Too many founders are overwhelmed—not because they’re doing the wrong things, but because they’re doing too many things alone. In this episode, we unpack how hiring (and properly using) an Executive Assistant can transform your time, focus, and impact. You’ll learn when to bring on an EA, what tasks to delegate, and how to set up the relationship for long-term success. Whether you’re considering your first assistant or trying to make better use of one you already have, this episode will show you how to turn an EA into your most valuable productivity tool.
TRANSCRIPT
Greg Alexander: Hey, everybody. This is Greg Alexander, the host of the ProServ Podcast. This is a show for those that are in the expertise business. So if you market, sell, and deliver expertise in some version of the billable hour, this is for you. We try to help you make more money, make scaling easier, and make an exit achievable.
Greg Alexander: On today’s show, we’re going to talk about how a founder can contribute more to their firm by leveraging the use of an assistant. That might be an executive assistant, a virtual assistant, or a personal assistant. The challenge that founders of boutique pro serve firms have is time. Very often, they become what we call the founder bottleneck, meaning they constrain the growth of the firm because everything runs through them. If you partner with a fantastic assistant, you can prevent the founder bottleneck from limiting the growth of your firm.
Greg Alexander: We’ve got a member with us today. His name is Kyle Walbrun, and Kyle runs a firm that specializes in virtual assistants. So, Kyle, for those who don’t know who you are, would you please introduce yourself and your firm?
Kyle Walbrun: Yeah, thanks so much, Greg, for having me on. I’m Kyle, and I am the founder and visionary of EfficientAide. We are an assistant company, and really what we do is we’re in the business of buying back time. We solve that in a variety of ways—ultimately by providing virtual assistants, as Greg mentioned. We also provide training for folks that already have an assistant and want to up-level that experience. We can also help on the recruiting side if you’re looking to hire more of an in-person, full-time executive assistant.
Kyle Walbrun: As Greg mentioned, we’re really in the business of buying back time and eliminating worry for business leaders so they can focus on tasks that are the highest and best use of their time.
Greg Alexander: Okay, fantastic. I’ve prepared a few questions here that hopefully represent the information needs of our community. First and foremost, Kyle, I think our community has an outdated and obsolete understanding of what an assistant can do for them. I think it’s a legacy understanding, and I’d like to update that. So, if you would, tell us—what is an assistant capable of these days?
Kyle Walbrun: That’s a great question, Greg. We do a lot of education around this topic. There’s this old “Mad Men” mentality—someone sitting at a front desk pushing papers—and that just isn’t the case anymore. A well-trained executive assistant or virtual assistant is not only there to check tasks, do data entry, check your email, and schedule your appointments, but they should also be managing your well-being, being the gatekeeper of your time, and contributing to more strategic initiatives.
Kyle Walbrun: It’s an outdated model where you had to say, “Assistant, here’s what I want done, how I want it done, and when I need it done,” and then double-check to make sure it’s done. In today’s age, with technology and the high caliber of assistants available, it’s now, “Assistant, here’s my problem. Here’s the goal I’m trying to achieve. What can you do to help me solve that or reach it?” In short, Greg, it’s a much more strategic partnership rather than simply checking off tasks or pushing papers.
Greg Alexander: Yeah, that’s a great updated definition.
Greg Alexander: You know, I will say that we’re living in a digital era, and it’s coming like a freight train, especially as we add artificial intelligence to it. Our members are founders, which means they are world-class bootstrappers. They get a lot done with very little. They’re hesitant to spend money on this because they view it as an expense. So how do you overcome the expense objection?
Kyle Walbrun: Yeah, you know, Greg, in a couple of different ways. I’ll tackle that question first. It goes back to what most leaders know as the Pareto Principle, right? Eighty percent of your outcomes come from twenty percent of your efforts. Time is your most valuable asset. I always tell founders: the reason you’re successful is not because you’re great at checking email or managing your calendar — those tasks fall into the 80% that don’t drive the business forward. The true cost isn’t in hiring an assistant. The true cost is all the opportunities you’re missing by not having a high-caliber assistant. Every minute spent checking your email, booking travel, or scheduling appointments is time not spent nurturing relationships, closing deals, or doing the high-impact work that made you successful in the first place.
