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Small Business Owners: Here Are 5 Questions You Should Ask and Answer Before Making Your First Hires

Person hanging employee of the month photo for Staffing Your Small Business

A quick guide for staffing smart, and picking the right people to move your small business forward.

Unless your first hire was in HR—you’re probably looking for a little help, as you start to staff your small business.

And that’s a good call. It costs companies $4,000 to recruit a new employee, and 52 days to fill a position. Which put it on top of the list of “things you don’t want to have to do too often.” We’ll break down all your burning questions on early-stage hiring: from “who first?” to “which one?” to “how though?”

What roles should I hire first?

Of course, this is hard to generalize. But you can think about your first hires in three different categories: “capacity hires,” “expertise hires,” and “ugh, I don’t want to do this anymore” hires.

  • “Expertise hires” are the people who have skill sets and experience that is out of your range, and who do things you’re incapable of tackling yourself. They are generally the most difficult to hire—because you may have a hard time properly defining their role, goals, and scope. But, expertise hires can fill essential knowledge gaps—making them instrumental to the growth of your business.
  • “Capacity hires” are the people who hire to do the things you can do—but lack the time, or energy, to do. They’re generally easier to hire, because you know exactly what characteristics and skillsets are required to get the job done. Choosing a generalist as your capacity hire often makes sense—because they might be able to take a more diverse array of things off of your plate. For example, you might look for an administrative role that can handle social media. Or a server with bartending experience.
  • “I don’t want to do this anymore hires” are the folks you hire to tackle the tasks you just plain don’t like. Ask yourself: what work do you avoid? And who might actually enjoy those things? If the answer to the second question is “no one”—think of ways to lump those tasks in with similar “capacity hire” positions.

Once you better understand your hiring needs—you can start deciding on budget, and an order of operations. Which of these roles will save you the most time? Which of these roles will allow you to access new streams of revenue. Are you turning away customers (or underwhelming your current customers) because you lack the personnel? Who can do the most to minimize that?

Sometimes, your “expertise hires” (an accountant, a lawyer, a marketing consultant etc.) are necessary, but out of scope at first. In this case, working with them as contractors might be the most practical way forward. Regardless of whether your expertise hire is full-time or freelance: it’s particularly important they have experience working with startups, and businesses with similar challenges to yours.

A quick note: remember that your first few hires are not just hires you make to fill roles. They’re hires you make to establish company culture. Think about the values you want your company to have—and make that value-fit a top priority.

How do I make people want to work for me?

boss talking to employee about quick growth is an advantage small businesses have when staffing their small business

So out of the gate you’re not Apple, or Starbucks, or a 3 Michelin star restaurant. And you might be thinking: “Well, great. Those are the places where the top talent is going.”

But the truth is, there are a lot of advantages to working at startup or small business. And a lot of ways to make your business look attractive.

Here are some differences to remember, when approaching potential hirees. Make sure to stress them in your job listing, and throughout the hiring process.

Company A: Small Business Company B: Established Business
  • The “resume building” advantages of getting to own high-level tasks, or high-impact decisions
  • The freedom and autonomy to build foundational building blocks of a company
  • Capacity to scale up quickly and be promoted from within
  • Flexibility—being pushed to work outside of their comfort zone or expertise
  • The “resume building” advantages of working with an established brand with name recognition
  • Learning to work within established systems and processes
  • Set timelines and structures for advancements
  • Established goals, tasks, and expected outcomes

You’ll note that the type of person who wants to work for Company A, is a very different type of person than one who wants to work with Company B. That’s okay, and these differences are okay to stress. Most likely, employees that are most fulfilled at Company B, won’t be the right fit for your startup.

The important thing is to create a value proposition for future hires—and to live and breathe it throughout the hiring process. Do you offer serious growth potential? Do you offer stock options, or bonuses? Can you carve them out a bigger leadership role? Do you offer perks—like unlimited PTO, or remote work? Find out what you offer that’s special.
When you’re hiring your first employees, you’re soliciting their trust. This means you’re also being hired, and you’re also being interviewed.

Lead your job description with why someone should join you—not the list of tasks they’re supposed to perform once they do. Start your interviews with a transparent overview of your company, your vision, and what you can offer your employees as you grow.

Person sitting at computer with notification for annual progress review part of staffing your small business

Where do I look for candidates?

There are a few classic recruitment methods for startups—which all fall differently on the “effort it takes you” and “money it costs you” scales.

