KJ outside

The moment I hired some help, I forged a more powerful future. But it’s not the most simple thing to do. Like most other skills, hiring requires practice. Practice I didn’t have.

Thankfully I have no horror stories to tell, but lots of “on-the-job” training. Let’s just say I’ve gotten way better at hiring over the years. 

I hope you can hire someone to help you soon. To get you started, here’s some of my hard-earned wisdom.

Trial by fire

My very first hire was pretty impulsive. Same with the third. I was just starting out in my new role as a team leader, and one was introduced to me by leadership and the other came from me sifting through hundreds of resumes. They were both people I immediately liked at the interview and connected with — I felt like they understood me. 

I also knew I needed help, but didn’t give much thought to how someone was going to help with everything I needed help with, whether or not they were truly qualified to give me the right kind of help, much less whether or not my somewhat laissez-faire attitude toward the decision would result in a good match for my business. I figured the only way to know if this is going to work with this person is to try it out.

Consequently, there was no formal hiring process, just a coffee conversation in good faith. They agreed to the laundry list of items I needed help with, eager to learn the business from someone like me. The (perhaps unspoken) understanding was that they would come on to work for me, and we’d figure out the rest together. 

I was definitely in denial about my hiring practices. I thought if they were hungry enough and smart enough — and by my guesstimation they were — everything would be fine. 

It was an exercise that was destined to fail. And through no fault of theirs, it eventually did. I didn’t know it then, but my lack of clarity and experience in management combined with my unconscious assumptions was a recipe for a short-term engagement, not a long-term personnel solution. 

20/20 Hindsight

Reflecting on those first three hires, I realize where I went wrong. Here’s the post-mortem:

The job description was overly ambitious and unclear.

Because I was unclear as to what I needed, the job description was too. Did I need an administrative assistant or a personal assistant? How many hours a week should they work? I had a nice, long job description I had written out, but as far as how to prioritize the tasks, I didn’t know the answers. I laid out specific responsibilities, but did not plan on training. It was baptism by fire, just as I had learned. My hires did not have an order of priority for their tasks or any understanding for how someone who was just getting into the business would actually ACCOMPLISH it all. The result was an eventually overwhelmed hire, because my expectations probably covered too many things and nothing about how they would “ramp up” to learn to do the job..

My expectations were unrealistic.

I picked the first few assistants because I saw things in them that reminded me of myself. This seemingly innocent perception led to one giant erroneous assumption: If they’re like me, then they’ll work as hard as me, work long hours like me, and be just as committed to the business as I am. They will have a brain just like mine and also telepathic powers. Right? 


The line between personal and professional was blurred.

Line? What line? I hired an assistant and I assumed they would do assistant-type things. Afterall, what’s the difference between asking someone to schedule a showing vs. asking someone to mail your sister a birthday present? The difference is not everyone wants to be a personal assistant. Not to mention, most people new to real estate don’t understand that there is no difference between your personal and professional life — there is no “switching” between the two realms (and back again). 

I hired off of feeling only.

There’s nothing wrong with trusting your instincts about a person. And it is helpful to like the person you hire. But they don’t have to be someone you would go out for drinks with after work. Even if they ARE going to be all up in your personal business, feeling like you are best friends is not part of the hiring process. 

There will be people who will interview well, but don’t have the right skillset. There will be people who look great on paper, don’t make you feel warm and fuzzy inside right away, but grow on you. And, there will be people who you like, who have all the right qualifications and want the job. However, it’s unlikely you will find that magical combination based on your instincts alone. The best practice in this regard is to employ both your heart and your head. Follow your intuition and then verify by vetting.

On my next hire, I stepped up my hiring game

Big time. I put bonafide hiring practices in place. I came up with a job description, used a personality test to find people who complimented my personality and had the type of personality best suited for the role. (I like Wizehire.)

I, you know, asked for references. 

Perhaps most importantly, I adjusted my expectations. 

My most recent hire has the title of Chief of Staff. It may sound ridiculous coming from a real estate agent, but you know what? This is the closest title that describes my expectations for someone in this role. I finally embraced that who I envisioned hiring was in fact disconnected from the title and package I was offering to an applicant. Also, if you are not going to be great at training your hire, you need to have extra patience around how long it takes them to onboard — and that’s ok. 

You can’t expect someone to be you and do all the things you might do in the growing stages of your business. There is a reason this is YOUR business, you have the skin in the game, and everyone else is on a steady paycheck. You can and should expect integrity, loyalty and diligence. But do not expect your world to become theirs — unless of course you are ok with burnout and turnover. 

Please get excited and take the plunge. Remember, my first assistant helped me triple my income in one year and that was even with all of my terrible hiring practices. It is YOUR time to take YOUR business to the next level. 

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