All Things Assistants—Do You Deserve One?

March 9, 2023

Shannon Waller

Do you ever wish you had an assistant, but feel like it’s a luxury you can’t afford (or don’t deserve)? For many entrepreneurs, investing in a support person can feel like a selfish and even frivolous expense, but the reality is, a good executive assistant can mean the difference between constant burnout and a thriving entrepreneurial life. It may be one of the easiest relationships to overlook, but it can also be the most transformative—and profitable. In this episode of the Team Success podcast, Shannon Waller and Superpowers partners Steven Neuner and Ryan Cassin talk all things assistants: why you need one, what to look for, and common mistakes to avoid. Listen now to learn more!

Show Notes:

Many entrepreneurs feel like they don’t deserve an executive assistant (EA) or that it’s a luxury they can’t afford, but the fact is, you can’t afford not to have one.
It’s one of the easiest relationships to overlook, but also one of the most important to the health of your business.
We often resist the idea of being supported, but fail to realize that we are stressed (and stressful to be around) when we’re not.
Your life and business transform dramatically when you’re freed up to work on your business rather than stuck working inside it.
Having a good EA allows you to lean in to your Unique Ability^® and gives you the space to focus on being a leader and visionary.
It’s also a highly personal and rewarding relationship—they get to know things about you that others don't.
There are two types of people: those who’ve had an EA and recognize the value and impact they’ve had on their life and business, and those who haven’t had one and are not only stuck doing work that they hate and aren’t good at, but feel guilty for how poorly they’re performing at those tasks.
There needs to be a mindset shift around the work being given to an EA. Just because it’s not work you enjoy doesn’t mean someone else won’t enjoy and excel at it.
We often offer the position with the promise of another role "after they've put their time in" when we should be seeking someone who actually wants the role and is excited to grow within it. It’s not a punishment.
A good EA will be able to anticipate how you would respond in different situations and take action on your behalf.
Productivity will double, triple, or even quadruple when you’re focused on the right tasks.
EAs empower everyone to achieve their highest potential.

Resources:

Superpowers

Unique Ability

CliftonStrengths^®

The Gap And The Gain by Dan Sullivan and Ben Hardy

The Kolbe A^™ Index

The Impact Filter^™

Episode Transcript:

Shannon Waller: Hi, Shannon Waller here and welcome to Team Success. I am very excited to launch a brand new six-part series with Steven Neuner and Ryan Cassin of Superpowers HQ about all things assistants. They are experts. They are world class at what they do, and they have a lot of experience. And as we were talking about, we thought this would be a super fun collaboration because we both deeply, deeply care about entrepreneurs and really deeply care about assistants and want to help make that connection even stronger. So here's some of the things that you can look forward to. Episode number one, we talk about how do you know whether or not you need an assistant and whether or not you deserve one? Episode two is what kind of assistant do you need? Virtual EA, basic assistant. We'll go through all of that. We're going to talk about in episode three, the first 90 days, number four, all about how to avoid the pitfalls: what not to do.

I always like when people give me direction about this. Number five is the winning formula, really the success criteria to make sure that you're successful. And then number six is what other high performers are doing, and I love learning from example and what other people are doing really well. So we want to share all this wisdom with you. So, stay tuned for episode one where we talk about how do you know whether or not you really need a Strategic Assistant or, as the conversation in some people's heads is, do I deserve one or not? Stay tuned.

Hi, Shannon Waller here and welcome to Team Success. Today, we are actually kicking off a series, which I am super excited about. We don't do that many of these, so this is kind of a big deal, with two of my very dear friends, colleagues, and peers who are just as passionate about entrepreneurial teamwork, particularly with regard to assistants as I am. And that is Steven Neuner and Ryan Cassin, both part of Coach. Steven's also one of our wonderful associate coaches. So, thank you, guys. You guys are from Superpowershq.com and I am very excited to kick off this series talking about one of the most important entrepreneurial team relationships ever. But I think it's also the one that gets overlooked the most and is underappreciated the most, if that makes sense. So on that note, thrilled to be talking with you. Before we jump in, why don't you guys introduce yourself because you'll do a much more thorough job than I ever will. And Ryan, if I could start off with you: who are you, how'd you get here, and what is your passion with regard to assistants?

Ryan Cassin: Yeah, of course. So thank you Shannon for having us. Really excited to share this time with you and to be a part of this series because I am extraordinarily passionate about the relationship between entrepreneur and executive assistant. I think it is one of the most important, and as you said, one of the easiest to overlook, one of the most often neglected relationships, but it also is one of the ones that can have the biggest, greatest transformational change in a business. And so, relationship I had with my executive assistant in a previous business is what really cemented this for me. I was so lucky. I hit a home run on my first try. I found an assistant who was a great values fit, was proactive, was thoughtful. She anticipated me and she really grew in the role, which was so important. I had a very basic idea of what an executive assistant could be. And over the course of working together for years and years, I was completely transformed by that relationship.

And now Amber, who is my executive assistant in a previous business, is now our Chief Happiness Officer at Superpower. So she's taken on a leadership role within our business to help other people find that entrepreneur-executive assistant relationship and make that match happen. But I'm passionate about it because I've seen the transformation it has on the lives of the people who have a truly great executive assistant. It not just helps grow their business, it also helps them be a better husband, a better father, a better spouse, a better parent, a better friend to people that they care about. It really does impact every aspect of life. And so we started Superpowers two years ago, gosh, going on three years ago now. And since then it's just been such a joy to help fellow entrepreneurs form this relationship and really see the growth that comes from it.

