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Hiring, Training, and Retaining an Administrative Assistant

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Working a luxury business is intense especially when you need to be available 24/7 for luxury clients or their handlers. Many of you need to hire an administrative assistant or virtual assistant (VA) to ensure your productivity and service is where it needs to be. Some of you have an admin or VA already but could use additional help. The question of the day is, “When do I hire my first assistant and when do I add my next one?”

For years, luxury clients have asked me this question. When I was looking for my first administrative hire, many years ago, I was told that when you hit 40 deals you need to hire someone, and then each 40 deals you add, hire another.

In my opinion, in today’s complex real estate world of lengthy contracts, long inspections, and massive amounts of disclosures, marketing programs, and technologies, each client/file takes ten times the amount of time and work that it took in the “old days”.

So, what’s the right answer to when to hire? That really needs to be evaluated on a case-by-case basis. For example, if you are selling 5 million-dollar properties and only sell 20 a year, you will need an assistant. If you want a better quality of life, have the money to hire someone, and are willing to spend the money, you may choose to hire someone early on in your business, or at least to hire a virtual assistant, transaction coordinator, or some other type of part-time help. 

Ultimately, you will need someone, and eventually more than one, if your goals are big. 

In this blog, I want to share a few general thoughts about hiring, training, and retaining an assistant, and then you can view some specific job descriptions and other helpful tools on our site I know you will find helpful.


Where to find them—ask everyone you know, look at your closings, and think about the administrative person that was on the other side of the deal. Should you recruit them for your team? Craigslist ads can yield resumes, and some clients hire an agency to assist them.

If you want to find someone quickly who is qualified, you will need to fire the jets on the hiring process. If you don’t have time to do it yourself, you may want to hire someone to help you.

Something I learned early on in my career is to always be on the lookout for talent. Keep a list of amazing people you meet so that when you need them, you can go grab them.

Once you have some candidates, review the resumes carefully. Look for red flags, job-hopping, too many instances of layoffs, etc. Look at where they live. In my experience, anytime I have hired someone who lived more than 15 

minutes away, it was a mistake. Look at the duties they performed in their last job; if they sat in a cubicle by themselves, working in your busy and chaotic environment likely won’t be a good fit.

Just because they have a real estate license doesn’t ensure they have the administrative skills you need. In my ads I like to say, “real estate license a plus but not required.” You can always pay for them to obtain their license in the future.

Keep in mind people with a heavy marketing background and degrees in graphic design may seem like a good addition to the team; however, they typically do not like detail work, and if you don’t need them primarily for marketing, they probably won’t like the job.

So often we hire the wrong person because we are desperate for help. It’s best to have a process you follow and don’t allow yourself to skip a step.

Your process could include:
  1. Read resumes carefully.
  2. Set up a brief phone interview—talking on the phone is most of what they do with your customers, so if you don’t like how they sound on the phone, why go any further
  3. Have them take a DISC test or whatever personality profiling test you prefer. When you review the test, it may not be clear if they are the right hire, and yet it will give some indication of areas you should discuss with them when you meet. Remember, these tests are a great tool, but they are not 100% accurate. Remind the applicant to take the test when they are not under pressure, complete it in one sitting, and don’t overthink their answers.
  4. Bring them in for the face-to-face interview and trust your gut. You are good with people, so what are your instincts telling you? If they are late or poorly dressed for the interview, why go any further? After all, shouldn’t they be looking to make a great first impression?
  5. Do a skills test. Can they really do all the things they say they can? Some of my clients hire candidates to come in on a Saturday, and they pay them to work on some easy-to-delegate projects to get a sense of how they work and how fast they learn.
  6. If everything is good so far, be sure you are very clear about the job. In fact, be sure to tell them the good, the bad, and the ugly. Don’t hype them on how wonderful you are and how terrific it will be; just tell them the truth. If they are still in, great! Move to the next step.
  7. Take the time to check their references carefully!
  8. Have someone else conduct an additional interview to see what you, in your desperation to hire, might have missed.
  9. Do a final interview and review the job description and schedule. If all is still good, then hire them.
  10. Don’t be cheap. Talent costs money.  It is realistic to pay them less when they are not familiar with the industry, because the training investment is greater. Build in periodic reviews and raises as appropriate. If you are offering incentives and bonuses, short-term bonuses work better for most than an end-of-year bonus.
  11. Have a methodical training plan and training schedule. Understand it always takes longer than you think it will to ramp them up.
  12. Watch them carefully during the first 30 days. Are they attentive and trying hard? Do they seem happy? Are you happy with them? While we must be realistic in the time it takes to train them, if you see major problems early on then cut your losses.


