Are you an entrepreneur struggling to manage your workload? Are you considering hiring an executive assistant, but not sure where to start? Look no further! In episode four of this six-part series on all things assistants, Shannon Waller and Superpowers partners Steven Neuner and Ryan Cassin discuss the benefits of having an executive assistant and share practical tips for developing a successful relationship with them in the first 90 days. You’ll learn about coaching and scoring systems, the importance of communication, and the pitfalls of overloading your assistant. Listen now to unlock new levels of productivity, freedom, and growth in your business!
The first 90 days with your assistant will determine your future success together.
During this time, pace your expectations. Your assistant should progress from simply knowing your expectations to understanding and anticipating your needs.
They should be the leader in your relationship, but you’re the boss.
EAs are there to manage your workload and priorities, free up your mental energy, and give you the space you need to focus on your Unique Ability®.
You need coaching just as much as your assistant does. Many entrepreneurs lack confidence when hiring because they don’t know what makes a great assistant or how to coach someone on something they’re not good at themselves.
The EOS® scoring system resolves these issues by having entrepreneurs fill out a questionnaire on their needs and receive coaching on their relationship with their assistant that encourages progress and growth.
This process helps entrepreneurs focus on progress over time rather than a single interaction, and gives feedback to assistants that will help them improve their relationship with their entrepreneur.
Entrepreneurs often struggle to give feedback and don’t invest enough time into their relationship with their assistant.
Weekly coaching sessions and daily sync meetings are opportunities for assistants to lead the conversation and help their entrepreneur prepare for the day.
Building a great relationship begins with establishing great communication. You and your assistant should develop a common vocabulary and work to understand each other’s communication styles and preferences.
The better you understand each other and the more your EA is able to anticipate your needs, the more freedom you’ll have.
Avoid assigning additional tasks to your EA beyond their designated role. They’re there to support you in your Unique Ability. Everything else should be delegated.
Likewise, your EA should focus on their Unique Ability, which is supporting you. Don’t let them become a shared resource amongst your team.
Shannon Waller: Hi, Shannon Waller here, and welcome to Team Success. I am back with Steven Neuner and Ryan Cassin of Superpowers. I love this because this is our podcast number four in our special executive assistant series about how to really make this a win, how you can be successful in setting this up.
So last time we talked a lot about mindset and preparation and how to think about it, who you need to be, all the things. And the fact that it’s an investment, that the ratio is at least a hundred to one in terms of candidates that you would look at to actually get the one that is actually going to be your right-fit. So my first thought is “Let’s have someone else do that, shall we?” Because that’s a lot of work, and that’s your area of expertise.
But now, assuming that you have a great ‘Who’, a great someone, then what? And that’s really what we’re going to dive into today, and crawl, walk, run, the first 90 days. I’m excited because—and you mentioned this last time, Steven, or maybe it was you, Ryan, sorry, I don’t remember—where it’s like where does the QuickStart meet the need for immediate gratification, but in fact it does take some time? How can you really... I’m going to say pace yourself, but “pace your expectations” is probably the accurate way to put it? Then how do you set it up for success? Because how you start is how things tend to continue, and I think it’s really important to do it wisely.
So how do you guys want to kick this off? Where should we start with this “crawl, walk, run” conversation?
Ryan Cassin: Absolutely. Well, excited to talk about it. The first 90 days, probably in any relationship, is where you get the confidence, you get the feeling that things are on track. You begin to get the shimmers of view of what the future holds if the role continues to develop. That’s certainly the case with the executive assistants as well.
The biggest thing we have seen is that entrepreneurs are willing to put the time in. They will look at things through a 90-day lens and say, “I understand that this quarter is building the relationship for great things to come,” but they still want to know that they’re on track. They want to know at the 30, 60, and 90-day mark that the relationship is growing in the ways that we would expect it to for good things to happen.
And so, the way that we think about it is in the first 30 days, your assistant should know you. We’ll talk about that a little bit more, but the second 30 days, so that’s 60 days into the relationship, your assistant should understand you. Then at 90 days, they should anticipate you.
And so, when you think about know you, this is the basic stuff. What does your company do? Who are the key clients and vendor partners? Are you married and do you have kids? What are their birth dates? The basic stuff, but the really key information that’s going to allow the relationship to grow.
Understand you. What that is for us is common context and vocabulary is beginning to form. And so, when you say, “Email Bob about that one thing,” your assistant should know who Bob is and what you want to talk to him about. You’ve developed a shorthand and communication is now getting easier.
Shannon Waller: That’s what I was going to say. It’s like the little shortcuts, the shorthand. That’s even a better way to talk about it. Then it gets faster, which for a lot of people is really key.
Ryan Cassin: Absolutely. That’s where the relationship finally starts to get a little bit easier and you’re starting to get in the groove with your assistant. You feel like, “All right, this is going places. We are on track.” And so, understand you at 60 days and then 90 days anticipate you. That’s where it kicks into the new gear. That’s what everybody wants and is striving for. The number one quality that everyone asks us for in an executive assistant is taking initiative, is being proactive. They want their assistant to see around the corner. The assistant becomes the leader in the relationship while you’re the boss of the relationship, right?
And so, anticipate you is that magic moment that should begin to happen in 90 days. We can go through the specifics of what we’re asking our clients, the way that we’re ranking the relationship and putting value on it. But that’s the high level, know you, understand you, anticipate you.
Shannon Waller: So wise. I think we’re going to bounce around a little bit on this, but I want to make a distinction, because this is what you’re working towards. They become the leader. You are the boss. Can you please dive into this? Because I think this is an absolutely essential way of thinking about it and talking about it. I was even saying this today with a group when I was on with Katrina, who’s my EA. It’s like who do you think manages who? I’m not managing Katrina. Are you kidding me? That would be stupid and ridiculous. She’s managing me. Yes, I’m the boss, but she’s the leader of my day-to-day activities and my life, my relationships, all the things.
So is that what you’re talking about, or how do you guys talk about it? Because I think this is such a key distinction and it’s lovely when it happens. This is something to aspire to.
