How You & Your Assistant Can Work Better Together

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By Kristina Schneider, Executive Assistant


Trust in the workplace is always a difficult, but necessary, part of running a successful practice.  A lot of estate planners, regardless of his or her professional designation, struggle with this concept.  Although just about every single one of these professionals could benefit from having some kind of assistant or other administrative support, they have difficulty in trusting others to take on important tasks.  Unfortunately, estate planners are only ever making any real money if they are either meeting with clients or doing some kind of marketing or networking to develop potential new business.  Therefore, all of those other tasks that take up your day need to be delegated, such as: checking your e-mail, answering the phones, managing your calendar, sending out letters, filing paperwork, even drafting legal documents, etc.  All of these tasks can and, more importantly, should be done by an assistant or paralegal.

Here are some tips, for both the advisor and the assistant, to help build trust between the two and create a symbiotic relationship.

Trust-Building Tips for the Advisor

I will start out with some tips for the advisor to know how he or she may be able to assist in this process of building trust with an assistant.

  1. Train your assistant your way. Since much of the trust issues between advisor and assistant stem from not feeling comfortable that a certain task will get done properly or in a particular manner that you desire, then it’s imperative that you take the time to train your assistant to do things YOUR way. If you like something a particular way or if you want to ensure a certain level of quality, then take the time and effort to show your assistant how you like things to be done. Feel free to even record your trainings and instructions, so that the assistant can reference this if needed. It’ll also save you the time and hassle if you have to train a new assistant in the future. Some examples of this would be if you want your calendar structured a particular way, you have special preferences for flights or hotel stays, you have a policy (whether stated or internal) on how long a client should wait for a response to a call or letter, etc. There’s plenty of things that you could identify that are particular to you, the advisor, and the way you do things; so train your assistant on these things because they could be very different from how the assistant views them or was trained by others in the past.
  2. Be clear and straightforward in your expectations and instructions. Miscommunications may occur frequently in the office, so it is important that you are clear and straightforward in your instructions and what you expect. This is particularly important when you are starting out with a new assistant because they may not be clear what it is that you want or are asking. An example of an unclear and vague instruction: “Please register me for this conference and book my travel.” An example of the same instruction, but done much more detailed and clear: “Please register me for this conference by tomorrow, so that I get the early bird discount on the registration fee. Then, find out when and where I should fly in and fly out and what hotel the event is being held at. At our next meeting, we can discuss some flights you may have found and what the best hotel rate you can find.” See? Not that much more effort and time to give some added details, but with the first instruction, that assistant may not have realized there was some urgency and may have booked travel, not knowing your flight and hotel preferences. Both tasks will, of course, save you a great deal of time. But with the first instruction, you may have paid a lot more than you had intended and been frustrated that the assistant seemingly was “unable to do a task you gave to him/her” – – and that’s simply not the case in this situation.
  3. Give feedback regularly. It’s important that you give your assistant feedback. This feedback should be done on a regular basis and it should be given openly and honestly. Additionally, it should include a balance between both constructive feedback for areas of improvement and positive reinforcement on a job done correctly and as desired. This feedback is the only way for someone to understand you, what your expectations are, what your preferences are, and, eventually, be capable of knowing what you want and need before you even ask. This is often the outcome for advisors and assistants that learn to work together successfully.
  4. Set an example. It’s important, as the boss, to set a good example. It’s not to say that you don’t have the flexibility, as the owner of your own company, to choose the hours you wish to work. For example, if you prefer to work 10am to 5pm each day, that is entirely your prerogative. However, if you designate that your day is to start at 10am, be on time at 10am. If you say you’re going to get something done, meet your deadline. Obviously, stuff comes up and projects and priorities need to be adjusted, but the more that you can set the example of the kind of work ethic you expect of yourself, and therefore your assistant, the better.
  5. Make your assistant a priority. Last, but not least, you should always make your assistant a priority. This person is probably one of the most important employees you will have working for you, because they should be taking on tasks to free you up to be doing the things that are the best and most productive use of your time. If you didn’t have this person, you would be doing these tasks and then you would find yourself working inefficiently, which will ultimately hurt your bottom line. So, it’s important that you make your assistant feel important and like he or she is important to you. You should have a set time on a daily and weekly basis that you devote to your assistant, so that they have a dedicated block of time on your calendar. You should not be barking orders from your office. You should not be checking your e-mail or answering text messages while they’re meeting with you or asking you a question. This means you are giving them your undivided attention, so that you show them that they are a priority to you and that you value their time, as well as the outcome of the work that they do. If you want to sort of listen to them and give them a sort of answer, then expect them to sort of meet your expectations.

Trust-Building Tips for the Assistant

Hopefully, some of the above tips will help advisors in what they need to do to build trust, but sometimes it’s a bit harder to “train” the boss – – especially if he or she isn’t used to working that way. Here are some tips on things that you can do to help build trust with your boss.

