929 Alyson Caffrey:

Wings of Inspired Business Podcast EP929 – Host Melinda Wittstock Interviews Alyson Caffrey

Melinda Wittstock:

Coming up on Wings of Inspired Business:

Alyson Caffrey:

A lot of founders will come to me, and they’ll be like, well, my team isn’t doing the things that I need them to be doing. And I’m like, well, how often do we shift priorities? Because when everything is a priority, nothing is a priority. So, what are the priorities of this season? This kind of releases some of the rest of the ‘I need to do this all, or I need to make this all happen right now’. Identify a priority for the season and then just expand the time horizon. So, if the priority this season is relationships, and that’s the one thing you want to do, you may find yourself at lots of networking events or joining communities. If you’re one priority for this season is your family, you may have a full July of blank space, and that might not feel like you’re, quote unquote, being productive. But I’ve seen so many folks, whether it’s coming back from sabbatical, coming back from maternity leave, coming back from a month off in the summer with the kids who have totally fresh ideas and perspective on what direction their business needs to go.

Melinda Wittstock:

As entrepreneurs we often have more balls in the air than we can successfully juggle, yet we put so much pressure on ourselves not to drop any of them any time. No, you can’t do it all, so how do you prioritize your time—in your business, with your family, for yourself? Alyson Caffrey is an operational maven and founder of two businesses, Operations Agency and Master Maternity Leave and she’s well known for her Operations Simplified framework to unleash the power of small teams. Today we talk about streamlining operations to help ‘parentpreneurs’ kid-proof their businesses and live family-focused lives. Whether navigating a new baby, managing the chaos with young kids, or simply making sure you’re front row at all the wrestling matches, Alyson shares how she helps entrepreneurs give time back to their families while growing a successful business.

Melinda Wittstock:

Hi, I’m Melinda Wittstock and welcome to Wings of Inspired Business, where we share the inspiring entrepreneurial journeys, epiphanies, and practical advice from successful female founders … so you have everything you need at your fingertips to build the business and life of your dreams. I’m all about paying it forward as a five-time serial entrepreneur, so I started this podcast to catalyze an ecosystem where women entrepreneurs mentor, promote, buy from, and invest in each other. Because together we’re stronger, and we all soar higher when we fly together and lift as we climb.

Melinda Wittstock:

Today we meet an inspiring multipreneur, ‘parent preneur’ and bestselling author who has mastered the art of juggling motherhood with entrepreneurship—and helps others to do the same. Alyson Caffrey is well-known for her Operations Simplified framework that helps entrepreneurs streamline their operations to free up time to live their best lives. She’s the author of The Sabbatical Method and today we talk about how to plan and prioritize your business around your own needs, with each season a chance to reprioritize. With summer approaching, what a better time to figure out how best to juggle competing demands on your time?

Melinda Wittstock:

Alyson will be here in a moment, and first:

[PROMO CREDIT]

Eight years ago, I started this podcast because I wanted to help women succeed as entrepreneurs. Over the years, I’ve driven more than $10 million in sales to the women I’ve featured on this show, and this year I’m taking my investment in female founders to a whole new level as a venture partner of the new firm Zero Limits Capital, where we’re dedicated to investing in highly scalable seed stage startups founded by women and diverse teams – a mission more important than ever as the Trump administration cracks down on anything and everything DEI. We’re looking for innovators with exciting new applications of AI, Blockchain and other emerging technologies that make a social and sustainable impact to change the world. Is this you? If it is, take a moment and tell us about your opportunity at bit.ly/ZLCintake – that’s bit.dot.ly/ZLCintake – capital ZLC lowercase intake.

Melinda Wittstock:

Have you ever been on vacation, maybe at the beach, a log cabin in the mountains, or absorbing the wisdom of an ancient city, and suddenly felt clarity about a business challenge or opportunity that had felt foggy when you were at work? More often than not, we tend to have leaps of inspiration when we are not working. Maybe just out when you’re walking your dog, or singing in the shower, whatever it is, when the busyness of work clears away, we can suddenly see clearly.

Melinda Wittstock:

My guest today Alyson Caffrey is an entrepreneur with two businesses helping busy business owners streamline their operations and move faster and more effectively by freeing up time for themselves and their family. She’s the author of The Sabbatical Method, and with summer fast approaching, Alyson shares important insights about how you can balance your business with the demands of motherhood—while also creating white space and fun for yourself. She’s also an advocate for maternity leave, and one of her businesses, Master Maternity Leave, helps companies create flexible working conditions for women while increasing productivity.