Ryan Cassin: Who’s the more organized between you two? Who’s the more detail-oriented? Who understands where you want to be and how you’re spending your time, and all of the demands placed on you and your time and all the things that you need to get done? Your assistant is the person who understands these things. Your assistant is the person who’s keeping track of all of these things.
Of course they’re going to be the person who leads in the relationship, who helps you understand the big picture, helps you get a clearer view of the field so you can make the right decisions and set the right priorities. So your assistant is the leader and you’re the boss.
Shannon Waller: Oh, my goodness.
Steven Neuner: Even if they’re good, even if you truly are in command of those things, sometimes it’s hard to read the label when you’re inside the jar. And so, the assistant sits outside and has the broader visibility of all the things.
Shannon Waller: That perspective. That is so great. Even if someone... I’m thinking about Kolbe profiles now, which measures how you strive and how you problem-solve. Even if you do have a lot of mental energy for being specific and detailed and research-oriented and also organized, are you actually applying those talents to your schedule, to your time, or are you, I hope, applying those talents to solve your client’s issues, those complex problems that you are uniquely suited to solve?
Guess what? If you want to actually have mental energy freed up to take care of them, you need someone to back you up. We don’t have unlimited amounts of mental energy. It’d be far more profitable for you to be solving their problems than your own, if that makes sense. So that’s why it’s so important. Even if someone does mentally strive that way, is that where you want to be using your mental energy? Probably not.
Ryan Cassin: That is spot-on. That is so brilliant.
Shannon Waller: Yay. I love that story. This one conversation right here will convince some people, who are like, “Well, I do it.” It’s like you can, but will you and do you want to? Can, want, and will are all different parts of the mind. Yes. Are you capable? Well, sure. You’re smart, you’re not dumb. Of course you can. Do you want to? Probably not. Will you? No, because you’re too darn busy, hopefully, creating value for other people with your amazing talents.
Ryan Cassin: Is it your Unique Ability to be doing those things?
Shannon Waller: Probably not.
Ryan Cassin: Full stop.
Shannon Waller: This is a really key distinction. Just because you can doesn’t mean ... And I don’t use this word often, but doesn’t mean you should. And as a statement of capability, like, that’s nice, so what? What is the highest and best you should be, to use that expression? How can you create the most value and impact in the world? For someone else, it’s going to be managing you, but for you it’s going to be managing somebody else. So I think that’s really, really, really important to focus on. So just because you can doesn’t mean you’re actually the best person to be doing it.
Steven Neuner: We get hit a lot of times as entrepreneurs. We can be on a bit of a rollercoaster ride. We might be taking a twist and a turn and a loop-de-loop all at the same time. And so, it’s real easy for us to get disoriented. And so, again, back to that broader visibility and keeping the priorities in order so that you don’t get destroyed and start running off down the wrong course.
Shannon Waller: Oh yeah. A lot of us are “Squirrel!” We’re distracted by bright, shiny objects. Even Dan will ... If he gets distracted in the middle of something, he said, “Oh yeah, a squirrel and a boa just ran by.” He’s got this lovely, charming way of putting it. But it’s really true. When you’ve got someone who’s going to hold steady, who’s going to reflect back to you what it is that you said your priorities are going to be, that’s exciting. You’re like, “Oh yeah, that was the bright, shiny object. I need to refocus on this.”
I think we forget that, and we don’t necessarily look toward our EA to be the one to reflect that back to us. But in fact they’re the best person because they’re the closest to us.
Nice. This is so good.
All right, so let’s go back to the ‘crawl’. Let’s go back to the first 30 days. What does that look like? I love how you built it up, Ryan, like what we’re building towards. So what does it look like in terms of when we first get started with someone? What does it look like when it’s working really well? What kind of warning flags do we need to pay attention to if it’s not? How does that land?
Ryan Cassin: Yeah. And so, we’re borrowing the EOS approach to how we score individuals that we’re working with plus, plus/minus, minus. What we’ll do is we’ll check in with folks at the 30- and 60- and 90-day mark. Really the key is we’re teaching to the test. We want all of our assistants to know exactly the questions we’re asking in that meeting so they can proactively ... Again, taking that leadership role in the relationship, they can make sure that they’re on track.
And again, knowing that you’re on track, even if you’re not getting all of the world life-changing results that you expect in the relationship at 30 days, knowing you’re on the right track gives you the confidence to continue investing in the relationship. It’s that extra boost of energy.
The other piece of checking in at the 30-, 60-, 90-day mark, it’s an opportunity to reinforce that feedback loop of “curriculum, coaching, and community”. So if somebody is off-track on a particular dimension, then you can bring in additional resources. You can incorporate it into how you coach up that assistant and make sure that it’s a point of emphasis, because you may be a brilliant assistant, but of course everybody has different natural strengths and weaknesses and things that they’re going to have to improve. Or, conversely, the entrepreneur may say, “Hey, this is a really important point of emphasis for me for this relationship to work. I want to really dig in deeply here.”
Shannon Waller: Yeah.
The first thing that strikes me is that the entrepreneur is not left alone with making sure that that relationship is successful. So basically you’re their buddy. You make sure that it’s not just going, “Here’s your person. Bye.” It’s not like that. You’re hand-holding, and I don’t mean that in a disparaging way. It’s like you are really taking everyone by the hand, both sides, and making sure and building towards success. So that’s cool.
Again, I think this is really key, and I think this is a huge source of a lack of confidence for entrepreneurs, is they don’t know what makes a great assistant because they’re a terrible one. Let’s be clear. So how can you coach someone on something you don’t do a great job of for the most part?
Then there’s that horrible feeling of trepidation. You’re like, “I don’t know what the hell I’m talking about.” But you guys really alleviate that fear. You solve for that problem because you have the curriculum, the coaching, and the community and the check-ins. So you’re looking for all pluses.
