What Kind Of Assistant Is Best For You? With Steven Neuner And Ryan Cassin

March 23, 2023

Shannon Waller

Welcome back to all things assistants! In episode two of this six-part series, Shannon Waller and Superpowers partners Steven Neuner and Ryan Cassin explored why having an assistant is crucial for any entrepreneur looking to improve their productivity, profitability, and overall quality of life. In this episode, they discuss the difference between a virtual assistant, an executive assistant, and a virtual executive assistant, and share a simple formula for deciding which one is a right fit for you and your goals. Listen in to learn more!

Show Notes:

It’s important to recognize that not everyone is suited to work with entrepreneurs. They’re very growth-oriented and freedom-driven, and the right assistant is someone who wants to grow with you and can support that freedom.
A good assistant should also have a natural desire to be helpful and proactive.
Virtual is often better. In-person assistants can quickly become a shared resource or can become a crutch for the entrepreneur to procrastinate.
Whether in-person or virtual, your executive assistant (EA) is meant to help you get out of the office so you no longer need to have a physical attachment to an office or space.
Regardless of where your EA lives in relation to you, you can still build a system of collaboration and communication.
When everything lives in a virtual space, you’re also freed up to do your job, which is building relationships outside of the office.
An EA should help with other things as well, not just with work.
Your business is just one piece of you, and you may need support with other things like personal projects and even how you plan and execute your Free Days^™.
The difference between a virtual assistant and an executive assistant has nothing to do with in-person versus online.
Instead, you can think of an assistant’s function in terms of the 3 Ps:
Projects: If you have a specific project that needs to be completed, hire an assistant. Sites like Fiverr or Upwork are great for this.
Processes: This is where virtual assistants shine. They’re not improving or innovating, but rather offering consistent execution on a known, defined, step-by-step process.
Proactive: This is the definition of an executive assistant, and where you get the most growth and freedom. It’s the highest leverage relationship available to you. In the simplest terms, an EA is a personal integrator for your business and life.
More specifically, an EA is someone who knows you, understands you, and anticipates you, which means they have authority to act on your behalf. They should be the leader in the relationship, essentially managing you, even though you’re still the boss.
A great EA can also help you maintain and build personal relationships by updating you on what’s happening in your loved ones’ lives and briefing you on important personal details before meeting with someone.
Important tip: Find your complement, not your copy. You may get along best with people who think and act like you, but an assistant is there to fill in the gaps.
You have to really know yourself first—what your skills are, how you operate, where your energy goes (and/or should be going).

Resources:

Superpowers

Unique Ability^®

CliftonStrengths^®

The Gap And The Gain by Dan Sullivan and Ben Hardy

The Kolbe A^™ Index

PRINT^®: The Why Of You

The 4 C’s Formula by Dan Sullivan

Entrepreneurial Operating System (EOS)

Episode Transcript:

Shannon Waller: Hi, today I'm back with Ryan Cassin and Steven Neuner of Superpowers HQ, to talk about all things assistants. And I'm so excited because this is such a valuable strategic relationship between you and the person who supports you, but it's just rife with confusion. So today what we're going to do is dive into what kind of assistant do you need, what level of support? And one of the things I really like that Ryan outlines, as you'll hear, is all about projects, process, and how proactive does that person need to be. So stay tuned to learn more. I know you'll love it.

Hi, Shannon Waller here and welcome to Team Success. Today is episode two, which I'm very excited about, with my dear friends Ryan and Steven from Superpowers, and if you want to look them up, it's Superpowershq.com, and we are talking about all things assistants. And so last time we really talked about the mindset in terms of what to expect, why you would want one, what maybe mental hurdles you might have to get over, and just the incredible asset and usefulness, both for you and how you can actually elevate to be your best self by having that incredible partnership with an executive assistant. So today what we're going to do is dive into the different types of assistants there are, so let's get into some of the nitty-gritty of the difference between a virtual assistant, an executive assistant, virtual executive assistant.

And it's interesting, I was thinking about this getting ready for today and, put it this way, even if you have had an in-person assistant before, they're going to be virtual now, it's just the way it is, if not all the time, then at least some of the time, if only because you're so darn mobile, because we're all over the place, we're at conferences and all the rest of it. So the whole virtual thing I think is actually kind of funny because we pretty much all are now, so I think that's a fun thing to talk about. But I do think that communication changes, so I think we can get a few nuances into that. And then also kind of who you need to be and how you need to be, be a great person to work with and to, as I talked about last time, earn the support and be that great person that someone else wants to contribute their awesome talents to. Anything else? No, I've sort of jumped, I don't want to steamroll this.

So Ryan and Steven, just talk about a little bit for you, just to introduce Superpowers, we didn't even do that a lot last time. So tell me a little bit more about Superpowers and your reason for being, Ryan?

Ryan Cassin: Yeah, Superpowers’ mission is to help successful entrepreneurs achieve new levels of freedom and growth. And we think that freedom and growth, that getting both of those simultaneously, and I love talking to Coach folks because Dan has the Four Freedoms—time, money, purpose, and relationships. And so every time we're talking to folks who are a part of the Coach community, there's the shared vocabulary about what freedom means, and I find it to be such a rich conversation. But freedom and growth, because oftentimes I find that entrepreneurs are on this teeter-totter between prioritizing freedom but sacrificing growth or then being in a different season and prioritizing growth but sacrificing freedom to do it. And so not only does that create all sorts of whiplash in the business and make it difficult for your team members, it also creates whiplash in your personal life. It makes it really hard for you to enjoy the fruits of your labor as an entrepreneur.

So freedom and growth, and we think that one of the ways to do that is to have a really high leverage executive assistant on your team. And so what Superpowers does is it recruits, trains, and manages high leverage executive assistants for our entrepreneurial clients.

Shannon Waller: That is very clearly easy to understand. Thank you. Steven, what would you like to add to that?