Shannon Waller: You used the word transform with regard to yourself, and I could not agree more. I had exactly the same circumstance several times over. I feel like I've been very well trained and that was from which I'm really appreciative, but that is so true and that's actually what's possible, again, but not always what people are expecting. So thank you, Ryan. That's a great context for our conversation. Steven, tell us more about you.

Steven Neuner: Yeah, always great to be with you and I love being with this community. I love supporting entrepreneurs' freedom and growth. And so that has been in every part of every business that I've ever been a part of. This is really no different. My journey is a little different than Ryan's. I joined Strategic Coach, and I had qualified by $1. I barely qualified into the Program and that was including a rental property that was real income and it was mine, but I just barely qualified. And so I showed up, and I was the person in the room super eager, still not sure if I was an entrepreneur or not. And so when I showed up, a Strategic Coach changed my whole world. One of the first things that came as part of the early conversations at Coach was this idea of having an assistant. And unlike every other thing that's come up in Coach, this was the piece of advice that I resisted the most, this piece of wisdom, I gave it the Heisman.

I'm like, "Yeah, yeah, yeah, that sounds great, but we got to hire for all these other roles. We got to hire for all these people." And we had success. We grew, and a lot of hard work was blessed. And what happened was, I continued to ignore the wisdom, and every other piece of Coach you give me, Dan says, do something. I do it. Something about the assistant, though, I just kept pushing it away until one day my team came and they hijacked me. They basically said, "Hey, look, you are the bottleneck on everything. We so appreciate how much you love us and how you want to hire people to support us, but you're it. You're in the way on everything. You need help, and we are not letting you hire anyone else for this business until we hire someone for you."

And so literally my team pushed this issue and, boy, they were right. It was an incredible transformation and just very, very life-changing. And honestly, I still to this day scratched my head because the impact was so significant. I often wonder where I would've been if I'd not resisted it a period of four or five years.

Shannon Waller: Interesting. How much do I love the fact that your team actually did an intervention with you? That is fun. Then this is what I really want to get into in this initial conversation because we're going to talk a lot about the whys and wherefores and some of the real specifics about how to be successful with an executive assistant. So, if you don't have one, if you do have one, if you have an assistant that's not an executive assistant, or if you simply want to maximize what you already have going on, yes, this series is for you. But let's start at the very beginning, which is kind of what you're talking about, Steven, is we resist this idea of being supported, that we don't need it. I mean, your team was very appreciative that you chose to leverage them first as opposed to yourself. And it wasn't until they hijacked you and said, "No, you have to change your ways."

And I think that's really normal, actually. So your resistance is not unusual. For me, I know when I hired my very, very, very, very first part-time person—in other words, I took over a quarter person and made it a half—that was terrifying. And I was like, do I have enough work? I remember the fear and I remember the questions I had and the lack of confidence. And you guys know we have this amazing concept at Coach called the 4 C's, which is a growth formula, but it starts with commitment. And then you immediately experience this lovely feeling called courage. Not lovely. Problem is, it feels crappy, but once you're willing to go through that feeling of courage, what you develop really, really quickly, especially if you're fully committed and prefer short versus long courage, is then you develop the new capabilities, which gives you new level confidence, which just means you can do the whole thing over again.

So it very much is a 4 C's moment the first time you hire someone, I would say when you change out people, if they move on or you move on, I think that's very much a 4 C's one. And assistants are so personal, aren't they? They get to know stuff about you that other people just don't know. So I think this more than a lot of other positions in the company, like a CFO or a director of marketing or something, because this one is so personal, people tend to avoid it for the length of time. As you're listening, I'd like you to help leave this with just a huge sense of confidence and capability or at least commitment to go, "Okay, I've thought through having an assistant, what kind I want." You've answered the question for yourself, do I deserve it? You've answered for the question, what will it be like once I have one?

And to your point, Steven, it can be pretty wild when you're like, oh my gosh, this is the difference it makes now, what if I had done it before? And we can kind of beat ourselves up and go into "The Gap" a little bit. But the truth is, you are doing your best at every moment. Just recorded a podcast with Dan about this, actually, Dan Sullivan. Because we're all doing our best. And then sometimes, you go, "Oh, this is the new best." So let's talk about the difference it made. And Ryan, you talked about transformations. Steven, you too. So what is one kind of like measurable, because we are all in the same boat, we all have phenomenal assistants that have graced us with their support for which I'm grateful, but what are some of the really tangible, I was going to say, evidence or examples of what you could now do that you could not do before you had an EA? Ryan, do you want to start?

Ryan Cassin: Yeah, so you're exactly right. The transformation that you get with an executive assistant is incredible because really what you're able to do is lean more into your own Unique Ability. And so for me, that meant I've been able to be a better visionary for the business. I've been able to think more creatively. I've been able to bring better energy and lower stress to my team, which means I'm able to be a better leader for them. So these are things that don't show up maybe on a scorecard and you don't quantify. But I think that if I was being completely honest, those are the biggest transformations that have happened, the biggest changes I've seen in the business as a result of having a really fantastic team around me, of which my executive assistant is one of those people. And I think, you know, you mentioned the 4 C's before.

