In this pertinent episode, Valerie Trapunsky, Founder and CEO of ChatterBoss, shares how she and her team built a product that clients can trust to reliably deliver instant, personalized and thoughtful service..
You will discover:
– Why would should delegate even tasks you like
– What a Chief of Staff staff can do for you
– What 1000 assistants said are the top three things they need
Episode Transcript
Scott Ritzheimer
Hello and welcome welcome once again to the secrets of the high demand coach podcast. We’ve got a very special treat today and that is Valerie Trapunsky. After a decade spent working as a top level assistant for a list celebrities and as the Chief of Staff for high net worth individuals and CEOs, Valerie Trapunsk founded chatterbox in 2017. She developed a passion for effective problem solving and became committed to bringing that same level of excellence and service to solo entrepreneurs, business owners and executives that are ready to scale. At chatterbox they strive to solve their customer needs through a combination of intelligent technology, and intelligent systems and most importantly, intelligent people. Well, Valerie, I’m so excited to have you on had a chance to check out your website and see a little bit of your story. And there’s a lot to explore. But I really want to start there. I want to hear this story. What were you doing before starting chatterbox chatter boss? And again, how did that ultimately lead you to make the leap into doing what you’re doing today?
Valerie Trapunsky
Yeah, thank you so much for this intro. Thank you for having me. Um, before I started chatter, boss, I was working as a personal assistant. And as a chief of staff, I kind of fell in to this industry, it wasn’t something that I thought that I would be doing. But it ended up being this amazing adventure, I had an opportunity to work for a list celebrities and high net worth individuals. And it was a completely different world than I imagined. But also the assistant function was completely different than I imagined inside of that role. Now, before I started that position, I was under the impression that the assistant role is a monogamous one, that every person has one assistant, and that’s it. But very often I would walk into these homes and I would be the second or sometimes third assistants. And what I learned from that was that it gave me the opportunity to work with people have complementary skill sets in personalities. And where there was a weakness of mine, they had a strength and we were able to work together. And so when I started chatter boss, I wanted to create a model that mimics that. So the kind of attention and support in the way that high network and not high net worth individuals are able to use their assistance for small business owners and entrepreneurs to be able to have that same kind of access. So it’s been a fun journey.
Scott Ritzheimer
Fantastic. And so that’s what you guys do right at chatter boss. Tell us a little bit about how you help entrepreneurs and business leaders.
Valerie Trapunsky
Yeah, so we work with entrepreneurs and business owners, and we pair them to a dedicated and on demand remote executive assistant. So you essentially get somebody that knows you that knows your business. And that is that essentially becomes a part of your team. And we know that the entrepreneur that the average entrepreneur spends anywhere from 30 to 60% of their workweek bogged down with administrative items. And so we give you an assistant to be able to bucket all of these admin tasks and to run with them. But you also get a backup system. So it’s a two assistant model, you get a backup assistant in case your primary sick and as a way or something happens, you have someone else to rely on and and that’s what really makes us unique that we build these teams around you with the right skill set. We look at your personality, we look at the assistants personality, and we create this what we strive for this frictionless team experience
Scott Ritzheimer
That’s fantastic. So I got a couple of questions because I really want to dive into how to get the most out of a VA like how to get that relationship to work. So first question, I would have the, you know, entrepreneurs out there and they’re like, should I hire a va va or not? Well, let’s just jump right there. Why should they hire a VA?
Valerie Trapunsky
I, you may have heard of this thing. And it gets passed around a lot in the industry. If you don’t have an assistant, you are the assistants. And that’s just true, because 30 to 60% of your work week you’re doing administrative tasks. And there is for some people, part of that administrative burden is something actually that they enjoy doing. They just it doesn’t move the needle in any way. So they don’t grow meaningfully. But there’s definitely a percentage in there things that they hate, that causes them stress that they procrastinate. And then those things are actually at a detriment to your business. So the only way to really grow is to have that support. And I really encourage it’s a little bit counterintuitive. Sometimes people start a business and we say start with an assistant right away and they say well, I want to grow I want to first see this. And the truth is, if you wait too long to get an assistant to your business, what you’ve effectively done is you’ve trained yourself that you’re going to continue to do During these administrative functions, you almost don’t see them. So sometimes when I say that statistic, people are like, No way I spent 60% of the work. If you actually do a time audit you do, but you no longer even, you don’t no longer even realize that.
Scott Ritzheimer
Wow. You’ve trained yourself to be your own assistant. So I want to flip that around and say, what are some reasons that you shouldn’t hire a VA? And that may be what are some reasons why you maybe need to hire an employee on site or some tasks that are not appropriate to hand off? What are some reasons why you wouldn’t hire or delegate to a VA?
