The Evolution of Office Management

The Evolution of Office Management

What was once a one man team is now a small business with two separate branches under the same Ascend name. Over the years, I’ve hired, fired, maintained and changed the way we run our business. I’ve always been open to change because I can’t do it all myself, and there’s no point in pretending I’ve found the golden rule for any one way of getting things done. I’ve always felt like if we aren’t changing, we aren’t making any positive progress. It’s hard for you to understand the advice of a young guy, without truly knowing my experience and what I could possibly have to offer you as an entrepreneur just starting out. You’d probably be pretty surprised to know that I’ve been managing people for nearly a decade now, though I’m only 27. Here’s the quick version of the business world I came from.

My Management Journey

When I started managing people, I was just 19 years old. I hired my first assistant for real estate transactions, and just about anything else I needed in business. The ongoing joke in my office was that my assistant, who was a bit older than me, had to purchase the champagne for the closing gifts I was giving my clients, because I legally couldn’t. Over the years, the faces changed, but the job was the same, until I hired another realtor under me, to be on my team and represent me as my buyer’s agent, meaning he would now focus on showing homes to people looking to purchase a new home, and I would focus on people who wanted to sell their homes. I was dabbling with investor clients at the time, and just learning about property management and the requirements to get my broker’s license, so those were dreams in my future, but still a little ways away.

After getting my broker’s license, I began directly managing a handful of properties for one of my larger investors who lived out of town. I was personally taking maintenance requests, showing houses, and signing leases, and it got exhausting. I hired another assistant to help with property management and it’s growth. A short time later, I was approached by a local, well respected business owner in the area with his own real estate brokerage about becoming his sales manager. At this point in my career, I had been dedicated to the company I worked for, and it’s somewhat frowned upon to jump around companies in our town, but I saw this as a huge step for myself and my team, and we made the move within 6 months. We set up shop at this new place, and I began learning how to manage people much older than me, and what made them tick. Truthfully, the next few months were a whirlwind of learning and personal growth, as I educated myself directly underneath a very reputable broker in the area.

All good things of course must come to an end, and my team and I realized fairly early on that the relationship we’d been fostering with this brokerage was not sustainable. There were promises made that couldn’t be kept due to financial reasons within the business itself, and it was not going to create the environment I wanted for my personal team or business. With only the knowledge I had from the two brokerages I’d worked for, my experiences good and bad with my own brokers, and a passion to make it, I incorporated my two companies and opened our doors at Ascend Real Estate and Property Management. Ascend has changed substantially in the years we’ve been open, staff members have come and gone, and money has been reinvested in the company time and time again. We opened our doors with a receptionist, leasing agent, manager, and a slew of realtors, myself at the head of the company. Today, we have a receptionist, leasing agent, bookkeeper, marketing specialist, transaction coordinator, general manager, two maintenance workers, and myself as a realtor, broker, and owner of the company. Looking back now, I can see the mistakes and mishaps we had along the way, and if I could do it all over again, I’d make the same mistakes to learn the same lessons. I’ll share a little more on those later.

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‘Figure It Out’

Running a one man show is easy. When you’re the only one working on your business, you know exactly what you want done and exactly how you want it done. This, however, changes when you hire someone because they have their own methods, rhymes, and reasons for doing things ‘their’ way, which sometimes isn’t ‘your’ way. Sometimes they don’t have a way of their own at all, and they need your input on how you want it done. I have never been a micromanager and I have always had to figure things out on my own to start my companies, because, for whatever reason, many people think they have some kind of secret sauce they can’t share with anyone else. I knew sales. I knew the way I liked my day scheduled. I didn’t know a lot about accounting, marketing, managing, corporations, hiring, firing, or a really anything else it takes to run a startup business, but I figured it out along the way. This directly translated into my early management style that we now lovingly refer to as “figure it out” management. I assumed when hiring people, that if they didn’t know something or didn’t have the answer, they could do their own research, and figure it out for themselves too. I did it, and I liked the freedom to make mistakes and learn from them that this experience provided to me. The problem with this method of management is that many employees (especially type B personalities that encompass a LOT of inexperienced employees) need direction for how you want something to be, and they can feel a lack of training or support if they are left to navigate major decisions on their own. The people that are excellent at figuring things out on their own, without training or self help courses, are the people that do not work for anybody (type A personalities, business owners, etc), or they’re a salesperson. I quickly figured out that my employees had an internal joke of not asking me questions because they knew my response would be to “figure it out”. I learned this half joke one day and knew I immediately had to cut that slogan from my vocabulary. They didn’t see this motto as a helpful guide to learning on their own, they saw it as a disinterested owner that didn’t care about them or their problems.