I think one of the great challenges with this role is that ideally you're hiring for it once and you've got your assistant for life. And so you've had one turn on that cycle, but you don't necessarily develop that skill or that capability. But I think you're so right that the confidence that comes from finding that relationship, even if your executive assistant moves on, we work with folks who have said they understand the investment, they understand that if they've had an executive assistant in the past and they're looking for a new executive assistant, they understand the transformation it's had in their lives, and they know that they don't want to go back to a life without one. Often, it's sort of two categories of people. It's people who've had one before and understand the value and the impact that it has on their lives and their businesses.

And then there's a lot of people who come to us and they say, "I'm at the point that I can't tolerate any more brokenness in my business and my life, and I'm responsible for that brokenness." There are things that—sort of the Steven story—there are things I'm responsible for and I'm letting my team down. And so before you even get to the part where you're thinking creatively, you're a better visionary, you're seeing around the corner, you're building a better business and being a cultural leader in your business by leading the way that you want everybody else to show up, there's this element of just, "I can't be the person responsible for breaking things in the business and expect everybody to be a high performer around me."

Shannon Waller: Right. That is such a key point. And if you're someone who's constantly breaking things that doesn't feel very good as a leader, and if you don't know yourself well or you haven't done any of the profiles, it's going to happen. And at least when you know that, you can start to supplement and complement your teamwork with other people who are as... well, frankly more brilliant or as brilliant in their areas of expertise as you are in yours. But expecting us to be all things all the time is ludicrous, but we tend to function that way.

Ryan Cassin: Yeah. And I think you hit the nail on the head. In our conversations, we have a lot of entrepreneurs who mean very well and are speaking candidly. They say, "Well, I've got this menial work that I have to get done" or "I've got this crap work" or "this stuff." And I think that's such a trap of a mindset because the work you're describing is somebody's Unique Ability work. And I think the first step to getting that breakthrough of working with your EA, especially early on, is valuing the work itself. We know by definition it has to get done because it's on your plate as the entrepreneur. Otherwise, we wouldn't be having the conversation to begin with. So it's important work. It just doesn't happen to be your Unique Ability. This is a brilliant concept Coach gives us. It's not your Unique Ability work, but it is somebody's Unique Ability work. So elevating that work and assigning it to somebody who that's their Unique Ability, I think that's a critical mindset shift that has to happen before you can even unlock that first level of transformation in that relationship.

Shannon Waller: Okay. As you're listening to me, you can't watch me where I'm like, "Yes!" I've had this conversation forever. I started The Strategic Coach Team Programs in 1995 to help try and bridge this gap. And thank God there are companies out there now like you guys, Superpowers, who are helping put this entrepreneurial teamwork in place, which is why I love talking to you. But it's interesting. It's exactly what people say: "Oh my god, I've got this menial work, this crap work, this," other words I shouldn't say on a podcast. It's like, no, just because it feels that way to you doesn't mean it's someone else's gold. But no, you're like, "Oh, this stuff is so crappy, it's so blah."

And then no one else is going to go, "Oh great, let me have it." No one's going to respond that way. But if you're like, "Oh, I have scheduling" or "I've got filing" or "I've got data entry" or "I've got this." If we just leave it neutral, and you say, "I don't like it, I'm not good at it, but you are amazing." And there's something else, there's a trap that happens, Ryan, is that when we think it's crappy work, we think the people who do it are crappy, or if we're a nice person, we don't want to give it to them because we're not a crappy person and then nothing changes and we stay stuck. It is so not an invitation to teamwork. It's ridiculous.

Steven Neuner: What I would just see on top of that, what I see a lot of entrepreneurs do and have done myself before I understood this is you make promises. "If you'll just take this job, work hard at it, just get through the time, we'll grow the company and I'll get you into the next role." So that people are literally entering in with this expectation versus, "No, this is something I love to do. I'm going to do a really great job, and I want to continuously improve and grow in this role." And so it's sort of this recipe for, they already have one foot out the door before they even get one foot in. Also, I see people overpay for work versus investing into the person for them to grow in the role and actually earn the money. So it's like, "I'm going to overpay you because this is all stuff and surely nobody would want to do so I'll overpay you hoping you'll just keep doing it." But the truth is, there are people that love it. You can invest in them; they can grow.

Shannon Waller: That is such a key point. I hadn't thought about the overpaying, but you're totally right because again, if you're treating it as though it doesn't have worth, it doesn't have value. So it's kind of like danger pay just so you'll do this menial work for me and it truly isn't. And let's dive into some of those things because, again, I always relate to profiles as you guys have heard me talk about, but I know what my- I'm not unintelligent, that's not a problem. Personality's fine. But I know my mental energy. And I can do scheduling. I can send out one invitation and then if they send it back, and if it's not a yes and it has to go to another stage, I'm out. Literally nothing would be on my calendar unless someone else looked after this for me, and one of my Team Success podcasts is "Scheduling Is A Creative Act." Yes, there's some people's schedules who can be automated but not mine. Mine is a bloody work of art, my calendar.

Ryan Cassin: It's so true. And there are at least a dozen examples of things like that where on paper it sounds like this is going to be so simple and so easy. I'm going to email, I'm going to set up a calendar appointment, and we're going to get it on the calendar and we'll meet and it'll be done. But in reality, it's three or four emails back and forth, or it's following up with people when they don't reply or making sure that you have all the materials you need to arrive at the meeting prepared and ready to go, and then the follow-up materials that happen after the meeting or the action items, and then all of the unexpected things that really end up creating open files in your mind.

