Do you have a backlog of work that’s taller than a mountain?

If so, instead of moving forward, you’re probably playing catch up trying to whittle that mountain of work down. You know you need to hire a remote executive assistant, but you’ve been avoiding it.

It’s amazing how creative you’ll get to avoid the hiring process.

You’ll shuffle work around. Try to squeeze 26 hours into each day. Work through the weekends. Put more work on your current team. 

None of those are sustainable and aren’t going to make much of a dent in that backlog, but at least you can put off hiring for a while. 

And while it’s not the best thing to do, it’s understandable. Bringing on new employees takes time and money. Lots of it. The time you want to dedicate to getting work done has to be redirected towards recruitment, interviewing, hiring, and training. And let’s not forget the employment benefits and payroll expenses on top of that.

Yes, magically creating a 26-hour day can seem like a better approach sometimes. 

Maybe to avoid hiring, you’re even thinking of adding a few independent contractors to the team to get caught up.

Hiring A Contractor As Your Remote Executive Assistant

We get where you’re coming from.

Because the hiring process is time consuming and expensive, many people are going the independent contractor route. Hiring a freelancer seems like a no-fuss approach, and a good way to fast-track any backlog of work that needs to be done.

Instead of recruitment, interviews, and payroll, you hand over the work to the contractor and pay them when they’re done. Easy, right?

Hold on, though.

The considerations you face when choosing whether to hire someone as an employee or contractor aren’t just about convenience. It’s not only a question of what’s quicker, if in fact finding a contractor really is quicker. There’s the tricky little issue of employee classification compliance.

You might think you have an independent contractor, but do you?

Is Your Remote Executive Assistant An Employee Or Contractor?

If we use tax documents to define those working for us, a 1099 is a contractor and a W2 is a full-fledged employee. But the difference isn’t tax forms, of course. It’s in legal definitions.

The IRS has put out guidance on what an independent contractor is, and isn’t. Here are some ways to differentiate contractor from employee:

  • Behavioral. Are you controlling, or have the right to control, what your remote executive assistant does, and how they do their job?
  • Financial. Do you control the business and financial aspects of your executive assistant’s job? (e.g. how they’re paid, if expenses are reimbursed, if you provide the tools)
  • Relationship. Does your remote executive assistant have contracts or agreements with you that outline benefits, define a relationship, or indicate a sense of permanency in working for you? Are they working for you on an ongoing basis?

If you answered yes, your remote executive assistant is probably an employee, not an independent contractor. As you can see, there are blurry lines between the two. It would be pretty easy to ask too much of a remote executive assistant and slip into the realm of employee.

The U.S. Department of Labor has also released compliance information on how to define an independent contractor vs. an employee. Based on their guidelines, you should ask yourself a few questions to consider if there have been changes in your working relationship or expectations:

  • What’s the nature or degree of control I exert over my remote executive assistant?
  • How permanent is their working relationship with me?
  • How much have they personally invested in equipment or facilities to work for me?
  • What level of skill, personal judgment, or foresight is necessary for them to do the work?
  • What profit or loss, or risk or opportunity is there for them?
  • How integrated into my business are they? How much do I rely on their work to make my business run?

One thing that’s interesting to note is that changes in federal administrations have meant possible changes to these rulings. That makes compliance with the law even trickier. There’s the IRS, the Department of Labor, and ever-changing guidelines to contend with. Get the employee classification wrong, and you could face significant penalties down the road.

While both contractors and employees have their pros and cons, when it comes down to making a decision on which to go with, a W2 employee is almost always a better choice.

Why You Should Hire A W2 Remote Executive Assistant 

Maybe you think you understand the requirements, and you go ahead with an independent contractor.

An independent contractor has more control. 

They’re given the tasks needing completion, and get them done to meet deadlines. There might be some expectation around that narrow approach, but if you take too much more control over when, where, and how they do the work, you’ve suddenly veered into W2 employee territory.

They might not realize it. You might not realize it. Yet you know that the longer you work with someone, the more the relationship and expectations naturally change. It isn’t uncommon for long-term independent contractors to gradually become employees by definition, whether their job status reflects it or not.

A general rule of thumb, to be sure you’re in compliance, is to assume that when you hire someone to work for you that they are an employee.

We understand this problem, and it’s one of the reasons we took a unique approach here at Boldly. We wanted to offer clients the best of both worlds: speedy hires of highly qualified people without the concern of employee classification compliance.

The Best of Both Worlds

Our solution? Premium Subscription Staffing.

All of our team members are W2 employees of Boldly. We handle the compliance. We handle payroll. We do the recruiting and take it very seriously. When you come to us, you don’t have to worry about any of the concerns that come with employees or independent contractors.

Even better, using a subscription staffing model, you can access incredible talent that will fit your budget. Pay for the amount of time you need, get a remote executive assistant that’s perfectly matched for the work and ready to get started right away, and have zero headaches about hiring or compliance.

Are you ready to see that mountain of work start disappearing? 

You could have a new remote executive assistant on your team, one who comes with the freedom to get everything done without you having to worry about breaking any rules. 

Plus, you can get started right now.