Steven Neuner: What is there to add?

Shannon Waller: I know.

Steven Neuner: Well done Mr. Cassin.

Shannon Waller: Yep.

Steven Neuner: What I would say though is we come from a unique context of having both not just built businesses, but firsthand experience the difference that this role can make, done well, in the lives of our businesses and personally. And I think that that really is significant, it really, really makes it more of a passion project more than anything, for us.

Shannon Waller: I love it. And I think that's why the three of us got so excited about this idea for the series, is because it's something that is such a passion. I certainly have had my own strategic assistants and I'm blessed with that, but also I created the Strategic Assistant Program many, many, many moons ago, 1995 to be exact, because the gap was so clear and this was something key. And understanding entrepreneurs is actually not easy, it's different than a corporate relationship, it's different than a kind of much more bureaucratic kind of system, it's very much like who is an entrepreneur and how do you work with them and they're unique and interesting and growth-minded and freedom driven, as you were talking about, but not everyone is cut out for that, so I think really appreciating that distinction is huge. So let's jump into a virtual assistant versus a virtual executive assistant, what's the difference? I'm super curious.

Ryan Cassin: Yeah. And I love what you led with Shannon, which is that if you've had an in-person assistant in the past, there's at least some component where they will be virtual or remote or distributed or whatever word you want to use, in the future, and I find that to be so true. When I have conversations with folks about how they need an in-person assistant, I really like to dig in on that. It's not our business and so we want to be a good fit if that's an absolute requirement, but I love to dig into that because I think it reveals some of the blind spots or sort of the old way of thinking about how business is done, to absolutely require to have that person be physically in-person.

And so we talked about this before, but sometimes what I find is that in-person assistants can quickly become a shared resource. Good assistants have a natural desire to be helpful, they have a natural desire to be proactive. Entrepreneurs who are unconfident about having that assistant, then volunteer them out as a shared resource, and so that's so easy to do when it's in-person, are particularly social entrepreneurs, and that's a lot of them because entrepreneurs are typically the sales engine of their business, they love to have somebody that they can hold hostage and gab with all day long. And so in-person sometimes becomes a little bit of a crutch for having somebody that you can kind of corner and who's stuck there. And sometimes that manifests as a procrastination technique and so I don't throw that out to be judgmental, but it's just a reflection, something to be mindful of, is something that we see. But ultimately shifting this more productively, the idea is that your executive assistant is helping you get out of the office and you personally no longer needing to have this physical attachment to an office or a space. And so when you're working with somebody who is an executive assistant outside of the physical bounds of your business, then you have built a system where collaboration, communication all happens completely in the cloud. You are always on the same page no matter where you are physically, if you're separated, if you're in different time zones, if you're on Free Days and you're coming back for a quick Buffer Day or a Focus Day to check in on the business, you are never losing a step, you're completely in sync. And so we think that there's huge benefits to getting over some of the hurdles associated with working remote with an assistant because the whole idea is that we're getting you out of the office as well.

And really at the end of the day, your executive assistant should be supporting you as a person and the business is just one piece of you. It should extend to personal projects, it should extend to things that you have to get done around the house, it should extend to things like how you plan and execute your Free Days as well. So I just wanted to really quickly hit on this requirement that I see some folks have and I think it's earnestly held that the person needs to physically be there, but what are you missing in terms of upside and opportunity to have better collaboration, better communication, more effortless sync up with your assistant by virtue of having everything live in a digital place?

Shannon Waller: I love that. And you know what, I'm laughing as you're saying someone to talk to and that can be a procrastination strategy. I'm like, how many times have I seen this? And then so you've chatted with your assistant all day long, thinking that somehow that's turned into productivity, and then you're like, "Okay, do you have enough to do?" And they're like overloaded with all the work that you just laid on them, that they've had no time to do because you went there talking. I actually heard about this just a couple weeks ago. So I hadn't conceptualized it like that, but yes, that is a big danger. And I think this goes back, talked about last time a little bit about busy work and why we kind of hesitate sometimes. Well we also can misuse this incredible resource that we have because again, lack of confidence, lack of focus, lack of direction, and just needing that handholding sometimes, so that's a really great point. And the other one I like, which is your job is to be out of the office. Your job is to be going and meeting with and connecting with those high level relationships that are going to help you not only have a Self-Managing but a Self-Multiplying Company. I talk about that in our weekly planning calls. And so yeah, freeing you up and having systems that can work no matter if you're in-person or more likely, out and about is really wise. Steven?

Steven Neuner: Yeah, just a couple of more points, another way to think of it too is, what if you have Self-Managing Companies, which more and more entrepreneurs do now, and so which set of walls do they sit in? How do they know truly if they're tied to a business versus tied to supporting you? How do they really know how to leverage you best to get the best result? The second thing is, I'm literally sitting in one of our businesses now. We have a vineyard in Anna, Texas, which is north of Dallas. If I were to say, "Everyone, my assistant must drive to my office here," my talent pool for the best and brightest with the highest capability to support me, is going to come tremendously down in what's possible and available to me.

Shannon Waller: Yes, such a great point. I really appreciate people who articulate this. If you insist on it being local, what, the 20 square miles around you? Seriously. And there's some incredibly talented people who are 25, 30, 100, 1,000 miles away. I am a little bit keen on time zones being not too far apart, but it's like why would you want to miss out on that kind of talent? It's crazy. And I live in Toronto, Canada. Okay, Toronto, I mean my person, Katrina, lives not that far away from me, but she's a good hour to an hour and a half away from the office and I'm probably 45 minutes, depending on traffic and construction, so why would we do that? That makes no sense. Now do occasionally I want to see her? Heck yeah, I actually wanted to give her some presents I bought for her on my last trip, but it doesn't make sense and I'm out and about a lot.

