Growing a Team with Meg O’Leary
On this episode, Meg shares:
- How she knew that it was time to add someone to her team
- What traits and characteristics she was looking for in a team member
- What it looked like for Meg to grow her team AND maintain her brand at the same time
- How her pitch has changed from “me” to “we” and how that has ultimately made her business stronger
Links:
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Transcript:
Intro: Welcome to Becoming a Sleep Consultant! I’m your host Jayne Havens, a certified sleep consultant and founder of both Snooze Fest by Jayne Havens and Center for Pediatric Sleep Management. On this podcast, I’ll be discussing the business side of sleep consulting. You’ll have an insider’s view on launching, growing, and even scaling a sleep consulting business. This is not a podcast about sleep training. This is a podcast about business building and entrepreneurship.
Jayne Havens: Meg O’Leary is a Certified Sleep Consultant and Founder of A Restful Night. For Meg, being a sleep consultant means changing the lives of families each day by giving them the tools and confidence they need to get their children quality sleep. Meg has always been a sleep enthusiast and as a mother of three young children, she quickly realized how important A Restful Night is for both parent and child.
Meg received her certification from the Center for Pediatric Sleep Management and uniquely combines her expertise in sleep with 15 years of leadership as a marketing executive coaching large global teams at American Express. Working with Meg means you’ll get the best combination of parent, sleep enthusiast, and coach. Meg resides in Westchester County, New York with her husband and three children. She supports families both locally and virtually all over the world. Meg, welcome. I’m so pumped to be chatting with you today.
Meg O’Leary: Hi, Jayne. Thank you. I’m glad to be here as well.
Jayne Havens: Before we get started, tell us a little bit about your journey to becoming a sleep consultant. I guess, I’m wondering, what made you want to jump into this field?
Meg O’Leary: Yeah. As you mentioned in my bio, I have three young children of my own. So, I have a five year old, a three year old, and an 18 month old. My journey with loving sleep started way before I had kids. I was always very conscious of my own sleep habits. I remember being pregnant with my first daughter, and my husband saying, “You’re going to be the best mom as long as you’re rested.” I was like, “Okay. Great.” Anyway, Fiona was born and I dove into it as a new mom reading all the books and following all the blogs. I quickly got her sleeping independently. I think, unbeknownst to me, I sleep trained her but I didn’t even realize really what I was doing. Then we got pregnant with my second. I had her about 16 months later and bam, I did it again. I was just — everyone would look at me, like, “You’re so lucky. You have these great sleepers.” I’d be like, “No, I actually really worked on it from day one. We’ve just been practicing getting them down and focusing on good rhythm,” and all the things I coach parents on now.
Then, like many —COVID hit, the pandemic hit — life took a little bit of a turn for me. As you mentioned in my bio, I was working in the business travel sector at Amex. The industry took quite a hit, and I was offered the opportunity to leave the company on my own terms. I was pregnant with my third at the time, and so I left. I had my baby. I took some time off. My husband and I were kind of like, “Alright. Well, what’s next for me?” He knew I wanted to be a working mom. I knew I wanted to be a working mom. But there was something about corporate marketing and just this concept of a nine to five that just didn’t feel right or organic for me, just given where my family was at that time. Together, we were doing a lot of soul searching. We just kept coming back to like, “I’m so good at this.” I love helping friends. I love knowing that my kids sleep. That’s when I connected with you, if you remember. I jumped into the course and built on all the books I had read, all the blogs I had dove into. I became certified and launched my business shortly thereafter. So, I think it was a combination of things. It was just interest and passion but, more importantly, just some different drivers in the market that led me to this. It’s great. I’m happy I’m here.
Jayne Havens: Yeah, I’m happy you’re here, too. I was looking back. You actually finished your certification in July of 2021, and you launched your business in September of that same year. Then literally seven months later, April 2022, you were ready to expand your team, which is crazy and awesome. What did your business look like at that time? How did you know that it was the right time to bring someone on board?
