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7 Pitfalls to Avoid When Hiring an Assistant

This article originally appeared on the Freshbooks Blog on March 17th, 2015


Stop me if this sounds familiar… You’re sitting at your desk, staring nervously at your to-do list. The projects and tasks kept piling up, but no matter what you do, you never seem to be able to get ahead. Your business acquaintances kept hounding you to hire an assistant to help grow your business, but even the thought of going through the process of bringing on an employee feels overwhelming to your currently overburdened state.

Hiring an assistant to pick up the slack at your business doesn’t have to be complicated, but you can save yourself even more time and frustration by avoiding the following pitfalls:

Pitfall #1 – Failing to define responsibilities

Deciding to bring on an assistant is one thing – integrating that person into your business successfully is another thing altogether!

Too many entrepreneurs and business owners put the cart before the horse, bringing on an assistant before they’re fully clear on what they expect the person to do. Unsurprisingly, this can lead to frustration on the part of the business owner (who feels he isn’t getting his money’s worth from the arrangement), as well as the assistant (who’s frustrated by unclear expectations).

Avoid this pitfall by preparing for your assistant before you do your hiring. Look at your business processes and visualize exactly how your assistant will help you. What tasks will your assistant take on? How will he or she support your operation? Developing a specific job description with clear expectations won’t just help you avoid initial frustration, it’ll allow you to identify the ideal candidate for your needs as well.

Pitfall #2 – Creating busy work to fill your assistant’s hours

That said, as you look at your to-do list, be sure that the tasks you’re planning to delegate to an assistant are items that will actually make a difference to your company. It’s incredibly common for business owners to bring on an assistant without a proper plan, and then resort to “busy work” projects simply to fill the hours.

Remember, you don’t have to hire a full-time assistant at first if you don’t have the workload to support that schedule. If you only need ten hours of support a week, look for a part-time worker or a virtual assistant with flexible hours to meet your needs. You can always expand later as your available workload grows.

Pitfall #3 – Failing to provide clear instruction

No matter how good they are, assistants can’t read your mind! While a process might seem clear to you, you’ve done it day in and day out – your assistant is coming in to your company with a fresh set of eyes. As a result, it’s up to you to explain the project using clear language, pictures, and training examples (where appropriate).

Developing thorough process documentation can help with the instruction process, but it takes time to create. In fact, it’s not uncommon for business owners to report frustration with the fact that it seems like training their new assistants takes more time than it would have to just do the tasks themselves!

And while it may seem that way at first, be patient. Look at training your assistant as an investment; after the upfront cost of your time, you’ll see a positive return on your efforts.

Pitfall #4 – Failing to set performance expectations

Telling an assistant, “Research this issue for me,” sounds straightforward, but is quite open-ended in practice. Should the assistant work on the project for two hours or ten? What project will the research be used in, and should specific sources be sought out to help prove a point? These are the types of questions a good assistant will ask, and it’s up to you to answer them with a clear set of expectations.

Imagine that you’ve hired your first assistant and asked him to prepare a spreadsheet showing the impact of a client’s recent transactions on your company’s net worth. Your assistant puts hours of research into your company’s past performance and spends nearly an entire day creating extensive charts, tables and graphs – when all you really wanted was a simple line-by-line summary. All of this wasted time could have been avoided if you had set clear performance expectations from the start.

As a general rule, you should assume that any issues that arise during your first few weeks with a new assistant stem from failures to communicate on your part – not from any weaknesses in your assistant’s abilities. If performance expectations aren’t met or if projects aren’t completed to your liking, start by improving your own communication before placing the blame on your new worker.

Pitfall #5 – Underestimating your assistant

Bringing on an assistant can be a scary prospect for business owners, as it means shining a (sometimes unflattering) light onto your company’s inner workings. But don’t let this hesitation limit the number and scope of the projects you give your assistant.

According to research conducted by Wagner & Harter in 2006, employees who viewed themselves as “empowered” demonstrated higher levels of satisfaction than those in organizations with more structured, hierarchical, and less flexible work environments. As a small business owner or solo entrepreneur, you’re perfectly positioned to provide this type of working arrangement. Instead of underestimating your assistant’s abilities, give him added responsibility as his mastery of the existing tasks you’ve already assigned is proven.

Pitfall #6 – Micromanaging your assistant

On the subject of workplace environments, keep in mind that nobody likes a micromanaging boss. In fact, that’s probably one of the reasons you set out on your own as a freelancer or entrepreneur in the first place!

If you’ve provided instruction and set performance expectations using the processes described above, there’s no reason you should have to hover over your assistant’s shoulder while work is being completed. Doing so wastes your time and frustrates your assistant, so keep your eyes on your computer and use the time you’re saving on projects that will actually move the needle for your company.

Pitfall #7 – Failing to account for language barriers

Finally, while the power of the internet makes it possible for business owners to work with virtual assistants from all around the world, you need to base your hiring decision on more than just dollars. Usually any virtual employee is going to be cheaper than a local employee, but if you bring on someone whose first language is different than yours, you may run into language barriers that turn projects into larger, more complex initiatives because of hours going back and forth for clarification. If the projects you anticipate assigning to your new assistant require significant explanation, consider choosing someone who speaks the same first language.

Certainly, these aren’t all the potential pitfalls that could occur when hiring an assistant.