Melinda Wittstock:

Let’s put on our wings with the inspiring Alyson Caffrey.

[INTERVIEW]

Melinda Wittstock:

Alyson, welcome to Wings.

Alyson Caffrey:

Melinda. I am so excited to be here. Thank you so much for having me.

Melinda Wittstock:

Well, you know, it’s springtime, and as the summer gets going, I know, you know, if you have small kids or you’ve got all kinds of other stuff going on in your life besides your business, it can be hard to juggle all of that, and this is what you help entrepreneurs do. So, for anyone who’s like, oh, my God, how am I going to make it through? You know, why don’t we start there?

Alyson Caffrey:

I mean, yeah, we’ve all got life things going on, right? I don’t know any business owner who’s like, oh, I’m just a business owner. Once we launch and start a business, right, it needs us a lot, right. Like a baby, right. We have to spend lots of time with it. We have to nurture it into existence. We have to find product, market fit and all the systems in the team and everything, and then we end up in this position.

Alyson Caffrey:

I know I was. And I know a lot of our clients have been where they look around and they’re like, oh, my gosh, I’m being pulled in a thousand different directions. And I’m. I’m feeling like oftentimes, you know, summer is a really great demonstration of that, right. The kids are off school, things feel chaotic. There are a thousand things to be running to, and you want a little bit of a break.

Alyson Caffrey:

So oftentimes, you know, this is really the season where business owners are like, holy cow, I really have been going a mile a minute in a thousand different directions.

Melinda Wittstock:

Yeah, that’s it. We all juggle a lot. I think one of the traps that women fall into in particular, is thinking that we have to do it all right? And not only that, but, like, do it all perfectly. And that’s impossible. Like, it’s just a recipe for burnout.

Melinda Wittstock:

And it’s the figuring out what you can actually let go of without beating yourself up about it. Talk to me a little bit about the mindset that women go through at different stages of their business.

Alyson Caffrey:

Yeah. You know, and it happens in parenthood and in business and that’s one of the reasons why I love talking about both of them. You know, so integrated is, you know, in the beginning of your business, it’s like a baby. So, it does need a lot of you. Right. There really is no substitute for mom in those beginning, you know, months and years. When you have a baby, you’re very. You need to be very present.

Alyson Caffrey:

And I think the same is true about our business, right. I know a lot of people who have, you know, messaging that falls really flat in the marketplace, or a product that falls really flat in the marketplace because they don’t give enough of themselves to it. And it is really demanding being a business owner in the beginning. And I think that key shift that you’re talking about, Melinda, really happens in that shift. Shift between, okay, I’ve gotten past this hustle mentality of getting the business up and running, and now I need to make something that operates completely independent of me. Whether you want to build it as a lifestyle business or you want to build it to exit, I actually firmly believe that those are the same thing, because a business that is fun to run is also fun to buy. And so, I think that the main mindset thing that starts happening is it feels really good to be needed.

Alyson Caffrey:

We, like, don’t know how to be in our business other than everything to everybody all the time. I think it’s just a really tough place to be where you look at your business and you say, cool. I feel like we’ve got these key things in place. There’s a really solid foundation for the business now. I don’t have to be involved in every single email that goes out to my email list. Right. And there may be certain things, and this is the caveat I will make, is that every business owner is different, and every business is different. So, the areas of the business that you choose to stay very involved in or not, it’s not a one size fits all thing.

Alyson Caffrey:

It’s not like you should give up email marketing first. If you love writing the emails to your email list and your newsletter breathes life into your existence, then keep doing that thing. But if the metadata of your website is really throwing you for a loop, like, outsource that thing first.

Melinda Wittstock:

Yeah. This is all about doubling down on your unique genius. And also, like, often that aligns with what you happen to love to do as well and delegating or hiring out the rest. And I think it’s tricky to know the timing for that sometimes, and some people aren’t necessarily even aware of that. Like, what is the thing that they absolutely must do or the area in their business where they have the most leverage.

Melinda Wittstock:

What’s their level of awareness of this? First of all, like, just starting at the beginning, you know, bones of this, they come to you. I imagine they’re burnt out or they’re on the verge of being burnt out. They’re trying to do too many things. How aware are they of where they’re bringing the most value as a founder to their business?