Meg O’Leary: It was kind of crazy. I look back. I mean, I never thought I would be where I am now a year ago, to be completely frank. It’s been an incredible journey. When I launched in September, I was doing a lot of pro bono work. I was helping local families and just trying to get my footing. Then I started to charge for my services but charge a discounted rate — again, as I was trying to get my brand developed and get my experience. Then by October, soft launch was over. I was all in. I was servicing clients. By January of 2022, I was, on average, supporting six to nine clients at a time. I remember January being a very stressful month for me because I had this client load I was managing. Also, I was still a new business owner. I was only less than six months in, and there were still these demands around building my marketing channels and establishing different relationships and all the other things that went on.
So, I had this aha moment, that I was like, “I need some help.” For me, I was like, okay, I can outsource this. I can outsource that. But I love the business side, I love that part of my role. Of course, I love supporting families as well. So, for me, it really made sense to say, “You know what? Let me bring on someone who can help me with the client services side, who knows how to sleep train, knows how to support families. Then hopefully, that will free up some time for me to do all these business things and keep the pipeline going and keep business building going.” That was, for me, what happened. A lot of steps I’ve taken in my business. I was very like deliberate. This aha moment happened in January, but it took me really three months to get the right person and set myself up to bring this person on, which then happened in April.
Jayne Havens: I think when you’re successfully growing a business as a solopreneur, it can feel really hard to trust another person to help you grow. Personally, I’ve struggled with that. I don’t have anybody on my team helping me to grow, because I can’t seem to find it in myself to trust anybody else to help me to grow. I guess, I’m going to ask you, what things did you consider when you were looking to add another consultant to your team? How did you mentally deal with that?
Meg O’Leary: It’s really hard. It’s like our baby. It’s like you grew this. You found it, you grew it. It’s yours. So, bringing on someone meant giving up a tiny piece of that control, like you’ve said. It was definitely something I thought long and hard about. For me, the things that most of my time deliberating and considering were, number one, what is the purpose of me bringing this person on? What am I looking to achieve? For me, at that time, it wasn’t about scaling or making more money. It was really about freeing up my time so that I could pour more of my energy into the things I knew would build my business longer term, like I said, the marketing channels and all of that.
Jayne Havens: Hold on. I want to stop you there for a second, because that is so interesting what you just said. You said it wasn’t to scale. It wasn’t to grow your income. You also said that it was to position yourself to set yourself up. So, it was almost like it was to scale but not with a money drive. It was to scale because you have this passion to grow. Right? Am I understanding that right?
Meg O’Leary: Yeah, 100%.
Jayne Havens: Because I think that’s really an important distinction. I think the best way to grow is actually to grow — I mean, this is going to sound really cheesy — to grow from the heart, to grow from passion rather than to try and just reach a higher number in your bank account. I think what you just articulated was exactly that. You said you weren’t trying to scale but you were setting yourself up to scale.
Meg O’Leary: Yeah, again, so much of what I bring to my business comes from my 15 years of corporate marketing strategy. You have to think, too, what is three steps ahead that you want to get to? For me, this was one step in getting three steps forward. So, it was all about a long-term play 100%. Yes, of course, I want to scale my business. I want to help more families. I want to grow my revenue. But at the end of the day, you also have to remember you have to invest time, and you have to invest money to get there. For me, this was a stepping stone. That was the purpose, like I said, to free up my time.
I would say the second thing was really about my brand. How do I maintain the brand of A Restful Night when I bring someone else on? I spent a ton of time in those early months of business development working with a marketing strategist to build out my brand, what do I stand for. So, I wanted to make sure that with this move to adding someone else, that it wouldn’t change what I stood for in the market and that I was prepared across all aspects of my business to answer that question. I would say that was one thing.
Then the last thing was, what we need to do to make myself as comfortable as possible with this change? Like you said, change is hard, especially when it’s your baby and it’s your business. Anything — we can’t control everything, but there are things within the chaos that you can control. So, that’s what I was sort of focusing on. I spent a lot of time thinking about what changes do I need to make to my process, or how do I make sure that I have visibility into things so that my clients are getting the great service that I know I give them? But when I’m not the one doing it, how do I make sure?
At the end of the day, I would say those were the three big things that I kept coming back to. As long as I was feeling comfortable with those, I knew I could keep moving forward and keep moving forward. So far, I’ve seen it. It’s been great so far. Having someone, not only to be a colleague of mine under my business umbrella but also to be someone to throw ideas at and brainstorm cases in how to help families, there’s tons of benefits.
