biz ladiesLife & Business

biz ladies 09: The Control Enthusiast’s Guide to Delegating

by Grace Bonney

Hello, darlings — Lauren here, from The Boss of You, pitching in while Grace goes to the proverbial chapel to get married. (Woo-hoo!) I’m continuing on my “HR for the Self-Employed” theme (here’s the first installment, which discussed treating yourself to some well-earned benefits & perks), but this time rather than focusing on your own bad self, I want to address a more traditional HR angle: Hiring help. Come join me after the jump for the full post!

CLICK HERE for the rest of Lauren’s post on delegating after the jump!

Hello, darlings — Lauren here, from The Boss of You, pitching in while Grace goes to the proverbial chapel to get married. (Woo-hoo!) I’m continuing on my “HR for the Self-Employed” theme (here’s the first installment, which discussed treating yourself to some well-earned benefits & perks), but this time rather than focusing on your own bad self, I want to address a more traditional HR angle: Hiring help.

Hiring is a terrifying prospect for most creative entrepreneurs, and not only because of the financial risks it entails; in fact, I think often the thing that scares us more is sharing the responsibility for (and more importantly, control over) our precious product. I ran into a jewelry-designer friend in my favourite sandwich shop a while ago, and after a bit of catching up — during which I mentioned we were hiring a new employee — she confided in me that she desperately needed to hire help, but couldn’t bear the thought of having someone producing less-than-perfect work in her name. So instead of hiring, she was working herself to the bone trying to keep up with production demands.

I can’t tell you the number of times I’ve seen people in this situation, trapped by their own success. It’s really upsetting to me, because I’ve been there — and I can tell you, it’s no fun. Word gets out that your stuff (or service) is awesome, and the next thing you know, you’ve got more work than you can handle and not enough hours in the day — and all the well-meaning folks around you try to make you feel better by saying, “That’s a nice problem to have,” but you know better. You know you cannot sustain this for long, and that you’re approaching burnout, and you just want it to stop, but it doesn’t. And the idea of hiring someone gets both increasingly appealing and increasingly frightening, because by this point you are working yourself crazy and the idea of writing a job posting and doing interviews and reference checks and oh god, training them, is just mentally and emotionally exhausting.

That, by the way, was a rough transcription of the inside of my brain every time we have needed to hire staff at our web studio. And if (or rather, when) you find yourself thinking any of the above thoughts, please do me a favour and remember that they are giant flashing neon signs that you need help. And not the therapy kind.

It’s time to hire someone to assist you — and you can’t afford to hire anyone who won’t meet your exacting standards when it comes to the work you do so well. So how do you battle those perfectionist demons that insist that if you want something done well, you have to do it yourself? Here are a few tips (which I’ve learned from hard-won experience as a recovering delegate-o-phobe):

