Starter Steps to Hiring your First Assistant

“If you don’t have an assistant, you are one.” – Raymond Aaron

Who should I hire first?

It’s a common question among new business owners. And my coaching is pretty straightforward…

If you’re a new business owner, your first hire should always be an accountant.

After that, get a bookkeeper.

When you get those out of the way, I encourage you to hire a personal assistant.

 The Wrong (and Right) Hiring Order

I’ve heard some corporate-background business consultants spout off advice they’ve probably read in a book somewhere:

That your first hire should be someone who can bring in money – like, say, a salesperson.

I don’t even sort of agree.

Consider two things here…

Firstly, the typical left-brain corporate advisor type rarely has been in the trenches as a solo business owner like you, who is working out of your house, trying to run a family, plan meals, make a carpool and every other task under the sun. (AND he’s a man, right?)

In theory, yes it would be great if you could outsource the money-making part of your business…but that brings us to our second thing to consider, which is…

…which is that if you started your business with just a great idea and your skillset, you’re probably not ready to outsource the selling part – which is probably still a very delicate part of your business. (Exception is made for artists, writers and musicians who hire good agents.) Hiring a salesperson or marketer usually isn’t hiring. It’s abdicating…most likely because you’re hoping it’ll all just go away and never bother you again.

The problem is that you need to get better at sales, you need a system for how you sell, you need to understand your voice and message in both marketing AND sales before you can outsource them well. So, give yourself time to master this stuff while your business grows.

In the meantime, get other items off your plate. What takes up the bulk of your time? What gets in the way? What little nose-bleed tasks keep tugging at you? And most importantly, what do you use as a procrastination excuse every single day?

Wait. Before you answer. Let me share my own ridiculous story. This way you’ll feel much better about yourself…

All the Ways You Procrastinate (Or…My Stupid Toothbrush Story)

Long ago in a galaxy far, far away, I worked out of my home when I wasn’t on the road. I was a performing songwriter running my own record label, and I never had enough time. (And this was before Facebook.) There were always a million things to do, and I could never even find the time to do them.

And yet…

I managed to do the dishes and complete a total clean up of the whole entire kitchen pretty much every day I wasn’t on the road.

Then one day, I caught myself scrubbing the kitchen sink with…ready for it? A toothbrush. You know those times where you glance at the edge of the stainless steel where the faucet meets the sink and discover what could only be a black plague of death hiding in there? Well, that’s what happened to me.

So, I did what any average obsessive distracted person would do who’s avoiding doing her work.

I grabbed an old toothbrush, bleached it and started in on the sink, scrubbing furiously to get rid of the offending substance.

That’s when I woke up.

I was literally drowning in to-do’s. I had money to deposit, songs to write, a producer to call, dates to book, checks in the mail for CD orders. (Like I said, this was before Facebook!) And there I was, toothbrush in hand, bent over the kitchen sink giving my whole spirit (and precious time) to something that really didn’t matter.

Which is precisely when I hired my first personal assistant.

I was nervous. After all, nobody I knew had a personal assistant! But in only a few hours per week, she took on the kitchen, the laundry, and the grocery shopping. (And presumably, the black plague of death in my kitchen sink.) She later did my bank deposits and CD orders.

I showed her what to do, and I made myself use the time to do the work that would ultimately pay me way more than her hourly wage.

I haven’t looked back since. I now have a personal assistant 30 hours a week. She helped me create an Operations Manual for my home, pets, husband and life. At first it was in a binder. Now it resides in Evernote.

It’s never easy to hire someone. It seems there’s always a one-woman-show in your head with the never-ending monologue about how you should just be able to do all of this stuff. Or that by the time you show someone else how to do it and blah blah blah –

So, let’s bring up the house lights, stop the drama, and get started removing stuff from your plate, so you can actually, you know, focus on your business…

 Five steps to hiring a personal assistant

1 – Brain dump.

This part’s fun. Grab a piece of paper or open Evernote – and write down every single thing you do in a week. Everything. Personal and business. Let fly, my sister. And don’t leave anything out just because it makes you embarrassed, or you’ve been meaning to stop doing that. This is all about seeing clearly.

2 – Identify your biggest (or most subtle) time thieves.

Now, look at your list. Identify which items steal your time and energy that could easily and quickly be outsourced. This is often the “low-hanging fruit.” These tasks could take anywhere from 5 – 50 hours of your time each week.

3 – Create a master list.

Create a list – not just of the tasks that you can outsource – but also the time you will be adding to your week just by letting them go. This will train your brain to see that you can actually take this time to work. (Once I started paying someone to do these things, I was less prone to wasting that time because I challenged myself to generate the income I was paying!)

4 – Determine how many hours you could outsource for starters.

You don’t have to get it ALL off your plate. Start small. How many hours could you hand off? How much is worth investing so that you can begin training yourself to focus on building your business? Write it down, make a plan.

5 – Create an ad and post it.