Jayne Havens: I think that bringing someone on and maintaining your own brand identity is really challenging and, frankly, really impressive that you’ve been able to achieve that because — at least, I’m just going to speak about my own business because that’s what I know. People don’t say. “You should hire Snooze Fest, or you should even enroll in CPSM.” People say, “Take Jayne’s course.”
At least, for me, my entire brand is wrapped up in my own identity. I think it’s really, frankly, very impressive that you’ve figured out a way to create a brand that’s beyond your own name, your own face, and your own personality because — I don’t know. That just feels really impressive to me. Props to you for figuring that out. I guess you had some help figuring that out, and you hired somebody to help you figure that out and navigate it. It’s really impressive.
Meg O’Leary: I think this is not us talking about branding. But I’m a marketer, so I’ll throw the branding plug in here. I think people think about a brand like a logo, right? Like, “Oh, I’m going to brand my company. My logo is going to look like this.” That’s not your brand. Your brand is what your customers feel when they work with you. It’s what process for them looks like. It’s what the output looks like. It’s your mission, it’s your value propositions. All these things boil together. Of course, there’s a logo that people recognize you for. But that’s what, for me, is most important. I know we’re probably going to talk more about what do I look for and all of these things. But for me, that’s most important. It needs to be the ‘A Restful Night experience’ whether you’re working with me, or you’re working with my colleague, Sarah, or whoever else may join my team down the line.
Jayne Havens: So, on that note, what traits or characteristics were you looking for when you decided to bring somebody on? Was there a personality type that you had in mind, or even just like an image? Is that fair to even ask?
Meg O’Leary: Yeah, I think those are all fair images. Having worked for 15 years, I’ve hired a ton of people over the course of my career. I always hire people who have skill but, more importantly, have ambition and have a good energy to learn and grow. For me, you can tell right off the bat when you speak to someone whether you’re going to click, whether they’re going to jive with your philosophies, et cetera. So, I think all things aside, you have to click with the people that you’re working with. That’s the only way you’re going to make it work. You have to trust each other. You want to have coffee with this person, right? That’s important. I’m not looking for a particular image or anything, but I do think personality plays a big role.
Other things that I was looking for — plug for CPSM — that, for me, that was very important, that whoever will work with me and work under my brand, be certified in the same program that I was certified in, and that we could be talking the same talk and applying the same methods and having the same philosophies. That’s part of what I talked to parents about on discovery calls and how I explained how our team works. I lead with that. I lead that we’re under the same certification. We’re doing the same work. It’s just about who’s leading your day to day program. That was, for sure, important.
Passion, wanting to help parents as much as I do, not approaching every family the same, really taking the time to listen and become part of their family for those two weeks that you’re helping them, and work ethic. Like I said in the beginning, I think you can sniff out a hard worker pretty quickly. If you’ve interviewed enough people in your life and you’ve hired people, you can tell pretty quickly. So, I work really hard at this. This is my full-time job, and I pour a lot into it. I don’t expect someone working for me to maybe have that same drive every single day, but I need them to show up when I need them to show up. Those are things that I’m looking for. I want someone to treat the business like it’s their own because they care so much.
Jayne Havens: How is your experience bringing somebody on to your team changed the way that you do business? If you can think back to the way that you used to operate as a solopreneur and now you’re a team, what does that look like day to day or week to week, month to month?
Meg O’Leary: I wasn’t doing it that long by myself. I guess that was an advantage, because I hadn’t created too many concrete systems that I needed to change. But I would say that workflow is, for sure, something that’s changed, as I think about it being just beyond me. So, I had to take a real close look at my processes and the workflow and figure out what needs to change, what do I need to keep control of, and where do I need to maybe modify things so that I have good visibility? I use HoneyBook, which is a customer relationship management platform for everything. That, as a tool, has been instrumental in terms of me being able to see what’s going on, manage the pipeline, and make sure that clients are getting similar communications.
Workflow has definitely been a big piece. Personally, when you think about the workflow, I handle all of the discovery calls. So, that’s something that I choose as part of my workflow to always direct to me. Because I find that it’s really helpful for me to see the types of families that are coming through, be able to see which program is going to be best for them based on what I hear. Then also tee up who may be the best consultant for them to work with and manage the pipeline that way based on caseload and technique or availability. So, that’s an example of something that I’ve deliberately kept in my wheelhouse so that I’m overseeing that.