Kyle Walbrun: I also like to challenge founders and leaders to consider their hourly rate. Most are worth $300, $400, or even $500+ per hour. So when you put it in that context and think of ROI in dollar terms, every hour spent on a task that could be effectively delegated is money lost. Those are two different ways I typically address that question, Greg.
Greg Alexander: Okay, my next question is: for those enlightened founders who understand that hiring an assistant is the way to go and are ready to invest—but still want to spend as little as possible—they might outsource the job to Vietnam or the Philippines. And then they have a terrible experience. They lump the entire idea into that failure and say, “Well, this didn’t work for me.” I chuckle when I hear that, because as much as these founders think they’re unique, they’re not. Assistants are working for founders everywhere. So if it’s not working for you, maybe the problem is you. I have a hypothesis and I’d like your opinion: when it doesn’t work out, it’s usually not the assistant—it’s because the founder doesn’t know how to leverage the assistant correctly. Do you agree or disagree, and why?
Kyle Walbrun: Absolutely agree, but I’ll add a caveat. When I talk about executive assistants, I’m assuming we’re discussing someone with proven experience working with founders. I’ve seen cases where a founder goes the budget route, but still hires a high-caliber assistant—and it works. But that only happens if the founder invests time into that assistant. What I see more commonly is that founders bring someone on, give them no time, no resources, and no context, and then expect immediate results. After a week or two, when it’s not working, they say, “Why aren’t you controlling my life yet?” and jump ship. That’s not setting the assistant up for success.
Kyle Walbrun: It’s the classic “help me help you” scenario. You have to invest in the assistant. The key is finding someone who already has experience working with founders. They know how to manage complex schedules. They know how to use bullet points instead of paragraphs, so when they have your limited attention, it’s used effectively. That builds trust. If founders give a little time and truly buy in, they’ll see results. But more often than not, they can’t let go of the vine, and that holds everything back.
Greg Alexander: I’ll use myself as a case study. Forgive me if I’m a bit long-winded, but I want to put this out there. I’m a serial founder and entrepreneur, and I could not have accomplished what I have without my assistant, Alana Newell. When I hired Alana, the first thing she said was, “Greg, I need you to define what a perfect day looks like.” We talked it through in detail. Now, every day gets graded—A, B, C, D, or F. An A means we achieved 80–100% of a perfect day, which for me means spending time with members and reviewing my investments. B is 60–80%, C is 40–60%, D is 20–40%, and F is anything below 20%.
Greg Alexander: My first meeting every week is with Alana. We look at the calendar and ask, “Are we going to have a good week or a bad week?” At the end of the week, we average out the five weekdays to evaluate. Then we look 30 days ahead for landmines—those calendar items that will drive me crazy—and she proactively starts editing them out. Because of this methodical and regimented approach, my calendar is never overbooked. My inbox is empty.
Greg Alexander: The end of every day. Just let that sink in for a moment. Listen. I have a zero inbox every day, and my to-do list is short. I am completely dialed in because I have an assistant—an accountability partner—who does not let me off the hook. Now, I had to be vulnerable and have this conversation, and this supports what Kyle was saying: we’ve got to invest in your system to be successful. This is not just something to pencil in and dump a bunch of crap on. Because if that is your approach to an assistant, all you’re going to do is create more noise in your life. Your activity will expand to consume the time available. You’ve got to be really intentional about it.