  1. Be an avid note-taker. This is often times a personal preference. All throughout school and into my career, I was always a big note-taker. However, as an assistant, my personal preference for writing things down has proven to be an invaluable asset and skill set that has ultimately allowed me to better support my boss and make sure that I don’t miss any details. Not only that, but it gave my boss added reassurance that what I was being instructed to do was important enough for me to write down and that it would not be forgotten or overlooked. (Check out our newsletter article, “7 Tips for Taking Better Notes & Being More Efficient!”, on some tips for better note-taking).
  2. Ask questions. Another tip to help you develop and build more trust with your boss is to ask questions. Some people are not very good at giving instructions and some people are afraid or hesitant to ask questions. Unfortunately, there may be little that you can do to change your boss, so if something is unclear or you need further guidance on how to do your job well, then ask questions. If your boss seems frustrated or flustered when you ask questions, reassure your boss that you’re only trying to do a good job and make sure that you do things correctly. I don’t think any boss would have a problem with that and, hopefully, it will help develop the way the two of you communicate so that he or she provides you enough instruction that you need and you eventually know what he or she wants. Personally, I would prefer to ask too many questions and get it done exactly as desired than to make assumptions and have to re-do it or disappoint my boss.
  3. Give updates on projects and tasks. Giving updates on the projects and tasks that you are assigned is an important part of the process of building trust with your boss. This is particularly important when you’re first starting out. Whether it’s simply telling your boss that you took care of X, are almost done with Y and plan on taking care of Z next week. These updates will help keep your boss in the loop about your progress and even help identify tasks that may need to be bumped in priority. Eventually, you will develop a strong relationship with your boss where he or she may be comfortable with your work and assume you handled everything assigned unless you bring it up. Until you’re at that point, updates and progress reports are a great trust-building technique.
  4. Keep yourself organized. Organization is also a personality preference that varies from person to person. Regardless of whether your boss is organized or not, as an assistant, it’s important that you keep yourself organized. Your boss is giving you client files, legal documents, confidential materials, personal materials, etc. There has to be nothing more frightening for a boss, who is trying to develop trust with you, to walk into your office and find it completely disheveled and chaotic. You may even be one of those people that has an organization to your disorganization, but for the sake of building trust, confidence and reassurance with your boss, you are better off keeping a neat and tidy office, with organized inboxes, piles, shelves, or whatever organization tool you need. This will also make it easier to locate things when requested, as it can be quite embarrassing having your boss standing in your office while you frantically look for something he or she gave you. Don’t let this happen to you! (For some further assistance on how you can better organize yourself, check out our articles entitled, “Five Simple Tips for Being a More Organized Assistant” and “How ‘Electronically’ Organized Are You?”)
  5. Be honest and learn. As a final tip here for you, the assistant, be honest and open to learning. The assistant process is a huge learning process, which means that you may initially make some mistakes. Just be honest about your mistakes and bring them to the attention of your boss as soon as possible so that corrective action may be taken. Then, be sure to acknowledge the “takeaway” you got from making the mistake. Doing this will make your boss feel more comfortable with you, your character and trust-worthiness as a whole, and will bring the two of you closer as boss and assistant, even if there is some initial frustration or stress caused by the mistake. Hang in there and do the best that you can do – – it’s really all that your boss (and anyone else, for that matter) can ask of you.

Whether you’re the boss or the assistant, I hope that the above tips are helpful to your working relationships.  Trust is never an easy thing to build, but if you can understand the power in building more trust in people at the workplace, it’s amazing what it can do.


Pssssst… are you an advisor reading this article?  If so, that’s fine.  While this article is written for staff members, many professionals would benefit from it as well.  But be sure to pass along this article to your assistant.  Click here to forward this article over to your assistant so that he or she can read it and benefit from it, too.  Also, you may wish to encourage your assistant to sign up to receive our monthly newsletter directly so that they can get these helpful tips and articles each month, too.  To sign up your assistant to receive our e-mails, click here.


Kristina Schneider is the current Executive Director of The Ultimate Estate Planner, Inc. She graduated with a Bachelor’s Degree in Business Administration from Pepperdine University in 2004 and was hired right out of college to work for the Law Firm of Kavesh, Minor & Otis, coordinating and facilitating Philip Kavesh’s “Missing Link” Boot Camps while also providing administrative support to Mr. Kavesh as his Executive Assistant for over 7 years. With a combined almost fifteen years of administrative experience and her direct experience working at Mr. Kavesh’s law firm, Kristina has been able to assist numerous estate planning professionals through The Ultimate Estate Planner, Inc. And, equally as important, she has assisted the executive assistants and staff members of many of these estate planning professionals to provide better service and support.

You can reach Kristina at (424) 247-9495 or by e-mail at

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