Then, I would say, the second thing that’s changed quite a bit from ‘me’ to ‘we’ is the pitch. Like, here’s what we stand for. Like you said, everyone knows you as Jayne Havens. So, everything before Sarah, who works with me, was very me, me, me. Like I, I, I, Meg, Meg, Meg. So, I had to make a very conscious effort in communicating about what we do but also in my marketing materials like my website, other places, to change all of that to very we, we, and our team.
For me, it’s incredibly important to make sure that when I’m on that discovery call with a parent that they know in full transparency that someone else could be servicing them. I don’t want it to feel like a bait and switch. Like, you connected with me and all of a sudden, I pass you off to someone else on my team. That’s not what it’s about. So, I’ve had to change a lot about how I think about that discovery call, both in terms of how I position it and how I talk about how we’re set up to support them.
Jayne Havens: Do you find that certain families, like they talk to you and they only want to work with you because they spoke to you? Have you successfully figured out — have you mastered that, where you can have a great conversation with a parent and then just gently nudge them right over towards working with Sarah, and that works just fine?
Meg O’Leary: Yeah, I can honestly say, I haven’t — I think there are certainly parents that will say like, “Hey, I’d love to work with you if you’re available.” My availability is oftentimes farther out than maybe Sarah’s availability. I think there’s trade offs with everything. Some parents will say, “I’ll wait.” Other parents will say, “I’m just excited to work with your company. I know you guys are great. So, who’s next and available?”
I always equate it to going to get your hair cut. If you go to get your hair cut and you end up working with the owner of the salon, you may have to wait longer to get that appointment, or you may have to pay a little bit of a premium for them to cut your hair. It doesn’t mean you’re going to get a bad haircut if you go and get your hair cut by Suzy, but it just means you may be wanting to wait for someone else. I equate it the same way. But generally speaking, I’ve never been hit with that, I guess, rebuttal or whatever. But I feel I’m so confident on my discovery call, that whether it be me or Sarah can service them in the same exact capacity, that it never feels like a hurdle to me to overcome. Do you know what I mean?
Jayne Havens: Yeah, I would imagine that, actually, now that you’ve built a team — this is something that we actually didn’t talk about offline at all. I would imagine that to some degree, it’s just giving your business, as a whole, more credibility. You’ve established this company. You’re not just some person that sleep trains babies and toddlers, but you have a company. You have somebody under you working for you. I would imagine that that positions you to probably close easier.
Meg O’Leary: Yeah, I think we’re definitely getting more exposure without a doubt. We have two networks working for us now, as well. The more you grow, the more opportunity you have to reach people. I think it’ll be interesting to see how things pan out over the next several years. I’ve mastered what’s working now. But I’m sure in a couple of months, something may change. I may need to think about something different. I think that’s part of being a business owner who’s got a team underneath them. You have to be ready to pivot at any point in the game.
Jayne Havens: Let’s talk about growing pains, and just like pros and cons of being a solopreneur versus having a team. I feel like you’ve talked a lot about the things that are working really well. But have there been growing pains? Are there things that have been really hard as you’ve taken on somebody else to work with you?
Meg O’Leary: Yeah, we talked about the pros, right? The biggest pro of all is having more people to do the work and being able to, hopefully, broaden the impact that we have, I would say less cons, more considerations, if we can call them that. Because I truly haven’t seen — I went into this very deliberately. If I thought there was a downfall, I probably would have maybe tap the brakes a little. But I would say the biggest consideration has been, I think, two parts. One is, it’s an investment of time to bring someone on. I can only expect someone on my team to be as successful as the time I’ve put into them. It’s not like they start on a Monday, and on Tuesday, you’re handing them their client. You’re saying, “See you.” I spent a lot of time making sure that we’re in sync on processes. We’re meeting weekly to talk about cases and how things are going. So, I went into this thinking like, “Oh, I’m going to have so much time now that I have someone new on to do all this marketing stuff I want to do and spend time business building.” The reality is demand increased when I brought on someone. So, I actually haven’t seen time yet. I’m hoping to get there, or that I can bring on someone else so I can get there.