Alyson Caffrey:

You know, that’s a really great question. I think to some extent the folks that come to me understand one of two things to be true. Either or both. A, they need help, right. They’re like, I can’t physically do all of this by myself. Cue in kind of that burnout. Or B, everything feels like a priority, and my team isn’t meeting expectations for that reason.

Alyson Caffrey:

And a lot of founders will come to me, and they’ll be like, well, my team isn’t doing the things that I need them to be doing. And I’m like, well, great. How often do we shift priorities? Because when everything is a priority, nothing is a priority. So, the very first thing that I try to help them understand maybe isn’t necessarily where their time is most valuable to the business. It’s what are the priorities of this season? And so, anchoring this whole discussion in, we’re preparing for summer. What is your priority for summer? And priority is singular for a reason. It’s a singular word in nature. There can be one priority at this time.

Alyson Caffrey:

And I think this kind of releases some of the rest of the ‘I need to do this all, or I need to make this all happen right now’. Identify a priority for the season and then just expand the time horizon. So, if the priority this season is relationships, and that’s the one thing you want to do, you may find yourself at lots of networking events or joining communities or doing those types of thing. If you’re one priority for this season is your family, you may have a full July of blank space, and that might not feel like you’re, quote unquote, being productive or you’re quote unquote, having best use of your time. But I’ve seen so many folks, whether it’s coming back from sabbatical, coming back from maternity leave, coming back from a month off in the summer with the kids who have totally fresh ideas and perspective on what direction their business needs to go. Total clarity on their messaging or total clarity on the launches that they’re going to run. And it doesn’t happen by sitting and blocking yourself out in a room and having a thousand priorities and changing links on thousand pages.

Alyson Caffrey:

It really just is with white space. I think back to kind of land this all down is identifying a priority first is where I always come in. And if the priority that season doesn’t necessarily align with something that you’re excited about or something that you’re good at, you might need to ask yourself, cool, well, is this actually the priority? So always go over everything with a fine-tooth comb. And then the second thing is, who might I ask to help me in this season if this doesn’t feel like my exact, you know, genius or my exact skill set, right. Because it doesn’t always need to be you.

Alyson Caffrey:

Right. The highest leverage activities in the business might be somebody, you know, who is a partner or somebody that you bring in or a teammate or something like that. I think back to Who, Not How. I think it’s Dan Sullivan. Super. Great read.

Melinda Wittstock:

That’s a great book. Who, Not How.

Alyson Caffrey:

Yeah.

Melinda Wittstock:

Really game changing, actually.

Alyson Caffrey:

Yeah, it’s fantastic. And I think as owners, right, I was challenged recently, actually in a group that I’m a part of, of CEO Moms. You know, one of the gals who was speaking into one of my problems I’d brought to the. She said to me, she was like, Ali, I think your skillset isn’t necessarily in all of the things in the revenue side of the business. It might actually be the people side. Right. So, the who, not the how. And it’s really, really interesting to think about that because as business owners oftentimes are mastering the skill set of putting people strategically in the business.

Alyson Caffrey:

Not us, actually is what might get us to that very next level.

Melinda Wittstock:

Yeah. With founders, there are so many different skills that we bring to the table. I mean, we may be amazing kind of product visionaries, right. Or just like sort of ideas people. We may be very operational, like you’re saying about yourself. You’re obviously an operations person and a people.

Melinda Wittstock:

So, making sure that, you know, the hiring is right, and people are in the right seats, they’re onboarding reported correctly, they’re doing the right things that, you know, the, the results are clear, the objectives are clear, you know, these sorts of things, right. Somebody else may just be a sales machine or an amazing marketer. And whatever that that gap is, like the business has to hit all those notes and different emphasis at different times. And so, it’s just having that awareness. I like what you said about the white space. If you walk away from it, sometimes you can, you can see like where there’s a, you know, a gap, but you can see more clearly from 30, 000ft, I guess, to mix.

Alyson Caffrey:

Oh, wholeheartedly, wholeheartedly. And you know, I think a lot of us are scared of white space again, going back to that headspace that if you’re not hustling, your business isn’t growing. It was very much like that in the beginning. And I think we’re petrified of white space because that would mean maybe that we’re not booked up with sales calls or that we don’t have as many investor meetings or any of those types of things. And in reality, the seasonality that is business, once we move to a position where, you know, we’ve harvested, let’s just say, I mean, to even get into kind of the seasonality of nature, we have winter that comes right after. So, after a big launch, you know, folks who are, you know, going through some of these, you know, really, really heavy projects, lots of copy, lots of pages, lots of one-on-one time with people answering questions, it’s really natural to shift into a winter mode. And I think as business owners, we miss that, and it leads to burn, leads to regret. Time not spent with family; time not spent focusing on self.

