The One Hire To Transform Your Business And Your Life With Steven Neuner And Ryan Cassin

May 4, 2023

Shannon Waller

In part 3 of Shannon Waller’s interview with Superpowers partners Steven Neuner and Ryan Cassin, they get into the details of finding and training a Strategic Assistant^® who will grow alongside you and free you up to achieve more, faster. Listen in to learn how to overcome resistance, invest in the perfect partnership, and foster open communication for long-term, transformative payoffs.

Show Notes:

Overcoming Resistance To Hiring An Assistant

Ryan and Steven note entrepreneurs often resist hiring an executive assistant because they wonder if there’s enough work to give them or how it would free them up, amongst other concerns.
Ryan’s process starts with identifying the entrepreneur’s Unique Ability^® and how they would spend their ideal day.
Ryan then asks the hiring entrepreneur about the types of people they most enjoyed working with and what traits and skills they had in common.
Once entrepreneurs get a picture of how an executive assistant could positively impact their available time and energy, they answer their own question of why they should hire one.

After Committing To Hiring An Executive Assistant, You’ll Need Courage

Steven refers to the Strategic Coach^® concept of The 4 C’s Formula^® and how it applies to entrepreneurs who make the commitment to hire, then must face the fearful stage with courage. Only when you pass through that phase will you develop new capabilities and experience the confidence of having achieved something difficult and new to you.
Shannon describes how each new Strategic Assistant hire was a new 4 C’s cycle for her that required courage to get through the fear stage of not knowing if she would find the right person.
The discomfort during the courage phase is worth all the new capabilities and confidence that result from finding the right-fit assistant.

Hiring An Executive Assistant As An Investment

Shannon emphasizes that entrepreneurs should have an investment, not cost, mindset and allocate the time and money into building a long-term relationship with their assistant.
The investment is not only in the other person, but in your own growth, productivity, freedom, free time, etc.
As with most investments, allowing time for the relationship with your executive assistant to develop is key to maximizing the payoff.

Where To Find An Executive Assistant

An executive assistant is not a virtual bot who only does the same handful of tasks over and over.
Ryan believes the goal is for the executive assistant to lead in the relationship, while the entrepreneur stays the boss.
Superpowers originally hired assistants from the U.S., but transitioned to exclusively hiring and training people from the Philippines.
Ryan compares the pros and cons of hiring locally versus internationally and recommends hiring assistants from the Philippines for their long-term career commitment, English fluency, and willingness to shift their work hours to match their overseas entrepreneurs.

Executive Assistants Who Want To Grow Their Career In Their Role

Superpowers cultivates the long-term career growth of their assistants through their Three Cs training focused on curriculum, coaching, and community.
If you’re planning on growing as an entrepreneur, you need an executive assistant who is also eager to grow alongside you.
The right executive assistant for an entrepreneur must be as aspirational as their entrepreneur.

Set Up A New Executive Assistant To Win

Along with the core activities to delegate—email, to-do, and calendar management—entrepreneurs should prepare how they will communicate with the assistant (using the Communication Builder tool) and what role they expect the assistant to grow into.
Entrepreneurs must be willing to be open, transparent, and coachable.
Entrepreneurs must be prepared to share the company goals and their personal ambitions with their assistants.

The Key Difference Between An Assistant Who Is Life-Changing And Somebody Who Helps Around The Business

If entrepreneurs want to accept an assistant’s help to achieve their stated goals, they have to accept their coaching in the necessary areas that will better serve those goals.
Sharing more personal habits and preferences may be uncomfortable but being transparent with their assistant is essential for success.
Entrepreneurs must give permission from the outset for open, two-way conversation about the work and also how to best work together.
With a solid relationship foundation, the assistant can create the most value for you, eliminating dangers, capturing opportunities, and maximizing strengths on your behalf.

The Best Time To Hire An Assistant Is Now

Entrepreneurs frequently say they need to get everything cleaned up before they can get an assistant.
In Ryan and Steven’s experience, this never happens, and it’s a terrible excuse anyway.
Consider that, for someone whose Unique Ability includes organization, no matter how you clean up your mess, that person will end up reorganizing and restructuring your processes to maximize efficiency anyway.
he activities that you’re incompetent or passing competent in may be a chore for you, but they’re actually a fun challenge for someone with the right Unique Ability.

Logistical Concerns

Because of the amount of access assistants must have to be effective, entrepreneurs must have non-disclosure and employment agreements in place to safeguard privacy.
Cross-device password software such as 1Password or LastPass will help assistants access various accounts without having to know the specific passwords for each.
Technical training has to include cyber security awareness training about phishing and other social engineering threats and sophisticated AI scams.

Finding The Right-Fit Assistant Takes More Work Than You Think

Many entrepreneurs take shortcuts during the hiring process, only interviewing a handful of people and asking the same questions they would ask for any hire.
Superpowers averages about a hundred candidate interviews for every position they fill.
Top candidates will complete at least four rounds of interviews and performance tests.
Though it sounds like a lot of time and effort, it’s absolutely worth the investment to transform what you can achieve.

