Guest post: How do I know when it’s time to hire some outside help?

May 5th, 2008

The Boss of YouAre you a business of one who’s wondering whether it’s time to hire an extra pair of hands? Torn between whether you should hire an employee or a subcontractor? Fairly certain that if you don’t start delegating soon your head will implode, but not sure what tasks to farm out, let alone where to find a capable set of extra hands in the first place?

Not to worry. Lauren Bacon and Emira Mears are here to help. Lauren and Emira started Raised Eyebrow Web Studio, Inc. in 2000, so that they could be their own bosses and continue to work with the not-for-profit and small business clients they loved. They became so dang good at it they decided to write a book — The Boss of You: Everything a Woman Needs to Know to Start, Run, and Maintain Her Own Business. So without further adieu, here’s what Lauren and Emira have to say on hiring your first employee…

There comes a time in every successful self-employed gal’s life when the question arises: How do I know when it’s time to hire some help?

The first step is to look for the warning signs that going it alone is not working out. For most small enterprises, there’s a good long stretch where you (and your business partner, if you have one) are your only employee(s). Of course, if you’re successful, you’re likely to get busier and busier, up until the point where you stop being able to juggle all the work you’ve got coming in.

We hit this point in our business about three years in, but we didn’t see it for much, much longer. It’s our hope that our tale of woe will inspire others to act promptly when the time comes to bring in an extra pair of hands.

See, between client work and the administrivia of running our business (answering email and phone calls, managing our books, and so on), we found ourselves working longer and longer hours and feeling like we were getting no further ahead. We were losing our weekends at the office, and losing sleep over the prospect of missing deadlines if we slowed down. Our success was killing us — the more work we did, the more referrals our clients sent our way, and we couldn’t keep up with the demand.

So why didn’t we hire someone right then and there? Three big reasons:

1. Fear of financial risk. We were terrified that the moment we hired someone, our workload would drop off and we wouldn’t have enough work to keep everyone busy (and the business profitable). The thought of being responsible for another person’s salary on top of our own was just scary enough to make us hesitate.

2. Fear of change. We liked our little two-person, best-friends-and-business-partners-forever setup. And we knew that dynamic would change the moment we brought another person into the mix. We weren’t ready to step out of our roles as comfortable equals and into being the bosses of someone else.

3. Fear of losing control. Yeah, we were hardcore control freaks. (Or, as our hero Joss Whedon prefers to phrase it, “control enthusiasts.”) We were completely stressed out at the thought we might hire someone who wasn’t as perfectionistic as we were, and see the quality of our work deteriorate.

So where did that leave us? Stuck in overwork hell for another couple of years. Yeah, that’s right, I said years. It got pretty ugly; there were emotional breakdowns on both our parts on a fairly regular basis, due to too much work and not enough play, rest, and perspective. People kept telling us we needed to hire help and we kept arguing with them, telling them we didn’t want to grow, and that we’d find some other way to cope.

(Now, by the way, that’s a perfectly legitimate strategy, but only if you’re comfortable turning down work so that you can stay sane. We weren’t doing that.)

So how did we get over our fears? In short:

1. We discovered that not only will a hard-working employee pay for themselves (in our case, by working a reasonable number of billable hours per week), but will speed up production times (duh) and thereby quicken up the cashflow cycle (because when projects finish faster, the billing date comes sooner).

2. We hired someone we liked. A lot.

3. We peppered our job posting with phrases like “detail-oriented” and “meticulous,” and hired someone just as careful and quality-conscious as we are.

That’s the short version. There’s plenty more on the subject of hiring help in our book. But meanwhile, please feel free to post your questions about hiring here, and we’ll do our best to answer them.

Entry Filed under: Q&As,She's the boss

5 Comments Add your own

  • 1. Marie D  |  May 6th, 2008 at 10:23 am

    oh it’s funny Joss Whedon is your hero, he’s mine too!

  • 2. Felicia Sullivan - Author&hellip  |  May 7th, 2008 at 11:10 am

    [...] Emira here, one of the co-authors of The Boss of You, and guest poster at this here lovely blog while Felicia continues her world domination tour. This post is Part 2 of a four stop blog book tour we’re rolling out this week in support of the book release. For Part 1 on knowing when it’s time to hire an employee for your small business, you can visit Michelle Goodman’s Anti 9-to-5 Guide website here. [...]

  • 3. All Things Girl » A&hellip  |  May 7th, 2008 at 11:39 am

    [...] How do I know when it’s time to hire some outside help? [...]

  • 4. Felicia Sullivan - Author&hellip  |  May 8th, 2008 at 6:50 am

    [...] Yesterday, you met Emira Mears, author of the must-have book that should be on any entrepreneur’s bookshelf, The Boss of You. The gals are on their whirlwind blog tour, and their giving inside dish on how they launched and grew their incredibly successful web design business. On Monday, you might have caught them chatting on Michelle’s site about making the decision to hire outside help, which can be frightening to a new business owner. Yesterday on this fine space, they gave you tips on figuring out exactly who to hire (once you’ve made that all-important decision) , and today they’re hitting Lor’s space with more scoop. I’ve begged the gals to come back this week, so who knows, they very well might return. Until then, why not buy their book? [...]

  • 5. Jack  |  May 12th, 2008 at 9:44 am

    I’m a freelance web developer and tech support person and have recently been freaking out about this very topic – too much work, too little time, too little money to turn new work down. I appreciate the perspective of this post and may even buy that book (despite my name, I’m a woman, plus I think it’s probably a helpful book for folks who aren’t women!)

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Hi, my name's Michelle Goodman and I've been freelancing since 1992. I'm author of My So-Called Freelance Life and The Anti 9-to-5 Guide. Read my full bio here.

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