Alyson Caffrey:

Time not spent asking what do I really want out of this business? What do I really see this thing being as a part of my life and the ecosystem as a whole. Right. If everything’s in service of the business and the business never turns off, then we never turn off.

Melinda Wittstock:

Yeah. One of the things that I learned very early on because I, I launched my first business without knowing I was pregnant.

Alyson Caffrey:

Love it.

Melinda Wittstock:

You know, and so like, literally, like we got our funding, and we literally launched. My daughter was six weeks old, like at the launch, but I did not plan this. Okay. So, I had to get very, very clear with myself because the business was at that early stage, it demanded so much of me and obviously my daughter did as well.

Alyson Caffrey:

Yeah.

Melinda Wittstock:

And obviously I needed a nanny. I needed different support things. But I had to just let certain things go, like, no the house was not going to be perfect. No. I wasn’t going to be, like, entertaining. I wasn’t really going to be socializing as much as before. I’ve got to really hire the right people to take some things off me. But my biggest epiphany was when I’m with my daughter and ultimately I had a son also, when I’m with them, I’m 100 with them.

Melinda Wittstock:

And when I’m in the business, I’m 100 in the business. And I found the juxtaposition of the two made me better. It made me a better mom and made me a better entrepreneur. And I’m not saying it wasn’t like a show sometimes, but, you know, mostly, you know, it was good.

Melinda Wittstock:

Having the clarity, I guess, about the priorities were critical, and then having the confidence to actually set the schedule that was going to work for you. So not being driven by other people’s agendas, but really just deciding what you wanted and. And doing what you want, like, at the end of the day.

Alyson Caffrey:

Yeah. I think that’s so incredible. And let me just take a sidebar here and tell you how many women have told me that they’ve either started or launch, launched a business while they were pregnant or postpartum. It seems to be the, like, incredible forcing function, which is why I love a lot of the work that I do at Master Maternity leave is just because this is such a transformational time in life. I believe that becoming a parent makes you a better business owner on virtually every level. And what you’re describing, those boundaries, that focus, that priority, that’ what ushers you, I believe, into the next phase of entrepreneurship and ultimately unlocks all of the new levels that you are seeking. I personally went through a transition like that when I became a mom. And honestly, both of my kids were just surges of massive growth years in my business.

Alyson Caffrey:

And it’s not because I did more stuff. It was actually because I embraced these winter seasons, right? Seasons where I was totally focused on them, and I wasn’t focused on the business stuff. It gave me time to reflect, to distance, to get clarity. And we decided not to make a ton more things. We were just getting better at the stuff we were already doing, Refining, going deeper with clients, establishing better, you know, partner relationships, and those types of things are really, you know, where I see some of the business owners that have been in this thing. I mean, I’ve been a business owner now for eight years and this is where folks, you know, kind of get past those plateaus, right, of either length of time in business, revenue, overall impact. And it’s a really, really cool thing to see.

Melinda Wittstock:

Yeah, it’s so interesting what you say that there’s this correlation between women going into business when they have kids. I think, do you think part of it is just that there’s, you have more flexibility to set your own agenda. Like if you’re corporate, you can’t do a lot, you can’t set your own schedule. Do you know what I mean? You’re stuck a little bit, do you think? Totally sort of an impetus why a lot of women become entrepreneurs when they have kids.

Alyson Caffrey:

Oh, you’re about to get me up on a soapbox here. So, my belief, especially around maternity leave, so let’s just take that particularly, you know, every, every woman who is going through, you know, maternity leave planning or thinking about how that situation could look for her and her family. I believe that even as business owners, we still look around to the majority of our friends and family who are employed, either with corporations or small businesses and things like that. And, and we let that tell us how we can take leave, right? Eight weeks, super competitive. 12 weeks, super competitive. Even though in the grand scheme of things, taking six months off for maternity leave would be incredible for families. Right. Especially if mom wants to do it that way.