Resources:

Superpowers Services

Unique Ability

The 4 C’s Formula by Dan Sullivan

The Gap And The Gain by Dan Sullivan

The Communication Builder

The D.O.S. Conversation^® and R-Factor Question^®

1Password

LastPass

Episode Transcript:

Shannon Waller: Hi. Shannon Waller here, and welcome to Team Success. I am back with Steven Neuner and Ryan Cassin of Superpowers. I'm really psyched because last time we talked about what kind of assistant is best for you, and now we're going to get into some of the, I want to call it nitty-gritty, of really, what does it look like when you have somebody? First of all, how are you going to find them? How are you going to prepare to hire an assistant or get some help, get some "Whos" to help you, which the two of you are brilliant and expert at.

Then in our next podcast, we're going to actually talk about the first 90 days. 30, 60, 90, which you guys have both very cleverly called crawl, walk, and run. So that's something to look forward to. So stay tuned for that. But today we're going to jump into actually doing some of the legwork, the preparation to make sure that this new investment that you're making is really going to pay off. So, I'm excited to jump into this topic. Welcome back, Steven and Ryan, and really happy to jump in today.

Ryan Cassin: It's great to see you, Shannon. Thank you.

Steven Neuner: Thanks, Shannon.

Shannon Waller: Great. So let's jump in with what's really important in terms of hiring and preparing for an assistant. How do people need to think about it? Then, we'll obviously get into what they need to do. I know for me, it feels like kind of like a big deal. How do I go about doing this? I may have decided I need this type of a person. But what's the next step in the thinking or decision-making process that someone needs to be aware of?

Ryan Cassin: Yeah, so we talk to a lot of folks who are at the very beginning of that journey. They sort of have this sense that they need an executive assistant. They're bought in on the idea of an executive assistant. But for them, the gap oftentimes is, "Well, how much time do I need with an executive assistant? Do I have enough for them to do? What would I have them do? How would we work together?" All of these sort of foundational questions, and those are great questions to think about and ask. But what we do in our process is actually zoom out to get started a little bit.

We love anytime we can talk to Strategic Coach clients because we all have this shared vocabulary around Unique Ability. That's really where we start the journey, is getting crystal clear and oftentimes reminding entrepreneurs of their Unique Ability and going really deep on that and asking, "What are the activities that are in your Unique Ability? What is your Unique Ability ideal day look like?" We get really clear on what a great day with none of the distraction looks like. Then we say, "Okay, well, what gets in the way of that?" This, for us, is the low-hanging fruit of what an executive assistant could start to help with. They say, "Wow, well, I would spend all my time building new relationships and being out there and being an advocate for the business and being a culture warrior in the business, except for email gets in the way. I'm always going back and forth on calendaring appointments. I've got to-dos coming out every which direction. These are the things that get in the way of me spending all of my time in my Unique Ability."

Then, we go one step further. We say, "Okay, well, think about all of the people you've worked with in the past and the people that you work really, really well with. What are the common characteristics or personality traits of the folks that you just have a great working relationship with?" Then, we bring all of that together and we say, "Okay, so let's get this straight. If you're spending your day in your Unique Ability doing these things, and the stuff that gets in the way right now is being handled by your executive assistant, and that 'Who' is really proactive or detail oriented or whatever it is that you really appreciate in the people that you work well with, what impact would that have on you?" That impact, that's your "why." That's your north star for why you're going to go through all the trouble of finding and onboarding and training up an assistant because, at the end of the day, that impact is the thing that you're looking for.

We've had some incredible feedback in the calls that we've had about what impact it would have on folks' lives. We've had people tell us, "I'll be able to do the work I'm good at, leading to the life I want," that, "I'm able to free up time to spend with my family, explore new opportunities, and recharge," or, "I'll be able to gain two new hours per day and stay on track and accomplish goals that are getting pushed to the side and keep important tasks moving forward." Those are the sorts of things, that that "why," it pulls you in the direction of the next step.

Shannon Waller: Oh my gosh, there's so much brilliant stuff in there. But the question, "What is getting in the way?" Oh my gosh. So first of all, reminding people that they have a Unique Ability, what it is, and the value that that provides, and then what is in the way. It's almost like you have this road in front of you with this big—I keep using the word "sexy" today—this big, appealing goal that you have, but it's cluttered up with all the stuff that you're not good at. And all the things you mentioned are 100% on my list—email, scheduling back and forth, all the things. And then, what impact would it have on you? By the way, to surround yourself with some of those best people, and I've just gotten a good reminder the last couple of months how critical it is to have people around you with whom you resonate.

It's, in my word, fun—because that's one of my core values—and nourishing and supportive and just what a difference that makes. It's hard to forget, but I manage to do that. Not that I took it for granted, but it's what I'm used to. So all of a sudden I get something where I'm not used to it. It's like, "Hmm, hmm, hmm, that's not fun." But that truly is your "why," and that's what's so important because if you don't know why you're doing it, you're going to get off track. You're going to stop. You're going to, I was going to say fail, but you're just actually not going to have the right mindset to make it a successful venture. Ooh, thank you.