And so one of the beauties with an executive assistant is that you're on the same page, that this person is able to anticipate you. They understand how you would respond in a particular situation. They're taking proactive action on your behalf. And so you're able to say, "Hey, let's make this thing happen." You can describe the world in terms of the results that you want to see and not worry about all of the details and steps necessary to bring that to fruition at a really excellent level.

Shannon Waller: Mm-hmm. That's perfect. And again, we're going to talk about not micromanaging in a little bit, but we'll get there. So we're talking about specific results, and I really like what you said, Ryan, especially the less stressed part because one of Dan's books is Not Being Bothered. There's a small, narrow area of activities that give us energy—Unique Ability, to use a Coach term as you talked about—and then anytime we step outside the line, we're almost automatically bothered because we run out of mental energy for it. And when we do that, we're stressed, and we're stressful for other people to be around. And I think that's overlooked, byproduct of not being supportive. We're running around chickens with our heads cut off and people are like, "Oh, I'd love to support them if they would just let me." But no, we have to do it this way. So, the impact of a stressed entrepreneur, business owner, team leader even, if we actually take that into account, we probably would take action a lot sooner. Steven, what are some of the really tangible things that you have seen after the intervention?

Steven Neuner: Yeah, after the intervention, what I would say is, the more common thought that I had even going into this process was getting rid of competent and incompetent activities. Things that are really, really bothering me. Things that are depleting me, drawing me, so I couldn't show up my best.

What I really have found, and what I think where a lot of entrepreneurs can miss this, is this idea of actually, my assistant helps me not just avoid things that draw me out of my best self, they actually help me live my best self. They help me live my core values. So as an example, we're recording this on Valentine's Day, and I sent flowers to my wife yesterday, Corey, who also has been in Coach, and I could have just sent flowers and that would've been like the thing, but because of my assistant, because of her knowing what's important to me, she knew that this was our 20th-year anniversary of being married, and she put the extra entrepreneurial spirit into ordering flowers and found out what is the flower for 20-year anniversaries? It's asters. It's asters. And so she elevated that through her entrepreneurial spirit.

Shannon Waller: That is so cool. I never knew it was asters. So she's got this awesome entrepreneurial attitude. And again, I love this because my brain's expanding as you guys are sharing. Yeah, it actually allows you to be even more your best self, who you aspire to be and more your core values.

Steven Neuner: Yeah. And another core value of mine is having a growth mindset. I've been in Coach for a long time, and now I have the privilege of being an associate coach. I want to walk the talks. I want to not just have a growth mindset. I want to have a growth identity. I want evidence that I'm growing in life. And so my assistant is in a unique position to help me grow, help me with my weak spots, my blind spots. And so she enhances my core value of growth mindset and helps me turn that into a growth identity.

Example: health. I always have avoided doctors. There's a whole story behind that. I've really, really struggled with that. I signed up for The Lifetime Extender series, joined InsideTracker. And so this idea of being able to go to my assistant and say, "Hey, this is something I struggle with. I have head trash around it. I need you to help me make sure that I'm staying on plan for these, that I'm going to the doctor, that I'm getting my blood drawn, that I'm doing the things that keep me in motion on something that I might procrastinate on."

Shannon Waller: Ooh, I so love that. There's so much to talk about. Good thing we're doing a series, is that a really great executive assistant, and I played around with the names. Strategic Assistant is the name of one of our programs, which we like to use. Mind you, when you're going out into the world, you must advertise for an executive assistant; otherwise, they have no clue what you're talking about. Just saying. So that's the world's name for what we're talking about, but Strategic Assistant. And then I actually changed it to be Support Partner because that's what they are. Nicole Pitcher, previous assistant to my wonderful person, Katrina, now, she educated me, and this was actually in the interview process. She goes, "I have realized that I am best in a support role." She goes, "I've done other things." And this is a wicked smart human, and CliftonStrengths, she's got four strategic thinking strengths out of five. This woman has it all going on.

But she goes, "I know myself." And sure enough, her DISC profile showed that she was super supportive. Her biggest danger was being bored. I'm like, "That is one problem you will not have with me. I promise you will never be bored." But I always felt very, what's the best word to describe it? I felt very honored that she had chosen to support me. She was really picky about who she would spend time with, and she'd already gone through a couple of different employment opportunities. So it's interesting. I really feel like when I actually got out of my own way and figured out, okay, I don't have to be all things to all people all the time. There are certain very few things that I "should" be doing that I can create the most value and everything else. I need all the stuff to happen beforehand so I can do what I do in the moment and all the follow-up afterwards.

And then our partnership was dreamy. It was just so gratifying. And my measurable, just to share that is it's part of our Weekly Planner booklet in Strategic Coach. We have a list of strategic projects, which you'll work on five to six per week. And there's a "Who" there in that column. So you make sure you're not the only one. But there's room for up to 24 over a quarter, which is a lot. So, about six weeks into my working relationship with Nicole, she goes, "We need to have a meeting to talk about what you're going to be up to in the next six weeks, three months." I'm like, "Okay." So with most meetings, I'm used to being a fairly dominant personality. It's like, great. I thought I was in charge. That lasted for five minutes. And she goes, "Um, actually, this is my meeting." I was like, "Okay, awesome. You're in charge."