Do not avoid writing the ad. Writing the ad will make you a better employer. Writing an ad will sell YOU on the idea, as well as the ideal employee.

Then post the ad on a site like Craigslist or Indeed.com.  Or ask your network for any suggestions.

6 – Interview and audition.

Do a series of interviews. Do the first interview outside of your home. That way, you don’t invite strangers to your home. Do not just do one interview. Do several interviews and make the prospect audition for a week, doing set projects – like the laundry. Or the black plague on your sink. Sit down and get their input, how they liked the work, if they noticed that something could be done better. See if they think like a helper. You don’t want another diva in your house! You’ve got that role covered!

 The 5 Top Fears and Challenges of Hiring a Personal Assistant

Of course you have concerns and mental challenges with this simple process. Let’s address them head on…

Fear #1 – “Like I could find someone to do my shitty personal tasks.”

For some people, it’s mighty embarrassing to think of offloading the stuff that you hate doing.

Enter The Litter Box Rule.

I created The Litter Box Rule when people wanted to know my secret for finding personal assistants who have stayed with me for so many years.

The answer is that I’m clear and honest from the start.

First, I’m honest with myself. I’m unafraid to get clear about the menial tasks that need to get off my plate so I have time to run my business and have a life.

Second, I’m honest with my prospects. I don’t sugar-coat the truth about my life. (ie, cleaning the house before the cleaning lady arrives.)

That means that the ads I post are like any good marketing. They’re relentlessly honest so that prospects can self-select. In other words, if they’re going to be scooping the cat box, then I tell them up front. In fact, here’s a screen shot from an actual craigslist ad I posted a few years ago:

The Litter Box Rule means that being relentlessly honest about the role in any job description will set you up for success. When we hide who we are and what we need, we serve exactly no one. Least of all ourselves.

Fear #2 – “But I’m really picky about how I like things done!”

When people tell me this, I often discover that they’re terrified of being “found out.” They’ll be labeled a control freak. Or worse…a bitch.

Why not just own it? You like things the way you like them. This is why you have your own business, right? You’re not a bitch. You just know how it should be done.

I’ve found that the people who work for me love it when I am clear up front and can share exactly what a task looks like when it’s done and done well.

As with the Litter Box Rule above, let prospects know in your ad copy that you are picky – but that you’ll provide clear training and feedback to help them succeed. (You can always throw in a sideways smiley face to indicate that you at least have a sense of humor. )

Fear #3 – “But they’ll judge me for the way I run my life and house!”

Confession: I now have a team of nine people. As I’ve added to my team over the years, one of my biggest fears has been the fear of being seen. Every. Single. Day. Being seen in my ups, being seen in my downs, being seen in my Lululemons – whatever.  So I am intimate with this fear.

So guess what…they may judge you. But more likely, they won’t.

I have discovered that in my interview process, I can ask them questions like, “Tell me something about you that I just have to know.” And I will find out if someone is critical merely by how they answer.

Fear #4 – I don’t know if I can trust someone to do all of those tasks. What if they steal from me?

This is why you begin your relationship with your personal assistant with only a few hours a week, a few projects a week. Go slowly – and watch the person work.

Then, if tasks involving money are required, start by using cash. (Remember cash?) And let the role evolve.

As the position expands into more hours, you can activate credit cards from your bank that are not connected to your main account. That way, if the person suddenly goes batshit crazy one day, you won’t wake up to discover your accounts have been drained.

Fear #5 – “I just feel guilty for hiring someone to do this stuff. I mean, Who am I?”

Buried deep within the DNA of some of us is a well-developed addiction to struggle. When we aren’t struggling, we feel bad. If you’re not doing it all, then you’re not living up to some ridiculously high bar you’ve set for yourself.

Okay, so I’m not going to argue with this part of you. She is probably many years old, and will fight me tooth and nail for her right to feel guilty for not struggling.

So, let’s start by hiring someone for just a few hours a week. Challenge your struggle-addicted self to use that time to be genuinely productive and focused. See if it rebalances how you view the need to have someone helping you.

Lists of possible tasks a personal assistant could do for you…

Let’s close with a list of the kinds of tasks a personal assistant could do for you each and every week.

• Chopping vegetables
• Grocery shopping
• Picking the kids up from school
• Walking dogs
• Filling the bird feeders
• Scooping the cat box
• Dropping off dry cleaning
• Picking up dry cleaning
• Hand-washing delicates
• Unpacking your luggage after a trip
• Vacation prep work
• Light cleaning
• Cleaning the dinner dishes from the night before
• Emptying the dishwasher
• Folding the laundry
• Filling your gas
• Oil changes
• All car service items
• Random errands you always do on weekends
• Vacuuming
• Post office runs
• Bank runs
• Creating an Ops Manual for your house

Some of these items are things you may not want to take off your plate. (Picking up your kids, for instance.) But notice which items make you think, “Wow! You mean, I don’t have to do that anymore?”

So tell me how this makes you feel. Why would you (or would you not) hire your own personal assistant?