Unlocking New Levels of Freedom and Growth with an Executive Assistant with Steven Neuner & Ryan Cassin

0:01Boom! Shake the room, Fire Nation! JLD here and welcome to Entrepreneurs on Fire! Brought to you by the HubSpot Podcast Network, the audio destination for business professionals with great shows like inclusion and marketing. Today, we'll be breaking down how to unlock new levels of freedom and growth with an executive assistant. To drop these value bombs, I brought Steven Nooner and Ryan Kassin into EO Fire Studios. Ryan and Steven are co-founders of Superpowers. Together, they are unlocking the incredible leverage of executive assistants and helping fellow entrepreneurs achieve new levels of freedom and growth.

0:37And today, Foundation, we'll be talking about do we deserve an assistant? We'll talk about finding and training the right assistant, avoiding the top mistakes, and what high performers have in common, and so much more. And a big thank you for sponsoring today's episode goes to Stephen, Ryan, and our sponsors. Sales Evangelist, hosted by my friend, Donald Kelly, is brought to you by the HubSpot Podcast Network, the audio destination for business professionals. Each week, Donald interviews the world's best sales experts, successful sellers, sales leaders, and entrepreneurs who share their strategies to succeed in sales right now.

1:11A recent episode you should definitely check out is the five ways to do daily outbound with LinkedIn. Listen to Sales Evangelist wherever you get your podcasts. Hostinger is among the top web hosting and website creation brands in the world. See for yourself. Head to hostinger.com slash onfire and use code onfire for an exclusive 10 % discount. That's hostinger.com slash onfire and the code onfire. What's up, Fire Nation? As I mentioned in the intro, we're going to be talking today all about unlocking new levels of freedom and growth with an executive assistant. And as I mentioned, I have both Steven and Ryan on the mic today.

1:52We're going to start with Ryan today because, listen, Ryan, a lot of people in this world have something that I like to call worthiness issues. So tell us now, do we deserve an assistant? Yeah, it's a great question. And the answer is probably yes. And I'll let Stephen hit on the psychological traps we see some entrepreneurs get into in just a second. But the one thing that might make you undeserving of an EA is the wrong mindset about this person's role. The best EAs are combining organizational savvy, strategic thinking, follow through. So, you know, in our conversations with entrepreneurs, we often hear things like, I've got this menial work, this low value work, stuff that just has to get off my plate.

2:42But that is a mindset trap. If you have the right EA, the work you hate doing and probably aren't even very good at is someone else's superpower. So in terms of deserving an assistant, that perspective of valuing the work itself and elevating the work you're not good at to your EA is a big distinction. It shifts what you're looking for from a warm body you can find anywhere to demanding a highly selective and thoughtful process about it. And from what I would say, what I'd add to that, just from a psychological standpoint, a lot of times entrepreneurs have uncommon paths. That's how they end up being entrepreneurs through life.

3:21Sometimes those paths are related to some sort of trauma, and that trauma can lead to people feeling like they're not good enough or not worthy. And while that is a blocker to a lot of really great things, as long as you see yourself as not good enough, you'll always view an assistant as an expense and not an investment. I love that phrase. In fact, I think you may know that I have a book called The Common Path to Uncommon success because there always is that both uncommon and commonality that's surrounding us all when we're doing these things, which Ryan really leads me to the next question because there are all kinds of assistants that are out there.

4:02And I think that's one thing that is incredibly overwhelming to a lot of people. They're like, man, I don't even know where to start. So how do we know what kind of assistant is right for us? You hit it right on the head. And I think this huge range from VA, like virtual assistant, to EA, executive assistant, and even beyond, I actually think that that causes tremendous analysis paralysis for entrepreneurs. And it leads to them delaying or procrastinating on such an important hire. For us, we see a big difference between virtual assistant and executive assistant, even if they're both hired overseas.

