10 Questions to Ask Before Making Your First Hire

Before rushing to expand your business with that first employee, here are the most important things you need to consider first.

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By Alina Dizik


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You've launched your business, and it's beginning to expand. Now, you're ready to make your first hire--but don't be too hasty.

"It is easy to just want to fill that first slot and get things rolling," says Barbara Tallent, a serial entrepreneur and an advisor to Astia, a San Francisco-based nonprofit that runs programs for female entrepreneurs. "The wrong employee can become a huge burden for you and drag subsequent employees down as well."

Not sure where to start? Here are 10 questions to ask before deciding to hire your first employee:

Do you need to delegate some of your tasks?
To keep your eye on strategic matters, you can't be weighed down by too many mundane tasks. Ask yourself if you've reached that point with your startup and need to start delegating some of the work. The right hire can assume responsibility for everything from cleaning to shipping to dealing with social media, says Gregory Bier, director of the University of Missouri's Entrepreneurship Alliance, which tries to foster entrepreneurship at the school.

Do you have a defined role to fill?
Don't advertise a vague job title. Instead, take time to come up with a job description that spells out the specific responsibilities of the new employee. That will help ensure that you pick a truly qualified candidate. Also, the more detailed the job description, the easier it will be for you to set benchmarks to measure the new hire's performance.

Could an independent contractor be just as effective?
Rather than committing to a full-time hire--with a regular salary and benefits--some businesses are better off retaining someone on a freelance or contract basis, says George Deeb, managing partner at Red Rocket Ventures, a consultancy that advises startups in Chicago. If an executive assistant can easily handle the tasks you need help with, such as scheduling or bookkeeping, then a contract worker may be a good call.

Can your network help you find your employee?
Hiring an employee recommended by someone you trust in your network can take away much of the uncertainty and increase the chances for a successful fit, Tallent says. So, check to see if you have connections on social media sites, including Facebook and LinkedIn, who could recommend a candidate--or even who could be your first hire.

Are you hiring someone with your skills?
Be careful to avoid hiring a candidate who excels in areas that are too similar to your own skills. "The new hire should have strengths that compensate for [your] weaknesses," Bier says. For example, if your Web analytics or finance skills are not up to par, look for an employee with experience in those areas.

Can you make a multi-year commitment to the employee?
Hiring a full-time employee means you need to be prepared to provide steady income and developmental opportunities. "It moves you toward being an employer rather than an entrepreneur," Bier says. "You are responsible for someone else's motivation, pay, safety, training--and drama." So before you commit, be sure to have training goals in place, along with a plan for paying a salary over the long-term.

How will the new employee add to your bottom line?
Your first employee is a huge financial investment, so you need to understand how the person can help make your business more profitable, says Elyssa Sanders, New York-based cofounder of Godfrey Sanders PR, a public relations firm that was launched in 2012. Sanders hired her first employee to help maintain daily operations, so she could focus on bringing in more business. She says the new account executive has worked out well, garnering more media coverage for existing clients, which in turn helped attract new clients willing to pay the monthly retainer fee.

Would you spend time with the employee outside of work?
Because startups are known for long hours, it's especially important to get along on a personal as well as professional level. "One question we often ask ourselves after interviewing a candidate is, 'Could you go camping with them,'" says Robin Thurston, CEO of MapMyFitness in Austin, Texas, a platform for fitness websites. When you interview candidates, look for shared interests and approaches to solving problems.

Will the candidate be a good model for future employees?
Before committing to a new hire, make sure the employee possesses the necessary qualities to serve as a model to the workers you may hire down the road. "You really set the culture of the company with your very first employees," says Tallent, who looks for people who understand how to be part of a small team but also can work independently.

Can you count on your first hire to stay a while?
The first employee will come to know the company inside and out, so it's important that he or she is eager to grow with the business. "It's all about loyalty," says Thurston, who adds that several of his early employees have stayed with the company. Make sure you understand the person's reasons for joining and the experience he or she is seeking with your company. Less employee turnover means you'll save money on recruiting and training costs.

Alina Dizik

Alina Dizik is a freelance journalist and writer based in New York City. Her work has been published in The Wall Street Journal, iVillage, More magazine, The Knot, BusinessWeek and the Financial Times.

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