That's the view of Becky Casstevens-Bellury, Senior Client Success Consultant at BELAY, who says the fix starts on day one: document your preferences, give regular feedback, record how you complete recurring tasks, and set a weekly meeting cadence so your assistant learns how you work before a transition ever happens.
In this episode of The Perfect RIA, Matthew Jarvis talks with Becky about how advisors can start an executive assistant relationship successfully, communicate preferences, handle friction, and prepare for the reality that turnover eventually happens. Becky has been with BELAY since 2021 and has more than five years of experience as a Senior Client Success Consultant. Before joining BELAY, she was an educator, which she says is part of why she enjoys teaching clients how to get the most from their Executive Assistants.
Becky's advice is to treat turnover as something that can happen in any human relationship or business. Preparation starts with documented preferences, secure access, recorded processes, regular meetings, and ongoing feedback.
Matthew’s experience reinforces that point. He has worked with multiple EAs over the years, including situations where turnover happened because someone wasn't the right fit, someone's contract was bought out so they could work full-time, or life simply happened.
The practical takeaway is to build the relationship so that its most important knowledge doesn't live exclusively in one person's head. When preferences and processes are documented, a new assistant has a much clearer starting point.
Becky says advisors need to identify their own preferences before they can effectively train an assistant. A BELAY assistant may already have experience managing email, calendars, travel, or other tasks, but that experience comes from working with other people. The assistant still needs to learn how you want those tasks handled.
Becky recommends treating feedback as a muscle and building it into weekly one-on-ones. Instead of only asking what's going well, she likes asking, “What could be even better?” That question gives the assistant specific information about how to better match the advisor's preferences.
Matthew provides a good example of why these preferences matter. He says he doesn't like frequent communication and prefers to receive most updates during his weekly meeting. He only wants to be contacted outside that meeting for a “911 emergency,” such as a canceled flight. Other clients, Becky explains, may want constant updates throughout the day. Neither approach is inherently right or wrong.
The same principle applies to details that advisors may not realize are preferences until someone gets them wrong. Becky points to calendar layouts, meeting buffers, color coordination, email folders, inbox zero, and whether emails should remain unread as examples. Jarvis also explains that he prefers flights to be blocked for their entire duration because of time-zone issues.
Matthew says his preferences have also become clearer through experience. One week, he had 27 meetings across three companies and realized that level of meeting volume was beyond his capacity. His assistant, Anne, can use that information to help him stay below 20 meetings by asking which seven meetings can be cut. Jarvis also discovered that flights arriving after 9 p.m. leave him too tired the next day, another preference that became useful once he communicated it.
Becky says documentation makes turnover easier because the next assistant doesn't have to start from zero. BELAY's Client Guidebook gives new EAs a starting list of questions about preferences, including details such as calendar buffers and travel.
Matthew points out that this matters even when an advisor has worked with the same employee for years. He has worked with Colleen, his office manager at his practice, for about 15 years. After that much time together, Colleen knows his preferences “inside out.” But those preferences haven't necessarily been recorded, which could create a significant obstacle if Colleen eventually retires or moves on.
The lesson from Matthew and Becky is simple: don't rely on institutional memory to preserve personal preferences. If only one person knows how you want your travel booked, calendar arranged, or email organized, turnover puts that knowledge at risk.
Becky recommends setting up a password management service from the beginning. She says securely sharing passwords through a password manager makes transitions easier because advisors don't have to change every password when an assistant leaves.
She also recommends recording recurring processes with tools such as Loom. Instead of creating a polished training video, Matthew demonstrates the kind of “brain dump” Becky recommends. An advisor can record themselves completing a task while explaining every detail that comes to mind.
Matthew gives travel booking as an example. He might explain that he primarily flies Alaska Airlines, followed by Delta or United, then walk through the entire booking process. He can include details such as his known traveler number and frequent-flyer information, including where those details are stored.
Becky says advisors shouldn't overthink these recordings or try to create a script. The goal is to capture the process as the advisor actually performs it. A simple recording can then become a one-page resource such as “How to Book Matt's Travel,” putting the next assistant “90% of the way there.”
Matthew also recommends giving an assistant access to most systems while maintaining appropriate boundaries around sensitive information. For example, he doesn't give his EA access to his bank accounts. Becky agrees that boundaries can vary by task and service. For BELAY bookkeepers, she says the company recommends read-only access to bank accounts.