So she came in, we did a Positive Focus, we did an Experience Transformer, and then we went through this list. And as a result of working with her and now Katrina, six weeks before last, there were not 24 items on my strategic projects list, there were 60. 60. That's a lot. And that wasn't even the full quarter. So I was like, whoa, is there any possible way that I could have organized and pulled that off without her partnership? No, not a hope in hell. This would not have happened. So I'm actually measuring it that way, which I find really interesting. So double, triple, sometimes quadruple. By the way, 60 is not the goal, it was a bit of an insane six weeks, but it was so powerful to measure just how much more I was getting done as a result of having the support we're talking about. Ryan?

Ryan Cassin: I love that your assistant was pushing you from the 24 that you thought was going to be the number to 60. And I think embedded in that, and the way you describe your relationship with your assistant, is that you have high expectations of her, but she has high expectations of you as well. And I think that is a characteristic of a really high functioning, high leverage assistant support partner type relationship. Because what we find is that the most important intangible in an executive assistant is, do they possess a growth mindset? Because Coach does such a good job for all of us entrepreneurs swimming in this ecosystem of helping us envision a future that's bigger than our past and bigger than our today.

And so if we're meeting here today and we're as big as we are, we know that in the future, if we were to meet one, five, or 10 years from now, our future would be even bigger than what we have today. That's just in our nature. It's hard-coded into our DNA. But if we want to have a long lasting relationship with our executive assistant, somebody who knows us really, really well, who understands us and who can anticipate us, and take action on our behalf, to have that long, high functioning relationship, your assistant has to have a growth mindset as well and grow with you. Otherwise, that delta between where you are and where they are from a mindset perspective gets set in place on day one and only grows over time.

Shannon Waller: Yeah. Oh, that is such a phenomenal point to make. And it's interesting. It goes back to something that Dan and I actually were just talking about this on our podcast: grow or go. But Babs has always said the growth of our company is really predicated on the growth of our team. So if our team's not growing, neither is the company. And I think that's so true. So if we aspire to have even bigger and better clients and to deliver new and better value or even stronger value and more connections. Dan was saying this today, he goes, "Then the team has to know that every single quarter there's going to be new things to absorb, new challenges, new fun things to do, sometimes new hard things to figure out." But that's the name of the game. And it's so critical, especially for the person who's so connected to you in your leadership role, is to really let them in because you're going to be growing, so they need to be growing, and vice versa is also true. So that's such a great point, Ryan, thank you. I love that.

There's so many different directions I could go right now. So let's talk about some more mindsets that prevent people from seeing the value, although I think we've done a pretty good job of addressing a lot of them. But let's talk about the whole thing, whether or not people are thinking that they deserve an assistant. And I think, Steven, this might go back to your story a little bit, and the deserving conversation's kind of an interesting one. Mine wasn't so much deserving as, could I keep them busy? Could I afford them? What would they do? And those questions that I didn't have immediate answers for just left me kind of frozen. I was kind of pushed into it the first time. So, Steven, what's your take on the whole kind of deserving conversation?

Steven Neuner: I think it's really common. In fact, in certain parts of the U.S., I think it's even more hardwired in, this Midwest work ethic mindset, period and mindset. Like, I'm going to do it. It's a luxury. It's this idea, it's this luxury, I'm not there yet. And the problem is, we know from The Gap And The Gain, they're never there. If you're listening and you're saying that and you're just so committed to that, I would say then, at a minimum, please write down when you are going to be there because that is going to continue to move on you, my friends.

Shannon Waller: Oh my gosh, that's so true. Yeah. And the other thing is to actually treat it as a real question. The answer is yes, absolutely you do, especially if you've got big goals. If you want to stay the same or do less than you did yesterday or last week or last year, sure, maybe you don't need or deserve one, but if you have a growth goal... We've talked about this before, if you don't have an assistant, you are one, and you're probably way too overpaid for the quality of work that you're doing. So seriously, it's a business decision if nothing else.

Steven Neuner: And I think, again, back to this idea of my assistant helps me live my core values. If I have big goals, but honestly, I'm a little bit afraid, I'm in that courage standpoint. You know what? Staying really busy on the wrong work is a really great way to procrastinate. It is. It is. I can work really hard, and I'm working for that goal that I keep telling everyone we're going to achieve, but am I doing the right things and am I doing them for the right reason? And an assistant is that unlock for that.

Shannon Waller: Damn, mic drop right there. Yeah, we're doing busy work till all hours of the night, which is by the way, compromising your personal life and your family and your kids and your partner, and it doesn't allow you to be that visionary that you were talking about, Ryan, to have those new big ideas that are going to help grow the company. And one of the big mindset shifts that I know I went through in my career at Coach, which is a while now, is that it's about the future. It's about building for the future. It's not about staying locked in. It's not just about me and my personal productivity. No one gives a flying you-know-what.

What they want to know is, how am I being efficient, being effective? And I'm most efficient and effective when I'm doing what I'm unique at. And frankly, I'm slow as molasses on scheduling. I'm slow as molasses on what Kolbe would call Fact Finder and Follow Thru activities. I ran out of energy for those things by 9:30 in the morning. By the time I've turned on Zoom and had my first meeting, it's used up. My productivity goes down the sink if I'm doing those types of activities. Mind you, I could talk to you guys all day, which I do. So it's really interesting just how that mindset shift has to move in order to be able to make this work. Ryan?