Steven Neuner: One of the other things I think is interesting to this, Shannon, too is that for many, this is a "4 C's" moment, especially if they haven't had an assistant before. They're making a commitment. They're really going to have to lean into courage. New levels of freedom of growth require something that they haven't done before. The more that you're really clear on that purpose, it gives them that staying power to really take those next really important steps.

Shannon Waller: Fantastic. Just if anyone's not familiar with the 4 C's, it's making that commitment, which means you've really got to be clear on your "why" or you're going to back off that commitment. And then you immediately go through the courage phase, which feels terrible, does not feel at all like what you want to get to. Then, out of that, you develop the capabilities, and out of that comes the confidence. We all want to feel capable and confident, but we kind of forget that the actual "how we got to where we are now" is we were willing to make that commitment and willing to go through that period of courage.

As you were talking, Steven, it reminded me that every single time I've had a new assistant, I go through another version of this. I remember the very first time—I told this story earlier—of when I took over a part-time assistant by myself. I had a quarter, and I went to a half-person. That was scary as heck. But even when I decided, I shared an assistant with somebody else and then I decided, "No, I really do need my own full-time person." That was terrifying. That was a decade later, and that's when I worked with Nicole. Even when Nicole left and hiring Katrina, it was still scary.

You might think that once you've done it once, you're fine. It's still a 4 C's moment every time there's a new one. They could be different. Are they going to like the work? Are they going to be fun to work with? There's a whole new set of 4 C's, so it's a good reminder, but there's no reason not to do it because the payoff is so important and so worthwhile. I even thanked her today. It's like, I don't think I'd be sane unless she supported me.

Steven Neuner: In a future episode, one of the things I know that we'll talk about is that that is pain that I've gone through and there's some learning that I think that we're going to be able to pull forward for people to minimize how much time they have to spend in that courage phase.

Shannon Waller: Which is great because one of our episodes is going to be how to avoid the pitfalls, which will be very fascinating. Cannot wait for that one. Then, also what the best people do, how to make it win. So can't wait for those episodes.

But I'm not going to jump ahead. So that's fantastic. Thank you. The whole approach, how you are thinking about this, and again, I want to go back to our conversations earlier. This really is an investment, and it's not only an investment in another person, it's an investment in you. It's an investment in your future. And the cool thing about every entrepreneur is, what do we want to do with investments? We want to make them pay off. It's a completely different mindset than treating someone as a cost. If you're thinking about this as a cost, stop now. Don't progress any further. Do not pass go. Do not collect $200. This is just not the approach that you want to take. But this is an investment, and what we're talking about is how to really maximize that investment. The cool thing is, it's an investment in your own growth, productivity, goal achievement, freedom, time with your family, rejuvenation, clarity, all the things. That's really what it's an investment in. So again, that's another part of the thinking that I think is so key.

Ryan Cassin: Yeah, I think that's absolutely right. Investments come in the form of both time and money. Obviously, hiring people, there's a monetary cost associated with that. But the best investments, they don't pay off in 24 hours. We're not day trading for our executive assistant here. It takes a little time to develop that. So one of the things that we talk about is that the investment mindset needs to meet the Quick Start energy of entrepreneurs here, that we're going to have Quick Start and we're going to get lots of early wins. The onboarding process, it's something that you can bring that energy to, but you have to understand that it takes time for it to ultimately pay off. And one of the things that we try to talk about is, think about this as your personal quarterly rock. It could be your business quarterly rock as well, but that's kind of the timeline you're thinking. We'll talk more about what the specifics of that 30, 60, and 90 days, that first onboarding quarter, look like. But you've really got to make sure that that investment mindset, you're allowing the time for that relationship to develop.

Shannon Waller: That is so true. I literally cracked up when you said we're not day trading. That is so wise. It's like we want a quick win, but it's not going to be that quick. But there are things you can do to stack the odds in your favor, and I cannot tell you what a difference it makes. Holy mackerel. I would never not do it this way again, just saying. I would never not have a support partner, aka Strategic Assistant, aka executive assistant. Love it.

Now, the first thing to figure out, just to go back to the beginning, once you've got the mindsets in place, super important. The first thing that you guys talk about is, where will you hire your assistant? So you've determined the type, we talked about whether or not you're going to have virtual or what have you. Are they going to be U.S. based or something else? Then, you have to figure out what companies provide these services, so that's one of the important things to do. You guys actually have examined what's out there and what other companies are doing before you even got started, and you've really designed your process to address some of the issues that you saw. Do you want to talk about that for a minute?

Ryan Cassin: Yeah, of course. The first and foremost thing for us is that when working remote, a lot of folks think virtual assistant. For us, there's actual meaning to that definition of executive assistant. I think we've talked a little bit about this before, but it's so important, we reinforce this. Virtual assistant—that's somebody who can do that rote process again and again and again with no thinking. You can find those folks for $3 or $4 an hour, practically, online. That's not what we're talking about. We're talking about an executive assistant who ultimately can lead you in the relationship, where they're the leader and you're the boss.