4:43If they're domestic, it doesn't matter, right? There are lots of different services in this space to help you find your VA or EA. But also, depending on your need, that person might be on a community marketplace like an Upwork or Fiverr, or you might need a search partner to find that really perfect fit. And I think the most important thing is to know who you're hiring. And for us, there's a three-piece framework we talk about. The first P is projects. And for that, dedicated marketplaces where you match a specific need to someone willing to do that work is perfect, right? So design, video editing, copywriting, projects.

5:23Go to the marketplaces for that. The second is processes. And for that, a VA is a really great fit. This is where you need consistent execution on sort of a known step-by-step process, right? You don't need the process to improve. You don't need creative thinking. You've got known inputs and outputs, and you don't need the critical analysis about the work itself. And the third P is proactive, and this is where you hire an EA, an executive assistant. That's where we think you're getting simultaneous freedom and growth from, by the way. This is a person who sees around the corner, your assistant's taking the lead in the relationship.

5:56They're making decisions on your behalf. They have context and skills to use good judgment for you. They're really working side by side in the trenches throughout the day with you on your most important goals and tasks. And what I would just add to that is a proactive EA, this is where, to me, it really gets fun. This is where freedom and growth occur, which is a proactive EA knows the distinctions between all three that Ryan talked about. And without you even prompting them, they know when to pull in other people. They know when that fiver person's needed. They know when it's outside of their unique ability or skill set.

6:30One thing that a lot of people freak out about is like, okay, now that I'm understanding, how do we know what kind of assistant is right for us? And, you know, there's obviously some good processes about how to find the right VA, EA, et cetera. And I want to kind of talk a little bit about that, Ryan, but I really want to get into the process of the training, the right assistant. Because I think a lot of people are like, man, I don't have experience that I'm not trained to train somebody. I don't have education in that. So let's talk about that process, you know, of the finding, but even more importantly, the training of the right assistant.

7:06Yeah. So our experience has been that the big unlock here is the, what we call three C's, coaching, curriculum, and community. Those are the three things that make such a huge difference in this role. And so, you know, one of the big challenges with hiring for this role is that you can't go to college or university. There are very limited training programs available to say, I am a great executive assistant, right? And what often happens is people make the mistake of taking past experiences in EA and thinking that that is setting someone up for success. Our experience has been that oftentimes you're hiring someone else's work style, someone else's mistakes and bad habits.

7:48Those all creep into the relationship. So curriculum, coaching and community, so critical. You can find great curriculum resources online. There are programs dedicated to developing executive assistants, coaching that can either be from somebody you're partnering with to find this person or one-on-one, but the key there is feedback and closing the feedback loop frequently, especially early in the relationship. And then community, that can be online communities of fellow executive assistants on Facebook, LinkedIn, And Instagram has these types of communities. But having that peer support and learning is so critically important.

8:24And what we've seen is in the first 90 days, there are sort of three different phases. And it helps set the expectation for what you're getting in the relationship. The first 30 days is dedicated just to knowing you. Basic stuff. What's your company? What do they do? Who are your direct reports? Key customers? That sort of thing. Next 30 days, sort of at the 60-day mark, understand you. And what we mean by that is you're developing common context and vocabulary. So when it's email Bob about that one thing that you tell your assistant, your assistant says, oh, OK, I know who Bob is and I know what that one thing you're talking about you want me to email about.

9:00And then the next sort of highest peak of that first 90 days is, are we seeing anticipate you? Is your assistant beginning to look around the corner? Are they proactively taking things off your plate? Is the nature of the relationship changing where the assistant is leading in the relationship and you're getting the leverage and the freedom that comes from that? Wow, I love that idea of the proactively taking things off of my plate. Sounds like gold. Stephen, what do you want to add? What I'd like to add is I just have the incredible privilege of getting to coach a lot of entrepreneurs. And I've lived in this community for a long time.