Alyson Caffrey:

And I believe that a lot of the reasons why corporate doesn’t work for families is because they don’t get to create things on their own terms. Right? It’s kind of that top-down enforcement of this is what the company can afford, so this is what you’re going to get. And I mostly empower the women that I work with through my company, Master Maternity Leave, where we think about, hey, let’s just blow up this corporate idea of you should work nine to five, or you should take eight weeks maternity leave and then come back, or you should pay yourself full for eight weeks and then half for the other four, or whatever that looks like. And so, I actually think that it’s an invitation. And I do think that creating life and business on your own terms as a business owner is just so incredible. And I’ll say this as well, it’s harder. Like, it’s absolutely harder in, in a. I guess hard is different, right? Choose your heart, I guess a lot of people say.

Alyson Caffrey:

So you can either be externalizing your power and have somebody telling you, hey, listen, this is what you get, but you for sure will get paid and you have to work 9 to 5 or all of those things or you can choose your heart on the business owner side and say hey, I gotta make revenue appear and I have to test product market fit and I have to hire a coach and I have to manage a team and I have to figure out what HR is and who I can have help me with that. And there’s lots of different problems and different circumstances, but it’s a different kind of hard and I think both are appropriate for different types of families.

Melinda Wittstock:

Yeah, it’s interesting even, even as an entrepreneur, as your business grows and you hire women, it’s an opportunity for women led businesses to really rethink maternity leave even for their own employees. And, and it is tricky when you’re trying to balance like your cash flow and like the results, especially if you’re venture backed or something like that. Gotta hit these results, but you want to kind of remake that. Do you have any clients that are trying to figure that out like actually from the point of view of their employees and how to make you know, you know, maternity and, and, and balance like just in your, in your workforce actually work better than what we see from corporate?

Alyson Caffrey:

Yeah, of course. I mean a lot of I’ve advised many companies one on one about their maternity leave policies for their employees. And the one thing I’ll say is number one, it has to be important to them. I mean the same way you crystallize mission vision values for any sort of funding, any sort of startup, anything like that, your investors need to understand that they’re also buying into this mentality of my people get this time my people only work four days a week or whatever that looks like for them. And I believe that there are an even in a venture backed company, I believe that there are investors out there who will get on board with something like this. So just be as clear as possible is the first thing that I always tell my folks who come to me with this issue. The second is insurance. Insurance, insurance.

Alyson Caffrey:

Like if you don’t feel like you have the cash flow to sustain a 12 week maternity leave or something like that, getting insurance as quickly and as early as possible in whatever state your employees are in is going to be incredible because what you can do is you can have them, you can pay into this insurance and then you can have the state support through maternity leave and then you’re only supporting a fraction of their pay and maybe not the entire thing. So that’s another thing I would personally want to build in and then the third is more of a life.

Melinda Wittstock:

What type of insurance is that? What’s it called?

Alyson Caffrey:

Usually a short-term disability. You can also opt for long term. So long term disability would cover I think up to like six months. But it depends what provider you go through. I personally love that option because it does play into being able to fund a portion again right. Of that time, time off and then you can just supplement with whatever the rest is. So oftentimes what, what I personally do with for my team is we have short-term disability insurance and then say one of them wants to take a maternity leave. The short-term disability insurance will cover up to like $2,000 a week of maternity or of pay.

Alyson Caffrey:

And then if they make more than that, then my company is responsible for the rest.

Melinda Wittstock:

It’s good to know there are things like this to do because I think people just get trapped of, oh, it’s always been done this way. And they don’t, they don’t necessarily know about what’s to them and, and, and how they can do that. I mean, I think there’s a real opportunity for women led and founded businesses to really change the corporate culture in this way. And change always kind of begins with you. So, if you as a founder haven’t mastered this yourself, it’s very difficult to do that for your team. Totally starts with you like what’s the example that you’re setting.

Melinda Wittstock:

And a moment ago we were just talking about having to learn things like boundaries. I was thinking of man, the quickest way to overcome any kind of people pleasing is to just have kids in a business at the same time.

Melinda Wittstock:

And so, and so talk to me a little bit about how you actually work with your clients because you’ve got these two different businesses, right. One on the kind of operations side and one specifically about maternity leave. And so, tell me the process of really what you go through and how you help your clients. Give me an idea of your clients and what they’re grappling with and what the kind of before and after, I guess looks like.

