8 Signs You Need an Assistant

When you’re just launching a business, no one blinks an eye if you’re balancing your own books, cleaning the office bathrooms or taking packages to the post office yourself. But the day will come when you’re going to need some help. Because no one’s ever been able to squeeze more than 24 hours out of a day, and your hours are literally too valuable to waste on small stuff.

The key, says Allison Hemming, CEO of The Hired Guns, a talent agency for digital creatives, is to make a hire that maximizes your business—whether it’s in a traditional assistant role (virtual though he may be), a bookkeeper or even a part-time tech guru. “A great assistant should be a ‘one plus one equals three’ equation, where because they’re so much better at booking and organizing and prioritizing your life, you are able to do way more of the work you get paid the big bucks for,” she says. So how can you tell you’re ready? Look for these tell-tale signs:

  1. You’re working as hard as ever, but feel like you’re not getting anything done. “Analyze your personal productivity by tracking everything you spend time on for two weeks,” suggests Hemming, who uses this exercise regularly at the Hired Guns. “If you see anything you can outsource, do it. Your core business, what people are hiring you for, should be between 40 and 50 percent of your workload.” Two areas commonly outsourced, she says, are administrative and financial tasks.
  2. You’re having trouble keeping track of meetings, deadlines and work details. You can try technological solutions like setting alarms and using task-maker programs. But if those don’t work, Hemming says, “You might need an assistant; you might need a project manager, but you have to do something. You don’t manage this, you don’t have business.”
  3. You can’t take on new business because you’re already so busy. If you’re turning down clients—but still spending hours dealing with grunt work—something’s out of whack. “That’s when you raise your rates,” says Hemming. “And if you still need help, that bump might pay for your assistant.”
  4. You’re avoiding necessary tasks. Procrastinating on sending out invoices, just because you hate dealing with them? Um, that’s a problem. “You may be getting tons of work, but if you don’t follow up on this stuff you could still be broke,” says Hemmings. “Hand it over. Just make sure you don’t detach completely, because it’s still your business, and you need to know what’s going on.”
  5. You’re hopeless at certain (necessary) parts of your business. “I work with the digital creative class, so profit-and-loss statements and balance sheets aren’t the things that get them up in the mornings,” Hemming says. “If you know you’re bad at that, outsource it as soon as you can afford to.” (Her first hire was a once-a-week financial manager, for example.) This rule does have one caveat: “If what you hate is at the core of your business, then you need to think about whether you should really be working for yourself,” she says. “You’re not allowed to suck at sales if you’re a small business or solopreneur, for example.”
  6. You’re too busy to be creative or think about your business long term. When you’re down in the weeds, it’s tough to come up with that game-changing product or marketing idea. Shift some of the work to someone else. Just make sure you use the extra time for more than surfing Facebook.
  7. You don’t get social media. Even if you run a black-smithing school or sell home-churned butter in a prairie dress — in fact, maybe especially then, considering your customer base — you need to have a web presence. “It’s amazing to me how many people don’t,” says Hemming. “Your website, your blog, your Facebook, your LinkedIn, your Twitter—these are things that serve as marketing, that drive people to home base.” If you’re a Luddite by accident or vocation, hire out.
  8. You can afford it. Of course, one key rule of business still applies: Don’t spend money you don’t have. Before you staff up — even just to one person — make sure you’ll be able to pay the agreed-upon hours. If you need to, start slow, with a few hours a week, and build from there.

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