When to Hire an Assistant

by | BiggerPockets.com

Have you found yourself caught in that mental ping pong yet:

“I need to hire some help. But I can’t afford to hire help. But I can’t get everything done on my own. But it would cost too much bring someone in. I mean, I can’t afford to pay…”

As your business grows, you find yourself becoming busier and busier.

Question: At what point should you consider delegating some of the day to day office details to some sort of hired assistant?

Answer: When you get to the point where you’re overwhelmed – or overloaded – or there’s something in your business that you Just-Don’t-Want-To-Do…, it’s time to look outside yourself and hire an assistant.

The first time you run into this should-I-shouldn’t-I-hire scenario, it feels hugely overwhelming and most people wait longer than they should to bring in their first assistant. Be aware, it slows you down in the short term to train an employee, so don’t wait until you’re totally covered up or you won’t find the time necessary to spend training them!

As your business continues to grow, the second and third hires are easier to justify and happen much faster.

When and whom to hire varies, naturally, with each business. It depends greatly on where you’re headed and the results you want. Maybe it’s time to notice that you’ve already created the business you want so it’s time to stop growing and start slowing.

If, however, you want to grow, there comes a point when the business outgrows a single operator. Celebrate!

For us, the first person we hired was a bookkeeper. I HATE bookkeeping (even signed up for accounting classes at a local community college until I came to my senses). I finally recognized that some people love bookkeeping and I should be paying them to do mine. Bookkeeping, as vital as it is to your company, generates NO income, so hiring a bookkeeper will free up your time to do more income producing activities like negotiating with sellers.

The second person we hired was someone to help with property management. At that time, we had close to 30 properties and I was overwhelmed with the day to day dealing with tenants and rent collection. Dealing with tenants was my second biggest pain point so that’s where I wanted relief. Letting someone else be the buffer between me and the tenant calls, filing, and going to court made me a much happier person (and much more pleasant to be around). First, look for ways a new hire can relieve your pain points.

Next, evaluate where it is in the business that you generate income. Those are the positions you personally hold onto the longest. Typically, you generate no income swinging a hammer or wielding a paint brush. Pay someone to do the manual labor so you can be out finding and negotiating deals.

THAT’s where your income is created.

Related: BP Radio Podcast 002: Starting Out with Karen Rittenhouse – Subject To, Direct Mail, and Investing from a Woman’s Perspective

Some people recommend outsourcing as a way to save yourself time and aggravation. Rather than bringing someone into your office to assist you, offload some of your work to companies set up to handle it. As an example, after the first year or so of chasing down deals, we began to outsource our marketing so the calls came to us (big time saver). And, with out direct mail marketing, we created a set-it-and-forget-it approach. We paid for a year’s worth of postcards in January and scheduled our mailings 12 months out so we only had to think about direct mail marketing and prepare it once a year. HUGE time saver.

If you’re currently thinking about hiring someone to help with the load, why not? Bring in a part time person and, if it doesn’t work out, you can easily stop using them. If you increase your business because of an assistant (which is what should happen), you can afford to pay for more hours or additional help. By the way, when you pay an employee, rule of thumb is that they should generate three times more income than what they cost.

Should you hire? Think about this: if your business is totally dependent upon you, you can’t get away. We just went on vacation for 15 days and our business ran flawlessly without us. There’s a lot to be said for being dispensable….

When you begin to anguish about spending the money for office help, what you’re feeling are growing pains. CONGRATULATIONS! Your business is so successful that you need help. I say go for it and let us know how it works out.

About Author

karen rittenhouse

Karen Rittenhouse has been investing in real estate full time since January 2005. In that time, she has purchased hundreds of single family properties, opened a full-service real estate company, a property management company, a coaching/training business, and written three books on real estate.


  1. Interesting post Karen. On your marketing, how do you predict in January how many pieces to send 12 months out? Also, do you refresh your lists during the year or add new target markets? Seems like these would change what you’ve set up. Would be interested in how you handle marketing changes during the year.

    • karen rittenhouse

      Hi Alison:
      Great question! We market to specific areas where we want to own properties. For 4-1/2 years we marketed to the same 5200 houses (they met all of our search criteria) every 6 weeks. We mailed 1000 post cards per week and the list just rotated over and over. You really don’t need to change your marketing piece very often because the important thing is that the clients recognize over and over that it’s you.

      After 4 1/2 years, we changed our business plan and our target houses, but we still set up our direct mail marketing on an annual basis.

      Direct mail, of course, is only 1 of about 7 different ways we hit our target audience.

      Thanks for your question!


  2. Karen, investing in properties the way you do, one has to have help. The right people will not only save you time but, make you more money in the long run. As for me, I like swinging a hammer. Hire a PM to take care of my headaches while doing what I enjoy. Figured out what was needed to retire on, double it and now mostly retired watching my orchard grow and produce more fruit every year.
    Nice post.

    • karen rittenhouse

      Jim – You rock!