So if anyone’s not familiar with the EOS scoring, and this is on their people analyzer, plus is “Thumbs up, all good”. Plus/minus is, “Comme-çi, comme-ça, okay, adequate, whatever”. Then minus is “Things aren’t working so well”. That’s how you use it, too. Is that right? And so, are you looking for all pluses? What’s your scoring ratio? How do you encourage people to be successful?
Ryan Cassin: Yeah. We’re certainly looking for all pluses. In a perfect world, that would be what we’re striving for. What we’re really looking for is things that are plus/minus or minus to become pluses by the time we have our next meeting. We want to see that progress, because one of the other things that we’ve noticed about entrepreneurs, with the growth mindset, with the expectation that their team continues to get better and more capable as they grow and they learn, is entrepreneurs are really patient if they know that progress is being made on the things that they care about. They have confidence that the relationship is growing and developing, and the person is growing and developing in a way that’s going to lead to the good outcome.
So you can be a QuickStart individual and want to get right to work and get right at it and be full of ideas that you want to go execute on right now. But I don’t think QuickStarts get the credit they deserve with being patient with their people if they’re seeing that signs of progress and growth. So we’re looking for those signs of improvement.
So in the first 30 days, for instance, we’re making sure that the assistant is, again, leading in the relationship, coordinating regular meetings with their entrepreneur, making sure that that regular communication cadence and that muscle is being built, that they know their entrepreneur’s likes and dislikes, that they know their routine, they know their personal strengths and weakness.
Overall, it’s about 20 different dimensions that we’re scoring on, but we always ask the same question at the end of every one of these, and that’s “I have confidence my assistant will help me achieve new levels of freedom and growth in the future”. And that confidence question, that is the big one that we emphasize because it tells us “I’m willing to keep investing, I’m willing to keep growing, I’m willing to keep spending the time, because I’m confident that the future looks better”.
Shannon Waller: Damn. So this is a questionnaire that the entrepreneur fills out on their assistant.
Ryan Cassin: They’re getting a one-on-one meeting with our Chief Happiness Officer. Our Chief Happiness Officer, she’s responsible for having these conversations. What’s so interesting is that by having the same script in these 30-, 60-, 90-day meetings across hundreds of entrepreneurs is that she gets to be a really great coach to them, to their specific situation, their specific needs.
So that coaching, that coachability, it certainly has to happen in the direction of the assistant, but this is our opportunity to get three really strong opportunities to meet with our entrepreneurs and coach them on how to be better in the relationship as well.
Shannon Waller: I’m sure your Chief Happiness Officer finds areas of improvement. “Does the entrepreneurs ever score themselves?” is a question I have.
Ryan Cassin: That’s a good question. No, we don’t ask them to score themselves. That would be a great addition.
Shannon Waller: It might be a shorter one, but it might be interesting.
Steven, I know you’ve got something to jump in with.
Steven Neuner: Well, just a couple of things. One, what I really, really love about this process is oftentimes this is the stage where there’s a lot of fuel being burnt. And so, oftentimes instead of measuring the progress, it’s really natural for highly successful and ambitious entrepreneurs that are burning fuel to judge the experience, plus or minus, off of the very last interaction they had. “Oh my gosh, they did this for me and, man, it’s going great.” And so, there’s real missed opportunities for coaching improvement for the assistant or in that teamwork.
The converse can also be true. They can actually be making a lot of progress. They had one thing that maybe didn’t go well, and because of that most recent experience, then it’s just like “Gap City”, this isn’t going well, and everything else. And so, this is just adaptation for us to really try to center and give really constructive feedback.
Ryan Cassin: That also happens... It’s incorporated back to the assistant as well. And so, oftentimes entrepreneurs are giving activity- or task-based feedback in the moment, which is tremendously helpful. But this is an opportunity to zoom out on the relationship, and we incorporate the feedback from this meeting into the next four weeks’ worth of coaching for the assistant as well. So they’re getting that feedback.
We’re trying to make it easy, as easy as possible. So you think about playbooks. You think about sourcing the candidates and finding the right fit and all of the work that goes into that. Then you think about the onboarding process and teaching to the test, like we do, to make sure that the relationship’s on track.
But then the feedback piece of it, that’s another thing that entrepreneurs, they don’t typically have a lot of experience giving feedback for this specific role. And so, we’re taking the leadership position in that and giving that feedback back to the assistant in the weekly coaching.
Shannon Waller: What a fabulous partnership this is. You relieve a huge burden when you’re the ones doing it. You can be that intermediary between the two. It’s like having a dating coach, relationship coach between it. You’re not left alone with it, which is fabulous, because you’re totally right, they’re not used to giving feedback.
Steven Neuner: Well, I was just going to say, to your point there, is that oftentimes without that coach in the relationship, it’s easier at this stage in the game to wipe my hands, break up, “I’m done”, versus it could be just a little... Because we see so many and we see so many entrepreneurs work with... We can see the curve-ball and it just looks like a fast pitch at them, like at the head. And so, we can help them learn to see it, make an adjustment, and it can totally transform the relationship.
Again, conversely, the entrepreneur may be loving certain things so much, but there’s real opportunity for improvement that we know because we’ve been down the path. We’re trying to extract that out so we can make sure that we’re addressing that early on in the relationship, so they don’t get six months down the road ... which is what happens to a lot of entrepreneurs on their own device, because they don’t put the tension, they don’t put the focus, they don’t set it off on the right foot. They get six months down the road before they give up on it, and then they wait two years before they do it again because it was such a bad experience.
Shannon Waller: Oh, the amount of scar tissue people have built up is huge. So that’s a really great point. You can actually round things out so you can catch red flags sooner. You’re like, “Okay, you’re saying great things about this, but you have not talked about that.” So you can see where there’s potential cracks or things that need to get solved way before an optimistic entrepreneur might. So I love that.
Ryan Cassin: We can also see where somebody’s holding too tightly to certain things and not letting go and not inviting the assistant in. And so, those are the opportunities, too, to include the coaching.
