or unrealistic to expect of them?

    Caitlin Hofherr: Absolutely. It's always good to establish the boundaries of being able to separate your work-life balance. Although some personal assistants, going into a job, understand that this is 24/7. If it means getting a phone call at 2:30 a.m. to go buy some toothpaste, they're willing to do it. But it just depends on what role you want to go into. I think a lot of it comes down to that chemistry and matchmaking. Looking at your employer and understanding their needs and being able to see if you'd be able to fill it. In the event that it's a position that's going to require a lot more hours and whatnot, you kinda want to know that going in. And you want to obviously establish a great rapport with that person, because you are involved the most intimate aspects of their lives.

    What we always say is that trust has to be established immediately. Nowadays, personal assistants will have to sign a confidentiality agreement, they'll do a background check and whatnot. It is one of those things that you have to adjust yourself and adapt yourself to their personality and see how they work. You may need to come on a little less strong at first and maybe not be talking about financials. As your duties increase, maybe it turns to book-keeping. There's a lot of duties that a personal assistant handles, and obviously at first you're not going to be able to do everything, but most good personal assistants would want to. You have to establish that communication and trust with your employer at first.

    What are some of the other misconceptions you find yourself running into?

    Caitlin Hofherr: It's not as glamorous as people think. [Laughs.] We receive hundreds of resumes a week from people who are interested in getting into the field. Some of them have great qualifications. Some of them are entry-level and are not as aware of what is involved and we have to educate them that even if you set those boundaries, you are running this person's life. If they are traveling over the holidays they might be calling or e-mailing you. Most personal assistants don't really take a full day off. They're always checking their e-mail. That's something that comes with the territory.

    There are obviously, on the flip side, wonderful, great perks. Most employers recognize that if you have a great personal assistant, you should treat them well. The salaries are very competitive and whatnot, but it it's definitely not as glamorous as people think. And it's also not something that just anybody can do. Especially with the economy right now, we get so many applicants. It might be someone who was in real estate before, and that's not to say that they're not qualified, but as an agency we have to have some sort of grounds to qualify them. We need to see that they've done this for a certain number of years. We require three years experience.

    The other thing, too, is that a lot of people think because they organize their own life that they'd be great handling somebody else's. While you're organizing it, you don't necessarily get to call all the shots. I think that can be difficult, too, to check your ego at the door and understand that this is my boss' life, not my own.

    You mentioned when you interview candidates you ask them why they want to do this sort of work. What are some reasons that would make you wary or doubtful of a candidate?

    Caitlin Hofherr: If somebody is looking for a 9-to-5 job, something where they can check in and check out, usually it's a big sign that they're not going to be great for every position. A good personal assistant should be a clock-watcher. That's the No. 1 thing that we ask: "How do you feel about occasionally putting in long hours or having to travel with your employer?"

    The other thing that we look for is longevity. We want to see that if they have experience, how many years have they stayed with every employer? Is it every two years they get bored or after 15 years with one employer the person has retired? We're looking for longevity on their resume because with a personal assistant you want to establish that trust for years to come.

    You said it would be unreasonable to expect to be paired up with George Clooney as a personal assistant if you're just starting out.

    Caitlin Hofherr: [Laughs.] Well, if you have no experience, it's probably, I would say, a stretch.

    What would be a little more reasonable to expect or shoot for with your first gig as a personal assistant then?

    Caitlin Hofherr: We always say network locally.

    So R. Kelly then, maybe?

    Caitlin Hofherr: [Laughs.] Right. Exactly. But, obviously registering with your chamber of commerce. Every different type of person seems to be adjusting to their demanding schedule by hiring a personal assistant. So one of the big things is networking with other business groups and whatnot, and getting involved with your church, whatever it maybe. Sometimes it might take volunteering and helping a person out one day a week. Or working part-time at a much lower hourly rate than you normally would just to establish some sort of references for yourself. A lot of household organizers, people who take freelance positions, end up transitioning into personal assistants. And the best way to do that is to maybe take those positions that are only three days or a week so you can start to have a portfolio of your work and be able to show employers what you've done.