  1. Put “perfectionist” in the job description: When Emira and I hired our first employee, we peppered the job posting with phrases like “attention to detail,” “careful,” and “verging on picky,” in a conscious attempt to attract a coder with the qualities we were looking for. We still got some resumes with typos (a good sign they weren’t right for a job requiring precise syntax), but we also found a stellar employee who’s still with us almost four years later. Don’t be afraid to ask for exactly what you’re looking for — you’re the boss, and you’re allowed to aim high.
  2. Hedge your bets: If you’re wracked with nerves at the thought of being responsible for someone else’s regular paycheck, get creative about the arrangement. Part-time staff, subcontractors, or limited-time contracts (say, two or three months, during which period you can evaluate the pros and cons of having an employee) are all great ways to ease into being the boss of someone else.
  3. Always, always, always, always check references. ‘Nuff said.
  4. Make their first project a system. If this is your first hire, and you’ve been doing everything yourself until now, you probably don’t have much in the way of systems. Ask your new employee to start systematizing important processes. They’ll have a fresh, outsider perspective, so just ask them to take notes while you explain how you do things, and to ask all the questions they can think of. Then have them draft up a document outlining the process as they understand it. (You can re-use that document later, when you hire more people.) The process could be anything from order processing, to answering email, to updating your online catalogue — all that matters is that the better you do at explaining it (and the better they understand it), the more likely it is you can hand off the execution to them and take it off your to-do list. (Bonus: if they’re smart and creative, they’ll probably have intelligent suggestions on how to improve and streamline your processes.)
  5. Make sure they earn their keep. A lot of us are tempted to have our staff take care of administrative work that feels less rewarding and easier to delegate — but in fact it’s especially fabulous to get your employees working on things that generate revenue, because it improves both your cashflow (as you push out more good stuff faster than you were previously able) and your overall bottom line (because if they earn more than their salary and overhead costs, then you’ve got yourself some profit). So think about what money-generating tasks you can pass off to your new best friend; I promise that answering your own email will feel a lot better when you’re spreading around the other work. (That being said, if the admin tasks are really the ones causing you headaches, get thee a virtual assistant and stop worrying.)
  6. Be gentle with yourself. Look, you probably went into business for yourself because you like doing things your own way. That’s okay. In fact, I applaud it! So don’t freak out at yourself when you find yourself having trouble letting go, and letting someone else get their hands on your carefully-crafted, treasured work. Just breathe into it, feel the stretch, and enjoy the knowledge that what you’re doing is very, very good for you.

So, here’s my perfectionistic moment: I’m sure I’ve forgotten to include something crucial. Any of y’all got some good delegating advice to share? Leave it in the comments! (And thanks for reading!)

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  • Hiring has always been the most terrifying prospect to me… I finally feel like I am not alone now – this anxiety is somewhat normal?! Thanks for the reassurance and great advice!

  • Thanks!
    I manage 13 employees at my bakery and I STILL have trouble delegating. I’ve recently promoted two employees to manager status and they are slowly prying projects out of my death-grip! I’ve learned a lot from them about letting go and trusting their ideas and common sense, but an article like this is still a much-needed reminder for me… and I’ve forwarded it to them!

  • The idea of having a new employee help craft the system is brilliant, not only because you’ll get a system out of it, but also because it makes the employee feel part of things. As hard as it is to let go for fear that someone will wreck your brand, image or reputation, it is important to show an employee that you trust them to be part of the building, not just part of the doing. Let them generate ideas and run with one, whether it’s the system they help create, or a new product idea, or they will feel like just another worker bee.

  • Brilliantly said! I deal with this all day long at my day job (managing finance, HR and ops). Then experienced everything you mention during the holidays, unwilling to hire an hourly helper, even for button sewing or packaging or shipping, because of the training time and potential loss of quality. Geesh. And burnt out. (I am so totally hiring some help this holiday season!)

    Reference checking is truly truly essential. And not just “did they work for you.” Ask what you need to know as a potential employer. How did this person resolve a conflict? Did anything prevent them from being on time and reliable? Which areas do they need development in? What makes them truly acceptable? You’ll get much better, and more authentic, feedback from your referees!

  • I’m getting really tired of seeing that same large “We can do it” banner over and over again. It’s distracting from the otherwise tranquil beauty and thought provoking images found on this site.

  • great great GREAT advice. and isn’t it funny how many resumes come across with typos? who doesn’t go through that with a fine toothed comb? if that isn’t looked at in detail – and it is their business – how then can they take interest in YOUR business?

    Great advice.

  • I love this article. As someone looking in from the other (worker bee) side, how important it is to trust the people you’ve hired, and recognize (sometimes even actually use!) some of their ideas. If you’ve done everything you can on the front side to find a creative and intelligent helper, you really owe it to yourself, as Lauren points out, to capitalize on that employee’s energy and abilities. Please do not exploit their contribution to your business by mismanaging their skills and only allowing them to take care of administrative work. Admin work is a necessary part of running a business–and it can often be the key to learning the ropes. However, if you allow your staff to stretch a bit beyond the quotidien paperwork and data entry, you will inevitably cultivate happy employees, and save yourself time and money by retaining good support staff. No one wants to work in a suffocating, dead-end environment for a perfectionist egomaniac!