Shannon Waller: I just pulled out my baton in this interview I just did for a book chapter, is like the delegation death grip. They just don’t let go. They hand the baton over to someone and the other person’s trying to take it, and they’re still hanging on. So that happens a lot. It’s very fun demonstrating that because I literally have someone on a rolly-chair in the workshop room and I’ll pass and I’m like, “Don’t let go.” I pull and I pull and I pull and the chair starts coming across the room. It’s such a fun sticky model because people go, “Oh yeah, that’s me.” Around a few activities. It’s not everything. It could be opening mail, if people still have mail. It could be booking flights, certain types of appointment scheduling, all the things. We have our things that we’re so married to. That’s really interesting.
Before we leave the “crawl” stage, I really, really want to emphasize, I think we even talked about this in a previous conversation, but the cadence of meetings, because I’ve had meetings with this about Katrina. We see how some other people operate, and we’re like “How do you function?” Because they don’t talk enough, in my opinion.
So what do you recommend? Can you please be prescriptive? Please be... I was going to say bossy. But what do you find works in terms of the cadence of how often and for how long that an EA and an entrepreneur connect to meet together?
Ryan Cassin: Yeah. So the bare minimum, and this is the true lowest-effort bare minimum, is once per week. That’s the weekly meeting, looking ahead, trying to figure out what the next week looks like. Our recommendation is a daily sync.
Shannon Waller: Thank you.
Ryan Cassin: This can be five to 10 minutes. It doesn’t have to be painful. It can be over Zoom, it can be over a telephone call, so you can incorporate with other activities. Maybe you’re coming back from the gym and you want that drive to be your daily sync. “All right, let’s talk about what’s on my mind and top of mind for me, and run me through what my calendar looks like for the day.” That’s your assistant’s opportunity to really talk about “Here’s how we’re going to be prepared to take the day on strategically”.
Now, again, I think what happens with suggesting the daily sync is that it feels like a burden to the entrepreneur because they don’t realize that the assistant’s role is to lead that conversation. So I’ve gotten this feedback, it’s like, “Well, I’d like to have a meeting with my assistant every day, but I don’t want to have to prepare for that”. I totally get it. It is a lot of work to prepare for a daily meeting, and a lot of people generally try to optimize for as few recurring meetings as possible. And I understand that, but this is your opportunity for your assistant to lead in the role, run you through what’s going on. And it’s a great place for your assistant to batch non-time-urgent questions. And so, your assistant early on in that first 90 days is going to have a lot of questions, but very few of them are going to be ultra time-sensitive. So give your assistant a place to batch those questions in that’s easy for you to just knock them out.
Shannon Waller: Awesome. A way to think about this might be starting a race. By the way, Katrina and I are all over the daily sync. I hadn’t called it that, but the daily meeting, the daily huddle. We start our day together. We both grab our cup of tea or coffee. This is a tradition that I started with Nicole, too. But it’s like “On your mark, get set, go”.
So if you think about that meeting in the morning, it’s actually the “On your mark, get set”. It’s your launching point for the day. It’s so cool to be asked, “What’s on your mind? Here’s a reminder of your calendar.” It’s a chance for you to say, “Oh yeah, for that meeting, I need this,” because some of us don’t remember till the last minute what we need. That at least gives the person a couple of hours, hopefully, to get that into your in-box or however it is that you communicate. So it’s so important.
The other thing, which I think is genius, is that the entrepreneur’s not the one responsible for organizing, setting up, or leading that meeting. It should feel like a support. It should feel like a cup of coffee in the morning. It should feel like a boost. It’s how you get focused. It’s how you get really clear and confident about your day. If it’s a pain or a drag, there’s something wrong with how it’s being set up as far as I’m concerned.
But I’m like “I need to be reminded”. I am so good in the moment. You know where I’m not good? Before and after. I’m really, really good in the moment. I can trust what I’m going to pull off. Before and after, not so much. So my assistant is the person who’s really great at setting me up for success and making sure, “Okay. What did you promise, Shannon? What is it you said you would send out?” That’s where I need help. It’s powerful. When you’ve got someone who’s just going to be the yin to your yang, life gets so much better.
Ryan Cassin: And when you’re looking at the daily sync, I think the through-line, I would say, when folks get this relationship wrong is that it’s very, very small-task-oriented, and it adds up to, “Oh, it’s supposed to be a great life-changing relationship”. And so, it’s really easy in that daily sync to be like, “Okay, well, what have we get on the agenda for today and what to-dos do we have to get done and everything else?”
But, again, we’ve scripted out all of these “icebreaker” type questions that your assistant can ask one a day and be very thoughtful about building the relationship. So when you start the call in the first 30 days and the icebreaker question is “Just briefly describe the best vacation you had”, that’s a great opportunity to build connection and relationship. But it’s also strategic because your assistant is listening for details, like did you visit family in Oklahoma or did you go to Paris, France for a week? Did you go travel first class, or what was special about that experience is what we’re looking for.
Shannon Waller: You go on an African safari.
Ryan Cassin: Exactly. Were you gone for three days because that’s what you like for your Free Days right now, that’s the highest number of Free Days you could tolerate, or did you go for two weeks? And what happened when you were gone for two weeks? How was that? So there are these intentional icebreaker questions that we’re asking that are really easy to answer, build the relationship, build the camaraderie and the relationship and all of that, but they have strategic purpose so that assistant can do better in their role.
Steven Neuner: I find that oftentimes where people struggle is they can go super-relational, and then burn through 30 days of just purely relationship-building, or they can go super hard at just like, “You’re here. We’re going to just get to work.” It’s a wonderful blend, that that purpose is just a wonderful way to ignite potential, because each one of those conversations is essentially helping that assistant build a profile for the entrepreneur that allows them to make decisions in the future for them. So I love the intentionality around those questions.
Shannon Waller: I love it. I think, you’re right, there does need to be a balance with the relationship and the doing, the feeling and the doing side. Some of us... Like Katrina’s very much relationship-focused. I’m both. I have two relationship strengths out of my top five, but I’m also very task-oriented.