I was just in Palm Springs, I was in Palm Beach, I'm going to be in Dallas, I'm going to be in Chicago. So if we can't figure out how to work another way, we're kind of toast. So I think that's a really good point and that's really essential. So one of the things as we were, again, planning, plotting for today, is the difference between assistant and versus an executive assistant, which I think is funny because I'm like, when I read your definition, I was like, why in the Lord's name would anyone want anything but an executive assistant? Just talk about assistant versus executive assistant, what is the difference?

Ryan Cassin: Yeah, so it's a distinction for us that's really important. What does this mean, executive assistant? And there's a big difference between, in our mind, a virtual assistant and an executive assistant. And it doesn't necessarily have to do with the physical place in which the work gets done. This isn't the difference between somebody who's in office versus not in office. When we're talking executive assistant, this is somebody who can know you, understand you, and ultimately anticipate you. I love this line that Strategic Coach has about, and we've adapted a little, that in the relationship with the executive assistant, your EA should be the leader in the relationship and you should be the boss. They should be pulling you forward, anticipating you, acting proactively on your behalf, and they have the authority to be able to act on your behalf as well. That the nature of the relationship between you and your EA isn't such that they're constantly coming to you for approval, it's that they're voting your proxy on something, that they're taking care of things in your absence or without your explicit approval on every little detail.

And so there's a lot of different services in this space to help you find help. And an assistant can be anything from someone you find on a marketplace site like Upwork or Fiverr, to someone that is a dedicated individual that you work with, someone you hire directly for. We have kind of a three Ps, the way that we think about the use case for each of them. The first is projects, and so that's where if you have a project, I need to get a podcast edited, a video edited, I need an illustration or a graphic created for me, a flyer done, some sort of atomic piece of work that needs to get done, go to those dedicated marketplaces. You can match a specific need to someone willing to do that work.

You can get really predictable, high results, fast turnaround times, very affordable, fantastic. Projects is sort of the base of the pyramid, the simplest thing to go knock out. The next is processes, and that's where what we would classically say a VA would be good at. It's consistent execution on a known, defined, step-by-step process. So you don't need to improve the process or you don't need creative thinking brought to the process, you've got known inputs and outputs and you don't need critical analysis about the work itself as it's happening. There's no meta layer of thinking about your thinking while you're doing the work, it's just a square peg into a square hole and just hit it.

And then the highest end, and this is where we think EAs are, it's the proactive. So projects, processes, and proactive. This is where we think, as we talked about before, getting simultaneous freedom and growth comes from. This is the seeing around the corner, your assistant is taking the lead in that relationship, they can make decisions on your behalf, they have the context and skill to use good judgment. They're working side by side with you throughout the day so they see things through the lens that you see them through. They're right in on your most important goals you have for the quarter, for the year. It's the highest leverage relationship of the three, that’s what we're focused on.

Shannon Waller: And what a brilliant way to break that down, projects, which are tasks, so things to get done. And as you said, there's some great talented resources out there. Processes, we have a distinction which we've all talked about, which is make it up, make it real, make it recur. So visionaries make it up, what we call innovation managers or project managers, kind of put the flesh on the bones and make sure it can move and walk and talk, and that's kind of where revenue comes from. But then people who can make it recur, I actually think this is where profit comes from, because if I'm involved, I'm changing it every time, not a profitable activity, but those people who can make it recur, that's what you're talking about. The systems people who can run in a system that has had all of those questions and niggly one-off circumstances, those questions have been answered, they just have to run it.

Then you've got proactive and this is where you truly have that partner, and it goes back to what you were saying earlier, and I joke about this all the time. It's like I don't want to have to manage someone, I want them to manage me, I'm the squirrely one. It's like yes, technically in the power structure, sure, I'm the boss, not even a word I like, but really I'm the one whose time and activity and attention needs to be managed, to your point, and to do that, good lord, so of course they have to be proactive. I want a person, I want a thinking partner, I want someone who is intelligent and going to put that intelligence to work. Not to say there isn’t intelligence involved in the other things, but that kind of like, handle the new stuff, figure things out, be my proxy. Great way of articulating that. I'm not good enough actually to break things down to just the project level, I actually need someone else to do that, so I cannot imagine working with someone who's not proactive. It would drive me batty. Steven?

Steven Neuner: We all are very familiar with EOS and Gino Wickman, and in the EOS world you have what's called an integrator for the business and they're removing roadblocks, obstacles, and they're keeping the ships running on time and all the function of the business connected. I like to think of the proactive model, the executive assistant, the EA, as a personal integrator for your business, for your life, all those pieces. How do you remove obstacles, keep the ships running on time, keep all the pieces moving, versus us having to get in every single detail?

Shannon Waller: That is a great way. And again, if everyone's not familiar with Entrepreneurial Operating System, EOS, please read Traction, then go do it. Better yet, hire an implementer to help you, and Strategic Coach runs on EOS, anyone wants to know that. But the idea of having a personal integrator, and actually I want to go back to this point that, and I love it because I don't get to have this conversation with very many people, that this, your EA is attached to you, not just your company. And again, Steven, it goes back to your story in the first podcast, which is where your team hijacked you or did an intervention, to use my language, and said, "Great that you're hiring people to support us, but you are the bottleneck." And it's probably because we think about ourselves in the context of the company, but really we need support, period, in all aspects of our life.

So let's delve into that because I think that's even a bit of an expanded thinking for me. Yes, there's a few Free Day things just to make sure they're protected, but I don't tend to do that as much. So let's talk about having that assistant is look, you are their project, you are their focus activity, is one distinction I know is really helpful. So let's talk about that, what's the thinking behind that and how can people really be leveraged when someone actually manages all aspects of your life?

Ryan Cassin: Yeah, Steven, I think you've got so many great firsthand stories, the way that you work with your assistant to manage social media presence, to get inspiration for ways to have date night or go have really memorable nights out with your kids. I think you've got some phenomenal stories around this.