And so we originally started hiring exclusively from the United States. The business was born out of the pandemic. We literally incorporated in March of 2020, which perfect timing for a going remote kind of world. But we have recently transitioned in the last 12 months to exclusively hiring in the Philippines. There are pros and cons to both approaches, but in the U.S., what we found is that generally there was sort of a stepping stone attitude about the role.

So while you get lots of pros when you hire from the U.S.—you get the ease of communication or at least the assumption that it's going to be easy communication. You assume written and spoken English is going to be fluent. You assume that culturally there's going to be a lot of alignment. What we struggled with is there's an attitude we found in the United States about this being a stepping stone role in some cases. Where we've gone with the Philippines is that this is a very career track, long-term, top-of-the-economy type role. What we gained was long-term relationships with our clients and our assistants, and we didn't sacrifice. We thought we were going to sacrifice English fluency. Not at all. We thought that we weren't going to find a servant's heart. In fact, we found a country with incredible servant's hearts, and it's just been a tremendous change.

One of the other things that I think sort of throws people off a little bit when they think about hiring internationally for this role is working the same time zones. There's very much a culture in the Philippines ... Now, you can also go to South American countries and you can find time zone overlap ... But there's very much a culture we found in the Philippines of working overnight hours. They'll turn their nights into the day and work exactly the same hours as you, so it's not sort of this asynchronous, never-building-a-relationship sort of thing. Everybody's comfort with Zoom and all of the digital communications tools, you wouldn't know where the person you're hiring is physically located. It really is completely seamless.

Shannon Waller: Wow, that's fascinating. And you're not the first company I know whose main, I was going to say staff, but team comes from the Philippines. It's interesting and some very, very, very successful companies. One of our coaches, her team comes from the Philippines. Person who coaches coaches that I work with and a good friend of mine, also his team is from the Philippines. And they just rave. I think it's interesting that the culture of the country is very much that servant's heart, as you talked about, and it's an esteemed position. Whereas I think to the U.S. and I'm in Canada, it's not. It's not seen as a high-level role that people aspire to. I think kind of what you're saying, it doesn't attract some of the right-fit people, but there, it's like you're held in high esteem if you have this role.

Ryan Cassin: Yeah. When you are career minded about this role, you seek proactively ways to grow within it. Our sort of secret sauce has been what we call our three Cs—the curriculum, coaching, and community. So the core playbooks and ongoing education, the one-on-one coaching that helps develop and feed the growth mindset, and the community of support that's so necessary for assistants who typically are in sort of an isolated role. They're usually the only assistant or one of very few assistants on the team. They don't naturally have peers on the sales team or the operations side of the business. So having a community is so critically important.

When you have a career mindset about it, when you want to grow, then you're actively seeking out more curriculum, you're actively accepting more coaching, and you want to be a contributing member of a community. The most important part in our hiring process is that growth mindset. It is making sure that you're hiring somebody who, because if we spoke a year from now together, my expectation is that every person in this podcast will have grown over the course of that year. If your assistant isn't growing with you, then the gap in skills and expectations and workload, that's growing over the course of that year as well. You need them to grow with you to be able to have success in that role.

Shannon Waller: Again, such a key point. If you're listening to this, you can't see my face, but I was like, "Oh my goodness," because one of the biggest dangers for entrepreneurs is when their team doesn't grow with them. Why did I create The Strategic Coach Team Programs? Because I saw the flipping gap between where entrepreneurs wanted to go and what they were aspiring to, and the team—because they didn't have an effective way to communicate— was way back in the woods trying to figure out, where is this dude going? Often, it was a dude. And so bridging that gap and finding people who are growth minded and then having means not supplied by the entrepreneur, let's be clear, what do they know about being a great executive assistant? Not much, but you provide that coaching and that training, and if they're aspirational, which they are, and see it as a career, then this is fantastic.

I love this because the entrepreneur's growth oriented, again, or they wouldn't be talking to you or us. So we're very like-minded in that way. Then, you give the actual executive assistants a means and a track where they can grow and get better through the curriculum, the coaching, and the community. So, great. I love this parallel growth track that you're talking about. Exciting. All right, so that's how fabulous your team can be. So say I'm hiring an assistant, trusting the people that you find will be great. What do I have to do? What's on my deck to be able to actually set myself up, set the other person up for success? How do I need to prepare, somewhat mentally, but also practically in terms of making sure that the i's are dotted, t's are crossed when someone starts?

Ryan Cassin: Yeah, absolutely. I think this is an opportunity to first and foremost dust off that Activity Inventory. If it's been a little while since you went through the Activity Inventory exercise, then this is an opportunity to refresh that and update it. And in addition to the core playbooks that we'll bring—email management, to-do list management, and calendar management and all those sorts of things—knowing how you're going to interact with the assistant and what you expect them to ultimately grow into, it's a really important road map for getting that relationship started. But I think beyond the activities, and the temptation is always to focus on the activities, and that's where everybody's head goes. But I think you really need to have a spirit of openness and transparency. That is so critical because if you're just giving your assistant the tasks, you are capping their ability to serve in that role for you.