So there’s almost a conscious shift of gears in our conversations where it’s like we do our Positive Focus and, “How are you?” and, “What’s going on?” and then we’re like, “Okay, what do you got to get done today?” It’s almost a shifting of gears, but it’s so critical.
But I love you’re getting to know one another. I mean some of us naturally do that, but it can be awkward at the beginning of a relationship. So really strategic. I love that story.
Oh my gosh, there’s so many good things that you guys... By the way, there’s a ton of stuff we’re not covering, because I have a long list. But that’s for someone who wants to get involved with you guys.
So let’s talk about the “walk”. Let’s talk about understanding you, which is 30 to 60 days. So any minuses or plus/minuses have been converted to pluses. We’re keeping going. We flagged anything that needs some TLC. So the understanding you is really interesting. What does the second 30 days look like?
Ryan Cassin: Yeah. This is again where we’re looking for that common vocabulary, common context, and we’re asking questions like “My assistant has a good understanding of the best and worst use of my time. My assistant understands my communication style and needs. My assistant knows which projects drain and energize me. My assistant is organizing things in accordance with my routines and preferences”. Then, of course, in addition to a few other dimensions, I really want to reinforce this. We’re once again asking that key question. “I have confidence my assistant will help me achieve new levels of freedom and growth in the future”, because it’s just such a powerful tell.
Shannon Waller: Oh my gosh, so smart. All I can think of is why wouldn’t someone want to be doing this? That’s where I’m at right now in my head.
A couple of other things that you say is that openness, just to touch on that for a moment, because that’s what leads to that confidence for freedom and growth. You need to feel free to ask questions and make statements, and they need to feel free that they have the same permission. You need someone that you can be honest with at work and someone who can be honest with you.
Let’s talk about that honesty. What would keep someone from being honest? Because you guys have delved into this a little bit. You’ve seen relationships that worked and you’ve seen probably some of them that have not as well. So let’s talk about honesty, because I think that’s probably an obvious but underappreciated aspect of this dynamic.
Ryan Cassin: Yeah. So I’ve never encountered an entrepreneur who says, “I’m going to be dishonest in this relationship.” So when we talk about honesty, it’s really about “I’m willing to take the time to share how I think about things, how I see things. I’m willing to invite you in”, and that it’s also the willingness to be transparent. It’s the willingness to share the things that might be uncomfortable.
I think one of the things that folks struggle with is giving that feedback early on and making sure that they’re giving an honest assessment of the work. I think to the extent that dishonesty enters the relationship at all, that’s the biggest area where we see it, is they accept good enough when, with just a little bit of feedback and a little bit of time, they could have helped their assistant understand what ‘great’ looks like.
Shannon Waller: Oh, that’s so good. Steven?
Steven Neuner: Of the stages, to me, this is one of the most dangerous, because the assistant now is reaching the level what... They know, they’re starting to understand. There’s real opportunities for them to even start to mirror little pieces of anticipation. And so, entrepreneurs will tend to dump more here without having, like, the confidence increases, and sometimes they’re trying to delegation or dump too early. And so, that can create complication because there’s time that needs to be given to working through that process.
The other thing that I think is dangerous here is the entrepreneur starts to get a little bit of relief. “Oh my God, I’m not in my emails. Oh my God, I can finally have a Free Day.” They’re starting to have these real things, but there can still be underlying issues that need to be just strengthened, components of—maybe not be issues, but just things that need to be strengthened in the relationship. But they’re now afraid to give that honest, candid feedback because they’re afraid they’re going to run off or lose the lifesaving oxygen-breath that they finally got a grasp of.
Shannon Waller: I mean the beginning is the new blushes on the relationship and we’re all happy, honeymoon phase of something, and then probably the “run” phase, you’re like, “Okay. They’re anticipating this. Great.” This is probably the most dangerous, the trickiest to get through, because if I think about me, I can either jump ahead. It’s like, “Oh, first 30 days, we’re great. Bam! We’re ready to go.” So I’m like running a million miles an hour and they’re like, “What’s happening?” or someone else... I can imagine this 30 days is so key, and to have patience and to take a breath and to not go too crazy, not too slow, not too fast to make sure that this actually works. That’s fascinating. Ryan, what’s your experience with this, with the walking stage of the journey?
Ryan Cassin: Yeah, I would agree with Steven. I mean I think he was exactly right. For me, this is one of those stages where you’re trapped between, all right, my assistant knows enough and has enough access and familiarity with me that things are beginning to move forward. I’m seeing the traction, the excitement that comes from it, and I want to jump right to “anticipate”. I start to have really, really high expectations because I’m beginning to feel what “anticipate” looks like. I’m seeing around the corner. I’m excited for the relationship to continue to grow, and I get really impatient with the relationship because that’s what I want right now.
Shannon Waller: Yes. It’s getting good, but they want it to be great.
Some people, I imagine, can even get stuck at “good enough” and they actually don’t want to risk all the good stuff they’ve had, like what you were saying, Steven. You’re like, “I don’t know if I really want to say this because it could mess up all the benefits I’ve already got.” I can also see that happening, too.
Ryan Cassin: Don’t settle. That’s the most important thing in the first 90 days.
Shannon Waller: Don’t settle. I love that story.
Steven Neuner: We do a lot of coaching around that, too. I mean sometimes we’re the intervention team for that, for some of the entrepreneurs. Don’t settle for “good enough”.
The other thing that can happen here with that expectation is, “Oh my gosh, they’re so capable. So now I’m going to turn them into all these things that are not an assistant”. Then if we’re not careful, then you start throwing them out of their Unique Ability and what they’re actually hired to do and some of those other things.
So we’ve got some pitfalls in a future one and how to avoid them and some techniques to get what you want out of the relationship. But I just think this is also one of those phases you could start to try to lump in new things before the relationship’s ready for it.
Shannon Waller: Don’t give them a different job. I can totally... I’m laughing my rear end off because I can totally see that happening. I’ve seen it happen. Occasionally I’ve been tempted. You’re like, “Oh, well, if you’re so good at this, then you’d be great over here.” Of course, they’ve got a pain point from there. So like, “Oh yeah, could you be the marketing assistant, too?”