Steven Neuner: Well, back to Coach, I've been in Coach, Strategic Coach 18 years, and the first thing we do in workshop one, we talk about the Lifetime Extender and My Plan to Live to 156. So those haven't read the book, you need to go check it out. But the idea of buying back time on the things that are most important that we tend to just push off, push off, push off. What is the evidence, what is the evidence today that what I say is important in the future, how do I connect those two? That means for me, what does it look like to be a great husband? Well, I use a certain level of, my wife fell in love, Corey, because I have an entrepreneurial spirit and I would move heaven and earth to create unique creative experiences when we were first dating, well, we're 20 years now. I don't want to give all that to the business, I want to continue to find ways to bring that to our relationship. However, I only have so much energy and so much time in the day, so I have The Better Husband Playbook. My assistant literally will go every month and look, she has a preferred list of the things my wife loves, the kind of foods, places she likes to eat, music, gifts, et cetera, events coming up. And so she'll literally go and do research and create a list and I get a report that she puts together and we have a little bracket of time in our weekly check-in and it's like we go through it real quick and I'm like, "Yes, yes, no, no, yeah, and we should do this." And then she goes and makes it happen.

I have collision courses for really great exceptional date nights that have creativity to them, I give thoughtful gifts, and it's just a little bit of extra thinking. I'm still making the decision, sometimes I'm like, "Hey, not this, but that," but it's empowering, something that's really important to me and that is changing our family tree. I have the same thing for each one of my kids. When's the Monster Truck Rally coming in town? I go research that, but I’m a 5 Fact Finder, I got other things to do, but I want to show up. One of my values is that. And so to know that's there, to make the plans, to coordinate it all requires effort and energy, but I get to be blessed by the opportunity to show up and live into those things.

Shannon Waller: Oh my gosh, first of all, Better Husband Playbook, please package and sell that, if you haven't already, be really good. And that's so powerful, and it's interesting, most of the assistants I know actually really enjoy those types of activities. You might think it's only business, but that tends to be the person who's looking to actually only treat this as an entry level job. Again, we talked about that last time, first episode, so go back and listen if you haven't yet. But for someone who actually owns it and loves supporting you, this is fun because first of all you know there's going to be kudos coming, lots of gratitude from you, from Corey, from your kids, from what she's helped to enable to make happen.

Steven Neuner: And she loves it. And I see so many entrepreneurs, when I think about this role sometimes and I see this in all the businesses, the entrepreneurs I hang out with, and sometimes even in Coach workshops, where people have this real sense of guilt of like, well, if they knew what I was really buying my wife or the type of trips we took or whatever, they get this hangup and this head trash that causes them to live a very small life. And so instead of get a freedom of growth, they build a prison, they have success and then they're trapped because they can't enjoy the success. What I would say is the typical, oftentimes the right assistant, they don't want your life, but they want you to have a good life. And if we really care about them, that is returned.

And it's not just family relationships, other ways that I've put this into motion, to Ryan's point, is I don't go on social media. My assistant creates a Better Friend Playbook, I get literally a report every week of all the things of my most important relationships, “Hey, so-and-so had their anniversary, Ryan had this incredible date night with Carissa. We call him Mr. Casanova.” And so knowing those, I have a quick report, so I haven't seen all the political stuff, all the hate, all the nonsense stuff that just throws me into The Gap and makes me think the world's on fire. I can literally just focus on those really key crucial moments and be able to say, "Hey, you know what, Jason had a baby. Let's send him a gift. Send this note to him."

And so she replies on social media on my behalf, and it's not marking, it's keeping me in the loop because this is where a lot of people make announcements now. Literally, this came to be because I missed a wedding of a friend and the invite came through Facebook Messenger and I just don't go on there very much and that I would've never missed their wedding.

Shannon Waller: Wow, good point. Okay, so you The Better Husband playbook, The Better Friend Playbook. Are there any other playbooks we need to know about? This is awesome.

Ryan Cassin: Two that I get a ton of value from, and actually I'll make it three because one of the things that I think highlights the idea of this being Unique Ability Teamwork, where the activity that your assistant is doing, they're bringing excellence that you don't possess to it. And so I'll give you the example of my assistant going through on social media for me as well and seeing that there was a close friend of mine that had a baby and I don't know what the right gift to get that person is, and I am cursed with the High Fact Finder. And so what I would've done is gone and spent an hour or two researching “perfect baby gift” and reading every listicle there is on that, gone truly down the rabbit hole. And my assistant not only found a perfect gift, it was custom to the name of the baby. And so it was this really cool wilderness scene jigsaw puzzle type thing, where every letter of the baby's name was a different animal on the scene and it was really, really cool. It was creative, it was unique. It definitely stood out as a gift. And it's something that in no world would I have found this gift and it was just perfect. It made me look so good and it made me feel so good to be able to gift in that way because even though that's not in my Unique Ability to find that and to deliver on that, it's definitely reflective of the way that I want to show up in that relationship. And so my assistant helped me show up the way that I really wanted to, but my capabilities don't naturally lend themselves to it. And so the two other playbooks that I get a lot of value out of are our Personal CRM Playbook. And I find that entrepreneurs, I mean they're so good about their business CRM, they know the stage of every deal, they know how close are they on the two yard line to getting the next deal done and money in the bank. The achievement oriented nature of the CRM can be very addictive for naturally salesy personalities that entrepreneurs often are. Well, what gets sacrificed in that oftentimes is their personal relationship, the best friend that you say you'll call tomorrow and then you make that call two weeks from now. And so having your own personal CRM and logging the last time you communicated with somebody or having your assistant be able to see their activity on social media or know what their interests are and be able to see news or articles or opportunities for you to naturally just reappear in their lives and let them know that you're caring and thinking about them. That's a really, really valuable thing because I value my personal network, but I struggle to feed and water it the way that I'd like to.