9:40And what makes us great is also our Achilles heel. And we have the ability to really get inspired by little things, such as we meet the girl at the coffee shop and we say, she's the one. She would be the perfect assistant for me. It would be so wonderful. We just totally connected and she's got all the right skills and I'm just going to hire her. That is a quick shortcut to short circuit, a really potentially high impact hire. If I could just say anything on this, I would just say, do the work or get someone to do the work. There's so many institutional best practices, but you got to be intentional if you really want to get the leverage out of this relationship.

10:26Fire Nation, value bombs are being dropped everywhere, both Ryan and Steven in full effect. We have so much more of this coming when we get back from thanking our sponsors. Happy 2024, Fire Nation. Q1 is here and that means new goals, more growth, and upgrading your day-to-day workflow. While most sales folks are stuck in the mud of manual scheduling, digging into data, and tracking down leads, let me share a better way to win so you can get a jumpstart on your year. The new HubSpot Sales Hub is smart sales software for today's multitasking reps. It's built to help you manage every stage of your sales pipeline with ease.

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12:44Gentlemen, we're back. And Ryan, I want to talk about avoiding mistakes because when we avoid mistakes, it's amazing. It saves us time. It saves us energy. It saves us money. So tell us, what are those top mistakes that we can avoid? Totally. And avoiding mistakes in this role means that you can potentially have a much longer, much more productive relationship with somebody who is going to be working side by side with you. The average tenure of a typical executive assistant in the U.S. is only 23 months. But all the best EA relationships we know are like years and years and years, right? It's practically the point where you couldn't imagine working with anyone else, right?

13:26Most commonly, we see entrepreneurs hire their EA only after their redlining. And all that does is take it from a strategic hire to a reactive hire. So we're no longer fireproofing our businesses, right? You're calling in a five alarm structure fire here. And it's made worse by entrepreneurs' tendency to have really high quick start energy and then low follow through. That's a winning formula for growing a business, of course. Like we need that entrepreneurial energy, but it's a disaster when you're already overwhelmed and then, you know, hire an EA after the fact. So there are five big categories of mistakes we see when hiring an EA.

14:05The first is a lack of trust. So think of trust as like a bank, not a vase. Mistakes happen. So when they do, it's a withdrawal on that trust that's been built, not a complete shattering of that trust. The second is impatience. We believe good relationships happen in a crock pot, not a microwave. Cloning, that's a biggie. Entrepreneurs say, if only I could find someone just like me, things would be better. But we think that you have to look for your complement, not your clone, someone who possesses the skills you don't have. The fourth big mistake is low expectations. Is this person going to be menial or is the relationship going to be meaningful?

14:44Is the work they're going to be doing menial or is the work they're going to be doing meaningful? And then the last one is insecurity. So projecting yourself as perfect and having all the answers. Being in control is usually how that shows up. And that undermines your assistant's confidence, but it also dramatically reduces the activities he or she can help you with. And related to that, I would just say that shows up another way, which is looking good. Entrepreneurs, especially they bootstrapped it, they get in the habit and maybe a trap of trying to be all things to all people. The more they can kind of put down the persona of seeming like they have it all together, the more the EA is able to support and fill in those gaps.

15:23My assistant knows when I'm likely to get hangry and when I start acting like a turd, that it might be time to like, hey, let's schedule in some breaks for him or he needs some free days. Get him that Snickers bar. Come on. Get him to Snickers bar. I love this. And what's really cool is that Ryan and Steven have been able to see and work with, and they are high performers. And so they've recognized that high performers have a lot of things in common. So Ryan, let's start with you by going through some of the habits that the highest performers all have in common that you've identified over the years.

16:04Yeah. So two things that we've observed that I want to share. The first sort of a quick start hack for entrepreneurs looking to take that next step, but feeling overwhelmed by it. And the second is a mindset to be more effective in the relationship over time. So that hack, right? One of the easiest tricks is in this remote work world, being able to find somebody, whether they're remote in the U.S. or overseas, wherever they are, is that you can have your assistant shadow you through Zoom throughout the course of your first week together, right? So just share your screen in an open session throughout the day and let your assistant learn through osmosis.