Alyson Caffrey:

Yeah, you know, I was saying before I’ve been in business eight years, I can’t even actually believe it’s been that long. And I always joke that I’m an accidental entrepreneur. So I was in operations for three years before starting my business with, you know, fast growing PR and marketing firm. And one of the biggest things that I learned is that operations doesn’t need to be complicated. And in fact, especially if your team is like under 70 in size, operations should be very simple because you likely need to be more agile at that stage than you do really formal and supported by a heavy operating structure. And so what I’ve done over the last eight years, you know, in multiple different kind of formats is really take a look at how is the business operating, what does it want to achieve, how do we need to adjust the operating model to support those goals and then how do we roll that out to the team so that everybody, everybody feels really good about managing that. It’s about that simple. And truthfully, when I was working in operations agency, so that’s my operations consultancy, people hire me typically when they have big growth goals or maybe they’ve just bought a new company or they’re going to get bought by a company and they want to kind of integrate operating models, team, all that stuff.

Alyson Caffrey:

So, I work with fairly high-level companies and operations agency, and I found that a lot of people were coming to me and asking lots of questions based on life’s circumstances. I had a client come to me a few years ago, her name was Lisa. And she said hey, you know, I was, I’ve been having some struggles with my health and I just got back from the doctor, and I’m diagnosed with an advanced form of lipidemia, and I need to lay down every few hours for the next few months to drain my lymphatic system. And now Lisa is a high-level executive coach. She coaches executives from GoDaddy and Airtable and tons of big players in the tech industry. And she was like, I don’t really know how I’m going to do this. It was her, her husband and one project manager that worked on the team at the time. So nice and lean, high profit business.

Alyson Caffrey:

And she was in a position though where she couldn’t take on additional clients because of what it required from her physically. And I noticed that she was really, really struggling with this, this. I mean she loved her business. You know, she was in a position where she just couldn’t make it work anymore because she had really deprioritized her health in that season to grow the company. And that’s what led to me writing my best-selling book, the sabbatical method. Like how to weave rest into how you operate inside of your business so that you don’t hit these walls. Right. That hit by a bus analogy.

Alyson Caffrey:

My one client loves to say what if we just hit the lottery and move to Ibiza instead. So really just thinking through, like, how can we make this business support your life and not the other way around? And when I took my second maternity leave with my second son, the first one was an absolute blunder, let me tell you, Melinda. I mean, it was all the things. I was stressed out. I was super tied to my business. I was fractional cooing all over the place. It was a total nightmare. And I was like, there’s gotta be a better way.

Alyson Caffrey:

I started researching some of these benefits that we’ve been kind of touching on here in this. In this conversation. And I launched master maternity leave on the heels of having my second son. And honestly, there has never been something that I’ve felt more excited and passionate about. I think operations is something that, you know, is somewhat slippery to a lot of small business owners. And to me, I’m like. Like, you guys, this is your permission slip. This is your ticket to rewriting and reorganizing the business in a way that feels like it supports the type of parent you want to be, the type of person you want to be caring for yourself, caring for your family.

Alyson Caffrey:

And I personally love this season of becoming and all of the transitions that it offers. So, our process is really, really geared into taking a look at the business, doing an audience, it. Making sure that we have a really clear plan on what needs to shift and. And what, you know, needs to be implemented to support the business’s goals, whether that be growth or lifestyle focused. And it doesn’t need to be, you know, choose between the two. Like, you could have both, I believe, and then, of course, making sure that those things stay managed over time.

Melinda Wittstock:

Yeah. It’s interesting what you say about operations, because a lot of people, I don’t know, you know, can get too heavy on the operations too early and, like, totally. And other people can, like, completely ignore the operations, and it’s chaos, especially in growth.

Alyson Caffrey:

Yeah, right.

Melinda Wittstock:

Where they, like, literally don’t know their numbers or don’t know what’s going on or, like. Or hire people but have no onboarding systems or they’re founders who think, oh, man, like, they. They can read my mind, you know, exactly. Like, there’s so. I don’t know. I. I’ve done five businesses now, so, like, I’ve seen. I just sort of feel like I’ve.

Melinda Wittstock:

I’ve seen it all, and I’ve, like, made all the different kind of, you know, mistakes or, you know, seen them or experienced them as an investor in companies. You know, and, and so getting that balance right is tricky. And also, because it changes, it changes as the business grows, too, in terms of your own role. Right?

Alyson Caffrey:

Most definitely.

