Pepper Design Blog

A little while ago I shared that a goal of mine is to create a true 32 hour work week. That means me finding ways to reallocate or reduce well over a third of my overall weekly work screen time. That’s huge! but I think also totally doable if I go about it in a smart way. It’ll take time, but I have a game plan.

Part of making the room to cut back (or expand) any business might mean bringing on an extra set of hands. This could be a virtual assistant or someone who shows up everyday at your doorstep ready to help. In my case it has been a little bit of both.

Hiring an administrative assistant isn’t new for me right now, but I thought I’d share my thoughts on it today since I’ve found it to be so life changing (truly).

I first began working with an assistant about two years ago. At the time I was the only one at my company doing my job and my responsibilities were growing fast. I knew that if I could just cut back on more of the daily duties to make time for the bigger projects, I’d be able to keep up with the outstanding responsibilities that needed my attention.

Also: cost-benefit analysis. If it’s more cost-effective to free up your time and if the benefits far outweigh the negatives to delegate, you will save time and money in the long run.

Around the same time that an admin assistant became imperative for my day job, I began to see a steady growth in some of my side work (aka not my 9-5 job but my *creative* marketing work with smaller companies). I needed not an admin assistant but a marketing assistant. I was on the hunt to fill TWO different jobs requiring two unique sets of skills.

Here’s how I went about finding the right assistant for each. To this day I love working with them and would offer the moon and stars if they ever asked. (For the record, I’ve been through maybe 6 or 7 assistants over the course of two years. I’ve had my last two – one in marketing/design, one in administration – for over a year.) When you find the right people, you can’t let them go. It’s easy to tell immediately if a candidate is a poor fit for you and for your business, and equally immediately if they’re perfectly matched (the heavens open and the angels sing).

A few things people forget about assistants…

–they don’t have to be full time (even 5 hours a week of help makes a huge difference)
-it doesn’t have to be just one person (using a tool like Task Rabbit may be perfect – it’s more about getting into the mindset of ‘it’s okay for me to outsource this’)
-your assistant doesn’t have to be local, they could be half way around the world as long as you devise a system that works (my creative assistant now lives two states away)
-you’re going to want someone highly skilled and organized (aka you’re not hiring your friend’s sister’s niece just because)

Let’s talk for a moment about that big topic of hiring.

I’ll share my thoughts specifically on hiring an administrative assistant today, and a creative assistant in another blog post soon.

ADMINISTRATIVE ASSISTANTS:

Where to look:

Local university and college career job posting boards, Craigslist, virtual assistant sites like Zirtual, apps such as Task Rabbit (and Handlr, which I’ve just heard about), word of mouth (just start mentioning to the right kind of people), professional organizations.

It can be really helpful to create a relationship with a career center representative at a particular college or even a professor – request that your job posting be mailed out to a class of sophomore marketing students, for example. If you build that relationship they’ll push the good candidates your direction. To create that relationship, check in often and be kind when they include you on a mailing list about career fairs (though you don’t need to go).

How to find someone great:

Spell out your expectations really clearly in a job posting: share EXACTLY what you’re looking for, use a bulleted list if you need to. Clearly convey the day-to-day tasks, and then offer examples of what that really means. ‘Seeking an energetic, timely candidate who is a grammar ace’ is great, but what you really mean is: ‘I am looking for someone to oversee the important deadlines of our company newsletter, proof marketing content for grammar/spelling accuracy in Microsoft Word, and filter emails for customer service.’

Be sure to especially include the gritty stuff like data entry, document management or whatever is least appealing about the job. I used to try and hype up the perks of the job and downplay the cons, but really you don’t want anyone to be surprised when you send them a link to a recording from an hour long meeting to transcribe. I hadn’t set expectations quite right with one particular assistant and I remember feeling terribly guilty asking her to take over some of the not-so-great items on my plate and then I ended up doing them myself because of it. Setting your expectations from the very get go will make all of the difference down the road.

Be willing to pay well: it’s so worth it. At the heart of every business are the people and it’s the people that bring the joy, hard work and expertise to their jobs. Whether it’s for retainment (the lost effort in repeatedly training a new assistant is crazy frustrating), in appreciation for someone who you know will work really hard, or for the warm and fuzzy feelings that you’re taking care of your people, you will appreciate the simple act of compensating well in the long run because your employees will appreciate you, too. I feel the same way when hiring for childcare – you truly get what you pay for in attitude, kindness and loyalty.

I had this brief notion at the very start of assistant hunting that I’d hire college kids for an exciting, unpaid summer internship or at minimum wage (not a single internship that I did in college was paid, not a single one). But times have changed and 20-something-year-olds have bills to pay, too. Plus, my job is just not that cool.

Now when a candidate that I know will do SO well asks for $12/hour (for example), I offer them $14 (just to witness that big smile and to know that I’ve just secured them looking forward to working really hard for me) and then reevaluate at 6 months and 12 months. If you’re more comfortable starting low and then offering a surprise raise a few months in, that’s awesome too.