Or this is another thing I’ve had happen. I don’t know if you guys have this because of how your structure is, but I’ve seen it. It’s like, “Oh my gosh, I’m feeling better looked after. But Joe or Joanne over there, they’re really struggling. Do you think you could go help them for a little bit, because they’re drowning?”
Ryan Cassin: 100%.
Shannon Waller: Then you’ve just given away this massive asset that you’ve been ... And the person been working towards supporting you and then you just gave them away.
Ryan Cassin: Yes. This happens way too much. There’s two reasons. A, and I think more often than not, it’s what you described, which is “This is a high-performing individual. They’ve done amazing work for me. Just think what they’re going to do for everybody else on the team. It’s going to be incredible”. You load up all of your hopes, dreams, and wishes into them.
The second thing I see, we don’t have to talk too much about it, but I do want to just bring attention to it, and it’s guilt. “I have an asset on my team that nobody else has supporting them, and I feel I have to give this person away to them, because if I don’t, I’m going to be judged for having the assistant”. And so, that is one of the things that we run into.
Shannon Waller: Oh my gosh, you nailed it. Guilt is huge. Okay, so I don’t want to leave this alone because I think this is super-important. How can we disabuse people of the word ‘guilt’? I was not raised with guilt. It was a four-letter word in my house. I could get away with swearing more easily than I could get away with guilt. Don’t ask me why, but that’s my mother for you. Marilyn Waller, praise be to you.
But how can we let people know that it’s totally fine to be supported, that it’s appropriate, that it actually is forwarding the business if they are supported? How do we shift people’s mindsets and get rid of that? Because guilt is blaming yourself. There’s blaming other people and when you blame yourself, that’s guilt. That’s a definition. So how can we disabuse people of this really bad notion?
Steven Neuner: For me, personally and in my own experiences, being reminded of the vision, of your vision, your ambition. The bigger that is and the quicker you move towards that, you are actually creating opportunities for other people to live into their purpose. Again, I’m not saying like, “Hey, you should feel guilty about something else”, but if you want to feel guilty about something else, rob people of their futures and their opportunities because you’re not secure enough to be investing in yourself in this type of way.
And, by the way, I’m a big fan of, if you’re getting that type of freedom and growth and you’ve got people that can be leveraged, we’re a big fan of providing those types of opportunities to other people on your team. But to me, reminding them of their future is the crucial part, and I think that’s the big unlock.
Ryan Cassin: Your team wants you to get help so you can be in your Unique Ability more. They need you to be in your Unique Ability more because that is probably, for a lot of businesses, one of the biggest levers to continued growth and success.
Shannon Waller: It’s interesting because we talk at Coach about the Time-and-Effort Economy and the Results Economy and having to cross the risk line. People who are in the Time-and-Effort Economy, which are occasionally called employees, what’s important to them is security. Now what’s interesting about entrepreneurs who cross the risk line in the Results Economy is they find it’s all about opportunity. Entrepreneurs find security and opportunity, not in working for somebody else. They don’t find any security in that.
But one of the things I think entrepreneurs don’t appreciate is when they’re freed up to do their Unique Ability and create the value that they’re best at in the world, that creates security for your team. You not doing what you’re supposed to be doing scares the living daylights out of them. Steven, I remember you saying in a previous conversation, your team did an intervention with you, right?
Steven Neuner: They did. They did an intervention. They said, “Hey, we appreciate you. We’re so grateful that you love us so much. You keep hiring for everyone on the team, but you’re the bottleneck for everything. We’re not letting you hire someone else until you get help for yourself.”
The things that were behind that was they knew when I was outside and doing these other things, there had been enough results in the business. They wanted me to go do more of that because that meant opportunity for them, bigger futures for themselves, more autonomy versus me complicating stuff by me getting involved in things I shouldn’t get involved with.
Lastly, many of them were having to become my assistant. They were having to fill in. So I had really, really high-performing, high-functioning team members that are like, “Hey, I love you. I don’t want to be your assistant. And so, that’s not my Unique Ability. That’s not why I came here.” So they were a big push into me leaning into this.
Shannon Waller: Oh my gosh, this is so brilliant. If you really do have a commitment to your Unique Ability, here’s the interesting... It’s a little bit of a paradox, I think. So if you do your Unique Ability, you’re like, “Oh my gosh, I’m doing what I love to do and I’m best at. That creates the most value. I’m here with other people. I just create a lot of positive impact in the world.” People have a lot of guilt about that.
But here’s the interesting thing, in my experience, and I think yours too, is that there’s no way any of us can be freed up to do our Unique Ability unless we’re surrounded by people who are unique in their areas. This is “Who, Not How”. And so, when we force other people, because we’re too guilty or shy or not believing, or whatever the phrase is, to invest in our Unique Ability, we force other people out of theirs.
That makes no sense. It is not a strategic and profitable way to run a business. The most profitable way to run a business is you have everyone doing what they love to do and do best, because they’re going to run circles around people who are merely competent, who are merely okay.
So there’s a strong logic behind it, but I find that this conversation gets hijacked by emotions like guilt. When you look at it from the outside, you’re like, “Oh, Lord, what are you thinking?” But when you’re in, it’s totally legit. So I can appreciate both sides.
Ryan Cassin: So we’ve gone to all this work now to find the right-fit individual, to get them the curriculum, coaching, and community they need to be successful, to get them the game-plan for the first 30, 60, and 90 days to be their most effective. Then by making them a shared resource, we blow all of that up. Then on top of it, no one team member has a complete view of what the assistant is doing. So now I only see this small sliver of activity, and I feel dissatisfied. Why can’t this person do more?
Meanwhile, the assistant is, unfortunately, in the position that they’re getting burnt out because they’re pulled in 10 different directions. The success metrics they were working toward are no longer the exclusive success metrics. They’ve got other people’s success metrics now that they’re responsible for. It just becomes a compounding problem. It is the fastest thing that unravels that relationship.