  • Using a recruiter: There are a few cases in which relying on a recruiter can be a huge time and money saver. If you’re hiring for very specialized “expertise” positions–recruiters often have a niche they know, understand, and can hire for, well. If you’re hiring en masse—recruiters can be a necessary expense, as you struggle to do the legwork. But if you’re hiring for a few roles—and understand your needs and requirements for those roles well—you might be able to save a bit of the budget by taking outreach on yourself.
  • Posting on hiring boards: Nowadays, there are a nearly endless supply of job posting websites. There are the “in general” sites, like Craigslist, LinkedIn, Indeed, Zip Recruiter, Glassdoor. But each career track also has niche hiring sites that get viewed by top talent. There’s Tech Ladies for women in tech, or Idealist for nonprofits, or Angellist for hirees that specifically want a startup job.
  • Direct outreach through your network: Regardless of where your listing lives, it has to be distributed. Aside from your personal network (friends, family, former colleagues, etc.) and your professional network (community organizations, mentors, networking events, partner organizations)—considering engaging in some direct outreach. Use LinkedIn to find professionals who fit your requirements—and send them a personalized message to gauge their interest. If you’re looking for one or two “rockstar” candidates—a warm intro can go along way.
  • Attending a career fair: If you’re hiring for entry level talent—and are in the vicinity of a university—ambitious students make great first hires. Most cities also have career fairs you can take advantage of to get your country out in front of eager talent. If you’re hiring for a new retail opening, or restaurant, and need to make a lot of decisions quickly—hosting a career fair of your own might help expedite the process.

How do I determine which candidates are the strongest?

Side by side of two candidates illustrating how to figure out if a candidate is strong as part of staffing a small business

Likely, the most time-consuming part of your hiring process isn’t interviewing, or handling the post-hire paperwork. It’s figuring out whom to interview in the first place.

There are several points throughout your hiring workflow when you’ll get an opportunity to screen. Each step of the process should get you a step closer to determining which candidates are a fit.

1. During your application: At this point, you should be screening for: “Can this person do the job?” If you have requirements in your listing, you should be able to skim their resume, or their cover letter, and find reference to that required experience.

If there are particular skills you expect, or challenges you know your employees will have to handle—adding a brief form to the end of your application can go a long way. Questions like…

  • Tell us about a time you dealt with…
  • Describe your experience using…
  • What makes you a good fit for this role…
  • Please give 2-3 examples of projects where…

…are easy to digest, and should make the initial filtering process easier.

2. During a phone interview: Depending on how many potential hirees you have after step one, it might be worthwhile to set up brief phone interviews—before bringing people in office. These can be 15 minutes, and cover the basics. Why do they want this position? What’s their current employment situation, and relevant experience?

This can serve as a solid gut-check on a candidate’s experience and give you a bit more insight into how they approach the role. Mainly, it’ll serve to confirm what their resume and cover letter told you about their qualifications—and save you both some time if “what they can do” and “what you need” doesn’t line up.

3. During an in-person interview: At this point, you should have weeded out anyone who can’t do the job (or would need a lot of handholding to do the job). It’s time to bring in a few candidates (likely, 2-4) that fit the bill, and drill deep into what makes them a fit.

It’s important to remember that with your first hires, you’re not just looking for skill fit–you’re looking for culture fit. A star candidate with lots of corporate experience may be really impressive—and still not the right bet. If you’re a “Company A,” and they thrive in a “Company B” culture, it might take longer than you think to get them up to speed. And if you need someone who can pivot fast, and work autonomously—those skills are as important to ask about, as the bullet points on their resume.

Aim for a good mix of “talent” questions, like:

Tell us about an instance/project/situation in which you did your best work.

And “fit” questions, like:

Tell us about a work environment you found challenging, or one which you felt supported your growth.

Once you have an understanding of both their work capacity, and work approaches—compare it against your notes from their resume, and their phone interview. You should have more than enough of a foundation to make an informed hiring decision.

How can I speed this process up?

Hiring is a process—but it doesn’t have to be a grueling one. They key is to have a system, stay organized, and be consistent. A few tips:

  • Use scheduling tools like Calendly or Acuitiy to make scheduling easy—and save yourself a lot of email back-and-forth.
  • Have a separate email account for reviewing and receiving applications. It saves you from having to sort and sift your primary inbox for emails—and allows you to use tags and folders to group candidates by “yes,” “no,” or “maybe.”
  • Similarly: take notes. Store those notes in one place. Sort them by candidate name and position. Having a set desktop folder that contains a candidates name, resume, cover letter, and your thoughts—will save you a lot of time reviewing.
  • Make sure your legal ducks are in a row from the get-go. Have your contracts and other paperwork at the ready for signing, long before you make an offer. Readying any onboarding information early, is also a solid proactive idea.
  • Hold a brief hiring retrospective with yourself, once this is all over. Take stock of what worked (where your listing got traction, what candidate skills seemed most important, what sorts of candidates you can filter out earlier in the future).

Summing up staffing your small business:

Hiring decisions, as a small business owner, are some of your most critical decisions. But they’re also some of the most exciting.

Bringing on new employees also means bringing on momentum. And the time you put into the process now, translates to more and more time saved, as your business grows.