And so be prepared to read them into your company's goals, including the big, hairy, audacious goals. Make sure that they're completely read in on day one to what your ambitions are personally and professionally. Help them understand what your vision for the future is for yourself and your business so they can play an active role in helping you get there, so they can connect today's activity to why that makes a difference in the long run. And it is surprisingly difficult for folks to do because I think that Quick Start energy just overrides and says, "Let's get to work," but that limits how much your assistant can work for you.

Shannon Waller: It's interesting, as you were saying, I was like, "Oh, why don't people share it?" Well, some of them, well, A, they're looking at the relationship as being more transactional than they are truly a relationship, which means there's an ongoing ... and some of them don't want to be coached because your assistant might say, "How is this in alignment with your goals that you talked about again?" And they might coach you and you're like, "Oh, I wasn't really expecting that. Thank you very much." But it's so key. And if anyone's gone through EOS, because with EOS process, it's like you share your vision, your VTO, your Vision Traction Organizer, every quarter and keep people posted with what's key. And you need to have that same mindset when it comes to your assistant. So whether or not they're in those meetings, you still need to be able to share that. That's a really cool point. Thanks, Ryan. Steven?

Steven Neuner: Yeah, one other thing on the coaching, Ryan talked about it very succinctly in how it applies to our assistants. What I will tell you, and before Superpowers was a business, Ryan and I, our assistants had helped train and mentor other assistants because people would say, "I want an Amber. I want a Fern," who were our assistants at the time. And so we were doing this as a labor of love in the beginning, but one of the things we discovered is, sometimes we noticed that the assistants could sit together and there would be some shadowing, mentoring, training, coaching community before it was a thing. But the thing that was often the gap when we found out the relationship didn't work, and we love these people, they're friends of ours, but what we found was is actually they wanted a Fern or an Amber, but they didn't want to make the changes that Ryan and I made in ourselves to be great team members to those assistants. And so coaching also can be for the entrepreneur, right?

Shannon Waller: That's what I'm thinking. Yeah.

Steven Neuner: Yeah. Because especially if they're new to it, especially sometimes bridging that gap is a very important part of that puzzle.

Shannon Waller: So that's going back to the transparency part that you talked about, Ryan, and some of us are naturally transparent. I'm thinking of the PRINT profile and innate PRINTs are pretty transparent. What you see is what you get. But other people are much more "keep things close to the chest." And I think that's a pitfall to avoid. And something that successful people do is, they are kind of more open and more willing to share. But what does that look like, and what changes did you guys have to go through in order to ... Sometimes it's like, "Oh, you want to know that?" We don't always expect that from someone in a particular role, so that could just be an aha moment. But what changes did you have to make? That's a really interesting point.

Ryan Cassin: Yeah. So I think one of the things that took me a while to warm up to, it was really easy for me to talk with my assistant about business tasks in a business context, and then to bring Amber at the time into what my vision for the business was and then the quarterly goals and take the time to really bring her up to speed on that and how it related to me. Where I struggled the most was bringing her into the more personal items. And so, what are the tells when I'm stressed out? How can you know? I've got to have awareness of what the tells are when I'm stressed out, right? I don't want her have to learn those the hard way. Although, to be completely honest, I think she had a lot of patience to learn, unfortunately, the hard way on that one. So I tried to get better about what are the tells when I'm stressed, what are my personal habits and routines and how does that fit in with my business habits and routines?

So what does my perfect day look like? Not starting at 9 a.m. and ending at 5 p.m. for instance, but starting at, I like to wake up at a certain hour, and I like to go to the gym, and then I like to have time to think and pray and meditate. What does my ideal day look like? What are my tastes and preferences about travel and restaurants and gifts? When I'm traveling somewhere, do I like the cheapest seat? Give me the middle row next to the lavatory, or do I prefer sitting at the front of the plane? Do I like a hotel that's $200 a night or a lot more than that? So those are uncomfortable conversations for some folks to have because you tip your hand about what your station in life is, what your economic station is at any given time, and that's a really challenging one. But a servant-hearted executive assistant wants to know those things because delivering the experience that you expect, that you want, that puts you at your best and allows you to perform your best is ultimately their goal.

Shannon Waller: Oh my gosh, I love that. Yeah, it's really true. If you're self-conscious about your station life, if you think you should be a different place than you are. So in Strategic Coach, we call that "The Gap": You have an ideal of how you think you should be, and you don't feel like you're measuring up, as opposed to measuring all your incredible progress. And you might feel like it's a little quirky. There's certain things I'm happy to pay for, I don't know why, but when it comes to rental cars, I'm cheap. I resent having to pay for them. So we all have our weird little things, and it's like, "Oh, Shannon, just get over it." Right? You said this kind of earlier is that you kind of have to be self-aware. You have to know what causes you stress, what doesn't. And it reminds me of an exercise—I'll put this in the show notes—of the Communication Builder. It's available off yourteamssuccess.com, which is, what's the best way for you to give information? What's the worst way? What's the most effective and least effective way for you to receive information? Way harder to change how you receive it than it is how you give it. And then one of the questions is, what do you need when you're stressed? Do you need time alone or do you want reassurance? And it's great to know that about the person you're working closely with, aka your assistant, because what they might need is completely different. Just to give a quick example of that. So one, because I used to coach this live in a teamwork conference, and entrepreneur said, "Oh, I need time alone." Guess what his assistant needed? Reassurance. So what did each of them do?