Hint: young professionals appreciate being recognized. Another great way to remind them that you appreciate how much they are doing for you is to share a thank you note and a Starbucks gift card every now and then. Truly – a tiny investment such as this can keep your small team thriving.

Qualifications to seek out: 

An awesome attitude: a positive attitude is the best! It’s contagious. At the end of the day a really great candidate has to have an awesome attitude despite the really boring items that might be on their to-do list. I can’t put it into words, but a positive attitude just makes a working relationship so much better. I so appreciate an assistant who starts an email with ‘Of course! I’ll get right on that!’ and ends an email with ‘Happy to finish that up. Thanks!’. From a delegator’s point of view, it’s awful to have to apologize for work or to beg someone to reprioritize the non-exciting stuff first.

A punctual personality: the ability to meet a deadline is also equally key. There’s nothing like promising a deliverable and then having to renege on that promise when you don’t have the work finished by someone on your team. It’s terribly embarrassing, too.

Leadership experience: I don’t love to micromanage anyone else and I tend to be more hands off of the day-to-day. I love an assistant who sees what needs to get done and does it without asking. Likewise, I appreciate someone that I can explain a project to from a high level perspective and can count on them to figure out the minutia on their own.

Basic office skills and a love to learn: for me, it’s always been important for someone I work with to know how to build an awesome PowerPoint or to create accurate and clear charts in Excel. My admin assistant uses Excel a lot – if I ask in an interview if a candidate is okay using pivot tables, I usually can gauge pretty quickly how comfortable they are with the tool. PS my current awesome assistant didn’t know what a pivot table was but I had a gut feeling that she had the drive to learn how to figure it out and since then she’s taught herself many a tool (from Salesforce to Photoshop) using YouTube video suggestions (side note – YouTube is the BEST training tool out there!).

A degree in business or the Letters of the Arts (such as English or communications): this is purely as a broad characterization for who has been the best match of me in the past. For my needs, I value above all else excellent communication and writing skills – two areas where admin assistants are very valuable.

Previous experience working as an admin: Not necessary but could be a bonus if a candidate already been trained in basic admin skills like online research, organization and reporting. Have they worked with a law firm? You know they’re organized. An accounting firm? They have experience with numbers. In a creative environment? They think outside of the box.

They follow up: it’s important to hire someone that is excited for the new experience. A great way to gauge this is to let them follow up with you. (PS if you are interviewing, this is a must!)

Where should I start?

I recommend starting small. You likely won’t find the most amazing assistant right off of the bat. You’ll ‘practice’ what it means to manage your time and theirs with your first assistant. You’ll jot down notes on what to look for in a second assistant, you’ll find even more ways to improve communication/project timelines/training as you go.

One excellent way to get your feet wet is to hire for that summer internship. The bonus here is that if you haven’t found your perfect assistant match, you’ll each walk your separate ways three months later and it’s no big deal. Plus, students are young and full of energy. They are also tech savvy and willing to learn. Hint: after you’ve found the right person though, keep them for a long time.

If you don’t live near a college campus, state in your job posting that the position is for three months. This gives you an opportunity to say ‘thank you!’ and walk away (without having to fire someone) or to invite them on for a longer time period. You’re the only one who knows that this is secretly a ‘trial time period’ and for us that hate the idea of confrontation it’s ideal.

My honest thoughts:

I first worked my way through three admin assistants that were assigned through a local temp agency. I was nervous about hiring on my own and thought that I’d let a company handle the filtering and background checks, plus temp agencies also manage insurance, taxes and extra small business expenses such as disability and workman’s comp. My experience though with all three assistants was that I was but a stepping stone in their career journey and that as soon as they landed a full time job with a more exciting company they were gone. I totally get that and I wished them the best on their journey. What I realized though is that what I needed was not a temp but a long term solution. Now I interview on my own (sooo important) and use 1099s for tax purposes.

Next I sought out a college intern. Remembering my internship days from college, I imagined that this person would be a career-driven student with a part time schedule, flexible attitude and eager to fill a a resume. Perfect! I worked with local universities (we have three within 10 miles of my home) and interviewed at least a half dozen candidates on several different occasions. I made my way through two interns and learned a lot! but also realized that I would inevitably retrain for this position every three months (about the length of a semester) forever if I stayed with it. Not to contradict my advice to start small, but once you’ve outgrown an ‘internship’ position, you’ll know it. Internships are short term, seasonal solutions that rock for a few months. But then you have to start over again…

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I’ll leave it there for right now! I have some suggestions on what tools you can use (online and otherwise) for training, collaboration and timecard tracking. Also, a post on hiring a creative assistant coming very soon.

A footnote: one reason I feel really comfortable writing this post is because I’ve been that person, I’ve had that admin assistant job and I’ve learned a lot from it. All while in college and all while trying to figure out ‘what I really wanted to do’. Working as an assistant to a variety of different professions (fund manager, financial analyst, developer, magazine publisher and so on) is a great way to get your feet wet. I experienced a lot of different managerial styles and across the board each and every person helped me to move my career in the right direction.

ps. more related working mom articles and what does it mean to feel balanced. The real pros and cons of working from home.