Hiring Your First Employee: Terrifying but Necessary
Hiring your first employee is one of the scariest steps in growing a business. You're not just adding a salary — you're adding responsibility, legal obligations, and the terrifying prospect that someone else will touch your carefully built systems.
Before hiring, ask yourself: do I need a full-time employee, or can I solve this with a contractor, freelancer, or software? Many businesses hire too soon when automation or outsourcing would have been cheaper and less complex.
If you do need an employee, hire for the role that frees up the most of your time or addresses your biggest bottleneck. Usually that's an operations/admin person, not a second version of yourself.
Legal requirements: get an EIN (if you don't have one), register for state employer taxes, get workers' compensation insurance, set up payroll (use Gusto or Rippling — don't try to DIY payroll), and display required workplace posters.
The job description should focus on outcomes, not tasks. 'Manage customer support to maintain 95% satisfaction score' is better than 'answer emails and phone calls.' This attracts people who think about results.
Interviewing tip: ask behavioral questions. 'Tell me about a time when...' reveals more than 'What are your strengths?' Anyone can claim they're a hard worker. Few can give a compelling story about overcoming a challenge.
Compensation: research market rates on Glassdoor, Levels.fyi, or Payscale. Paying below market gets you below-market talent. If you can't afford market rate, consider equity, flexible hours, or remote work as part of the package.
The first 90 days are critical. Have an onboarding plan, set clear expectations, check in weekly, and give feedback early and often. Don't wait for the annual review to tell someone they're off track.
Your first hire sets the culture for everyone who follows. Choose wisely.