Again, it's not naturally in my ability to be in high communication with all the friends and the people I care about. So I really get a lot of value out of that one. And the other one is the background brief, this is the quick five-minute primer that if you're going into a meeting with somebody you've never met before, maybe this is a sales prospect, potential investor in the business, maybe this is a potential new hire. This is the quick five-minute primer that if all you had was the Uber ride over to the meeting or five minutes between Zoom meetings to read it, you'd know exactly their background, how you met, what common points of connection are. Maybe you both have the same school in your background or the same sports interest. I mean, there's so much you can find out about people online, being able to have that at your fingertips and then your assistant also know you well enough to say, "Hey, here are the common connection points and how you can build rapport right off the bat," that's really valuable for me.

Shannon Waller: Thank you. I love hearing about all that and it's inspired me because I'm thinking about, oh, okay, so one of the things I do, I'll meet clients and sometimes they'll come up to me and it's like, "Will you be on my podcast or can I have a call with you or something?" I'm like, "Great, sure." And I make sure Katrina knows, we get it scheduled. Then I'm like, "What did we want to talk about again?" I'll totally forget. I was very present in the moment and that just escaped me.

Ryan Cassin: Who are you?

Shannon Waller: Exactly. What was this again? So Katrina, she's the capturer of that information, and we've learned, the hard way, that everything goes in the calendar, it goes in the event. So my prep stuff for you guys for last night, everything was in that calendar invite, everything is synced up with that. I'll have a notes page with the additional things next to the calendar invite because where do I go? Well, in my lovely Quick Start short Fact Finder Follow Through way, I will jump to the calendar and then work backwards. That's how my bottom line brain works. So everything is in the calendar, and it's been a game changer, and especially with any Strategic Coach clients, I want to know their Kolbe, I want to know their CliftonStrengths, I want to know their Print profile. I'll get some of that background information, the name of their website. That's kind of the bottom line information I want to have because then I can really personalize and tailor and individualize, one of my strengths, my conversation to them. So yes, I haven't called it a playbook yet, but now I'm going to have to come up with a name for that, so I don't get caught short.

And all of this goes back to something that you've been talking about, Steven, and now I feel like I understand it better, it's really how to show up as your best and be in alignment with who you want to be. Ryan, you said the same thing, and I'm like, oh, that's what that means. And this teamwork allows you to do that so much better than what you could possibly do on your own. Especially as things get busier, as you grow, as you've got more things to think about, it's hard to deliver to the, it's not the quality standard, but it's hard to deliver at the level that you want to, and it takes teamwork to do it. So don't be frustrated that you can't do it all yourself, just get a phenomenal EA who's probably much better at this stuff anyway, and then you can actually show up as that person, that's what I'm hearing.

Ryan Cassin: That is all outside the realm of the blocking and tackling businessy sort of stuff that I think a lot of people have in their mind when they're introduced to the idea of, hey, I need an executive assistant. What are the to-dos I'm going to be able to shuffle off to you? What are the things that in the business I won't have to do anymore? But it misses this whole next level, this whole other opportunity to get so much more out of the relationship as you grow into it.

Shannon Waller: Well, and on that proactive point, hopefully this causes some anxiety to calm down. One of the things that I have learned is that when the right person shows up, they see the gaps. You feel them, but you probably don't have a great way of talking about them or figuring out how to fill them. That person sees the gaps and they're like, "Oh, I can do this for you. I can do that for you. You need help with this. This is a problem. You were late for this meeting. You were struggling because you weren't prepared and you got frustrated. You were a little cranky because you didn't get enough sleep or exercise," whatever it was, they see it and they want to fill in the gaps for us. And I think this is key to remember, we don't have to have it all figured out, in fact, we don't because it's not our Unique Ability. But for the person for whom this is, they're like, oh, their brain just goes crazy wanting to jump in with a solution, we just have to say yes and not get in the way.

Ryan Cassin: And this is why it's so important that you're finding your compliment, not your copy.

Shannon Waller: Yes.

Ryan Cassin: We talk to so many entrepreneurs who think that the executive assistant role is going to be most successful for them if they're able just to create a clone of themselves, which is the fallacy of entrepreneurs in general. If only I had a clone of myself for sales and a clone of myself for operations and a clone of myself for customer support and success and then a clone of myself for my executive assistant to boot. And of course, that's a recipe for disaster in every other role, it's a recipe for disaster in the executive assistant role as well. You want somebody who is not your copy, someone who fills in those gaps.

That's one of the things that we spend a lot of time on, is really learning who the person is and what they're really good at. So when we have conversations with entrepreneurs about their executive assistant, the first question is not what do you want your EA to do? It's what do you want to do? We start there, map that out, figure out their Unique Ability, and that begins to form the foundation of the conversation for who that complimentary personality is.

Shannon Waller: So you work backwards. Oh, I love this story. That is brilliant. And I cannot emphasize enough, find your compliment, not your copy. First of all, there are very few things that any of us should end up doing, like one, maybe two. And so if you're finding your copy, you're going to find someone who's not as good because you're not that great at it, find someone better. We have kind of an intuitive sense of a compliment. By the way, who feels best in an interview? Someone who's our clone.

Ryan Cassin: Absolutely.

Shannon Waller: We vibe, we talk, we brainstorm, I'm a 9 Quick Start, another 9 Quick Start, We just have a great time. Then we leave and nothing happens. So my compliment is someone who's got a different personality, a different set of mental energy, as per Kolbe, a different personality, hopefully they also still need to be smart. I'm not going to compromise on that one. But if I look for me, I am first of all an idiot, and I'm sunk. It's one of the worst things I could do.

