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What Entrepreneurs Need To Know – Hiring! With Roslyn Drotar-Cassidy

Episode Summary

Roslyn Drotar-Cassidy is an established marketer in a niche market. Her real specialty though is her honesty about her entrepreneurial experience. Join us as we have a really frank discussion about when do you hire? And how the dark moments of the entrepreneurial journey can eat you up!

-when it’s too late to hire
-the secret to hiring
-and how to avoid the chaos of your first hire.

Join The Community:
Win The Hour, Win The Day!
Podcast: Win The Hour, Win The Day Podcast

You can find Roslyn Cassidy on:
IG: digitalsocialstrategist
FB: Digital Social Strategist

NYB Guests_Transcription – Roslyn Drotar-Cassidy


Kris: (10:38)

Hey everyone. This is now your business and I’m Kris Ward. I am really excited to have this next conversation with our next guest Roslyn Cassidy has been in the legal marketing industry for 25 years and after getting a degree in marketing while working in a big law firm with over a hundred employees, she left and went to work in a boutique firm. Now Roslyn has a wonderful path that she just can share with you as we have a conversation going from $1 million practice to another and then you know what happens to most of us. She eventually opens up her own agency. Roslyn is a digital social strategist and she serves entrepreneurs and the legal industry to help them grow their business, generate leads and create marketing plans that work right from where they are. But we’re going to talk to Roslyn about something even more powerful. The behind the scenes stuff. Welcome to the show Roslyn.

Roslyn: (11:33)

I thank you for having me Kris. I am so excited to be here. 

Kris: (11:37)

I am excited to have you because you know what? I think you’re amazing on a number of levels. Okay, so you’ve got these successes under your belt and all this wonderful stuff. But what I really admire and appreciate about you is, you know, we had a conversation and you started to talk to me about, you know, the pains of having your own company and the demands that that was taking on you. And, and this is something I’m passionate about, that you know, business should support your life, not consume it. I say that over and over again. And what I want people to understand is you’ve got this amazing background with all kinds of, you know, systems and strategies and really leveraging in different arenas. With high volume and yet all the rules of engagement really changed when you started your own business. 

Roslyn: (12:24)

Yeah, 100%. Um, everything changed when I started my own business. Absolutely. And, uh, I didn’t know what I was walking into and I had to kind of figure it out along the way. Um, and it wasn’t always easy. Um, it wasn’t always rewarding. Um, but you know, you, you do what you gotta do. Um, and, and sometimes it, it takes you down a path and you aren’t expecting and you just kind of have to, you know, say what, what are we gonna do here? Right? Like what am I gonna do with what’s in front of me? Um, and I think we all do that on a daily basis as entrepreneurs. 

Kris: (13:01)

Yeah. And I think for me, what is really refreshing about your honesty and we’re gonna dive into, I think a really powerful part of your story as well in a moment where you talk about the fact that you, you really came very close to quitting. And why I think that is so hugely impactful is because you have this background that really is just created a, you know, as I said about systems and volume and stuff, but everything changes when you have your own business because you start off and you worry about money and you think, okay, I got to do this myself and okay, I got to wait until, you know, make sure I keep my head above water as far as revenue and I’ll just work really hard for the first year because that’s very admirable. And so I want people to understand is, you know, the power of building a team is so important and yet you saw that in the bigger firms, but you fell to the entrepreneur mindset of let me grunt it out, let me work really hard, let me save money and try to do it myself. And what happened? What happened? Tell me. 

Roslyn: (14:00)