I would say the other consideration is just that I have a second job now — not only am I a business owner — or a third job, I guess. I’m a business owner. I’m a sleep consultant. But now I’m actually a boss, right? I need to prioritize making time for the people who are working for me, so that they feel important and that they feel supported. So, yes, I’m trying to find time but I also have to give time. I think that’s the biggest hurdle for me — making sure that you continue to see your return on time overtime, and you get what you’re looking for. That’s why I think in the beginning of doing all this, it was so important for me to be like, “Okay, what is my goal? What is my goal in bringing someone on so that I can make sure I’m inching my way towards that?”
Jayne Havens: Let’s talk next steps. Are you planning to expand further? It sounds like maybe you are.
Meg O’Leary: Yes. I mean, I think any good — well, I shouldn’t say any good. But I think if you’re an aspiring small business owner, who maybe one day wants to be like a mid-sized business owner, you’re constantly looking to grow. Yeah, I would love to be able to bring on a third sleep consultant on the team, at some point. At this point, we have a waitlist. I’m booking three weeks out. Sarah’s booking a week and a half out. We’re not able to turn around the client in a couple of days. There’s pros and cons to that. But I think it tells me something that we are growing. We just need to figure out how to do more.
So, I guess with that, I would say if you’re listening to this podcast and you’re someone that’s passionate about sleep and teaching infants and toddlers, how to do this, but you’re not someone who wants to own a business, my message to you is to be like, there’s ways to do it without having to be someone who’s bogged down in the admin side of accounting, and marketing, and all of those things that go along with it. You can be an incredible sleep consultant and not have to be a business owner.
Yes, I have ambitions of growing my team over the next year and broadening the impact that we can have. I think our relationship, Jayne, is one of these ones, where it’s like you know I want to do this. So, you’re always looking for who could be someone that would connect with me and that would may want to be on our team. Hopefully, if anyone’s listening to this and is connecting to that message, of course, I’d love to talk to them about it and see where they’re at in their process. It’s something that, down the line, we can stay connected and make work.
Jayne Havens: Yeah, you know I always have my eyes up for you. I hope that somebody is listening and fits the bill, because you’ve really taken this and ran with it. You’ve positioned yourself to grow really, really quickly and yet, still have a control over your process and your messaging and your business as a whole. I think that that’s really impressive, because I also know what it’s like to grow really quickly. Sometimes I feel like I’m just throwing spaghetti at the wall and then cleaning it up, and then throwing more spaghetti at the wall. It sounds like you have really great systems in place. It’s super impressive.
Meg O’Leary: I think that’s like a style thing too, though, Jayne. That’s your style. You’ve grown so much, too, but you’re a little bit more like, “Let’s see if this works.” I do a little bit of that but in a very controlled environment. Do you know what I mean? So, I think that’s also a message to people, which is both ways can work, right?
Jayne Havens: Yeah, I think that that’s really what’s amazing about entrepreneurship. It’s that there’s no one right way to be successful. I think when you’re really committed to showing up authentically as yourself, that’s really when the magic happens. For you, I think that’s way more methodical and organized. For me, it’s like, “What should I do today,” and see how it goes. It all can work.
I guess, with that being said, I would love to ask you what you think sets those apart that make it from those that don’t? I’ve asked this on the podcast before to other sleep consultants, and I’m wondering what your take on this is. I trained many, many people to become sleep consultants. Some of them knock it out of the park, and others never really get their footing. I wonder, what is that? What’s the difference between those that figure it out and those that don’t?
Meg O’Leary: For me, I think you have to want it. For me, that’s everything. It’s been everything since I was a junior level in corporate marketing. You have to want it. You have to know what your next step is. I think self-drive is a big piece. I don’t have a boss telling me like, “Great job. You did awesome today.” I have to find that in the family that got a great night’s sleep, or the Google review that they posted, or my husband being like, “You did awesome this month.” You have to be self-driven to continue to motivate yourself and show up every day.
I think being flexible and nimble is important too, right? I am a sleep consultant. I’m a therapist for parents. I’m an accountant. I’m in marketing. You have to be able to wear a lot of hats, and you have to be nimble. I’m not good at everything, but I know who to go to if I need help. I think people who struggle oftentimes get bogged down in like, “I have to do it all myself, and I have to be good at doing it all.” The reality is it’s not going to be. You have to know where to go for your help. People can be successful in a variety.
