Hiring should make your life easier. But for many founders, it does the opposite. It adds stress, drains time, and still leaves you buried in the day-to-day.
If you’ve ever thought:
- “I’m tired of wasting time and money on the wrong people.”
- “Even when I hire someone, I still end up doing most of the work myself.”
- “I don’t even know what I’m doing wrong. I just know it’s not working.”
You’re not alone. I’ve been there too.
Before I built a repeatable hiring system, hiring felt like a gamble. After hiring 50+ roles for clients (and plenty for myself), I started seeing the same 8 mistakes pop up again and again.
This post breaks down each of those mistakes, with practical ways to avoid them so you can start hiring people who actually make your life easier.
Mistake #1: Rushing the process
I’ve talked to dozens of founders who’ve tried and failed to hire, some more than once. One told me they had hired five different assistants on Upwork and none of them worked out.
In almost every case, the same root issue shows up: they rushed it.
Hiring isn’t something you can knock out in a few hours. If you want someone great, you need to slow down and treat it like the high-leverage investment it is. That means carving out real time for each part of the process.
If you’re managing hiring on top of your normal responsibilities, aim for a 4-6 week timeline. If you want to move faster, I’ll show you how at the end of this post.
Mistake #2: Skipping clarity on what you really need
One founder came to me frustrated that they were constantly having to fix their team’s work and couldn’t figure out why. When I asked how they had made their hires, they said, “They reached out to me, and we needed help, so I hired them.”
This is so common.
If you haven’t gotten 100% clear on what you really need, you’ll end up hiring people who don’t fit and can’t deliver.
This particular founder had those same people in their business for years. That cost them untold amounts of expense, lost revenue, and a lot of unnecessary frustration. They were stuck in the weeds and constantly stressed about money for years, because of a problem that started at the hiring stage.
Most founders skip this step because they think it’ll take too much time. It doesn’t have to.
Want the same clarity tool I use with clients? Grab it for free here!
Mistake #3: Writing job descriptions that don’t attract
Another founder tried hiring through a recruiting agency but was fed up with the poor quality of candidates they received.
When I looked over the job description they’d been using, I immediately knew why. It wasn’t tailored to attract rockstar candidates. It was a bland, boilerplate job description with nothing that would make a great candidate say “I want this.”
There was no mention of company culture. No hint at growth opportunities. Nothing that showed why someone would want to work there.
Here’s what most people miss: great candidates aren’t just looking for a paycheck. They’re looking for purpose, ownership, and a work environment they actually enjoy.
You don’t need benefits like medical insurance, though they can help. You do need to clearly communicate what makes working with you a good experience. Is the role fully remote? Do you give a lot of autonomy? Do you move fast and value collaboration?
If your job description only talks about what you want and says nothing about what they get, you’ll keep attracting the wrong people, or none at all.
Mistake #4: Winging it with your application process
I was scrolling through Instagram and saw a business owner post about needing a virtual assistant. They asked people to email them if interested.
Within a few hours, they posted again. They had shut down the search because their inbox exploded and they had no idea how to sort through it all.
This is what happens when you use an unstructured format to collect applications. It becomes overwhelming, fast.
Not only were they flooded with messages, but everything was mixed in with their regular emails. People sent all kinds of material: resumes, personal stories, and long emotional paragraphs about why they wanted the job. It’s exhausting and makes it easy to miss the best candidates.
Here’s how to avoid that chaos:
- Use a tool to collect applications. Even a simple Google Form works, but a proper tool will make this process even easier for you. I’ll share my go-to tool at the end of this post.
- Ask the right questions. Good application questions give you consistent info across all candidates and help you spot who’s worth your time. It’s your first filter.
Mistake #5: Ghosting candidates or moving too slowly
A client of mine had two stellar candidates and was especially excited about one of them. But they kept putting off reaching out. When they finally did, that candidate had already accepted a role with another company.
Great candidates won’t wait around. If you disappear or drag your feet, they’ll assume you’re not serious and move on.
Staying in touch while juggling everything else in your business can feel like too much. That’s why I recommend using the right tool to help you streamline communication with candidates.
With just a couple of clicks, you can keep everyone in the loop. More on that below.
Mistake #6: Running unstructured, inconsistent interviews
A client once told me they “just went with their gut” during interviews. No plan, no questions, no notes. Just a casual chat and a good feeling.
They ended up hiring someone they really liked, who completely bombed the role.
Interviews aren’t just about connection. They’re about evaluation.
Here’s how to structure them effectively:
- Ask the same questions across interviews. This helps you compare candidates fairly and keeps personal bias in check.
- Watch the clock. Some candidates are talkative. Keep interviews on time to show you value boundaries.
- Leave time for their questions. This shows you how they think and what they care about.
- Stick to your structure, especially when you like someone. Just because you get along doesn’t mean they’re the right fit. Consistency protects you from making a charisma-based hire that doesn’t work out.
Interviews are one of your strongest tools to weed out bad fits and push the best candidates forward. Use them well.
Mistake #7: Ignoring employment laws
I’m not an employment attorney, so this isn’t legal advice. But I do want to flag some important things you need to be aware of when hiring:
- 1099 vs W-2 classification. Misclassifying a contractor can lead to fines. Know the difference and when to use each.
- State-specific laws. Some states, like California, have much stricter rules. What works in one state might be illegal in another.
- Salary transparency. More states now require you to list pay ranges in job posts. Failing to do this can cause compliance issues.
You don’t need to be an expert. But you do need to know what applies to your business. When in doubt, talk to a professional.
Mistake #8: Neglecting onboarding
You’ve finally found a rockstar. Amazing.
Now what?
If you skip onboarding or throw them in without a plan, even the best hire will flounder. And you’ll find yourself thinking, “Why aren’t they picking this up?”
Here’s what to prep before their first day:
- Tool access. Make sure they have logins and permissions.
- Company context. Help them understand how the business runs, what you care about, and how decisions are made.
- Clear how-tos. Show them how to do the key parts of their job, step by step. I recommend Loom for this.
- First-week and first-month tasks. Give them early wins to build confidence. These are quick wins for you too.
- Regular check-ins. Be available. Early support and feedback set the tone.
Pro tip: Record Loom videos of yourself doing core tasks. Have your new hire turn those into written SOPs. You delegate, they take ownership, and you end up with documentation. Win-win.
Want to avoid these mistakes and hire with confidence?
You don’t need to figure it out alone.
Talent Engine: Hire Rockstars is my program designed to walk you through every step of the hiring process. I’ve used these systems to hire 50+ roles for clients. Inside, you’ll get the tools, templates, and automations that make it easier, faster, and way less stressful.
🎯 Join the waitlist now to:
- Get early access before the public launch
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Hiring doesn’t have to feel like a gamble. Let’s make it a strategic advantage.