Yeah. Yeah. So, and it was interesting just to take a step back is when I was with one of the national organizations that I was with, that was one of the things that I did was I coached other entrepreneurs and we would talk about where they were and their practice and, and support them with your, you’re in a place where you need to hire somebody and getting them over that and taking that step and that leap of faith sometimes. Cause that’s really truly what it is. Most of the time it’s a leap of faith. Right. Um, and so there I was in my own business and I was fighting that. I was really too, I’m scared to let go. I think that, you know, when you have a business and you work so hard to get it to this, this spot, it’s like your baby and you, you, you know that hiring somebody is gonna. It’s gonna force you to kind of let go of some of it. Um, and so I fought that so hard. Like you were saying. I love what you said, the grinding it out part, right? Yeah. It’s almost like I thought of it. Like if I, you know, if I can’t leverage this on my own, am I failing? Am I not being efficient? Where’s the messier? Um, and so I struggled and struggled and struggled. And I got to a point where I, you know, my whole mindset around it was in such a place of paralysis, almost like an analysis paralysis that I thought I, you know, I’m done. I’m just gonna quit. I’m gonna quit. I’m gonna let go my business. And I literally started looking for a job. Like I was defeated. I thought, I can’t do this. I’m laying on the ground bleeding. Everything’s blowing up around me and I’m, you know, it’s just better if I go find a job. I’m just, I’m done. I’m gonna let the business go. 

Kris: (15:35)

Do you know what I love about that? That you shared with us and you’re so kind to share that with us is because there so many people, you know, probably listening right now that what happens is when you’re isolated, isolated, like that, you start to doubt yourself. Like, Oh, I thought I’d be good at this, or I thought I was smarter. And you are one smart cookie, you’ve got a lot of experience, you’ve got a lot of education, you’re surrounded by brilliance for many years, a lot of years in the field, and then yet you were struggling with the same thing because all the rules of engagement change when you have your own business, which by the way, if I must say that’s my pet peeve, is you, you see this all the time with government organizations helping entrepreneurs or you know, people with a job saying, I can train you how to put systems into your entrepreneurial, you know, a company, their entrepreneurial company, oxymoron there. But anyhow, but the point is until you’re in it, you know, it’s like talking to somebody, but I don’t know anything wartime say until you were there. You don’t get it, right.

Roslyn: (16:31)

I love that, No, it’s so, it’s so incredibly true. I love that you point that out because it’s true. It’s like kind of that, that whole thing where you’re like, if my kids ever before you have kids, right.

Kris: (16:42)

Oh yeah yeah 

Roslyn: (16:42)

As it years does it to you

Kris: (16:47)

I always say I was the best parent til I had kids. You know? And, and, and there’s something you mentioned all the time you mentioned that people mention all the time with, you know, it’s my baby, I didn’t want to let it go. And when do I want to say to that is people think like you say, Oh this is my baby. I work so hard and I, I want to make sure I do it right. Well there’s two things that I, I want to point out there. One is nobody’s saying like, like here’s your baby handed off. Leave it somewhere and never come back. But it’s almost like if we’re gonna use the baby analogy, well maybe you can hold the baby for a minute while I make dinner. You know what I mean? So the idea of everyone doesn’t want to let go. What I wanna say is, well gosh, there are things you can let go. Like there are little things every day that you know, if I could take 15 minutes, you know, this is what I coach people with win the hour, win the day is, we start off super small and say, okay, this is your zone of genius. This is your passion. I’m not gonna even touch that right now. We can be talking about this nuisance that you have to do 15 minutes of every hour and all of a sudden we’ve got two hours at the end of your day and it was really redundant work that you never noticed. So you, you have the same mindset as so many other entrepreneurs thinking it’s almost like all or nothing like I have to hold onto it all or let it all go. 

Roslyn: (18:05)

I love that. The way that you explained all of that is so huge because it’s, and just to kind of go back to the baby analogy, like you can’t be the best mom you can be without getting that break right. Without somebody to hold the baby while I make dinner or let’s, I need to go out. Like we, you know, I need to go out with my husband. I need to refresh. I need to regroup. You, I think have to step away from those things and give them to somebody that can support you and have your back. And when you do, and you show up back into that space where someone’s helped you grow your business manager and box, do your calendar, what have you. Sometimes they give you a fresh perspective too. They’re like, Hey, did you know? And they’ll give you this insight and you’re like, Oh my, I would have never seen that because I was so in the weeds. And it’s huge. It’s huge to make sure that you’re, you can’t do it alone. Nobody’s successful in this space. Does it alone. It’s just no. 