But I love it because in to your point, Ryan, you can't actually appreciate someone else's Unique Ability until you first appreciate your own. And so if I don't appreciate that I have unique strengths and talents that need to be focused and protected and freed up, then I'm not going to be able to appreciate my compliment and I'm going to look for everyone else to be like me. I just have to share a really funny quote from one of our old clients, he was talking about Kolbe, but it serves for any other profile or task as well. He said, "Before I knew about Kolbe, I thought everyone was just like me, only not as good," which kind of nails this.

Ryan Cassin: That's perfect.

Shannon Waller: I know. But when you actually have ... you can be super, super confident in the areas that you are superb at and love to do and are best at and have a ton of humility about everything else, and I think that opens the possibility for really tuning into that compliment and listening and believing what people are saying, as opposed to just trying to impose your will and your way on other people.

Ryan Cassin: You absolutely nailed it with the Quick Start energy because that's exactly what we see is I want somebody who's going to be as Quick Start and fired up and as excited and as distractable as I am, and it's the first thing we have to be kind of like, walk back, okay, do you really want that? Think about what the consequences are if you two got ping ponging off each other, I mean you'd spin off the face of the planet. Somebody's actually got to follow through on this stuff.

Shannon Waller: 100%. And I have examples, I actually gave a presentation at Kolbe one time, and we didn't have an intelligence profile, but we went through four different personality indicators, indices, and we were complete opposites. We went through Kolbe, complete opposites. We went through DISC, we went through Myers-Briggs, we went through CliftonStrengths. And then even, this was going a little far out, we even did astrology. We're compliments, we're opposites. It's like, okay, could it be anymore? And it doesn't look like it should work, worked brilliantly. But we knew how to do the yin and yang. We knew how to be the balance from one another. Whereas I was fast-paced, she was steady. Where I was outgoing, she was calm. It was phenomenal. In fact, she even wrote a guide called Teamwork Tips about how to work with me or people like me, which was really fun.

And the reason why she wrote it is because people were calling her and she doesn't like phone calls. She’s introverted enough that she goes, "I'm going to send this and then we can have a conversation if you still have questions after that." But she wrote this beautiful eight to 10 page guide on how to work with someone like me. So amazing intellectual property came out of that, partly out of her desire to not have to pick up the phone to answer a random phone call with people whose questions she didn't know what they were going to be, which I thought was really fun.

Steven Neuner: Well, and Shannon, I mean you're in the top 1% of knowers in teamwork and everything else. You got to think of a typical person that's hiring for a role like this, if they're doing it well, they may be doing it every five, seven years, something like that. There's no institutional knowledge, they're not living in the world you live in necessarily. And so they can take that Quick Start energy and the right person can mirror it, and then it's a successful hire, and then it just goes really, really solid from there. And it's really, really crucial to be able to know how to not just assess with the different tests and everything, but to really draw out, to almost have the person audition for the role. Can they be quick on the feet, not just can they tell you a story about it, but literally when tested, can they yield the results that they need to yield to be a successful support partner?

Shannon Waller: So how do you guys do this? Do you do this to help line up people and create that great partnership? How do you test people? I don't mean test and intending to have them fail, but how do you put this to the test, how does that work?

Ryan Cassin: Yeah, so the first piece of this is having a really great conversation with the entrepreneur themselves. You can't build a two-way relationship if half that relationship is closed off or doesn't understand the personal side of building that connection and the potential that is unleashed by that. So we have an initial conversation. Again, we work backwards from there, Unique Ability, to use the Coach term, we figure out what's getting in the way of that, some of the low hanging fruit for an executive assistant. We then ask them, okay, well what are some of the personality characteristics that would have to be true for this executive assistant to be a really good fit for you and for your team? And it shifts the question just a little bit beyond who they want to work with, to also thinking about, okay, this person needs to plug in with other members of my team as well. So what's the culture of my business and people who really thrive and succeed here, and how can we find somebody who's going to be a good culture fit?

So it's amazing when we have these conversations and we've had hundreds of them now, the words are there, folks know what they want to be doing, what their superpower is, they understand what's getting in the way of that really clearly, and they understand who thrives and succeeds in the organization. And so we've built a little bit of a profile just in our initial half hour or hour long conversation, and then what we do is we go and we have about an hour and a half long onboarding call, and that's everything from the very tactical, like what email platform do you use, just to make sure that we're training the person the right way, all the way up to more detail around culture, values, exploring some more of the personal playbooks and getting more meat on the bone there.

What do you expect in terms of your assistant being able to help on the personal playbooks from day one, and we're recording all of this, we're getting transcripts of all of it. And the amazing thing is that so much is revealed in these conversations just by having a really casual back and forth, you start to get a really clear picture of who's going to be successful. And then we're simultaneously running a search process where we're advertising for the role, executive assistant. But right now, I mean we genuinely are averaging 100 applicants for every one placement that we're making. It's really hard to find somebody who's the right fit of skills and capability and growth mindset and follow through, but also just enough pace and intensity to keep up with a growth-minded entrepreneur. I mean, you're talking sort of needle in a haystack here. And so what we'll do to test for that proactive sort of see around the corner, anticipate, is we've got a series of situational questions that we ask.

So for instance, I'm running into a sales meeting and I say that I want to get on the six o'clock flight home and I'm going to be heads down, phones off between now and five o'clock when the meeting ends, I need you to book that six o'clock flight for me to get home. And you see that there's no six o'clock flight. There's a 5:30 flight, there's a 7:30 or eight o'clock flight, which flight do you pick? And there's no right or wrong answer, we've heard it reasoned both ways, while the 5:30 one because it gets you home to your family or the eight o'clock one because maybe the sales meeting goes long or maybe there's traffic between the meeting and the airport, and so you need the extra time and you might as well have the later flight.