The one thing that we see work really nicely is that remote piece of it, because when somebody is in person, that person can become a shared resource much more quickly. They get things dropped off on their desk. The remote piece of it, I think, really helps make that assistant your assistant.
Shannon Waller: It protects the situation. Yes, good. I want to put a nail in this coffin. I don’t want anyone to take that having done it.
And here’s one other factor. You’ve described the circumstance exactly, because they no longer know what they’re being measured on. And no one has a full picture. I never thought about that.
But the other aspect is trying to really get to know... You talked about the icebreaker questions, trying to get to know three... In my case, we had one assistant supporting three of us. I’ll tell you the Kolbe profiles, three, two, nine, five. So initiating QuickStart. We had a six, eight, three, three, initiating the Follow-Through, and a seven, two, seven, four, Manager profile. So lots of Fact-Finder, lots of QuickStart.
The contortions this poor human had to go through to try and figure out these three friends... We’re all friends, we work well together, but three completely different unique human beings, and try to serve each of us in the best and the highest way possible was insanity. Please do not make my mistake. It was one of the worst things.
That was one of the things that prompted me to go, “Okay, I need to actually have the body parts, the courage, just have one person designate to me. I’m worth it. When I’m contributing to the business, it’s worth it to make that investment”. It was a big 4C’s moment, but it’s only because the situation was so messed up with that one person trying to support three of us. It was insanity. What the hell were we thinking? So don’t do that, right, Ryan?
Ryan Cassin: Please.
Shannon Waller: Please don’t do that. Yeah. Oh my gosh, I hope some people are listening, going, “Yeah, been there, done that.”
Ryan Cassin: Oopsy.
Shannon Waller: Oops. Hopefully everyone survived and doesn’t have too much scar tissue.
All right, so let’s talk about the “run”, because this is what we’re all aiming for. This is when your assistant starts to anticipate you. This is when you’re like the sky’s really opened up and the sun shines out and the angels are singing from the heavens. It’s when someone can actually have high beams and look down the road and support you. So let’s draw the picture, paint the picture of this experience, because it’s pretty flippin’ magical.
Ryan Cassin: Yeah. So the key things here are “My assistant anticipates how I navigate value judgments”. That’s the reading-of-my-mind effect. “They know and anticipate what I need in advance of my meetings to be prepared. They anticipate how I would choose to delegate tasks or emails. They anticipate what the next step forward is toward a goal. They anticipate how to organize my schedule and optimize for my energy.”
All of these anticipations, certainly again in the business context, in the quarterly rocks or annual goals context. But it also shows up in ways that are personal in nature. So they anticipate that I need to have a great Free Day because it’s been a long time since I’ve had a truly banner or a gold Free Day. And so, they’re anticipating that and coming up with suggestions. “Hey, here’s what a great date night looks like,” or, “Here’s a concert that’s coming to town that you would enjoy.” They’re looking for things where they show up and anticipate with that servant’s heart beyond just the work context.
Shannon Waller: There’s something about when someone anticipates you and... I was going to say it sparks joy, it creates joy. You’re like, “Oh my gosh, that’s better than what I would’ve thought of,” or, “How did he or she read my mind?” There is real joy in that when I’ve experienced it. It’s like someone really gets me. They know me. They care about me. They’re helping to craft my daily experience.
One simple example for me, a previous support person I had would organize my schedule the same way that she would want her schedule, which was really to space out the client appointments. I was dying. I was like, uh-uh-uh, I’m one of these people that’s high-energy, but for me to stay in that state, I need to be hopping across the lily pads. Don’t give me time to sit on one too long. It’ll start to sink.
So I’m like, “No, schedule 15 minutes between, that’s fine”, because I’ll probably run over. But it’s like “Let’s keep the pace high because that’s how I function”. We didn’t have enough connection meetings. I’m not saying it was this person’s fault, but we didn’t ‘get’ each other enough.
This is what happens if you don’t have enough connection meetings, back to my question that I asked you guys, because then someone doesn’t get a chance to know you. If someone doesn’t know you well enough, they’ll schedule it the way they would handle it, which I guarantee, because you’re going to have different approaches, Kolbe and CliftonStrengths and all the other ways, is not going to be your way.
Your schedule might be hell for them, and vice-versa. That’s okay. Their job is to anticipate you and make it work for you. Then your job is to let them alone to go do that. I’ve experienced this, so I understand just how important it is.
Ryan Cassin: The through-line there is a lack of communication. That’s the biggest risk factor, the settling and all of that. The through-line is lack of communication in the first 90 days. So you need to actually take the time to have that meta-conversation of sharing how you think through things, your reasoning process, what factors you’re considering when you’re making a decision. Until you share your mind, your assistant can’t read your mind.
So it’s not a heavy lift. The “Why” can be delivered in a minute or less, and it’s a great thing to incorporate into the daily sync. “Hey, that thing yesterday that we had to hit pause on, I want to talk about that. Here’s how I approach that. Here’s how I think about that,” or, “That email I had to rewrite. Here’s the ‘Why’ behind it.” “This is a high-value client that I’ve had a relationship with for the last 10 years. And so, I communicate with this particular person differently.” It’s so important not to be afraid to have those communications moments early and often.
Shannon Waller: I want to add to this, and it’s not explaining or justifying yourself, because a few of us are allergic to that. It’s actually sharing. If you do this well with this relationship, it’s going to make you so much better at working with the rest of your team as well. It’s really setting context. That’s a huge strength of Dan Sullivan’s, but you’re setting context. “Here’s why I changed it,” “Here’s how this needs to be,” “Here’s why I’m thinking this way”.
Sometimes people will add different contexts. They’re like, “Okay. Well, here’s where I was coming from.” I’m like, “Oh, that might be a good thing to incorporate.” But when you’re sharing the context, which is the “Why”, then people can get on the same page with you. To your point, they can read your mind.
But I think it’s one of those skills that just translates way beyond this relationship. This is the Petri dish where you actually get to get good at it, but the benefits, even to your spouse, to your kids, to your parents, to your siblings, it just is so critical to be able to effectively set context so people can be with you. I don’t want people to underestimate just how powerful that is.