Well, when she was stressed, he would leave her alone. And when he was stressed, she'd be all over him offering reassurance. Neither of them got what they wanted until we actually did this exercise. So it was really kind of fun. Do you get hangry? Are you just make really meh decisions at 11:00 and you need a snack? I mean, it's weird. People say, "Oh yeah, no, I don't go into so-and-so's office without a granola bar or energy bar of some kind because I just know she's always hungry." It's like, "Well, that's useful to know." Now that's not going to happen virtually or remotely, but it's maybe you arrange for food to be delivered, who knows? But it's interesting, just being able to accept your own foibles, idiosyncrasies, preferences without judging them yourself is key to being able to share them with somebody else.

Ryan Cassin: And the overarching concept on that is permission. You need to set from the very beginning of the relationship to have a permission to have a two-way conversation, not just about the work, but about how the work gets done, who the people are, what their needs are, what their wants are. That's what maximizes the relationship.

Shannon Waller: Love it. Great. Steven, do you want to add to that?

Steven Neuner: You talked about being aware of your hangups, your bugaboos, whatever. I'm using my words, those little things. That's great, that's powerful, all the things you said. However, it ties into permission, but coachable, the assistant, a really great executive assistant is in a position to see things that you might miss in yourself. And so, are you able to actually receive coaching? Every workshop, we're in Strategic Coach, before anyone goes to a breakout, I say, "Okay, we're all in Strategic Coach. Are we all coachable?" And everyone laughs, but the thing is, that permission has to be given to truly be helped because we all have blind spots.

Shannon Waller: I think that's a really key point, which means you have to stay back—to your earlier point, Ryan—you have to be so connected to your "why." And indeed we have to be willing to shift, be open, be coachable to find another way there. Before, most of us, in some parts of our life, were Rugged Individuals. We're used to doing the brute force method. And especially the thing that is so true about an executive assistant, and I say this in the professional way, but it's an intimate relationship. This person knows your personality. They get to see when you're happy and when you're unhappy more than most people do, right? They're aware of what you're great at and what you're not great at. So if you're not- Neither Dan nor I are huge fans of the word vulnerable because he and I both consider it to just be open.

But there's an openness that's really important and that willingness to shift to make things better. And if you're really connected to your goals, how you do it, whether or not you do it at 9:15 or at 10 doesn't really matter, you'll make those changes. But it means you have to be willing to not be rigid and to adapt and to learn and to grow in order to be successful in that relationship and coachable with someone who knows your foibles, to use that word. Yeah, that's such a great point that coachability is key. Ryan?

Ryan Cassin: I think that's spot on. It truly is, time and again, we had the benefit of hindsight on hundreds now assistant relationships that have formed over the last three years, and that level of communication and openness, that attitude, that mindset, that preparation beyond just the list of Activity Inventory tasks, which is important, but it is the 101 version of what we're talking about here. It's the difference between somebody who describes their assistant as life changing or just somebody who helps around the business.

Shannon Waller: Right. And I've been really blessed because Katrina now and Nicole before, both of them became my friends, some of my best friends, they see me more than any other professional relationship I have, some of my other friend relationships, I see them more and sometimes they're my confidant. They get to see me when I'm happy. They get to see me when I'm not happy. So for me, I have two relationship strengths in my top five for CliftonStrengths, it's really important to have someone who cares about me and that I can care about. That's essential.

It's a personal relationship as well as professional relationship. I know not everyone wants to go there, but for me to do my best work, I realized really early on, I think I said this in episode one, I need someone who is into support, who cares. I'm going to be moving so fast I forget to eat. So I need someone who's going to care about me as a person, not just as a professional. And that's made my last two relationships in the last, my goodness, going on 10 years, so much better than the time before that. Steve?

Steven Neuner: And Shan, I think also to that point, wherever they're at on that barometer of how important that relationship is to them, without relationship, we know thanks to Dan and the R-Factor/D.O.S. model, we can't get into the dangers, we can't get out, so we can't create value. And so whatever that relationship looks like, it's got to be strong enough, healthy enough that that value can be created to the point where I'm a little bit contrarian and I love certainly the Activity Inventory and everything else, but I also know really wonderful entrepreneurs that all of that is resistance and barriers to them getting an assistant to begin with. And the right person, if we get all these other things right, the assistant can come in and actually organize you. You know what I mean? So I want to make sure that we kind of double down on that point because all those other things are great, and they certainly accelerate the value creation, but without that, whatever it looks like for you, that relationship, there's no dangers, no opportunity, no strengths, hard to create value.