I sat with my staff one day after preparing a new management style that would make them feel more incorporated into the team as a whole, able to ask myself (or at least Kenzie) questions when they needed help. I explained to them that when they needed help from me, how I’d prefer for them to ask for it (short, straight, and to the point), and that I’d happily provide the best information I could. It was imperative for them to have a resource in the office, and know that I was advocating for their success, not just my own. When they felt empowered, my office began running a lot more smoothly. Things were getting done in a way that made the business better as a whole, gave them a mental check mark for a job well done, and made me happy that they felt like part of what I’d created. “Figure it out” management died the day I learned about it, but I had an inside eye when my wife started working at the company. People confided in her as her business attitude is a little more gregarious than my own. Together we were able to recognize the issue with FIO management and correct it, but not everyone is lucky enough to have their employees say something that red flags an issue like this, and many bosses are not receptive enough to pick up on it. If you notice yourself as a hands-off employer, there may not be anything wrong with that approach if you’re a sales manager or just a resource for other entrepreneurs like a coach, etc. But if you’re a true owner and operator of your own company, you’ll have to learn how to be more communicative of your wants and needs, how to give direct and specific guidelines, and how to actively listen, or at the very least, provide a resource for these things given your inability or lack of desire to do so.

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Managing Salespeople

For a brief stint, I was managing a little less than a dozen salespeople. Independent contractors that were 1099’d from the company, meaning they were not on salary and they were not technically my employees, just hosting their licenses under my broker’s license and making sales under my company name, of which I received a small fee for. This is, and I can’t emphasize this enough, VASTLY different than hiring an hourly/salary employee that has a set schedule and requirements for their job. Managing an independent contractor is a different beast of its’ own entirely, and I realized after a lot of hard work, some failures, and some time and money lost, that it just was not for me. While selling real estate is more glamorous and exciting, managing properties is more stable and has much more control as far as repetitive income earned. Managing other self employed people means that they each have their own goals, clients, income, problems, and everything else that comes with another type A personality in your office. Managing properties and a property management company means that all of the clients are my own, the staff’s goals are all the same and align with mine, we all share the same problems, and the income is more consistent. While managing properties isn’t as glamorous, it is much more controllable and reliable in income and office management. As mentioned previously, my personal view is to not switch companies often as an independent contractor because it can make you seem unreliable, however, this view is becoming less and less common these days, and everyone in the self employed realm always wants more money for less energy. Building a company is not a pyramid scheme. You won’t get rich quick. You may not ever quite reach your goals, and you’ll go back to the drawing board more times than you can count. That’s how you know, you’re building something from the ground up, not riding coat tails, and certainly not being given any breaks. The best thing about the hard work you invest, is that if you do it slowly, over time, and you have the patience and persistence to continue past where others have faltered, no one can take the success you’ve built away from you (though some will try!). One day you could have several people wanting to come work under your company, ready to share in your hopes and dreams, making you feel like the next Million Dollar Listing realtor, and the next, half of them moved on (in the same day no less) and decided that they wanted something a little more fun and a little less work. Managing ICs is a very extreme roller coaster of emotions. With that being said, I’ll stick to my 8-5 employees.