Ryan Cassin: Yeah. One of the other things that I see, it manifests as, "Well, an executive assistant is a luxury" or "I don't deserve one" or some of the head trash around whether or not it's a hire that you are worthy of is people will self-sabotage by making their assistant a shared resource on the team because they have guilt about being the only person oftentimes on the team who has an executive assistant. Now, I'm a big fan of assistants for more roles and more people on the team because I think that this is a concept that if it works well for you as the entrepreneur, it also works great for other key members of your team who can get leverage on their time and who can be in their Unique Ability more often and drive bigger and better results for the business. And we can talk more about that, but let's just focus on the entrepreneur and the CEO of a business.

And if you don't think that you deserve this role, and the way that you're going to solve for that is by making this person a shared resource, you're guaranteeing that you're not going to find success in the role, and you're going to guarantee that this executive assistant's going to get burnt out because they're reporting to five different people, everybody sees only a fifth of their work product, nobody feels like they're getting what this person's potential should be. And so I think that's an unfortunate way that I see folks who are a little bit anxious about having their own executive assistant undermine the success.

Shannon Waller: I am laughing and I'm putting my hand up like been there, done that. So three of us shared a person. There were three different personalities, three different Kolbes, Kolbe MOs. Can you imagine this person trying to be effective, supporting three completely different human beings? It was a disaster. And that's the polite way of putting it. She didn't feel like she could be very successful. She felt like she had to have a different personality every time she went into our different offices. None of us felt like we were getting the appropriate amount. It was disaster.

Ryan Cassin: Capital D disaster. Yeah.

Shannon Waller: Less polite terms come to mind.

Steven Neuner: And one step further on this, the other thing that we see from time to time, and part of the reason why my team mutinied is that if you have really rockstar players in other roles, they don't want to be your assistant. And so they end up picking up assistant-type stuff because you're really busy as a visionary and CEO, and that's not, to Ryan's point but in a different way, they're already having to handle their own stuff. They don't want to have to deal with yours too because you can't get to it.

Shannon Waller: Ooh, that is such a good point. And I have to say, though, a shared assistant is probably a half a step towards where we need people to get to. But I think the other one is, it still took a fair bit of commitment and courage to go from, "Oh, okay, this isn't working anymore. I need to have my own person." I remember that feeling. It was not a fun one. It was just almost 10 years ago now, and it was hard. It was still scary. So to go from that, even a shared assistant and then to a full assistant, it is still a leap. And afterwards, to your point, Steven, I'm like, "Oh my gosh, why didn't I do this forever ago?" Or when someone takes- they're doing half their old job and half supporting you. That's another version of this shared work, and other people who treat it as an entry level or as a stepping stone onto something else.

Because here's the other thing I've found, and this is kind of interesting. If someone does have bigger ambitions, create an environment where it's really safe to share that because sometimes people will look at working for you as a stepping stone to something else, which if you're both aligned on that doesn't have to be a big deal. But when you don't know that, it takes you by surprise. Because I know, people who work with me, Julia Waller who, she did that role before she outgrew me within a few months, but she said, "It was great working with you, Shannon, because I got exposed to the owners of the company. I got exposed to all the coaches. I got exposed to all the content." Because we're in senior level conversations and meetings, and she was with me.

And so there can be an advantage of hanging out with us, but is it the person who actually wants to just stay in that role and expand, or are they using it as a stepping stone as well? And what I think is really great about your system and your processes, you are actually finding people who this is their goal. This is what they want. They want to be a kick-ass assistant for a growing growth-minded entrepreneur. Yeah. So don't make that mistake either. Don't kiss a frog.

Ryan Cassin: And it's a phenomenal role for people who are career-minded about it. You get to be as close to entrepreneurship without being the entrepreneur yourself. You get to see every aspect of the business. You get to talk to every person, both internally and externally. You get to see every decision that's being made. It is a really, really fun role if you like keeping things organized, keeping things on track, and you get satisfaction from seeing a job well done. And so being in a position to enable everybody to do their best work, to be able to be that rare combination of organizational savvy and strategic thinking and effectiveness that helps people plow through their tasks, but also frees up precious time, anticipates needs before they arise. The bottom line for the right person is, they're a game changer. They empower their organization to operate at the highest level and achieve its fullest potential.

Shannon Waller: What a great description. Yes. Yeah. And to be so extraordinarily useful, what an amazing opportunity. So you're being super useful to someone who's really useful, and you can do things that other people can't/won't do. That's a huge opportunity for the right person. I love that. Steven, what are your thoughts on this?

Steven Neuner: My thoughts are that it's so easy to lose sight of the fact that the entrepreneur, the assistant are people. And I think that there's all kinds of evidence, all kinds of metrics, all kinds of things you can measure in regards of productivity. The way that I used my time, the way that we grew, and I can measure and I can point to a massive growth streak that occurred when I repositioned the time, the ability to be supported as a human being. And why does Coach have The Entrepreneurial Time System? To reduce a lot of things, but one of them being the tension that a lot of entrepreneurs feel between work and home. To be supported as a person and as a human being and not just a productivity machine that's driving a growth car forward for the business, I think is really important.

Shannon Waller: Yes. Okay, so let's talk about that for a moment because I think one of the things that I've discovered has been important to me is that the people supporting me, first of all, I am friends with them. It's a personal relationship. I need someone who's going to care about me. I need someone's heart involved, not just their head and not just their intelligence, but also I want to be working with my friends. I mean, that's true everywhere. Clients, team, doesn't matter. That's always who I want to be working with. But the person who's working with me that closely, I want to be friends with. Yes, we're still professional, all the things, but I want them to care about me as a human, and I really care about them as a human. And I make a point of stressing that. It's not a transactional deal. It's a true relationship from human to human.