Shannon Waller: 100%. You have to be clear on that or you don't give someone else the opportunity to create value for you, bottom line. But I don't think people actually get this until they've done it. There's something so liberating about saying, "Here's my mess, here's the stuff I really suck at, the stuff I don't enjoy doing." And their brains, because they're complementary and different than yours, are like, "Oh." You don't even have to explain everything. The things that are not up to their standards, they just want to go just fix it for you. They're like, "Your email's a disaster." I'm like, "Yeah, I know. Can you do something about that?" And they're like, "Yeah." And it's so phenomenal because you don't actually have to do all the figuring out, so you don't have to do the thinking for two people. You've got another very capable, competent, confident, intelligent human being who's going to look at it and go, "Oh, yeah, I got you."

Steven Neuner: When I've heard people say, "Well, I need to get organized. I need to get my house in order. I need to get everything cleaned up, and then I'll get an assistant." I'm like-

Shannon Waller: Forget it.

Steven Neuner: Yeah, that's not going to happen. I've known you long enough. It's just-

Shannon Waller: Don't clean the house before the house cleaner comes.

Ryan Cassin: I'm so guilty of that.

Steven Neuner: And truly in their Unique Ability, they would hate the way you organized it anyway. And if they're going to be in charge of it, in charge of you, right, then they're going to want to have more of a say in collaboration and how that gets formed and structured.

Shannon Waller: Yeah, and I'm sort of extreme. I'm really good or really not good. And so I just go, "Here." One story, and this was a physical example, but you can translate it into the remote. I work with one team, and this gentleman, this client was just a disaster when it came to organizing papers. His office just looked like a hoarder's mess, and it caused his team pain every time they walked by. And he kept feeling like it was so bad that no one would want to do it. They would have to physically restrain themselves from going in to fix it.

And I think that's just as true as inboxes as it is of physical piles. So when you actually really appreciate your own talents and other people's, then you're like, "Oh, you probably know what to do with this and I have no clue." And they're like, "Oh yeah." It's really fun. So let's wrap up with what else, preparation wise, you've talked a lot about how to think about it, being willing to be open, be transparent, be coachable, what are some other even super tangible things because there's legalities involved, there's pay involved, what are some other things that people need to set things up for success? And we talked a little bit about permission, but there's actually all of the logistical things that we need to get permissions for too.

Ryan Cassin: Yeah. So one of the things that is sometimes a mindset shift as well for entrepreneurs is giving permission to the assistant to come in and manage the inbox and a calendar. And for us, it's almost a red line that if you're not willing to open at least that up, then we're probably not the right fit for you, and you're probably not in the right place to get the most out of an executive assistant relationship. You might be thinking of that person more like a marketing assistant or a sales assistant, but not truly an executive assistant because that's the primary touchpoint. The calendar is your time, and the email inbox is oftentimes where the communication happens. So all that is to say, delegated access. A lot of people don't know that this is a thing, but your assistant will have his or her own login in their own email account, but they'll be able to see your emails and reply on your behalf and organize on your behalf.

So that's number one: full access to the calendar and the ability to manage it. And then just broadly, we like one password on the Mac or Last Pass, which seems to work well on all the platforms. This is a password-sharing tool, and it allows you to share passwords without somebody having the passwords themselves. So if you want to share access to information, then they don't necessarily have to know your password. This tool allows you to share it with them and fill in passwords for different websites that you have. So the more you can share passwords and access, the more equipped, the more tools your assistant has to help you with, literally. And then of course, non-disclosure agreements, employment agreements, all of those things. If it's not covered already in your employment agreement, you're going to want to have something that talks about non-disclosure and privacy.

And we get a lot of questions about that. Of course. And I understand the concern there. One of the things that we have found to be really important as part of the curriculum is at-length training about phishing attacks and the types of seemingly legitimate emails that your assistant is going to be seeing in your inbox saying, "Wire all of the money to these instructions." And that's the thing that keeps me up at night, is the overzealous assistant who's doing the "right thing," thinking that they're being helpful, but instead they're falling victim to a phishing attack. I worry about that a lot more than a truly bad actor. I think there are other ways that you can go about protecting yourself there. It's the good people who do the wrong thing that concerns me. So making sure that, you know, you can Google all sorts of different resources for training on how to avoid phishing attacks. But that's a really important one to us.

Shannon Waller: Yeah. Our tech team initiated a whole training, and getting everyone to do it, including the founders, one of them anyway, has been a challenge, but it's so key and it, they're getting more and more sophisticated, which is terrifying. Now this is weird, and I would imagine because people in the Philippines work remotely all the time, is that something that in general people are really up to speed with? Do you have a lot of additional training? What would you say about that?

Ryan Cassin: Yeah, we have some simulations, and we spend a few hours on what the most sophisticated, most compelling attacks look like. In the age of AI, it's only going to get more complicated, more challenging, more difficult to fight that. So, like so many things, it's a little bit of technical training, but more mindset training. Like, "Okay, contextualize what we're looking at here. Does this make sense? Does it connect to other things? What is the expected next step? And who should I authorize or get permission from? Who should I make sure I run this by to just get a second set of eyes on something?"

Shannon Waller: So wise and it's so cool that you're very proactive with that kind of coaching and training because when you said AI, I was like, "Oh lord," just going to 10 or 100x the complexity of it, and it's already pretty good. But yes, if you have the right thinking approach and you kind of know to look closely at the URL, it's pretty interesting. You can flush it out and if you know who to go run it by.