      I spend hours per week gardening. Makes me zero income – saves me tons on therapy.


      You’re so right to do what you love. Makes you a much better person.

      Yes, the way we do business we hire out the work. And, we didn’t always hire everything out, the business has morphed.

      Thanks for your comment and congrats on your success!

  3. Jeff Brown

    As Dad neared retirement, and most of my sainted mentors got older and older, I began asking them questions concerning what this excellent post discusses. Their wisdom came down to one invaluable common denominator. In a perfect world your job is to ONLY do what only YOU can do. Anything you do that others can? Your bottom line just took a hit.

  4. If possible, I think it is always better to hire help before you are overwhelmed and too busy. Hiring help is a job in itself and if you rush it, it can create even bigger problems. If you can’t keep up with your work now, it is going to be very hard to find and train someone to help you if you have no extra time. I find the more help I have, the more money making things I am able to do personally and it increases my bottom line.

  5. Karen, thanks for the reminder. I always like the idea that I can keep my VA working on marketing and income generating tasks. This is just a smart thing to do.

    I somewhat (just s tiny bit) disagree that the owner shouldn’t look to reduce expenses. Expenses should always be reviewed from a CEO stand point. All of our business grow wasteful and need to be trimmed back. Sometimes that the most profitable thing we owners can do with our time.

    Sometimes chasing more deals is not the most profitable maneuver.

  6. Great article. I have one assistant now and I have other developers working on my websites.

    The more PERCIEVED CONTROL you give up the more money you make and the more sanity you keep.

    I do commercial transactions and my own investments. My philosophy is the investment cannot create another JOB for me that takes away from my core business. It has to stand on it’s own without an owner operator and have a solid structure of systems in place to handle bi-weekly to monthly oversight.

    What do you think of a bonus or incentive program for your employees?? I think if they know they have a chance to make more than XX an hour it keeps them motivated to produce when you are not watching. If they get lazy it only hurts themselves and their pockets. They become part of the companies success with one focus instead of just collecting a check.

    Home Depot, Wal-Mart and many other companies followed the principal of giving back greatly to the employees to help the growth of the business. Today they do not really do that but when I worked for Wal-Mart as a teen and Sam Walton was alive it was incredible. Stock was splitting every few months and people were making tons of money and Sam came by to all the stores frequently. The energy was electric.

    I can tell you the number one thing I absolutely cannot stand is property management. There is little to no money in that business. There is a ton of demand but you can manage 100 doors and only make 60,000 a year after expenses. I would rather do one commercial transaction and make the same amount.

    I used to have a 20 unit apartment building but I got rid of it as it became a job. I might buy an apartment building again but it would have to be 50 units and higher for a full time manager and maintenance person on staff.

    • karen rittenhouse

      Wow, Joel, great information and great insight. You have quite a business running!

      Yes, I try to add incentive pay to every position. Naturally that’s easy with our real estate agents as they get commission but, even with them, we also pay if they bring in a property management home or a tenant. Anything they can bring to us they get paid for. I want happy employees and the more they make, the happier they are.

      And as you eluded to, when you give bonuses for additional work done, cost savings, increase to the bottom line, employees not only function at a higher level, they begin to look for ways to make the company more efficient. Win/win/win.

      Thanks for taking the time to write such a detailed response.

      To your continued success!

  7. Great post Karen. There is nothing like having great people working with you. I am looking for an assistant/office manager as my daughter is going back to school now. She really stepped up and did a great job when it didn’t work out with my previous one. Such and important position to get all those time wasting little things done for sure.
    The “devil is in the details” and you can’t underestimate that position.
    I have recently hired a high level consultant to overlook my growth and work out some planning during this stage. Have you ever hired a consultant during your growth periods.

    • Hi Michael:

      Our coaches overlook our growth and help us with planning short term and long term processes. One of them is our business coach, one our CPA who is now our CFO. It’s important to have someone who is much more successful than you look at your business from the 5000 foot level to give guidance you could never be aware that you need.

      Thanks for asking!

  8. Great article Karen,

    I have been working on getting some of my processes and jobs written out and systematized to be able to utilize outside help. Contracting out some stuff and getting VAs for others looks like a good first step.
    As much as I would love an office assistant I am mostly working out of my, very small, home office and I don’t think I could find a place for them to sit. 🙂

  9. Oh my gosh, Shaun – I so get that!! Starting out, I was working out of a very small spare bedroom in our home. When I hired my first assistant, she worked in the same bedroom with me. It was crowded and we were often on phones at the same time – landlines back then (only 7 years ago… mobiles weren’t “the thing” yet!). M-i-s-e-r-a-b-l-e.

    Here’s hoping you have more space soon!


    • karen rittenhouse

      Congratulations, Kelly!

      Remember, most people are too fast to hire and too slow to fire. As tempting as it is to hire the first warm body that “seems” good, vet them and give them a 30-60-90 trial period BEFORE the hiring process is complete.

      Here’s wishing you tremendous success!

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