Becky strongly recommends weekly one-on-one meetings, particularly during the first year of the relationship. She says that cadence may eventually shift to every other week, but she recommends weekly meetings until roughly the one-year mark.
Those meetings give the advisor and assistant a place to exchange feedback, address questions, and identify what matters most during the coming week. Becky says the more hours an assistant works, the more she recommends meeting, potentially more than once per week.
Matthew has developed a specific agenda that works for him. He starts by reviewing travel for the next 30, 60, and 90 days because travel has deadlines and is mission-critical. Then his EA reviews the items on her list. Matthew saves his own items for the end because he knows his attention span drops after he has gone through his list.
Becky says Matthew’s approach demonstrates the larger point: there is no single correct meeting agenda. Some advisors may want to discuss travel first. Others may save it for the end or handle it asynchronously. The important part is finding a cadence and structure that actually works for the relationship.
Becky says advisors should first determine whether a problem is a normal onboarding issue, a communication problem, or a genuine fit issue. She describes work-style compatibility as neutral. “Not everybody's work style is going to connect with every other person's work style,” she says.
For BELAY clients, Becky says the Client Success Consultant can help identify what is causing the friction and determine whether the relationship needs a communication adjustment or a different solution.
Matthew gives an example from his coaching program. An advisor was concerned about a small issue with his BELAY EA but hadn't contacted his CSC. Matthew contacted Karen, who helped get the issue addressed, and the problem was resolved.
Becky also describes her role as hearing from both sides of the relationship. She works with the client and contractor to understand how information is being received. Sometimes, she says, people simply need to be heard. Other times, she asks the client and contractor to talk through the issue and then follows up two weeks later.
That follow-up creates accountability. Becky says she wants clients to know how quickly they expect an issue to improve, while also making clear that they won't simply sit with an unresolved problem indefinitely.
Becky’s central communication principle is that “feedback is a muscle.” Advisors build that muscle by giving feedback consistently instead of waiting until a major problem appears.
Matthew asks whether positive feedback counts as exercising that muscle. He gives an example of telling Anne, “I really appreciated how you handled those 57 requests that came in this week. Great job on that.”
Becky says positive feedback can count when it's reflective. The point is to explain what worked and why it mattered, rather than giving shallow compliments simply to soften criticism.
Matthew also emphasizes that assistants are people, not AI agents. They have good days, bad days, and days when they question whether they're doing a good job. He says recognizing good work helps build “relationship capital,” which gives the relationship more room when constructive feedback is eventually necessary.
For advisors who struggle with difficult conversations, Matthew’s advice is direct: “Don't let that keep going.” Either develop the feedback muscle yourself or find someone who can help manage those conversations.
Becky says a useful threshold for delegation is whether someone else can perform a task at 70% of the advisor's level. The initial result may only be 70%, but regular feedback can improve the work over time.
Matthew uses bookkeeping as an example. An advisor who is preparing for an audit while trying to clean up a year's worth of books may be taking on a task that is far more expensive in time and risk than the cost of getting help.
Matthew describes an advisor who was in the middle of an audit with messy books and facing a potential $100,000 penalty. He argues that the cost of bringing in a bookkeeper would be small compared with that potential exposure.
Delegation also doesn't have to mean giving away 100% of the task. Jarvis says that after his bookkeeper prepares his reports, he still reviews them and makes corrections. Instead of spending hours going through a year's worth of credit-card statements, he can spend about 20 minutes reviewing the reports and moving a few categories.
Becky agrees: “Delegating does not mean it has to be full delegation.”
For advisors, that distinction matters. The goal is to remove work that doesn't require the advisor's full attention while preserving the decisions and oversight that do.
How do you prepare for an executive assistant leaving?
Set up a password manager from day one, record recurring processes with a tool like Loom, and keep preferences documented in a shared resource such as BELAY's Client Guidebook. That way a new assistant doesn't start from zero.
How often should you meet with your executive assistant?
Weekly, especially in the first year. Becky recommends shifting to every other week only after roughly the one-year mark, and meeting more often if the assistant works more hours.
What should you delegate to an assistant?
Anything someone else can do at 70% of your own level to start. Regular feedback brings that number up over time, and delegating doesn't have to mean full delegation. Advisors can still review and correct the final output.
How do you handle friction with an executive assistant?
First figure out whether it's a normal onboarding issue, a communication gap, or a genuine fit problem. Work-style mismatches aren't a red flag on their own. For BELAY clients, a Client Success Consultant can help sort out which one it is.