Kris: (18:58)

No, nobody’s success. Well, in the history of the world of business has done it alone because really what I also say too is we talk about this a lot with win the hour, win the day is, am I in philosophy as you think? Hm. Okay. You know what, I, I know how to do this and somebody else wouldn’t. Whatever. And, and there’s some argument where you say, well, if you can do an 80% as effective as you, that’s still a big, huge win. But I would say how effective the do they need to be when you start trying to learn new things, six, seven, nine o’clock at night when you start at work earlier and earlier when you can’t remember the last time you had eight hours sleep, you’ve got a whole bunch of file drawers open in your head. You’re so exhausted and, and yet you think, Oh, I have to do this and this and this and never mind. Don’t even get me started. That all the stuff in the history of mankind, on the grace inventions were done in times of creativity or play cause you’re at rest. So you’re far more, uh, your, your brain operates that way. When you’re chasing a clock and you’re under stress, your brain does not operate as far as our few creative options.

Roslyn: (20:00)


Kris: (20:01)

So we all think, Oh my gosh, I have to do it all myself and nobody can do it as good as me. But I would argue you’re not doing it that good anymore if you’re that frigging exhausted and tired. 

Roslyn: (20:12)

Yeah. And that’s where I was, I was in burnout, like not even overwhelmed or now like complete, I can’t do this anymore. I can’t even think. You know? And when you’re like that, you’re not the best. You can’t serve your clients. You can’t be there for your family. All of the balance goes completely out the window and you’re in survival mode. So I love, love, love that point. You’re so spot on with that. It’s you and I. 

Kris: (20:35)

I was told kindly after the fact that I also had lost a significant amount of my charm. So it wasn’t as charming as I thought it was when was beyond nauseous, tired and cranky all the time. Apparently the first thing to go with exhaustion is a lack of charm. So [inaudible] 

Roslyn: (20:58)

I love that. I, you know what? I always, I would tell my clients too, when I was coaching a, think about how you’re showing up when you’re like that. When you’re burnout love, when you show up, you walk into a meeting or you’re on a conference call or what have you, and you’re in that space. How are you showing up? How are you landing your best? You can’t tell your clients you can’t be happy. You’re, you know, exhausted and overwhelmed and it’s not, it’s not good. And thinking about what you’re doing when you’re, when you are onboarding a new person, you’re, you’re supporting another, another person that might be, you know, needing their breakthrough and all that. So it just kind of, it manifests when you step out of your whatever’s holding you back.

Kris: (21:37)

Absolutely. And tell me some of the other things, because I think you’re very articulate about these pain points and that’s what we all want to hear now is like, well, what can we do now for our business? How do we get into this now? And so you thought it was like, you know, letting somebody else take care of your baby. And what were some other things that stopped you from getting help? 

Roslyn: (21:59)

Mmm, there I had issues with the financial piece of it. I thought, okay, how much is it gonna cost me? The thought of even putting pen to paper and figuring out how much it was gonna cost, narrowing down the candidates, right? Like let’s say you put this out there and you’re like, I need somebody to help me with this. And then you get flooded with all of these prospects and all of them look great and you’re like, now I have to spend how many hours weeding through all of this stuff. And that in and of itself is overwhelming. And then training, all of my efficiency’s gonna go down. So I’m gonna put a tremendous amount of time. I’m gonna put a tremendous amount of money. And what if it doesn’t work out right? Like that’s the scariest part of it all. And, and, and I, you know, I was like, I would think to myself, I just, I’m just gonna do it. I’m gonna do it myself. It’s so much easier. I’m just gonna do it myself. 

