3 Rules I Learned from Hiring the Wrong Person (Twice)

UPDATED: May 13, 2022
PUBLISHED: April 13, 2022
3 Rules I Learned from Hiring the Wrong Person (Twice)

As an entrepreneur, I didn’t think hiring a team would be that big of a deal.

Step one: Figure out what I needed someone to do.

Step two: Find someone to do it.

Voila! Good hire. Right?

Um, yeah, not so much.

The process of hiring the right person has been one of the most challenging parts of growing my once-solo operation into a team of happy, productive people working toward the same goals.

There are two massive mistakes I made early on that I want to warn you about so you know what to pay attention to—and then I want to give you three little-known rules of making a good hire. Here we go.

Warning No. 1

When I relaunched my solo business into an LLC, one of the first people I brought onto my team was a certified professional accountant. I got a recommendation from a trusted colleague. I contacted my CPA, asked for a few more references, then hired him.

Within a month, I fired him.

Look, I don’t know about you, but before owning a business I had never hired a CPA in my life. I had no idea what that relationship was supposed to look like. Nor did I understand that each relationship looks different depending on CPA style and client needs.

Turns out, I am a very needy client for a CPA.

I’m decent with numbers and for years did my own taxes. But I am terrible at dates, organization and regulations. For me, this means that the date when my quarterly taxes are due will fly right by me, even if it’s on my calendar. And if I happen to catch it, I have no idea where I put that form I’m supposed to fill out. And if I get that filled out, I’ll probably have to look up the rules of filling it out again, even though I just filled it out three months ago. Dates, organization and regulations are my weaknesses.

The problem is I didn’t tell my CPA any of this. So when the date for my first tax payment came and went without any word from him, I called him. Long, uncomfortable conversation made short: He was subtly annoyed that I couldn’t remember something so simple, but promised to remember next time.

Then the franchise tax date came and went. Same phone call. Only this time, I fired him.

I felt bad, too, because it wasn’t his fault. It was mine.

There’s a myth that if you do your due diligence, it will give you enough information to find and hire the right person. But I had asked peers for recommendations. I had asked my CPA for references. I had even called those references and asked if they were happy with his work. It was not enough.

I didn’t ask what their relationship was like with their accountant. How information was passed along. Whether they had to remember all the requirements while their CPA just processed the paperwork. If I had spent more time learning about this kind of relationship and what was common practice, I would have realized that what I needed was a coach, not just a CPA.

Warning No. 2

The next hire I made was a virtual assistant.

After doing research through a professional VA organization, I narrowed my list down to three candidates. Then I hired the least experienced person on my list. We’ll call her Vera.

Now, I told myself that I chose her because I was strapped for cash and since she was just starting out, Vera had the cheapest packages. But the truth is it was a pity hire.

Vera had a blog. She didn’t advertise this blog as part of her professional online presence, but I’m a researcher and found it. In this blog, she talked about her family issues, her cat, her general lack of friends and her dream of making some money while working in her pajamas so she could finally feel some self-esteem.

There is a tiny Rescuer in me that immediately fell for Vera. (I should know not to listen to this Rescuer after a couple of interesting boyfriend experiences, but what can I say? I’m human.)

I wanted to help Vera get started. I envisioned a sort of mentorship relationship where I could pull Vera along and—oh my gosh, seriously, I can’t believe I didn’t see it.

I wanted to pull her along? What was I thinking? I was hiring a VA not a puppy. I should never have to pull her along. Encourage, train, even coach? Maybe. But pull her along, no.

And pull her along is what I did. She couldn’t master the app I was using for project management. She couldn’t create the payroll spreadsheet I needed. And she didn’t respond to my other team members promptly.

It was a disaster—and I had paid for 10 hours upfront. I ended up using the last three hours on data entry and that was the end of a fruitless relationship and the teaching of a valuable lesson.

The 3 Hiring Rules You Don’t Hear

Since making these huge hiring mistakes, I’ve stuck with three rules that have saved me a lot of headaches:

1. Do your research on the relationship, not just the person. Ask for referrals, yes, but then ask more questions. Find out about the relationship style, the expectations on both sides, the duties of each and the level of professionalism vs. friendliness if that’s a concern for you. If the answers don’t jive with the style of relationship you’re looking for, why even bother to interview?

2. Never hire out of emotion. Never. Ever. Look, we all want to help out the new gal. We all want to bring on the funny guy. We love to be around people who make us feel good—whether it’s for our magnanimity or our sense of humor. And if you were hiring an intern or someone to MC your celebrity roast, I’d say go with your feel-goods. But you’re not. So hire for what you need, not just what you like.

3. Be brutally honest from the start. First, with yourself. If you are someone who can’t remember the due date for your taxes, you need to be realistic about this weakness. If you get a little snippy after a long day and expect people to overlook your rude emails—well, first of all you might want to work on that—but you need to admit that this is part of your current work style. Then, be honest with whomever you’re looking to hire. If you don’t give them an accurate picture of who they’re going to be working with and what you truly need from them—as a fallible human being, not just a boss with a to-do list—then they will end up disillusioned and you will end up without an employee.

Here’s what all of this means: The responsibility is on you for a bad hire. But it also means that the opportunity is yours to make a great hire. Take time today to get honest with yourself and make a list of questions that will guide you to the right person. I know you can build a team that you’re proud of and that makes you feel truly supported.

This article was published in January 2014 and has been updated. Photo by @Korneevamaha/Twenty20

Amy Anderson is the former senior editor of SUCCESS magazine, an Emmy Award-winning writer and founder of Anderson Content Consulting. She helps experts, coaches, consultants and entrepreneurs to discover their truth, write with confidence, and share their stories so they can transform their past into hope for others. Learn more at AmyKAnderson.com and on Facebook.