And when you treat it that way, there's just this unfolding or I don't remember what the word is that happens because you're not just looking at someone as a little transactional box. What can you do for me? It's more like how can we collaborate and support and be partners with one another? It's very, very different, but it is a very personal relationship. So let's dive into that for a sec because I think that creates safety for me. It also creates safety for the other person. I don't know if I'm unusual, but I'd love to get your input on that. On the personal nature of having an EA.

Ryan Cassin: I totally agree about that it's a personal relationship, and I think it is unusual. You'd like to think of your colleagues as generally folks that you're friendly with and you have good camaraderie and all of that, but the executive assistant role is one where you open the door a little bit wider and you share a little bit more of who you are and let a little bit more light in. But I think the key is that when you've got the right person, there's a genuine care that extends both directions. And so that manifests in big and important ways, but also manifests in lots of little ways on a day-to-day basis.

For instance, you're scheduled back to back today and I'm going to find this 15-minute or 30-minute block that you have this gap in your calendar and make sure that you have lunch, and I'm going to make sure that we get a DoorDash lunch to your house or your office to make sure that you've got time to recharge and to be at your best. Because really the relationship is so much more than the confines of the calendar and the to-do list. That when somebody who is on your team and who knows you really well and knows what makes you tick and makes you effective, when they see the full picture and when you let them in and you have that type of relationship, you're able to accomplish so much more than whatever's on the checklist for today.

Shannon Waller: Right. Yes, exactly. It's that, we could all go all day and then forget to eat when someone remembers to- Entrepreneurs and leaders need to be fed and watered, and we're not always great at doing that. So when someone else is looking out and they can kind of figure out when to make that happen, or even just catch your breath for a moment, it feels so nurturing, and I think that's really important.

Ryan Cassin: It does, but I also see that there's sometimes a level of discomfort with that too, and there is some resistance to easing into that aspect of the relationship, but I think that's where, again, things that are hard to quantify, but over the course of time when people have really phenomenal executive assistant relationships, they're not often talking about how they're plowing through their to-do list or how the schedule is always taken care of. Those things matter, of course. It's always the really, really great relationships, the ones that last a decade. There's a deeper personal connection there that that's the first thing, folks I talk to, that's what they clue in on really quickly.

Shannon Waller: I love it. Steven, what's your take on the personal nature of EA and entrepreneur leader position?

Steven Neuner: I think it's the difference between commodity and transformation. It's getting work done, bang, bang, bang, bang, bang. How do I get an artificial intelligence to do this or whatever, some sort of technology versus a truly transformational experience where they can actually anticipate you. They can act on your behalf. They can make decisions. They can help leave you into collision courses.

My process, after I go to every Strategic Coach, I spend and I tell everyone this, I spend at least a half a day the day after. And I'm re-completing my Pocket Coach, and I'm really just kind of thinking through and sitting with all the conversations from the previous day. And then I give it my assistant and I hand that off, and then from there, she knows the conversation's like, "Steven doesn't really like to have these difficult- we're going to put this person on a performance improvement plan." Or, "He's not going to want to let this person go." Or, "Him and his mom-" That you may not want to call Mom, and so let's make sure that there's collision courses or have lunch with or whatever, so that I, again, can live my values and so that I can do the things that are hard that I'd want to procrastinate on.

And again, that is transformational. That is not transactional, that is not just the schedule. All that stuff's important, like Ryan said. That's the "freedom from." The "freedom to" is I think what we're all reaching for.

Shannon Waller: I like that. So they're both an accountability partner, helping you stay accountable to your goals and to your values and to those sorts of things. They're a support partner. They help to nourish you and protect your time and make sure that your energy is looked after. And then they're a strategic partner as well, right? Because they're looking ahead, they're looking behind, they're making sure that i's get dotted and t's get crossed, all of those things and that you can show up at your best. That's really the part that I really like.

Yeah, I love looking at all the different dimensions of what this teamwork can be like because it's really fun. And the other thing is, I know from assistant standpoint, because I've had this conversation a lot, is the opportunity to do that scheduling for me, as I said, after one exchange, I'm done. But for Katrina, scheduling is like playing Tetris. It's fun for her. Nicole used to say she's scheduled to calm down. I'm like, "God, if I start scheduling, I'd become anxious." They have such totally different approaches and thank goodness. So I'm really good. I don't mess with it. And I say, "She's in charge of my calendar. Talk to her. I have no clue." And it's very liberating. It's really actually kind of fun to go on that transformational point to say, "Yeah, my security clearance doesn't go that high," which is a line that I learned from Dan, but it's so useful.

Steven Neuner: And to your point, Shannon, scheduling it would be the transactional, but hey, are they prepared? Do they know the purpose in the media? Are they going to have everything on time? Is Shannon going to have had time to do her Impact Filter to think through how she wants to show up, what she wants to do. That creates a transformational result that's hard to measure. It's hard to measure in just the, "Oh, we got something scheduled." Right?

Shannon Waller: Yes. It's funny because last night, last half-hour of the day, there was time for me to do the Fast Filters, and the notes that I needed from our previous multiple conversations were in there because God knows I would take half an hour to try to figure out where the notes were. She just had it all organized for me. I'm really good if it's all in front of me. I'm awesome. Going to find it, not so much.