Kris: (22:50)

Those are some really great points I’d like to unpack. And I it just, this is why I’m, I mean that’s why I wrote my book win the hour, win the day, and that’s why I want to do this podcast is just to give people opportunities because to learn, because when you’re there and nothing breaks my heart more when I see somebody really working so hard. Like it’s not like you’re not doing anything or you’re lazy, but when somebody is putting all their might and force into something that’s not executing for them, that’s what breaks my heart is like you’re over here killing yourself and you’re, it’s kind of like trying to plant a tomato and cement. Like I see you, you’re working really hard digging that cement Dell, but that tomato is not going to grow there. Right. And what have you just went over here you would need, it would take so much less effort to get a little pot of soil and put one little tomato seed in there, but you’re over there trying to dig through cement. So those are some really great points. I want to sort of dive into one is, man, there could never an easier time. I mean, I cannot believe that the resources you can afford in this day and age as far as hiring somebody that would allow you, like, you know, I know there’s always this thing if you could afford a coffee, but literally you can hire somebody even, especially when you’re new at it and you’re like, okay, I don’t really know what it is. Which by the way, sidebar conversation, by the time you need help is almost like too late. Like you need help. That’s not the time to be looking for help. 

Roslyn: (24:13)

Oh my gosh. That one needs to be like honorable horn. Like literally you have to, you have to pay attention to your gut, pay attention to your belly, pay attention to your calendar, your inbox, everything, and act sooner. Love that.

Kris: (24:25)

You’re right. Because by the time you need help, it’s too late. So not too late, but it makes it a much harder, harder, harder climb. So then I would say to you, you can hire somebody when you’re like, Oh, I don’t really know what I want to do, whatever. So when I start working with clients, especially in the beginning when they’re unsure of this, is it’ll be like, well, hire somebody for like four hours a week and we’re talking like 40 30 40 bucks. And then that gives him like some relief, like Friday afternoons and then we see, Oh my gosh, Oh wow. So that clears up some time. And then they say, well, you know what else since sound worked out so well, I didn’t realize I could also outsource this and this. And so we started real small things because what happens when you’re doing it the old school way like you is, okay, I need to hire somebody for 20 hours a week. I need to go through all these candidates. Then I need to set up a very sophisticated, you know, system to train them. Whereas I might say to one of my clients, okay, show me something, whatever. Maybe it’s social media stuff where they say, look, okay, I want you to go in and post on my groups that I’m doing this. Here’s one post re posted a bunch of times or whatever. There’s so many things that can show you that are labor-intensive, that needed to be done, but once you do it once, somebody else can execute it, whatever. Right? So then you know, you might say, all right, so that’s like 30 40 bucks a week, whatever. And then when we set up the hiring process, it’s so small. It’s so, I mean it, I know I made mistakes in the beginning and it took me months when I work with my clients to say I’m about to save you a year of your life because we’ve got it down to such an art form that we can get really rockstar people just by our hiring process. But then what happens is I might be asking somebody to do something and I’ve done it once and I just screen capture it, save the video on my computer, send it to them and they can see it. And then they can transcribe it for 10 cents and they’ve got the steps written out and they’ve got the video. So there’s the hiring process. I had to do it anyhow. I screen captured it with a free application. Screen capture took me five minutes, hit 10 cents on Temi. Now they’ve got notes and we’re done. 

Roslyn: (26:28)

Yeah. See and that’s what I love about what you’re doing though. Cause you make it sound so simple and easy, right? Cause it’s what you do. Me as a marketer, like I just want to market. I want to grow people’s practices, I want to generate leads, I want to be doing all this stuff. So that’s where the win, it’s letting go of those things that are your unique ability and cause it makes, it’s painful to me. I just told you, Oh my gosh, doing all that sounds so painful. But it’s because I don’t like it. I’m a business person, I want to run my business and I want to generate leads. I want to talk to my clients, I want to, you know, look at the dashboard and see where the money’s in the budgets and all of that stuff is. And I want to leave the rest to somebody that’s just going to save me in the places that I need to be saved. And so yeah 

Kris: (27:10)

That is exactly what I want everyone to do. You have a zone of genius, you have something that you find interesting and passionate about. So you want to just dive in and look at that numbers that I would probably want to scratch my eyes out for. And so you want to go in and look at budgets and all this other stuff. And so that’s where you should be. So the stuff I’m talking about now, you know, I’ve been doing this for awhile and I teach other people how to do it, but I will tell you now, my assistant does the hiring. 