It’s common that when they come in to work on their first day, we dump everything on them. Then we wonder why they quit after only a few weeks.

Map out a training plan and teach them piece-by-piece, starting with what you need their help with most. Block out time in your day to spend a couple of hours in focused training. Turn off your cell and give them 100% of your attention. 

Ask your vendors to assist you in the training process. Have them come in and spend an hour or two with your new hire to explain how they fit into the process and to teach your new person how to work with them effectively.

Also, review your office training calendar and plug them in when you can.

Each month you should do a review of the last 30 days. How do they feel they are progressing? Where are they struggling? And what additional training do they need? It may be necessary to pay for additional classes to boost skills in the areas where they are weak.

How long will it take? This depends on their experience level when you hire them. I would say that for most people 6 months to 1 year is normal.

The more precise and clear the job description and expectations, the faster they will master the job.

Retaining Talent

Let’s face it: it’s not easy to be a great boss. The real estate agents I coach struggle with this. They struggle with delegating, they struggle with patience, and they often have unrealistic expectations.

Staff turnover is one of the biggest drains on resources and a huge cause of stress for most of you. One of the new skills you must work to master is the skill of being a great boss. I found a simple and practical little book years ago called “How to Be a Great Boss” by Jeffery Fox. Read it and highlight the areas you need to improve.

The Things That Drive Our Assistants crazy

  1. They don’t take the time to provide the training I need and are upset if I don’t do it right.
  2. If they do train me, they are on their cell or constantly dealing with other interruptions, which makes it hard for me to learn.
  3. They pile too many things on me in a day and I can’t possibly complete them all.
  4. They don’t take the time to meet with me daily and they don’t provide me with clear priorities for the day, week, or month.
  5. They don’t listen when I offer suggestions or new ideas.
  6. They dump new ideas or projects on me without really understanding how long each will take to implement.
  7. They constantly interrupt me, call me, text me, or email all day long. I can’t get anything done.
  8. They second guess everything I do.
  9. They don’t delegate as much to me as I can handle.
  10. It’s a negative work environment. They are crabby and stressed out, and that stresses me out.
  11. They don’t compliment me, thank me, or reward me when I go above and beyond.
  12. They are cheap. When I deserve a raise, I feel like I need to grovel for it
  13. I don’t know if I have a future or what my career path or opportunities are. They never discuss it with me.
  14. I don’t even know what the team goal is. They never share it with me.
  15. They don’t provide the level of customer service they should, and then I have to deal with the unhappy customers.
  16. When I do something they don’t like, instead of telling me right away so I can correct it they let all the little things build up and then they blast me with them.
  17. If I do make an honest mistake, they blow their top and throw me under the bus to clients and vendors.

Next Steps

Ask yourself, “Do I need an administrative assistant or virtual assistant?” Jot down your areas of pain. What are those gaps in your business where you are leaving money on the table? What hats are you wearing an assistant could wear so you are free to do what you do best—work with luxury clients who have a need to buy or sell real estate.

Next, review your budget and determine if you can afford someone full-time or part-time. Write a clear job description and start following the process I listed above. When you do hire your assistant, ensure they receive adequate training, have clear direction, and that you do not overwhelm them and frustrate them with poor leadership. Turnover will cost you time and money, so patience is key here.

If you need help, talk to us and we will help you. We have the pleasure of working with some of the brightest and best luxury agents in the real estate industry across the nation. We will help you analyze your budget and your needs to determine when you should be making that next hire.

Go to to book your complimentary session.


    1. Author

      Thank you for your comments – we will have Debbie’s team reach out to assist you.

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