It doesn't matter what your answer is. Did you reason to get to the answer? Was there a mind at work there? And then B, did you also sort of think about it from your entrepreneur's perspective? Did you think, okay, well I'm going to get the eight o'clock flight, but I'm also going to let his family know, I'm going to let his wife know proactively. I'm going to also have some suggestions on where you can get dinner, either with the client or on your way to the airport. And we see this in the initial interview, this kind of thinking, is there are ways to not just take a simple yes or no, do you take the 5:30 or the eight o'clock, you can actually fill in the blanks and build on it, that's the kind of thing we're looking for. It's a mindset, it's a way of approaching the role that says, no, I'm going to answer the question, but I'm also going to see the opportunity to do so much more.

Shannon Waller: Okay. I would flunk because I would get them on a flight and then I'd be done.

Ryan Cassin: Yeah. Well, the worst is indecision, where you say, "Well, I'm going to text the person and try to figure out what they would like me to do." It's like, well, no, we actually said as a pre-condition, they are heads down, they're in the sales meeting, they're dedicated, that for us is an easy reject, right?

Shannon Waller: Right. Oh my gosh, that's so clever. And I just wanted to compliment you because you pull out all of that information because of the quality of your questions. When you're meeting with your person, even before you find the candidate, you're getting what they need, he or she needs, just on the basis of your question. And because you've done this hundreds and hundreds of times before, you probably sort through and sift through those answers really quickly, to go doo, doo, doo and find the pattern of what will be a great successful hire for this person.

Ryan Cassin: One of the coolest things is being able to have the conversation 100 times with 100 different high achieving entrepreneurs, who are all up to stuff, doing really cool things, living really big lives and hearing their ideas for how they want to get more out of their EA relationship. They inspire and lead us as well in the development of new capabilities and playbooks that we can bring to other entrepreneurs. And so kind of the coolest part of being a part of this really, really ambitious community is you get a front row seat to their bigger future.

Shannon Waller: Well, I'm so excited, and I actually really hope, this wasn't part of my initial plan for our series, but I hope actually that there's someone listening to this who is this kind of EA, who goes, "That's what I've been looking for." Do you know what I mean? Because you have curated such a powerful, who uses Superpowers, who you are superb at finding, who are you superb at matching people up with is rare air, and you have unique intellectual property, which I'm dying to know all the playbooks. I think that's IP that I would more than happily buy. Hint, hint. But then there's also, I'm sure, playbooks for the EAs that they're creating, and I know you have amazing training program to help people get even better at what they already kind of have natural capacity and capabilities to do and probably some experience, but then you help stack that as well, which I think is really interesting.

Ryan Cassin: Yeah. And this is one of the things that, we talked earlier about how important it is to find executive assistants with a growth mindset, so that they can track with their entrepreneur. One of the cool things that we get to do then is feed that growth mindset for our EAs, we constantly get to roll out new capabilities and new playbooks, and instead of this being just one more thing to do, it's a opportunity to further grow the relationship and accomplish more together. And so it's one of the really neat byproducts of working with growth mindset people.

Shannon Waller: Yes. On both sides, entrepreneurs and EAs, which is really exciting.

Ryan Cassin: Absolutely.

Shannon Waller: Oh my gosh, there's so much to talk about. So it's interesting, I want to go back to, again, your whole projects, processes, and proactive, and I just really want to make sure that we really hammer in that distinction assistant, if you just have a project assistant, this just that transactional task type of role or maybe even process. But it really is having that thinking partner, that proactive person who's going to anticipate you, look ahead, and probably challenge you.

One of the things that you guys have written some notes to me about is, you need to show up, if you're going to be growth oriented, you have to show up as someone who is willing to learn, who is willing to grow, and that means sometimes being willing to be uncomfortable. In our last conversation, we talked about the Four C's and commitment, courage, capability, and confidence. This means you can't just flip back to old tired behavior that didn't work, you have to be willing to grow as well. So I'd love to get your take on that because you've worked with clients for a while now, so what have you seen in terms of the growth of your clientele, from the entrepreneur side?

Ryan Cassin: Well, I'll start with an example or an experience. And I think there's also humility that has to come in the relationship, a willingness to be wrong. I can't tell you how many times I've gotten frustrated about something that was on my calendar that wasn't supposed to be there, or was with the wrong person, when in reality, that's exactly what I committed to and exactly what I asked for just two or three days before, and I had long since forgotten that conversation, it could have never happened. But my assistant keeps it all straight, keeps it all focused, and has the grace to respond patiently and positively when I'm like, "What is this? How could this possibly be?" It's like, "Well, this was your idea and this is what you wanted." Then it all comes rushing back. It's like, "Oh yeah, okay, this makes sense to me," because now I remember what the original idea was.

And so the learning there, the experience is that it is probably the relationship in the business where I'm most fallible and where I am most often making mistakes in a visible sort of way. And you have to be willing to accept that, to know that that's going to be part of it, that your assistant is going to be positive in keeping you on track, on the rails, and remind you gently and again, positively, that, well, no, this is something you wanted or this is set up a particular way because this was your idea. And it sounds silly and maybe it's just me, but it happens countless times.

Shannon Waller: It's not just you. I'm laughing, again, we were talking about Mindset Scorecards today, Dan and I, and it was interesting because if you are focused on status, having someone remind you of something you forgot is a blow to your ego. Let's be clear. I was like, "I wasn't supposed to do that, I was wrong. I look stupid. I look whatever." If you have a growth mindset, you're like, "Oh yeah, oops, sorry about that." And you're much more open, much more coachable if you really do have that growth mindset. And you've been making this distinction through our conversations, but really that's part of what the growth mindset means, is that you're not focused on status, you're not focused on always being right. You don't have to be the big, I was going to say, man or big woman in charge. You're there to grow and get better and so are they, and together you're going to do it well, as opposed to always having to be right.

Ryan Cassin: Well, and every time that happens, it's always a great relief. It is a reminder of, thank goodness I have this relationship because I am clearly not very good at this, and thank God I'm not the one doing it.

