7: Frustrated with Your Executive Assistant? The Fix Might Be Simpler Than You Think

Are you feeling like you still have to do everything—even with an assistant? 

Do you find yourself waiting hours for a response, chasing down unfinished tasks, or wondering if your EA is truly the right fit? 

You’re not alone. 

In this episode of Scale Smart, Stay Grounded, I dive into the most common frustrations founders have with their assistants and, more importantly, how to fix them.

I break down:

✅ The #1 reason most founder-assistant relationships fail (hint: it’s not a skill issue—it’s a communication issue)
✅ How to set crystal-clear expectations from the start to avoid misalignment
✅ Why texting and emailing your assistant is sabotaging your productivity (and what to use instead)
✅ The simple 30-minute weekly meeting that solves 90% of assistant-related frustrations
✅ When it’s time to hire a Lifestyle Manager to streamline both your business and personal life

If you’re feeling overwhelmed, stuck in the weeds, or just frustrated with your level of support—this episode will help you pinpoint what’s missing and take action to fix it.

Tune in now and learn how to create a truly efficient, aligned, and proactive support system that helps you scale without stress! 

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Transcript

Hello friends.

Over the past six months, I've had conversations with two serial entrepreneurs who share their frustrations about their current assistants. And here are just a few of the concerns they voiced. 

"I still feel like I have to do everything."

"She isn't available when I need her."

"She doesn't respond in a timely manner." 

"I feel like her other stream of income is taking priority."

 "I feel like I'm being taken advantage of!"

"Sometimes I call and she doesn't call me back for hours." 

"I have to ask someone else to help me with things my assistant should be handling."

"I'm starting to wonder if the role has outgrown her."

"When I ask about invoices that are weeks old, she responds...I was just about to work on that." 

"I want to replace her, but we've been together so long, I don't want to make it feel weird."

"Maybe I should hire another assistant to help her." 

"She isn't proactive. I have to tell her what to do." 

I love when serial entrepreneurs feel comfortable enough to vent to me.

As both an entrepreneur and a fractional executive assistant and lifestyle manager, I approach these conversations from both perspectives. That means I'm a neutral party. 

I understand the expectations of a founder and the realities of an executive assistant. 

In these conversations, I asked both founders a few key questions, and together we realized that their communication with their assistants lacked clarity.

They hadn't defined what success looked like in the role. Clear communication, including explicitly outlining your standard of excellence, is crucial. 

Think about it. Two people can eat the same meal, but one might say it's delicious, while the other complains it's too salty. The same thing happens in work relationships. What you expect is great performance may not be as obvious to your assistant until you spell it out.

So from the very start of the working relationship, you need to establish two things, your preferred work hours, so your executive assistant knows when you expect them to be available, as well as your preferred response time. 

Is it 30 minutes, one hour, two hours? Set that expectation up early. For both of these entrepreneurs, their primary communication channels were text and email, which I explained to them is a huge mistake. 

And here's why.

It creates more emails, which both you and your executive assistant are trying to reduce, and it also opens you up for a security issue. 

Instead, I advise them to switch to Slack and then to integrate it into their Google workspace for easy file sharing. 

Another issue that we addressed is neither of them had a structured weekly check-in with their assistant. Instead, they relied on random calls throughout the week to discuss various tasks. This lack of structure was causing unnecessary frustration. 

And here's a quick fix. 

Set up a 30-minute recurring weekly meeting. This alone will solve most of your frustrations. During your weekly meeting, your executive assistant should provide an update on last week's task, outline what's on their radar for this week, and also ask clarifying questions about upcoming projects.

This is also the perfect time to address any outstanding issues without feeling like a micromanager. For example, if invoices haven't been followed up on, you could bring it up in this setting and reinforce the expectation without feeling like a jerk.

Likewise, if your executive assistant is starting to feel overwhelmed or like the role has grown beyond their capacity, this is the space to discuss it openly. 

And before we move on, let me share with you my pro tip. Your executive assistant should create the weekly agenda, not you. If you see she's coming to the meetings each week frazzled, ask her to send you the agenda on Friday afternoon by 3 p.m. This is gonna serve as a gentle nudge to help her stay organized.

If you're constantly getting pulled into administrative duties or details due to dissatisfaction with your assistant, I have three things I want you to ask yourself. Have I set clear expectations? Am I communicating effectively? And do we have a structured meeting cadence? Addressing these areas can dramatically improve your working relationship. Now, once your business operations start to run smoothly, it's time to take a look at your personal life.

If things are chaotic outside of work, that stress will inevitably spill over into work. And guess who's going to be the first person to notice? That's right, your executive assistant. Now, some executive assistants handle both business and personal travel, and a few will even go beyond that and schedule things like haircuts and nail appointments, but most assistants don't go beyond that. If you need comprehensive support in your personal life, you really need a lifestyle manager.

As a lifestyle manager over the past four years, I've helped clients with a variety of tasks like home remodel coordination, where I act as a liaison with contractors and local permitting municipalities. 

I schedule specialized travel arrangements for family members who need extra accommodations, like an unaccompanied minor or a family member with mobility challenges. 

Event coordination is also something I handle, where I work directly with an event planner of my client's choice so that the client doesn't have to be the main point of contact. I step into that role and I also make sure that invoices are paid throughout that process so that there is no bottleneck up until the date of the event.

Vehicle maintenance is another thing that helps to relieve stress within your life coordinating pickup and drop up of loaner cars for routine services such as brakes as well as oil changes so there's no friction. 

What about your vehicle registration and your driver's license is it up to date? Well I've also handled those renewals for clients and the logistics behind it.

Scheduling gifts that are well known in advance as well as last minute helps to take the mental load off of remembering special dates. And once I know that something is of importance, if it comes up last minute, I make sure to make a recurring note on my end so that next year my client is well prepared.

I also handle dinner and event reservations. 

Out of state medical or dental visits are no problem. I connect with the medical provider and schedule the appointment and from there I coordinate flights, hotel, and rental cars if they're needed. All without it being a hassle to the client.

All friction in your personal life, a lifestyle manager can take it off your plate. 

In summary, if you're feeling frustrated with your current level of support, take a step back and evaluate your communication style. 

Are your expectations clearly defined? 

Do you have structured meetings? 

Are you using the right tools for collaboration? 

Making these small shifts will not only strengthen your relationship with your assistant, but it'll also show you how to scale your business without feeling like you have to do everything yourself. 

Okay, that's all for today. If this episode resonated with you, don't forget to share it with another founder who could use these same insights.

I really hope today's episode offered value. If you feel like you could use help with this process, I would be honored to have a conversation with you. I offer free discovery calls where we take a look at what is currently causing you the most stress administratively in your business and life. And from there, we'll come up with a customized, tailored solution for you. 

I enjoy working with post Series A founders, as well as serial entrepreneurs who are running businesses that are earning seven to eight figures annually.

I currently have the bandwidth to onboard one client this quarter. So if you're interested in working with me, I encourage you to book a discovery call. It's a low pressure conversation for the two of us to get to know each other better and to ascertain if we would be a good fit. You can go to www.daniellane.co to book a call or you can click the link in the show notes.

I'm also available on LinkedIn should you have any questions that you would like to ask. I'm active daily on that platform. 

And before we leave each other, I have one more resource for you. Do you need to delegate but are hesitant?

Please check out my free guide down in the show notes. It's entitled, Unlock 10 Plus Extra Hours a Week with Strategic Delegation. It's a quick read, loaded with actionable tips.