Valerie Trapunsky
Yeah, that’s a great question. So I’m of the opinion that businesses, starting businesses are going to require employees, we, as a company, have employees, we leverage a lot of our contractors, but of course, we have employees. So once there is a position that requires a certain amount of hours from one person, then that’s a conversation that you may consider, majority of the entrepreneurs on the virtual assistant side will need about, you know, 10,15,20 hours a week, which is great for an assistant, I think that that administrative function is so well done by a remote assistant, you don’t have to lock yourself in unless, again, you’re getting to those higher hours, when we talk about a Chief of Staff, right? People will go in and they’ll hire a chief of staff and the price tag can be 150-200,000. And up per here, that becomes a slightly different function. And even some of my assistants have held the Chief of Staff title. And our clients will say that they operate at our partner level, they operate on that Chief of Staff level. But what really separates a chief of staff that’s with you full time is the amount of time that they’re able to be with you. So that’s very crucial, right? Sometimes you can have the right person, but if you don’t have them for the right amount of time, then you are not able to leverage them to their to their full potential. So perhaps then we also do hiring we do recruiting for full time chief of staff roles, specifically in those instances.
Scott Ritzheimer
And that that actually segues directly into my next question, because you mentioned the very beginning, you did a personal assistant role you did chief of staff role, and I’m actually a really big fan of the chief of staff role. But I’d love to hear how do you how do you distinguish between those two? And the second part of it is when does someone know it’s time for a Chief of Staff?
Valerie Trapunsky
Yeah, it’s a great question. So I would say that the difference between an executive assistant and the Chief of Staff is one, it’s going to be the number, the the amount of experience, the type of experience. And specifically the Chief of Staff is where the executive assistant function catches all of the admin operational pieces that we have to run in the day to day, at the chief of staff level, it is more of a strategic people management function. And the chief of staff is the right hand to the entrepreneur or to the founder, and they almost have the same function. So we’re, as your assistant will be doing things that you’re not doing and shouldn’t be doing. Your Chief of Staff is almost like a duplicate of you, they’re gonna have some complementary skills, which is important, but their function is in the organization is to have your time expand. So we’re really looking for we’re always looking for a good match between the entrepreneur and their EAA, but at the chief of staff level, even more, so.
Scott Ritzheimer
Yeah. And what makes what separates a great chief of staff from the many if you will?
Valerie Trapunsky
Yeah. Um, the people management piece is so huge, at that Chief of Staff level, right? Understanding, understood, understanding the needs of others understanding how within an organization, you’re able to pull out and get certain things done. Because a lot of the time, you don’t really have that much leverage, right? You’re basically trying to do what the CEO does. But you’re not the CEO. Right? So it’s almost you have to work harder. It’s more of a challenge. But it’s a fascinating, it’s a fascinating position.
Scott Ritzheimer
Yeah. And you bring up an interesting point because Chief of Staff is in many ways an extension of the founder owner entrepreneur, we call them MSC, most senior executive, whatever, whatever title it is, but one of the traps I see them, the founder owner fall into and they’re looking for one is they have to be everything that I am plus everything that I’m not right. So where are some areas that that you find it’s actually helpful for the founder to actually relax their preference, right? Like, Hey, you don’t need them to be the best in the world at XYZ. What You really need them to focus on his ABC?
Valerie Trapunsky
It’s a great question. So when I recruit for the Chief of Staff function, the very first thing that I do is I build a comprehensive job description. So I will dive into the specific needs for this particular individual, a lot of the time in terms of competency, the Chief of Staff should have the same strain. So for example, if it’s as if it’s a sales company, and the CEO is very strong in sales, a lot of the times the job description in itself has a lot of that sales capability. And so in order to avoid friction, we want that to match. But then there are going to be both characteristics and job descriptions. So for example, if the CEO is someone that is not very organized, you in this area, you want somebody with higher level of organization, so that they can take the lead. If the CEO is struggling managing people, then you want the chief of staff to have that complementary skill set. So you actually want to, it’s almost like you want to look at your weaknesses, and you want to fulfill on them within this chief of staff, like we can’t change our character, right, it’s pointless to try. But when we get to the point in our business, where we’re able to bring on a chief of staff, we actually have that unique opportunity to expand and fill in the voids that we don’t have.
Scott Ritzheimer
Yeah, yeah. I want to circle back to the question of timing, what are some signs that you should start considering that Chief of Staff role?
Valerie Trapunsky
Yeah, it’s a it’s a really, really good question. Um, time. How much time? Are you spending? Are you feeling burned out? Are you working more hours than you should? Are you doing some of the day to day and just feeling frustrated? And maybe this is like, also signs of other things? Right? I’m like thinking like, pathologically, right? No, but you know, when when we start to be cranky with some of the people around us, right, like, we have to find the root cause. But sometimes that root causes, I’m doing too much. And I don’t have help. And I don’t feel that I deserve to be operating in this way. But it’s like a, I’ve created this situation for myself. So I think that our feelings tell us a lot about if we are if we’re ready, or rather, if we’re overdue, because really the best time to bring on an assistant is as soon as possible when you start your business, because the first thing that you do in your business, it is administrative, but the second best time is now.
