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5 Things to Consider Before Making Your First Hire

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A scaling business: is there anything more exciting? 🙌Sure, it’s a little scary to grow, but as long as you implement the right strategies, a team can multiply your efforts and put you on the fast-path to success. 👉It all begins with one: that first hire.

For many people with design agencies, coaching practices, or consulting firms, your first hire will be a virtual assistant aka a VA. Whatever the distinct role, it may or may not be remote, and you definitely need to be prepared.💪

Your first hire is something we have all kinds of ideas about, starting with advanced preparation. Believe it or not, long before you start asking for recommendations and sifting through resumes, you can set yourself up for success in hiring.

We’re giving you the 411 on the five things any biz owner needs to consider before making that first hire. Even if you already have a small staff, or are looking to scale into the next level, these hiring tips are well worth your time to review. It never hurts to circle back and tighten up your strategy, ensuring you’re completely covered and ready to roll, friend.

1. Define Your Organizational Structure

A first employee may cause your first real look at your organizational structure, and that’s a good thing. Most solopreneurs operate as a sole proprietorship or limited liability company (LLC). LLCs of any kind can get employee identification numbers (EINs) through the internal revenue service (IRS). Now that you have acronym fatigue, let’s talk about the different organizational structures, and how this impacts hiring and employee status:

Sole Prop  — if your only status as a company of one is that you are an independent contractor, you can still hire other independent contractors. Keep in mind, you are completely at risk for all of the company finances, which are technically your personal finances. There is no barrier between you and the IRS, and all of your personal assets are on the line and intimately related to the business. If you even add one regular employee, even an IC, you’ll want to consider the layer of protection afforded by an LLC.

LLC — the LLC is still the lone boss of a company, but the limited liability part provides some protection of assets. You also have some different tax declaration options, and may have to do quarterly earning reports and more. Sole proprietors, like we already said, get an EIN. This means that when you report pay for an IC, your EIN is on the statement, rather than your social security number.

S corporations — S corps are a great way to go if you want to separate your personal and business finances. S corps can have shareholders (up to 100) and owners can get common stock. This is a good option if you want a board of directors, but it is more complex (from a tax perspective), than just being a sole proprietor.

C corporations — in a sole proprietorship, your personal taxes are the business taxes, and vice versa. A C corp separates that. If you have big plans to go public, a C corp is the most serious structure to take on. C corps can issue shares and have unlimited owners or shareholders. Most businesses you interact with and buy from (including giant, name-brand ones), are C corps.

All of those options are on the table for you. This is a decision you have to make, and a structure you need set in place, before you start regularly paying someone to work for you.

2. Articulate the Role and Write the Job Description

The organizational structure bit is a major business decision that directly impacts hiring, and is something you should do anyway. This next point of consideration is our foray into defining and describing the actual position. It may feel like it’s solid enough for you to have this in mind, but we recommend getting it on paper. First and foremost, because you need to adequately communicate the job to prospects. Second, because writing it down will help you put words to your expectations and clarify roles and responsibilities. All good. All important. Here is where to start:

Job Requirements

List the requirements of the job, which sound easy enough, but you want to be thorough. For example, if you’re hiring a virtual assistant, job requirements may include:

  • Ability to communicate daily, between 9:00am-5:00pm ET, with some flexibility to accommodate clients in other time zones
  • Ability to do outbound marketing and direct communication with clients
  • Capable of scheduling meetings, then attending those meetings and taking notes
  • Willingness to coordinate non-work-related items, including scheduling, appointment confirmation, and managing tech devices and software
  • Professional appearance and communication skills
  • Ability to attend daily video stand-ups for assignments and updates
  • Capable of reporting project status and coordinating with other team members, as needed
  • Ability to work independently on assigned tasks

Job Qualifications

You may be tempted to squish these in with job requirements, but it’s advisable to parse out the qualifications section. For instance, if you are hiring a web developer, you may need to specify coding language. If you are hiring a writer, you may want to specify word count per hour or experience in the industry.

In keeping with our theme, here are some examples of job qualifications for a virtual assistant:

  • 2+ years of experience as a virtual assistant 
  • Strong phone skills
  • Experience with instant messaging communication and SMS texting services
  • Experience managing CRMs
  • Experience coordinating multiple calendars, scheduling, and confirming appointments

You can also add preferences in here, for instance, “prefer someone with working knowledge of Slack and Basecamp.”

Culture and Soft Skills

Last, it’s ideal to have a few statements about your company’s culture (even if it’s just you) and the kind of person you hope to hire. You may list characteristics like, enthusiastic, intelligent, fast-learner, passionate, focused, etc. 

It may be useful to Google, “job description for a virtual assistant” or other query, just to see how positions like these are generally worded. You may find things there that you missed.

