5 Hiring Mistakes Small Businesses Make (And How You Can Learn From Them)
May 9th, 2025 | 6 min. read
By Matt Patrick

Have you ever hired someone only to realize they were completely wrong for the job? Maybe you've felt that sinking feeling when your new hire shows clear red flags on day one. If you're nodding along, you're not alone.
Hiring mistakes cost small businesses thousands of dollars and countless headaches each year. But what if you could learn from someone else's embarrassing failures instead of making them yourself?
As someone who's made plenty of hiring errors over the years, I've developed expertise in what NOT to do. Today, I'm sharing the painful lessons that transformed our approach.
In this article, you’ll learn the five biggest hiring mistakes small businesses make (we know, because we've made them) and exactly how to avoid them—like hiring based on gut feelings, skipping role clarity, or rushing the process.
A Look at Our Most Embarrassing Hiring Failures
Oh, do I have stories for you about all the stupid things we’ve done when trying to hire new employees. The list is S-U-P-E-R long.
My favorite is the employee who was literally scared of computers. Not timid, not tech-averse. Actually scared. You would have thought that maybe, just maybe, we should have had some concerns from the get-go, but I can honestly say I think our optimism that this was a person that "may" work out was our prominent deciding factor.
And then there was the person who, on her first day, complained about her chair creaking, the ridiculous height of her desk, and the lights giving her a headache, which meant that she couldn't concentrate or handle details like taking notes. All of this within the first half day she worked for us.
Or the person who, after entering a transaction into QuickBooks, was genuinely confused about how the numbers got there. (What??)
So let me say, we have been right there where you are. Hiring out of desperation, eternally optimistic that this person is going to solve all our problems and will hardly need training to do so. They'll be our next best employee, and their skills will easily overcome the potential problems we see during the interview process. You know, like the fact that they can't carry on a real conversation. Yes, we’ve been there too…several times.
You see, I am an eternal optimist and just KNOW this person will be the one. Well, let me tell you plainly: they won't. That doesn't mean they can't be, but we need to realize that our gut isn't perfect.
Hiring is hard. But with lots of practice and mistake-making, we have learned many important lessons about how to improve our process. In fact, for six years now, we have been named a "Best Place to Work" by the Memphis Business Journal. So, we must be doing something right.
Here’s a look at what we’ve learned…
5 Critical Lessons We’ve Learned From Our Hiring Mistakes That Can Help Your Small Business
1. Focus on Character Instead of Just Skills: Hire for the Person, Not Just Their Abilities
We are huge Patrick Lencioni fans (almost fan-boy status, if I might say so myself). His book, "The Ideal Team Player" is our gold standard in identifying what we are truly looking for in all our employees. If you haven't listened to our podcast on this subject, we’d highly recommend it.
The ideal team player simply says we are to look for employees who are: hungry, humble, and people-smart. It doesn't mean they don't have any technical skills, but it emphasizes that technical skills can be trained while humility cannot. (It might be coachable, but that’s not an easy task.) You can't teach someone to be hungry. They either care about getting better or they don't. And you can't teach someone to be people-smart (aka, knowing how to treat others, when to be empathetic, how to be the right kind of a nag, and knowing when to pat someone on the back and when to kick them in the butt).
In the workplace, you have to be able to deal with ALL types of people—clients and coworkers—so this is a really important quality to have. Check out Lencioni's full list of hiring questions to start thinking about how you can hire for these values.
2. Use a Consistent Hiring Process Instead of Relying on Gut Feelings: Make Hiring Objective, Not Subjective
In recent years, we have come up with the "Whirks way" to hire, and it all comes down to having a repeatable system. Your gut can lie to you. You may be in a crappy mood when you walk into the interview. You may like the person but forget to ask the question that could lead to an answer that has you thinking, "Uh-oh!"
Systematizing your hiring process with a consistent, objective scoresheet and a clearly defined process is super critical to improving the overall success rate in your hiring efforts.
We believe in this concept so much that we've actually developed a Whirkbook to help you develop your own hiring process that aligns with your unique company values, including a sample scorecard. Get your copy here ⬇️⬇️⬇️.
You can also start revamping your hiring efforts by checking out our article on how to improve your overall recruiting process. These resources may not be a perfect fit for your organization, but they should act as a guide to help you develop your own objective system.
3. Take Your Time Instead of Trying to Fill Seats Quickly: Never Hire Out of Desperation
Yes, we've made this hiring mistake. The alternative of not having someone (we thought!) was worse than having someone who wasn't ideal. Turns out we were wrong. A bad fit for your team can create chaos, frustration, and mistrust between employees. It also happens to be costly.
Having a system creates a filter so this doesn't happen. And even when you feel overworked or overwhelmed, don't deviate from your system! When it's possible, you must have patience for the right person. Hiring the wrong person—no matter how good short-term—will hurt you in the long run. In short, don't let the idea of short-term pain relief outweigh the long-term pain and cost that having the wrong person on your team will cause!
4. Define What Success Looks Like Instead of Lacking Role Clarity: Never Hire Without Clear Expectations
Yep, we've made this mistake too. We rolled out a new service and I liked the person…a lot! But I didn't know what they would do exactly. I had not clarified the role, and that made it very hard to define what "winning" would look like for them in that role.
This leads to confusion about purpose for the employee, regardless of how good of a fit you think they might be. My optimism and "figure-it-out" mentality were a disservice to this employee because they didn't have the clarity they needed to do the job well. Thankfully, in this specific case, this employee was patient and trusting enough to stick around until we figured it out.
But to follow best practices, it is essential to figure out what you want winning to look like in any role you're hiring for BEFORE you hire the person. You can always modify it and let it evolve later, but be clear that you know what you are looking for first.
5. Prioritize Development Instead of Expecting Perfection: Remember That Nobody's Perfect
As you can see, there have been times (not often) I've been wrong. I'm not perfect. No employee you will ever hire is going to be the perfect fit, and that is perfectly normal. Every employee has insecurities, strengths, and weaknesses. And that's okay because you know new employees will need some training and development to be successful.
Don't assume everything is going to be sunshine and rainbows with each new hire. Ultimately, you are responsible for making sure they have a clear picture of what's expected of them. You need to be honest and open about areas of improvement. You need to be encouraging and a steward of their development. You want them to have the desire to learn, take feedback, act on it, and continuously want to get better. But this requires you to help and support them.
From Hiring Nightmares to Finding Your Small Business Dream Team: Take Action Today
Looking back at all our hiring mistakes, I can see how each failure taught us something valuable about building an effective team. Creating a clear and consistent hiring system isn't just about avoiding embarrassing or unfortunate situations. It's about building a foundation for your company's future success.
- Where we were: Making reactive hiring decisions based on gut feelings and immediate needs.
- Where we are now: Using a systematic approach that focuses on character and clear role definitions.
- Where you can be: Building a team of ideal players who embody your company values and drive your business forward.
Hiring the right employees is hard. And truthfully, not every employee will work out. Taking the time to create a clear and consistent hiring system, however, will save you time, resources, and cringe-worthy happy hour stories for years to come.
If you’re working on building a more intentional hiring strategy, check out these 3 Steps to Hiring the Ideal Team Player. Knowing what success looks like before the interviews start can help you avoid many of these same mistakes.
Not sure how to get started? Our Whirks People Services are a great way to dive into this process with the support of an HR expert.
Topics: