I’ve talked to dozens of small business owners this year, and most of them admit the same thing: their onboarding process is basically “here’s your laptop, good luck.” It’s not that they don’t care: they’re just stretched thin, and onboarding falls to the bottom of the priority list.
But here’s the problem. When onboarding sucks, people leave. And when you’re running a 15-person company, losing someone after two months isn’t just annoying: it’s expensive and disruptive.
So what are small businesses getting wrong? After seeing the same patterns over and over, I’ve narrowed it down to five mistakes.
- Winging it every single time
No checklist. No plan. The new hire shows up, someone gives them a quick tour, and then… nothing. They spend their first week figuring out who to ask questions of and where to find stuff. It’s chaos dressed up as “flexibility.”
- Treating onboarding like a paperwork dump
Yes, you need the W-4 signed. Yes, they need to read the employee handbook. But if that’s ALL your onboarding is, you’ve already lost. People want to feel like they made the right choice joining your team. Tax forms don’t do that.
- Cramming everything into day one
Here’s what doesn’t work: a 6-hour orientation on Monday covering every policy, tool, and process the company has. By lunch, the new hire’s brain is mush. By Wednesday, they remember maybe 10% of it. Spread it out over weeks, not hours.
- Ignoring the two weeks before they start
That gap between “I accept the offer” and “first day” is a golden time that most companies waste. You could be sending a welcome video, getting paperwork done early, or just checking in to build excitement. Instead? Radio silence. Then owners wonder why new hires seem nervous on day one.
- No clear expectations for the first 90 days
Ask a new employee at most small businesses what they’re supposed to accomplish in their first month. You’ll get a blank stare. Without real milestones, people drift. They don’t know if they’re doing well or failing until it’s too late.
What actually works
You don’t need an HR team to fix this. Tools like FirstHR exist specifically for small businesses: they handle checklists, document collection, task assignments, and more. You set it up once, and every new hire gets a consistent experience without you having to manually track everything in spreadsheets.
Onboarding isn’t glamorous. It’s not going to make your LinkedIn feed. But it’s the difference between someone thriving at your company and someone quietly job-hunting by month three. Fix these five things, and you’ll already be ahead of 90% of small businesses.



