Hiring Your First Employee

Before you post the job, ask: is this a W-2 employee role, or a 1099 contractor role? The IRS rules are stricter than most owners realize. If you control when, where, and how someone works — they're an employee. If they bring their own tools, set their own hours, and work for other clients — they're a contractor.

Misclassifying isn't just paperwork — it's back-pay, back-taxes, and potential penalties if someone files a claim. The default-safe move for someone working full-time for only your business is W-2. If you genuinely have variable, project-based work that they can do on their schedule, 1099 might fit.

Don't hire a generalist as your first employee. "I just need someone to help with stuff" is the most expensive mistake. Pick the one task that's eating the most of your time AND that you don't enjoy AND that doesn't require your trade expertise to execute. That's your first hire's job description.

Common right answers: scheduling and dispatch, admin/bookkeeping support, customer follow-up calls, social media + reviews management, junior tech who can handle straightforward jobs while you do the complex ones. Common wrong answers: "sales" (you should still own sales for the first 2–3 years), "marketing" (without specificity), "office manager" (too vague).

Look up market rate (Indeed, Glassdoor, your state's DOL data) for your specific role in your specific area. Then pay 10–15% above that for your first hire. The premium is worth it for two reasons: you'll get better candidates, and you'll lock in someone who's hard to poach.

Don't try to save on the first hire. The cost of replacing them after 6 months is roughly 50% of their annual salary in lost productivity, recruiting, training, and downstream impact on your reputation.

Indeed and Facebook Jobs are still the highest-volume sources for trades and admin roles. ZipRecruiter has higher cost per post but better filtering. LinkedIn is overkill for hourly roles.

Best source by a wide margin: referrals from your existing customers and crew. Offer a $250–500 referral bonus paid after the new hire's 90-day mark. People you know are far more likely to hire someone you can actually trust.

Most owners overinterview. You don't need a 5-step process for a $20/hour role. You need 30 minutes on the phone with these five questions:

Set explicit expectations for the first 90 days. Tell them on day one: "We'll have a sit-down at day 30, day 60, and day 90. If at any of those points either of us thinks this isn't working, we part ways with no hard feelings."

Use those checkpoints. Don't avoid hard conversations to be nice. Most owners wait until month 9 to fire someone they knew wasn't right at month 2 — and pay 7 extra months of salary for the privilege of being conflict-averse.