Ryan Cassin: That's right.

Shannon Waller: Even just personally with text messages, they're getting crazy. I'll get texts from family members, and my sister, Julia, will be like, "Nope, delete. That's definitely fake." All the things. But that's because the family member has people to check it with and that gives some confidence.

Ryan Cassin: Yeah. We're in the early days of all of this, but already you can see news stories about how synthesized voice is being used to make phone calls saying, "I'm in trouble. I need help. Please send me money here." And so it is multi-factor, it is getting much more sophisticated, much more personal, and that makes it a more complex challenge. That's the thing that keeps us up at night.

Shannon Waller: That's completely terrifying, just saying. But you're on it. Which is the most important thing. Steven?

Steven Neuner: Ryan can probably, in a minute I'll ask him, but what's the exact number of people on average that we interview before we hire? But I would just tell you that there's some work that needs to go into it, including some thought work that needs to be done before you interview the person because it's a different type of hire. And to really, really test and make sure that they're the right person for the right seat, it's going to take a little something different than what you would do for maybe other roles in your business.

Shannon Waller: Such a great point. Ryan, what would you say in terms of the number of interviews it takes to find a right fit?

Ryan Cassin: Yeah. Well, without exaggeration, our average is 100 to one. And so what we've had to build is an entire talent pipeline to find that many candidates. And then our first round of the interview process is to do an automated interview where the applicant records video in response to some of our initial questions. And that's really to kick out the people who are never going to be a good fit for this particular role. We then have a live one-on-one interview and then a second-round interview, and then we have a week of training where we get sample projects completed from them to make sure that we're seeing the performance that we can be comfortable with. So it's a really in-depth process and that's why that number of 100 applicants to start with, to get to the final right-fit candidate. That's why it's such a wide gap.

Shannon Waller: Man. All I could think of was, "I don't want to do that. I need a 'Who' for that." So I'm super impressed with your process, just saying, because that is a commitment. You were not kidding. I knew it was a commitment. I didn't know it was that big a commitment.

Steven Neuner: Yeah, it may be [inaudible 00:39:15] commitment for everybody, but the bottom line is, is it's something that should be taken seriously if you want to have a serious positive outcome.

Shannon Waller: Right. 100%. Just to circle back to the beginning of our conversation, when you realize the leverage that this person can have, when you realize it's a support person for you, right? Yes, it's for the business, but it's for you and how freed up you can be from the things you don't like doing. So you can focus that extra two hours a week or two hours a day even, that would be amazing, to focus on the business activities for which you'll actually have the biggest impact. It's not going to be going back and forth five times on the scheduling one appointment. It's clearing out your inbox so you're not stressed that there isn't money sitting there that you've just neglected because that happens, right? It's so powerful. So when you understand the real value of it, the "why" makes sense. The investment makes sense. The transparency and the coachability makes sense. But if you're not really clear on that, none of the rest of this would, I think is how I would look at it.

Steven Neuner: What it is not, looking at an email that takes 30 seconds to respond to 15 times in one day before you respond to it.

Shannon Waller: How did you know?

Steven Neuner: I know a lot of entrepreneurs and I am one myself.

Shannon Waller: Oh my gosh, it's so true. The amount of times we touch something, so to speak, is insane. It's because we don't know what to do with it. And it means I have to check my calendar, I have to go do this, and then I'm gonna lose track, and then I forget. Then I come back because I was switch tasking and it's like, oh Lord, yeah, I'm with you. Oh my gosh, this has been such an insightful conversation, and I love how broad we've gone with preparing for your first assistant. Well, for your hiring a new assistant because everything from the Activity Inventory, your Unique Ability, all the way down to one password and what's the name of the other one, Ryan? I didn't know that one.

Ryan Cassin: Last Pass.

Shannon Waller: Last Pass. What a brilliant idea. So that's a very cool way to share that. Be aware of some of the dangers like phishing and training people on that. I think your process really articulates how critical this role is and that if you're going to take it lightly, don't bother, is a little bit what I would say, but it can be so spectacular. Transformational is the word. Thank you for bringing that up again, Steven. This is an important investment. You're an important investment, and the process is worth investing in so that you can get that amazing right-fit human who's just going to blow things open for you. So thank you both, and I'm looking forward to our next conversation. Anything else to wrap up, Ryan?

Ryan Cassin: No. Thank you so much, Shannon. This has been a pleasure, and I appreciate you being such an advocate for the power of teamwork in this role.

Shannon Waller: It's my jam. I love it. Steven, any last words from you?

Steven Neuner: I would echo Ryan, and I would say, don't wait till you get your life or your house in order before you get help.

Shannon Waller: So true. Yeah. The right person will just look at that as food, as nourishment and opportunity to contribute and make a difference. So don't deprive them of it, is what I would say. I love it. All right, well, thank you both so much. Next time, we're going to talk about crawl, walk, run the first 90 days, and I can't wait.

Steven Neuner: Looking forward to it. Thanks, Shannon.

Shannon Waller: Thank you.