Greg Alexander: My last question for you regarding this—actually, I have two more. I’ve found that when I was an executive at a Fortune 500 company, I had an executive assistant, and that was appropriate because I was an executive. I’m a founder now, so I don’t have an executive assistant. I have a personal assistant, because my personal life and business life are so intertwined. Founders don’t have a black-and-white separation between personal and work life. My assistant would not be as successful if she didn’t manage both aspects. Is that a best practice, in your opinion? Do you recommend founders have personal assistants, or do you think it’s better to have an executive assistant?
Kyle Walbrun: Yeah, great question, Greg, and that’s a really common scenario. Real quick, before I address that question, I want to go back to your perfect day analogy, because I know some founders are thinking, “Great, Greg knew what that perfect day looked like—I don’t know what that looks like for me.” When you work with a high-caliber assistant, they should be able to share experiences of what other perfect days look like and be a thought partner during that process. I was recently talking with a client whose mindset around a perfect day or delegation was framed by what they thought they could get, not what they truly deserved. That’s a big difference. Your perfect day should reflect what you deserve—not “Well, I have someone offshore, and this is all I think I can get from them.” Think about what you truly deserve and source someone who can help you achieve that, like Greg described. Many leaders come to me saying, “Kyle, I don’t know what I don’t know. Tell me what this could look like.”
Kyle Walbrun: Now, going back to your question about personal versus executive assistants—absolutely. As a founder, personal and professional lives often blur. Your assistant should be in the business of buying back your time and eliminating worry, whether on the personal or professional side. It’s common for assistants to see your business emails as well as your kids’ soccer schedules or PTO calendars. These are often intertwined. Having one person manage both sides is not only effective but allows that assistant to build rapport outside of a purely professional scope.
Greg Alexander: One thing you mentioned that I thought was interesting—when I prepped for this, I didn’t realize that part of your practice is training assistants. I thought you were just placing them. So for those listening, they probably fall into two groups: either they don’t have an assistant—hopefully, this call is a wake-up for them—or they do, but maybe they’re not thrilled with the results. Tell us a bit about how you work with clients who already have an assistant but want that relationship to be more productive.
Kyle Walbrun: Yeah, thanks for asking that, Greg. We do one-on-one training, and not just for the assistant. Often, it’s as much about training the founder or leader. Common areas we address include setting up a proper meeting cadence—this is critical. Most founders talk to their assistant ad hoc, and some haven’t spoken with them in weeks. That makes it tough to build rapport. As Greg mentioned, he starts his week with a meeting with his assistant. I’d bet that if that meeting didn’t happen, things would get a little loose.
Kyle Walbrun: Another common area is task management. What is the assistant working on? What’s in progress? Where are they stuck? And equally important: what is the founder working on, and how can the assistant provide accountability? That includes nudging the founder: “Hey Greg, you have a deadline Friday—block time on Thursday to get it done.” A third common area is performance reviews. Founders usually have reviews for everyone else, but assistants—especially if they’re fractional or virtual—often get overlooked. Make sure there’s a review cadence, whether monthly or quarterly. Discuss what’s working, what’s not, and what’s next. This step is frequently skipped and leads to issues festering under the surface, and suddenly, you’re thinking it’s not working—when you never gave that feedback in the first place. Those are three things we always cover in our training.
Greg Alexander: That’s awesome. I appreciate you sharing that. Kyle, we’re going to leave it here for now—we’ve got much more to talk about, but I want to save some things for the private member Q&A you’ll host in the upcoming week. On behalf of the community, we’re very lucky to have you, and thank you for your contribution to the Collective this week.
Kyle Walbrun: Thanks a lot, Greg. Really appreciate you having me on.
Greg Alexander: All right, a couple of calls to action for those listening. If you’re a member of Collective 54 and want to learn how to remove the founder bottleneck by having a great partner known as an assistant, please attend the Friday role model session—Kyle will be our role model, and you can ask him your questions directly. If you’re not a member and want to become one, go to collective54.com and fill out an application. Someone will get in touch with you. Until the next show, I wish you all the best of luck as you try to grow, scale, and someday exit your firm.
Note: This transcript was generated by Zoom.