Shannon Waller: 100%. Dan has a term called delegated memory, which our assistants can often do that, hopefully there's technology involved too, it doesn't hurt. But someone who knows how to use that technology, to remind us, like, oh yeah. I'm like, "What did I say I was going to do again?" Just having that other brain is so key. Steven?

Steven Neuner: Well, I was just going to say, Ryan, you did want to meet with me, it was your idea for that meeting. So as much as you were triggered, you wanted to have that meeting. I'm glad you were reminded-

Ryan Cassin: I was trying to get out of it.

Steven Neuner: No, but what I do think is also in this is that most people have a growth mindset, we live in a fast moving, ever-changing world, and there's all kinds of chaos flying at us all the time. And so the ability to do that and receive that with a growth mindset and not be thrown into scarcity, I think is more important than ever, both for the entrepreneur and for the person supporting them. ChatGPT being an example, an assistant that is focused on just a project or something that they might be a little bit scared right now, like, "Hey, oh my gosh, scarcity, I'm going to lose my role." But a truly support partner, like what we're talking about here in this conversation, they're like, "Game on. How can I leverage this technology to better support my entrepreneur?" So it's that growth mindset that unlocks bigger and better things as the new things come up.

Shannon Waller: Yes. I heard a great word, which I've decided to adopt as my word for the year, and that is curious. So not to have those pre-conditioned assumptions, not to assume, like, "Eh, it's bad. Oh, it's a threat to my job." Good lord no, it can help save you hours if you know how to use it well. And so I think that's key to growth anyway, just to be curious, but that your executive assistant needs to be curious as well. And one of our brilliant clients at our Free Zone Summit, we had a ChatGPT panel, which was really fun. He made a really great point, he said, "AI is not going to replace team members, but team members who know and can use AI will replace team members who don't." And I was like, whoa, that just made so much sense to me. So it's like, get savvy, and Dan, he says, "I have a really smart human in between me and technology,” but your assistant can be that person.

Steven Neuner: Absolutely. And to that point, I mean, we want to make sure that the assistant's prepared to accelerate those learnings on behalf of their entrepreneur, because a lot of entrepreneurs do need the smart human or they just want it because it's just not the best use of their time, they know it's a rabbit hole that they could spend endless hours on.

Shannon Waller: Awesome. All right. There's already so many things I want to talk about for our next conversation, including curriculum coaching and community. So just whipping that out there, Steven, which is amazing. And then also just really preparing for that assistant, to do a little bit more of a deeper dive into that. So guys, this has been a very illuminating and enlightening conversation, I've learned a lot, especially about the fact that this assistant is for you, regardless if you have one company or five, it really is for you. And that whole idea of playbooks, man, that's a breakthrough. You can take it so far, and again, it just gives more depth to both of your comments, that this is really helping to elevate you and helping you be the person you are committed to being, and it's going to take some teamwork if you're going to keep expanding that impact. So those are some of the takeaways, I'm sure there's a bunch more too. Ryan, how would you like to wrap up this conversation?

Ryan Cassin: Yeah, my hope is, in that discussion of playbooks, my hope is that if what's holding someone back from getting an executive assistant, however they decide to make that hire, if what's holding them back is they don't think they have enough for that person to do to justify that, my hope is that the playbook expands their perspective of what's possible in the role, so that they get over that hump and they bring that key hire on board.

Shannon Waller: I just want to tell a super quick story. I've shared it in one of our previous podcasts, but I think it fits in here. And that is when I first took on my very first assistant, it was a sales assistant, and I shared a part-time person with the other salesperson, and Susan wanted to hire someone independent, she goes, "Can you take over?" Her name was Anan Kim. She goes, "Can you take over Anan by yourself?" And I was immediately thrown into fear. I was like, "Do I have enough for them to do? Can I afford it?" I already knew her. And so finally I deliberated for about a week, nine or 10 days, and finally I said, "Yes, I'm going to do it." I made the leap, went through the courage phase, and then three weeks later I said to Anan, I said, "How soon can you go full-time?" Three weeks, having her devoted to me was a game changer and she was instrumental in my and our success. So yes, you will find as soon as you get that leverage and that right person, and Anan was just a brilliant support partner and was particularly in sales that I was focused on, but it was unbelievable. And then she did go on full-time, which I was very happy about. But it doesn't take much, as soon as you get a little bit of that taste, you're like, "I need more." So don't be afraid of it. That was one thing I learned early on for which I'm grateful, but it makes so much sense. Steven, how would you like to wrap up?

Steven Neuner: I'd just like to say thank you for the conversation, as always. The encouragement I love to give is that if you are going to hire a really great CPA or tax professional, you would not relegate the talent pool to the immediate 20 miles around you. You would look for someone that can deliver the results. Bet on yourself that if you want to really commit to someone that can help you really achieve these new levels of freedom and growth that are possible through this role, get someone that can deliver the results, think bigger and broader.

Shannon Waller: Yeah, I think that bet on yourself could not be more true. A really superb EA is an investment, it's not a cost. You take it off that side of the sheet. Now it can be a good investment or a bad investment, but you have things very much stacked in the way to make it a fabulous investment, but it's an investment in you, that's really the key. And so betting on yourself makes so much sense. Oh my gosh, so much interesting wisdom coming out of this. I love it. So thank you both. Looking forward to recording our third episode, which will be coming out. When you're listening, if you have any questions or comments or things you would like us to address, situations you've run into that you think that we could help with, please let us know at questions@strategiccoach.com. We'll be more than happy to take those as we continue on with this series. So thank you so much, Ryan and Steven and for you, thank you so much for listening.

Steven Neuner: Thank you, Shannon.

Ryan Cassin: Brilliant. That was fun.

Shannon Waller: We would love this to be an ongoing dialogue, so if any questions that have come out of today's conversation, please let us know at questions@strategiccoach.com. We'll make sure to include them in upcoming episodes. Thank you.