Roslyn: (27:37)


Kris: (27:38)

And because we have a process, so she’ll post a job, she’ll narrow it down to three, two people. And then I go in and pick out because she’s followed the process and I go pick and say, okay, let’s try this person. And yeah, you know they have a trial period. So now I don’t even do the hiring because the system has unfolded. So that’s what I’m telling you when you say I just want to do my marketing. Yes. Everybody say yes. Whatever it is you love doing, that’s what you should be doing. You have the vision, you have the passion, and so all this other stuff, that’s what we want to do. We want to take more and more and more off your plate so that you walk in because I believe you should start work refreshed and leave fresh.

Roslyn: (28:19)

I love that.

Kris: (28:20)

And you start in, refresh and you do all that stuff that the rest of us find people in your job and everybody else does all this other stuff. So that’s exactly what I’m so glad you said that. That’s a very powerful point. I just want to do my passion, my zone of genius, right? So then you need a team. That’s why you need a team 100% and then when you do that zone of genius, which will then by the way, bring in more revenue.

Roslyn: (28:47)


Roslyn: (29:08)

Yeah. Yeah. I think one of the first things that when you and I were talking that I loved about our conversation that you kind of pulled out of me when we were talking was, um, when I got to the place where I said I’m limiting my ability to grow, I’m shrinking my future by sitting here and not getting somebody on board, on my team to help me out. Yeah. And it really, it really can be that simple, but I can’t do it. I know I can’t do it. Yeah. Because much time and energy and I don’t want to touch it with a 10 foot pole. 

Kris: (29:38)

But here’s, here’s the thing, and, and I love that you say that because what also I find heartbreaking is when people say, okay, you’re right Kris. All right, I’m going to go and I’m going to figure this out because all we’re doing now is you try to do things. You say, well, whatever, I’m going to try to learn SEO on my website because they’ll save money and then you spend months doing that and you’re exhausted and it’s not petering out and you should be doing stuff on marketing. Great. And now somebody says, well, you should have a team. Okay, I’m going to run off. I’m going to see what course I could take to learn how to do that. So you’re just putting the same dysfunction in a different area.

Roslyn: (30:10)


Kris: (30:11)

So you’re right, that is something you should be outsourcing to someone who knows how to build teams quickly and effectively and show you how to do it in three weeks instead of taking three years. Like most people will have to do because those three years eat up your profits and again, delay cause all it is is now you’re burning down a different path. It’s like me jumping up and saying, you know what, uh, what I really love doing is building teams, but I want my team when we have meetings with clients to show up looking good. So I should probably learn how to cut hair because that’s something really important that we should, you know what I mean? Like just because you hire someone, all of a sudden you think it’s yet another thing you should know how to do. 

Roslyn: (30:53)


Kris: (30:53)

But it’s a totally, totally different talent or skill set or expertise or you know, whatever. 

Roslyn: (31:01)

Yeah, it absolutely is. And you make it sound so easy when you’re talking about it. You’re like, Oh I just screen capture it and then I did this and I’m like, you know you, you can tell you’re in your zone because you’re just walking through it like you’re excited about it and it’s what you do and you know how to do it. And here I am, like I don’t even know where to be at, where to begin. So I’m going to stop doing that and I’m going to start going into my marketing budget. You know, you just kind of go away from what you don’t like to do. So you might as well get somebody to support you and get what you need to do because so much it’s an investment. 

Kris: (31:33)

It is an investment and it, but it’s an investment in freedom and in minimizes your frustration because, because like I said to the other day, until you build out your team, the best thing in the whole world you could hope for is that this time next year you’re in the same spot. But without a team, more often than not, you’re going to be further behind because you’re going to be more tired. You’ve been running longer, and you’re just gonna get buried in your own work. Right. So the reason it, I think when anybody does anything, well it does sound easy and that’s why, that’s why you lean on other people, right? It’s like, Oh, I look, yeah, that’s like when you watch the Olympics and you’re two days in, you’re like that guy who just did 47 flips on the diving board. You’re like, Oh, look at that. Too much splash. Look at that. I’ve been, I’ve been watching the Olympics for three hours and he’s been training for like, I don’t know how many years, but I’m like, Oh, so when anything is done well it does look easy, but what I really want the message here for people like yourself and everyone out there is [inaudible]. It’s not your fault. Stop beating your head against the wall. Stop saying, Oh, I just have to get more. Here’s the thing I hate hearing. I have to get more organized. I need to be more disciplined because. 