Ryan Cassin: That's a really interesting observation and just another way that I see assistants as unexpected value: activation energy. I find that assistance can be that spark that you need to be able to get your work done. There are so many things that aren't in your Unique Ability that block you. It's fact finding. It's gathering information. It's putting all the resources in one place. But if those conditions existed where everything was already ready for you to add your Unique Ability to it, amazing things can happen. And so that's certainly something relatable for me. I very much lean on my assistant to provide the activation energy when I know I want to get something done, but there's a dreadful piece to it that is required to get started right up front that I can get help with and then do the part that I'm good at.

Shannon Waller: Yeah, they help get you over the dread factor. Oh my gosh, and thank you for saying that because I was like, there's something I wanted to share and I totally forgot what it was. You helped me remember, and that is that sometimes if I have a lot of email to do, or that kind of, where I have to slow down—not great at that. You know, be super thoughtful, make sure I don't miss anything. Sometimes, I will have—used to do it in person occasionally before lockdowns—but now Katrina and I will do it on screen and I'll go through my email. She'll be doing her stuff on the side, but she's my buddy. There's whole apps for this, and then I'll say, "Hey, does this sound okay?" Some little thing like, how do I close this off? How do I say no gracefully to somebody? She goes, "Nope, that's totally fine."

She has different relationship strengths than I do, so she gives me confidence to get that done. I'll be in Quick Start mode, to use a Kolbe term, and then I get in front of Katrina or it was Nicole, and then all of a sudden, all the detailed stuff, all the Follow Thru stuff comes into mind because they're almost like they're sharing their mental energy with me. Sounds a little woo woo, but I actually think it's true. But they help activate that. Until they were there, they were not a prompt in my system, but all of a sudden they show up, I'm like, "Oh yeah, this, this, this and this need to go on the list of things to do." And it's, yes, they're an incredible prompt and activator for those types of activities. Thank you.

Ryan Cassin: There's research that actually supports this idea that working together improves the outcomes and the results. One of the things that I also, just building on this idea that you know can be in a shared Zoom room with your assistant and bouncing things off of them, one of the things I do is in addition to that activation energy piece is I just verbalize to my assistant, "Hey, here's what I'm trying to do right now. Here's the thing that I'm trying to accomplish." Because one of the things I run into that's a challenge is sometimes I'll have 40 tabs open or 100 tasks in my task list or any number of things that my Quick Start energy wants to glom onto in that second and gets excited about.

But the reality is that I'm working on this one thing, and I sometimes lose sight of what that one thing is. I get distracted by the other things I have going on, and so my assistant can also just do, and it sounds so basic, but just keep me gently focused. That is a way that I get more productivity, more effectiveness out of my own work product. My assistant isn't doing a whole lot to add value there other than just this really basic, gentle reminder of what to be focused on, and sometimes I need that. Sometimes, I'm just burnt out or I'm a little spun up, and it really helps me remain focused and then present.

Shannon Waller: Oh, I'm laughing my rear end off because that's exactly- Katrina's, like "Um." I said, "What was I doing again?" And then she'll remind me. Great. Steven.

Steven Neuner: Oh, and I was just saying for anyone listening that has that guilty conscious mindset, this is a luxury. Think about the things that are important to you that would really drive your business forward that you just can't ever seem to get to. That time of them just sitting there with you, almost forcing you to get it done may be the most valuable investment you can make in your business in the next five years. It's not a luxury. There is significant ROI when we're doing the right things.

Shannon Waller: Oh my gosh, I love it. Well, so what this conversation has done for me is really kind of expand the value because I think people have "assistant" in a box. In our next conversation, we're going to talk about the difference between a virtual assistant, virtual executive assistant. Can't wait to talk about that, and we'll get into more details about who you're looking for and who you need to be, but to me this has really expanded the picture of just how useful an assistant can be that relationship, but then also how much more creative and visionary and less stressed and doing what your values are and living up to your growth potential as you were talking about Steven, just how instrumental that relationship is—well, can be and is when you have the right person. We covered even way more than I thought we were going to. This has been really exciting. So just to wrap up, what are you left with after this conversation?

Steven Neuner: I always enjoy this conversation because it takes me back to where we started, and it just takes me all into The Gain. I just want to say I've really enjoyed it, and if you're listening, you're worth it. You are worth it. Don't be me. Don't procrastinate. Get help. Let someone help you. It's going to be fine. It's going to be okay.

Shannon Waller: Awesome message. Great. Ryan?

Ryan Cassin: Yeah, I think there is so much uncertainty and people tell stories or fill in the blanks and it's not necessarily from a place of experience. And so I think de-stigmatizing and making this a well-understood role and bringing attention and awareness to the value of it, I think is certainly one of our priorities. We're fundamentally in the people business and having respect for the role and the way that it has impact on people's lives and their businesses and the people. The second order and third order effects. The people you don't even know you're impacting when you're working with your assistant or you're at your best. That's really, for me, a source of deep fulfillment in the work that we're doing.

Shannon Waller: I love it. Oh my gosh, I so appreciate the work that you are doing. I love that we can have this in-depth conversation, and in episode two, we'll be talking about more details about how to set this relationship up for success so you can get all the amazing benefits that we've talked about. Thank you both.

Steven Neuner: Thanks, Shannon.

Ryan Cassin: Thank you.

Shannon Waller: So, we would love for this to be an ongoing conversation. Do you have any questions or comments? Please let us know at questions@strategiccoach.com. We would love to hear and address these issues in future episodes, so we love your participation. Thank you so much for listening, and as always, here's to your team success.