Scott Ritzheimer
So another question for you here. Let’s we’ll switch back to the VA role here for a second, what are some common reasons that, you know, entrepreneur VA relationships don’t work very well? And how can the entrepreneur kind of get ahead of that to help ensure success for both?
Valerie Trapunsky
Yeah. I love that you asked that question. I wish that everyone asked that question when they were getting started with an assistant and when they were exploring to get in assistance. We’ve asked over 1000 assistants, what’s the most important thing for them when they’re working with their clients? And we have a top list of 12. But the truth is that they all say the same thing. And what they say is that they want to know where they stand, they want clear communication, they want respect. At the heart of it. Good communication is the key to working and leveraging your assistance to the max. So that includes, of course, you’re listening, but a lot of it is your own communication. What am I sharing? Am I giving you enough information? A lot of entrepreneurs are super smart. They keep a lot of things inside of their head, the thing that they said something, but they actually didn’t, then they’re disappointed that that thing that they thought didn’t happen. And so we’ve also had chatter boss have spent years developing different kinds of tools to help educate the entrepreneur on how they can step with their best foot forward when working within a suspend.
Scott Ritzheimer
Yeah, that’s fantastic. Fantastic. I was a question I like to ask all my guests and it’s this what’s the biggest secret that you wish wasn’t a secret at all? What’s that one thing that you wish every entrepreneur business owner and leader listening today knew?
Valerie Trapunsky
Beyond the entrepreneur and the business owner and really like all of us as humans, I think that the biggest thing that came as a surprise to me that was kind of hidden from my sight is that the answers that we’re looking for in life and in business are always inside of us. If we give ourselves an opportunity to listen, we’re always going to know the answer and what we’d need to do next. And when we’re talking about business, so many hard moments, it’s hard to be an entrepreneur. And no, sometimes I don’t know about you. But sometimes I’m looking at something and my brain says, You should panic. But my heart says, you’re fine. Here, you’re fine. And sometimes I’m looking and I’m like, it’s fine. But I know that there is urgency. So we have this intuition. And we have to trust that if we built our business, we’re the right ones. We’re the right leaders for our businesses. And and we have to let our intuition guide us.
Scott Ritzheimer
Wow, wow. Yeah. That’s excellent. Excellent advice. It’s, and it’s interesting, because I think a lot of folks would say, yes, I get that. But depending on kind of where you are in the cycle of things that trust and confidence, it ebbs and flows, right, there are times when you couldn’t take it from us if you tried, right. And there are other times, and it doesn’t happen all of a sudden. And so I was just talking with a gentleman the other day, and he’s like, I’m an optimistic guy. And then he paused. He said, I think of myself as an optimistic guy. But I’m really struggling right now yet. And so I love that, that just that encouragement of, hey, trust your instinct, you know, even when it’s hard, is there’s so much wisdom in that. Another question for I’m actually gonna switch gears, I’m gonna have you take off your kind of advisor hat, and put on your CEO, hat, CEO, chatter, boss and tell us what’s the next stage of growth look like for you and your business and what challenges we have to overcome to get there?
Valerie Trapunsky
So one thing, our ambition as a company is to be the number one remote executive assistant agency in the United States. And we’re taking our time there, we’ve been around for 7 years now. And this is our ambition in the next 10 years. And so we’re taking our time. But I want that to happen for us because of the unique relationships that we provide assistance and clients, and the research that we do into their relationships. And so we go beyond kind of brokering that deal. And it’s fascinating for me personally, as a passion. It’s been fascinating to learn what makes relationships work, what makes relationships fail, and I would feel personally accomplished for having have created Chatter Boss, and for having it grow to these heights that I want it if we are able to meaningfully contribute to the literature and the research and to the knowledge base of what makes teams work of what makes entrepreneurs and assistants work and how we can have better remote relationships because that’s the future so yeah, that’s my big dream.
Scott Ritzheimer
Wow. Wow, when you figure that out, let us know. I don’t think there’s a someone in business today that isn’t scratching their head to some extent on getting remote work, relationships working better. So I love that you’re going after I wish you the absolute best in it. Well, Valerie, thank you so much for being on what a fun conversation and so much insight there. I really appreciate you being here. And for those of you listening you know that that your time and attention means the world to us. I hope you got as much out of this conversation as I know I did and I cannot wait to see you next time. Take care.
Contact Valerie Trapunsky
After a decade spent working as a top-level assistant for A-list celebrities and as the Chief of Staff for high-net-worth individuals and CEOs, Valerie Trapunsky founded ChatterBoss in 2017. She developed a passion for effective problem-solving and became committed to bringing the same level of excellent service to solo entrepreneurs, business owners, and executives ready to scale. At ChatterBoss, they strive to solve customer needs through a combination of intelligent technology, intelligent systems, and most importantly, intelligent people.
Want to learn more about Valerie Trapunsky’s work at ChatterBoss? Check out her website at https://www.chatterboss.com/
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