I listened to your podcast with Kelly Knoll the other day. What she said really resonated with me. It was like, success is different for everyone. I think that’s important, too. What does it look like? It’s not always a dollar amount. It’s not always how many families you’re servicing. It can be something different. So, I think it’s important to understand what that success is. But I think what makes people different is that vision and that ambition to get to that goal.
Jayne Havens: Yeah, and to your point that success looks different for different people, I think that that really is an important point to drive home. When I think about Kelly — just to use that same example — she truly loves what she does. She truly loves supporting families, and she loves having that little pocket money. As she always says, it fills her cup. If your work doesn’t fill your cup, then you’re going to go fill your cup with other stuff. I think we are sort of programmed to do what we like to do the most. You choose the things that feel easiest, or most fun, or most exciting.
The things that feel hard, we have to do those things in order to be successful. You can either just plow through and do them, or you can outsource them. But if the things that feel hard are a true roadblock that stop you in your tracks, then I think that’s where a lot of people get really stuck. It could be the tiniest little thing. It could be not being able to figure out how to make a sleep plan that they feel really proud of. For what it’s worth, I used to send my sleep plans in the body of an email until, actually, very recently. I didn’t have a pretty document that I share. My document is still not that pretty. It just has my logo as a header, and that’s it. You too?
Meg O’Leary: Yeah.
Jayne Havens: I don’t have this over the top, beautiful document that I’m sharing. But that doesn’t stop me from sending really valuable, well-thought-out, well-articulated information. I think some people would feel like, “Oh, I can’t send out this document because it looks like junk. So, I’m just not going to do this.” People get stuck on the silliest things. You either have to do it messy, or you have to hire someone to help you do it in a way that looks a little prettier. But either way, you got to get it done. Right?
Meg O’Leary: Yep, and I think we’re all our own worst critic. At the end of the day, people want to just sleep. They don’t care if you give them a pretty document, or if you give them a Word document that has a well-thought-out plan that you’re going to guide them through. At the end of the day, they just want to sleep. So, it doesn’t really matter.
Jayne Havens: Do you want to know what’s so funny? The other day, I sent my sleep plan to a new client, little six-month-old baby. I wrote my sleep plan. It was great. It was written great. It looked just like the way all my sleep plans look. My client actually reformatted it for me. She sent it back. She was like, “Hey, I hope you don’t take offense. But I just had some time, so I reformatted this to look more in line with your branding and your website.” It was great. I was like, “Uh, what else can you do for me?”
What’s funny is, it’s beautiful but I actually don’t know how to recreate it because I’m not tech savvy. I love it, and it’s saved to my desktop. If I can figure out how to do it again, I will. But it’s not going to stop me. I’m just going to keep doing it my normal way until, I don’t know, probably forever — unless I want to hire her as my VA, and she can change all of them for me. I don’t know. You just have to go with what works for you. You can’t let the little things stop you in your tracks, I think.
Meg O’Leary: This is so true.
Jayne Havens: Before we wrap up, tell everybody where they can find you — social media, website? If people want to connect with you to learn more about working for you, give us the scoop. Where can everybody find you?
Meg O’Leary: The Instagram handle is A Restful Night. I am at arestfulnight.com. That’s our website. You can always reach out on Facebook as well. I love to connect with anyone who has any questions about what it’s like to just do the work, not necessarily the business side of it. This has been great. You know I love sharing my story, Jayne, so thanks for giving me this opportunity to talk to your audience.
Jayne Havens: Well, thank you for coming on to chat with me today. I can’t wait till everybody hears this interview we did today. Have a good one.
Outro: Thank you so much for listening to this episode of the Becoming a Sleep Consultant Podcast. If you enjoyed today’s episode, it would mean so much to me if you would rate, review, and subscribe. When you rate, review, and subscribe, this helps the podcast reach a greater audience. I am so grateful for your support. If you would like to learn more about how you can become a certified sleep consultant, head over to my Facebook Group, Becoming a Sleep Consultant or to my website thecpsm.com. Thanks so much, and I hope you will tune in for the next episode.