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Getting Chummy

One of the gravest mistakes that myself and my wife made in building our companies, that I imagine a lot of new business owners make, is finding ‘friends’ in your employees. The second you let the confines of your relationship blur, with or without knowing it, you’re treating them differently. It’s okay to know the personal life details of your employees, but yours should be as much a mystery to them as what their doctor does for fun. It’s okay to let them into a few special moments, like inviting them to share in a special life event like a wedding, or baby shower, as we have done in the past, but once you have dinner with them on a weekend, the relationship becomes tainted, and it’s almost always for the worse. You want to keep your demeanor in the office as professional as possible. That will mean making people angry, sometimes so much so that they quit. That will mean holding all employees to the same standard, whether you ‘like’ them or not, because ultimately you have to think of what is better for your company and the others in your company. If you allow someone to stick around your company because you enjoy them as a person, but they don’t do their job well, you are sacrificing the rest of your team to pick up their slack, and they will notice, I can promise that much. If you have a great employee with a sour attitude towards others, you are allowing the company culture that you’ve built to be negated and belittled. If one person is allowed to break rules of conduct, everyone will follow and you’ll have an anarchy on your hands in no time. With a small office, we thankfully have been able to do damage control quickly and pretty discreetly because less mouths chit chatting means less drama, but drama will still ALWAYS exist in the workplace. Welcome to politics and the great state of California that protects employees before employers. We’ve called people friends and they’ve spread malicious rumors with no grounds, for no reason other than jealousy. We’ve invited people into our home and they’ve stolen from us. We’ve invested a great deal of time and money in education and well being, and literally had ex-employees disappear without a trace. We’ve been sued a few times, never resulting in anything against us because we truthfully have always had reason behind terminations, but even those lawsuits that drag us through the ringer feel like a knife in our backs. Rule of thumb, assume everyone is out for themselves. You will have to treat everyone the same. Be careful what you say around people, and familiarize yourself with human resource law. It’s also a good idea to know an excellent HR lawyer for issues that arise, and they will. Try not to be shocked and hurt when you get sued or stolen from, and try to protect yourself as best you can without being a robot to your employees. It’s a huge balancing act to hold people at arm’s length and to want to be genuinely involved in their lives and success, but once you find your balance you’ll never look back! You already have good friends, you don’t need to mix relationships; just remember that.

Managing A Manager

With the rapid expansion of the companies, I knew we needed a general manager that had the same efficiency, mindset, and my ‘figure it out’ mentality. We hired close to a dozen people for this position, from people with a lot of property management experience, to people with none. People with a exponential management experience, and those with solid, type A personalities but no true experience. People with a lot of certifications, degrees, and plaques, to those with a GED. We weren’t picky about who they were, or where they came from, only that they could adapt, learn, and properly manage to a standard that we approved, and of course that clicked with our company culture. After a lot of trial, error, and training, we found the perfect one under our nose the whole time, promoted from within, and invested into an employee that had shown us time and time again that though she was young, she could handle the stress and organization of being a general manager. Now, I recognize that many business owners can feel odd when trusting someone other than themselves to run any aspect of their business. I have never been that way truthfully, but it’s the number one reason I hear when entrepreneurs complain about lack of growth in their business. They want to run their business the way they want to, and they can’t find anyone else to run it or care the same way they do. Here’s some truth: that will never change. No one will care for you little baby business the way you do. No one is reliant on that income the way you are, they just assume the paychecks roll in because your pockets are full. No one advocates for expansion, tighter margins on overhead, and more income for the company, though you will find plenty of people advocate for themselves. But, if you accept the truth that someone can run your day to day operations better than you can in this time and place, you end up succeeding much more quickly. You really have to first understand where your time is best spent, and I can tell you, I was not cut out for answering customer service questions from tenants. I lack the patience to even hear their story in full, and I don’t enjoy this aspect of my business. You can see how this could be an issue. My time is best spent making community connections and fostering relationships with investors, growing our company a few units at a time, and leaving the clerical and service aspects to my dedicated team. From day one, I’ve empowered the managers I’ve hired by having manager sized perks that came hand in hand with manager sized responsibilities. I don’t assume they can’t do the job until they show me they can’t. I wait for failure to consume them, and I’ll watch from a distance to see if they ask for help, or if they can problem solve some other way, but ultimately the only true failure, is not realizing they’ve failed and taking new action to rectify the situation the company is in. I am quick to give them the keys to the castle, but still quietly watching over them, monitoring their subordinates opinions (without stepping on toes), and our clients views on their effectiveness. Basically, if I hire someone to be the manager, I allow them to be the manager. As much as I want to get involved in day to day problems or conflict, I have to allow them to navigate it and wait for them to ask for help. Much easier said than done. Managing a manger isn’t so hard, when you have the right manager, but you can easily scare them off if you over micro manage. That isn’t to say that you can’t offer training or outside education that clicks with what you believe in or the way you want the company to grow, just make sure to allow them to make mistakes, AND allow them to attempt to fix it. Jump in when you see them floundering, just to offer help, so they know that you’re accessible, but allow the ball to be in their proverbial court.


That’s been my journey thus far! From one person at a time to over a dozen at a time, it’s been quite a trek. I foresee more branched out businesses in our future, and assume I will have to manage multiple managers for different businesses, so I’m sure that I will then take on a new management style yet again, and I’ll of course share those tips too. The best managers can see that something needs to change; if you can recognize it, you can change it.   

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