Define Your Organizational Structure

3. Find the Right Talent

In a remote environment, establishing a pipeline for employees is as crucial as establishing one for clients. Find the right platform that is going to be your best bet for sourcing qualified talent in your price range. Different talent types hang out on different platforms: people who want a salaried employee position may be more likely to look on Indeed or LinkedIn; people who favor the flexibility of independent contractor status and freelancing may be found on Upwork, Fiverr, or a tech-specific platform.

A couple of sources are useful to sleuth this out: colleagues and Google. People in your industry may already have connections you can leverage to find an employee. Also, there’s always trusty old Google to help answer questions like, “how to find a VA,” or “where to hire a virtual assistant,” etc. There are plenty of digital platforms that exist to connect talent to employers. Once you find one, set up an account and get to networking, sis.

4. Write Interview Questions and Vet Candidates

Once you have people in the pipeline, you need to be ready to filter them. Fair warning: hiring a VA, designer, developer, writer, or similar supportive positions could invite an onslaught of applications. We’re talking hundreds, if not thousands. The freelance economy is a busy one, and you need to have some tactics in place to weed out people who don’t fit the bill, and identify the ones who do.

What to Look for in a Cover Letter 

A cover letter may be the only thing you really look at, unless it’s a good one that invites you to check out the resume. Cover letters are a good chance to get a first impression of a candidate. As you skim through them, here are some checkpoints:

  • Is it succinct and well written?
  • Do you get a feel for this person’s personality?
  • Do you like their energy and what they chose to showcase in this personalized message?

What to Look for in a Resume

If the cover letter was a win, you’ll flip the page and look at the resume itself. Here are some things to look for:

  • How long have they been working?
  • How many clients have they worked for?
  • Does their stated range of tasks and responsibilities align with what you want them to do?
  • Do they have the right qualifications?
  • What extra sources have they directed you to?

That last point is important, especially if you are hiring a creative: is there a portfolio or somewhere they are showcasing their work to you? 

Tips for Interview Questions

It is helpful to have interview questions prepared in advance. These should be open-ended and aim to get the candidate talking about who they are, what their working style is like, and convey their personality and abilities. It’s definitely a task you can do anytime and have ready to go, and we suggest some of these:

  • Tell me what you love most about this kind of work
  • Describe your working style
  • What are you best at?
  • If you could take any task off your plate, what would it be?
  • What kind of people do you like working for?
  • What would make this an ideal job for you?

Once they’re in, then the real fun begins.

employee onboarding

5. Establish Employee Onboarding Processes

To make it clear clear clear: we are still talking about five things to do before you hire. We are not being super extra: onboarding processes are not something to assemble on the fly once you’ve found the employee of your dreams. You are going to be shocked at the kind of work involved in getting these materials together, and just how valuable they will be if you have them in-hand from day one.

The nature of your work will, in part, dictate what kind of onboarding processes you implement. Almost without exception, you will need the following:

  • Contracts — numero uno: get that ink down and dried. We 100% do recommend our Independent Contractor Contract. It covers it all, so you don’t have to worry about a thing.
  • Employee handbook — conduct, expectations, guidance, and (yes) rules.
  • Training — even if you rip all of these from other sources, delivering a handy how-to for all of your calendars, systems, and tools is a powerful way to reduce the time you have to spend face to face with a new hire.

Bonus: Ditch the Startup Mentality

As you grow, you need to change your mentality. Solopreneurs operate on their own, totally autonomous and free, which is great. But as you scale, you’re on to bigger and better things (we love to see it!). When you sit across from a candidate, you are the boss. No matter how well you get along, or how friendly the work environment is, being in charge has responsibilities. That includes having real, legit legal resources to support and protect your biz operations.

Legal Contracts for Your Growing Business

Hiring someone new is full of opportunity and promise. It is a big step in growing your business, and one you should undertake with care. Of course, you should also have F-U-N, because growth is something to celebrate! That, my friend, always deserves a high five and some bubbles! *virtual champagne clink* Having all of your contracts, documents, protocol, and processes in place is actually what frees you up to enjoy the ride. 

That’s where we come in. Let us take care of the legal side, while you take care of expanding your team! 

Browse our online collection now, and check out other blog posts to get inspo and real world guidance on business development and more.

*Disclaimer: This blog post has been prepared solely for general information and educational purposes. It is not intended to provide, nor should it be relied on for, legal advice. Should you require advice regarding a specific matter, appropriate legal or other professional advice should be obtained.

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Hi, I'm Neesa.
Attorney-turned-entrepreneur.

I traded stuffy suits, corner offices, and corporate boardrooms to serve small business owners and other freedom-seeking entrepreneurs like you from a tiny island in the Caribbean Sea.

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