Steven Neuner: When you have the right person, you’ve done all the thought-work, you’ve brought them along, they’ve had the curriculum, you both had the coaching, you’re really now kicking into this new level, this taste of new levels of freedom and growth. It’s really, really where it begins to set fire.
I equate it back to this all that investment is now where you get freedom and growth, and you get off that teeter-totters, the seesaw that we talked about in... Well, one where a lot of people double down on freedom and they sacrifice the growth, or they double down on growth and they sacrifice freedom. Why is it... And this is the proof in the pudding.
Why is it... Workshop one, we talked about the time system, Entrepreneurial Time System at Coach. We tell people to take Free Days first, put them first, and it blows people’s minds. “I’m trying to grow my business. You want me to take more Free Days?” How much work do you get done before you take a Free Day? You’re insanely productive. There’s so much wasted time. So when people are anticipating you, teeing you up, keeping you in that flow, whatever that flow looks like for you, that’s where you can get new levels of freedom and growth.
Shannon Waller: Yes, I could not agree more. There’s freedom from all the stuff you don’t like doing, but then you get freedom to do all the things that you haven’t been able to get to because you’ve been so mired in those activities that you just don’t love, and take enormous amount of mental energy and subtracts from all the stuff you want to be doing. So then you get freedom to do all the fun stuff. The fun stuff is going to be growth, hopefully it’s going to be some Free Days. That’s the magic.
I have to tell you, in my own experience of it, is it’s life-changing. It’s transformational. You can’t imagine doing it any other way. Once you’ve had a taste, there’s no way you want to give that up. It’s way too valuable.
Ryan Cassin: That’s one of my most fun conversations I have with prospective clients of ours, is folks who’ve had an executive assistant in the past because they come to that meeting and they are dialed in. They know Unique Ability and what theirs is. They know all of the tasks that their assistant should be helping them with. They know exactly what they love about that relationship and what they’re looking for in that person, because, as you said, once you’ve had that relationship and once it’s been high-functioning, there’s just no other way to do it.
Shannon Waller: No. Well, otherwise you’re sacrificing your Unique Ability to do that.
Ryan Cassin: That’s right.
Shannon Waller: That’s just no fun. They’ve also had experience with successfully passing that baton and confidence that that can happen. People move on in their life. Sometimes they’ll stay with you for a while. Sometimes they get an opportunity to go live wherever. So things will change. Don’t expect that it’s going to stay the same forever. Or they have a new life aspiration. Who knows?
But once you’ve done it once and you’ve successfully handed over that baton and someone else has run with it fast and they help you win the race, you’re like, “Oh, okay. This doesn’t have to be a once-in-a-lifetime experience. This can happen more than once,” and they’re much more willing to let go. They also know what gives them energy, what doesn’t, and much more upfront and straightforward.
Ryan Cassin: I’ve never had a conversation with someone who said, “I had an executive assistant in the past. It was a great relationship. We did all the things that we wanted to together in that relationship. Now I’m thinking about whether or not an executive assistant is right for me in the future.” It’s never ever been the question. It’s “How do I find the next right-fit for me?”
Shannon Waller: Yeah. They’re like, “How soon can we get going?” They’re like, “Okay, yeah. What do we need to do next?”
Steven Neuner: True.
Shannon Waller: Yeah, because once you’ve had it, you don’t want to not have it ever again. No, I love that.
All right, so I love... We’ve done this deep dive into... And we’ve talked to some really cool other topics. Well, topics that are included, like guilt. So we talked about the “crawl”, first 30 days, the messy middle, which is that middle 60 days, where you could either go too slow or you can go too fast, or you can give them away—don’t do that—because you’re feeling guilty or you’ve lost the mission. You’ve lost the purpose of it. Unfortunately, that’s only 30 days.
But then you finally get to the 60 to 90 days, and that’s when things really hit the groove. You’re running in sync. You’re having those daily meetings. That person starts to anticipate you and you can anticipate them, too. I know I just have to copy Katrina on an email and I know she’ll know what to do. I don’t have to explain it. I love that story. Or she’ll chat me one simple question, “We just got a request today. Do you want to be on this podcast instead of the weekly planning call?” In this case, we’ll try and rearrange it.
So it’s just fast and it’s easy and it’s fun. It’s not effortless, but it’s very little effort. Like all the effort you put in, all the effort and time and heavy lifting you invested in the first 30 days really pays off and it gets so much easier. Then you just could go, “Okay, what other fun projects do we get to work on together?” That’s the goal.
All right, anything else we need to do to wrap up in terms of the first 90 days, crawl, walk, and run?
Ryan Cassin: Stick with it.
Shannon Waller: Yes.
Steven Neuner: If I could, I have a quote here that I have hung above my desk. I’m just a big fan of it because it’s really so tied deeply to my “Why”. How do we get new levels of freedom and growth for people? Because I don’t want people to 10X just their business. I want them to 10X their lives. And so, here’s the quote.
“The master in the art of living makes little distinction between his work and his play, his labor and his leisure, his mind and his body, his information and his recreation, his love and his religion. He hardly knows which is which. He simply pursues his vision of excellence at whatever he does, leaving others to decide whether he is working or playing. To him, he’s always doing both.” Mr. James Michener.
I just cannot think... When you have a really great right fit relationship and you include them into your personal life, this is what’s possible. Your work can become your play.
Shannon Waller: Thank you. That is a brilliant quote. What a great thing to aspire to. That’s precious. Thank you.
Well, gentlemen, thank you again. I feel like we’ve covered some very important ground. Also, our next one’s going to be pitfalls, avoid these mistakes. But we’ve already talked about a couple, so we’ll reinforce those and also how to avoid other ones. Then also in the following podcast, what winners do. So how to be successful for sure in this.
So I hope you’re having as much fun as we are in having this conversation. Any questions or comments, let us know at firstname.lastname@example.org. We’ll talk to you next episode. Thanks a million.