16:42And this is so great because, A, they get this beautiful window into your decision-making process, what your typical day looks like, how you work through your inbox or calendar or to-do list, whatever it is on any given day. But also, it's no additional work for you. You've hired this EA, and you're still sort of for the first week operating the way you always have, the way you were before you had the EA. It's a really quick way for your assistant to get a peek over your shoulder. And then the mindset. In this relationship, I touched on it earlier, but the executive assistant is the leader and you're the boss.

17:17So that means you set the parameters of the relationship, but your assistant is the one pulling you forward. That's what a high leverage executive assistant does. It means they're in control and accountable for areas that are their responsibility. So things that were previously your calendar, your task list, and your email inbox are now your assistants. And the most effective entrepreneurs, they understand this. They don't look down on those tasks as things that get in the way. They see them as elevations to their assistant superpower. As having had the opportunity of coaching some of the highest level entrepreneurs in the world, both ambitious and just growth-minded in general, the common DNA that I see of the very best entrepreneurs, are there others focused?

18:00And so what Ryan hasn't mentioned here is we have seen a pattern of more and more of the top level entrepreneurs, recognizing the freedom growth that comes from a great executive assistant role. And they're thinking of their key people in their business and looking to provide that same level of freedom and growth in their roles through this relationship. Now we've had value bomb after value bomb dropped, and you might think that I've squeezed you guys dry, but I know you have more to give. And Ryan, That's what I want right now. I want to start with you and have you give us one single key takeaway from our entire conversation today.

18:38And then, Stephen, you can use this time to kind of really stew and find the best one as well. But what's that one key takeaway you want to make sure our listeners really get from our conversation? You are deserving of an executive assistant. The right executive assistant will deliver new levels of freedom and growth. but you have to have the confidence to see the relationship through and put your assistant in the leader role. Freedom and growth can happen at the same time. Do not buy the lie that it's a teeter-totter. And if you go for growth, you have to give up freedom. Or if you go for freedom, you got to sacrifice growth.

19:12They are both possible. And the EA is a key piece of that puzzle. Fire Nation, you're the average of the five people you've been spending the most time with. And hello, You're hanging out with SNRC and JLD today. So you only need two more cool people to keep up that heat. So for links to everything we talked about, visit eofire.com. Type Steven or Ryan or both into the search bar. The show notes page will pop up with links to all that jazz. And Steven, Ryan, where would you want Fire Nation to go to learn more about you from you? What is your call to action for Fire Nation today? We love sharing our experience about EAs.

19:53We love sharing best practices. We'd love to have a conversation with any of your listeners who want to be able to take that next step. So visit superpowershq.com, superpowershq.com. And let's set up a call. Let's chat. Steve and Ryan, thank you for sharing your truth, your knowledge, your value with Fire Nation today. For that, we salute you both and we'll catch you on the flip side. Thank you, sir. It was fun. Hey, Fire Nation, a huge thank you to our sponsors and Steve and Ryan. and for sponsoring today's episode. And Fire Nation, successful entrepreneurs are great at not one, not two, but three things.

20:30I'm talking productivity. I'm talking discipline. I'm talking focus. Follow one course until success. That's why I created the Mastery Journal so you can master productivity, discipline, and focus in 100 days. Well, I almost said three days, but no, it's 100 days. Step-by-step visit themasteryjournal.com. I'll catch you there or on the flip side. Sales Evangelist, hosted by my friend, Donald Kelly is brought to you by the HubSpot Podcast Network, the audio destination for business professionals. Each week, Donald interviews the world's best sales experts, successful sellers, sales leaders, and entrepreneurs who share their strategies to succeed in sales right now.

21:07A recent episode you should definitely check out is the five ways to do daily outbound with LinkedIn. Listen to Sales Evangelist wherever you get your podcasts. Hostinger is among the top web hosting and website creation brands in the world. see for yourself. Head to hostinger.com slash onfire and use code onfire for an exclusive 10 % discount. That's hostinger.com slash onfire and the code onfire.