Roslyn: (32:47)

That one killed me. 

Kris: (32:48)

Yeah, because I was like, you know, I’m a pretty organized person, but what happens is you just reorganize yourself. You’re not changing the infrastructure. You just reorganize it. 

Roslyn: (32:57)

And it feels good for a minute. It feels good for a minute, but it doesn’t solve the problem. It feels good and you think you’re doing something but you’re not. I’ve done that so many times and failed massively on the underside of it. 

Kris: (33:11)

Yeah. So let’s talk a little bit about now people are going to assume as we move forward, you’ve heard my wise words, you’re going to turn your, you know, your business around, you’re gonna triple your time off, double your income, you’re going to build this chain team, it’s going to be super, it’s gonna be easy. And you know what? You’re just going to find the fun back in your business because I think business should be fun. Now that aside, tell our audience what people you work with best as far as your marketing expertise so that they can come to you. Um, and know like, Oh she’s got it all set up now with the team and she is here to help me. So what, what do those clients look like for you? 

Roslyn: (33:48)

Yeah, yeah. So we build funnels and well we do three levels of support. So it starts off with just social media management, which is making sure you’re getting consistent content out and staying top of mind and that sort of thing. And then we do a second level, which is paid traffic. I’m creating ad strategy within the platforms. And then the highest level is really creating a sales and marketing funnel that gets your phone to ring consistently and leads while you sleep and that sort of thing. So landing page ads, Facebook, you know, all the LinkedIn inbox strategy, lead generation for any business at all. Just creating a sales and marketing funnel online in the digital space. 

Kris: (34:28)

So there you heard people, she is one smart cookie and she should not be running around, tiring herself out because she’s got too much going on going on and I had of hers. So that is awesome. All right, so I can’t people you really should reach out and connect with Roslyn. She’s got a lot going on for her and she’s just been so wonderful and brave because so many people are struggling with what you’re struggling and yet they just put their head down and you say, how’s business? Everything’s fine. And then they just say, Oh, once they get past this next thing or once they get caught up. So what I think for you, aside from having a talent in your area of expertise, you’ve got some real business chops because those, that self-awareness, you can’t do anything until you understand what the problem is. So for you to say, look, I, you know, in order to, because we could just hear those 30 seconds you talked about your business, you got a lot going on, you’ve got a really good scope and lens of marketing. So we want to see you out there reaching even more people. Right? So thank you so much for being honest when so many of us are not brave enough to do that, but to talk about the real trials and tribulations of grunting and out by yourself. 

Roslyn: (35:42)

Well thank you for creating this space for it. Something that we all need to hear and we all need to be present to it because like you said, we can’t do it all. And so creating a safe place where people can share that and open up and have a resource for it is huge. So you’re doing great.

Kris: (35:56)

Well thank you very much. I’m just very passionate. I think business should be fun. And I just, you know, for this blood, sweat and tears you put into it there, you’ve reward to be so much bigger. Because I tell you, even just the other day, I saw somebody on Facebook and she’s like, Oh, I left my job. I’m gonna start my own business because I want to spend more time with my family. And I thought, Oh my God, good luck. 

Roslyn: (36:18)

I tell you, it gets less before it gets more.

Kris: (36:21)

Yeah. I don’t know how many people said I started my business because I had this passion and I wanted to spend more time with my family, and then they’re like family. Like they’re so mad at me. I’m always in the closet answering emails. Right. So, you know, I just thought, well, you better get your act together because in the history of, I think entrepreneur in German or, or Latin means spend less time with family. I don’t know. Right. Yeah. I don’t know. All right. Thank you so much again, Rosa. We appreciate you. Where can people find you? 

Roslyn: (36:49)

You can find me on my website and digital social Um, and if you’re in the legal space, feel free to go to law firm, marketing

Kris: (37:01)

Perfect. Thank you again Rosen. We enjoy this. Thank you so much.

Roslyn: (37:04)

Thank you