Obviously, no one can actually read our minds.  What we’re all really looking for is the kind of assistant who can anticipate our needs and fill them before we get a chance to ask.  But why is that so hard to find?  Is it some special, nebulous skill that only a few people possess?

The answer is “no.”  People with this potential are everywhere.  If you have a good recruiting and hiring process, but you’ve still been repeatedly disappointed by assistants, then you may actually be the problem.  That’s good news because it’s a problem you can solve!

The path to finding a fabulous assistant begins with changing your mindset and expectations in two vital ways:

  1. Don’t expect it to happen overnight.
  2. Don’t expect it to happen with no effort from you.

That second item is critical.  Too many of us think we’ve done our part to get a great assistant just by making a good hire.  But our work isn’t done yet!  The relationship between us and our assistant is just like any other relationship; it takes time and effort to get what we want out of it.  The work you put in with your assistant during the onboarding and training process can make or break your chances of success.

“Junk in, junk out.”

When I tell people what I do, they often want to tell me how good or how bad their assistant is.  Too often, I hear leaders complain about an assistant who’s just good enough not to fire, but not quite good enough to be truly helpful.  “She just doesn’t think like I need her to,” they say.  My question in reply is, “How much time do you spend with her?”.  The answer is usually either, “None” or “Enough to let her know what I need her to do.”  And therein lies the problem.

There’s a saying in tech circles about data: “Junk in, junk out.”  If you put bad information into a database, you’ll get bad information out of it.  The same principle applies with you and your assistant.  If you put minimal information in, you’ll get minimal results out.

Setting your assistant – and yourself – up for success

To get an assistant who thinks the way you want, you have to invest time in teaching and sharing information up front.  Here are three key practices for doing it:

1. Meet with your assistant regularly.

Block off a dedicated time to meet with your assistant to go over what he or she needs to know.  In the first week or so, you should have a brief meeting every day.  This may seem counter-productive; after all, you hired an assistant to save your time, not take up more of it.  But realize that an assistant who just knows what to do and does it can only be a person who really knows you and your business.

In these meetings, always talk about what he/she did that worked well and WHY it worked.  Likewise, if something didn’t meet your expectations, talk about WHY.  Every time you share a “why”, you are teaching your assistant how you think, which is key to developing the ability to anticipate your needs.

If you realize that you didn’t get what you expected on a task because you didn’t share all the information you should have, take responsibility for it.  This will build the trust your assistant must have in you to provide the support you need.

2. Allow your assistant to ask questions.

There are few things more frustrating to an assistant than a boss who spouts assignments in a hurry and is impatient with questions.  Don’t overestimate your own communication skills.  Realize that just because something is crystal-clear in your mind, doesn’t mean it’s so obvious to anyone else that no further explanation is needed.

3. Answer questions generously.

Share everything you can think of related to the question, perhaps providing more detail than you think is necessary.  Don’t fear information overload!  A good assistant is all about the details; the more the better!  Context is everything.  The more context you can give, the better and faster your assistant will be able to understand you and how you think.

Short-term pain, long-term gain

While it may be inconvenient to block off 15 minutes or a half-hour every day to meet with your new assistant, the payoff will be well worth it.  The better you follow the advice in this article, the faster you will start reaping the rewards.


Rachael HodoRachael Hodo is the Founder of ProAdmin Solutions, LLC, a VA firm that specializes in general administration, content marketing, and association management services.  Rachael and her team work by referral only.  You can reach her on LinkedIn at linkedin.com/in/rachaelhodo.