Melinda Wittstock:

And so, talk to me about those transition points because, say, okay, so it’s, it’s the early days, and you got your business, and your business is your baby. Like, it needs you, and it’s, it’s all of you. And then maybe you have a little bit of help, you got a virtual assistant, or you have, you know, that kind of thing. But then, in growth, and you suddenly say you have a whole, you know, you got a tech team, you got your marketing team, you got the, this going on, you got that, you got all this stuff happening. And all of a sudden, your time as a CEO is very much has to be focused more on making sure that those systems are actually, you know, working well. Or hire somebody that you trust. You got to make sure you trust that it’s, it’s, it’s not easy. It’s not easy.

Melinda Wittstock:

Right. So, talk to me about the transitions and how you help people with that because their role is transitioning, their family’s transitioning, their kids are growing up, their kids have different needs. Like, it’s, it’s constantly changing.

Alyson Caffrey:

Yeah, wholeheartedly. And, you know, I love that you bring this up, because it’s funny. Last quarter, so Q4 of 2024, we typically create a guiding principle at operations agency for each quarter. So, it kind of acts like our filter, through which we look at everything in the business. And our, you know, guiding principle for 2024 in Q4 was, just because we’ve always done it this way does not mean we need to continue doing it this way. And I actually thought that my team, my team’s wonderful. Like, I love my team, and I have never seen them rally around a guiding principle for the quarter like this in the past. I think, in my experience, folks don’t ask themselves that key question often enough.

Alyson Caffrey:

They don’t ask themselves, well, well, does this still make sense to be doing, even though I’ve always been doing it this way, and you can have something for a particular season that you don’t necessarily have to put into the business permanently. And I believe that having a system in place, like a good, solid quarterly plan, or like making sure that we understand our numbers and let our numbers guide where we go next with strategic hires or additional services or any of those big decisions inside of the business, you Know, there isn’t a one size fits all approach to how to do this. And I think we could have kind of that safety net catch all to say, okay, at least once a quarter we’re going to go through and ask ourselves the question, do we need to continue to do this? And if the answer is yes, do we need to continue to do it in this way? I think those transition points really look like when you go 0 to 1, I’m not kidding. Hiring that first person and getting comfortable delegating is a massive, massive shift. Once your team gets to about five, that’s another massive shift. Because it’s very, very likely that all of the relationships can’t be kept up just by meetings and, you know, conversations alone. There needs to be a little bit more of a formal structure. Then we got 10, 30, 50, 70, 100 and then doubling from there, 200, 305, 500.

Alyson Caffrey:

That’s usually the people structure that I see needing some significant transitions, whether that be in people operations. So how your people are structured, even in data operations. I believe that if somebody doesn’t have a specific number tied to their performance of their role, that they likely should not be in the organization. If you’re looking to hire somebody and there isn’t a number that you can book, both look at and agree, cool, this number tells me how well I’m doing, then we might just need to pause on that role and consider that we want to flesh that out a little bit more. The other thing that will likely change the trajectory are several other things. Right. First is the current market that you’re in. So, depending on what the business is doing, whether you’re a product or service or any of those things, whether you’re a venture backed or not, of course there will need to be other considerations in place and sizes and whatnot.

Alyson Caffrey:

Role restructuring if you have other people’s money or if you’re using your own. And then additionally it’s the goals of the business. So, if you want to scale super big and exit, that’s one consideration. Or if you want to stay nice and profitable and keep this as a lifestyle thing that continues to fund other things that you want to do. That’s a consideration.

Melinda Wittstock:

Yeah, just, just knowing. Doing what you want.

Alyson Caffrey:

Exactly.

Melinda Wittstock:

It’s huge. I think those transitions though, you know, in growth, I think a lot of people skip over that sometimes and like, because who you’re being with five people is totally different from who you’re being if suddenly you’ve got 21. It was me and then it was three people and then it was like seven people and then it was like 22 people.

Alyson Caffrey:

That’s a big jump.

Melinda Wittstock:

And like all in the span of like 14 months. And it was really hard. And like, I’m, I’m sure there, there. I mean, you know, I look back and I think, oh, yeah, okay, I would have done that slightly differently or. Because I was still very much in the doing and the running. Running fast. Yeah, right, right.

Melinda Wittstock:

And, and, and it’s tricky so like actually knowing who you need to bring in when, when you need to slow down to move faster. I think that’s, that’s something that I didn’t really fully appreciate in that particular business at that time. But it can be hard to know. So, this podcast always come back the same thing. We all need mentors and coaches. Like, yeah, every time, time, like almost every show. Like, because it’s really true. Like, you know, there’s a limit to what you can do, and you need sort of an outsider’s perspective.

Melinda Wittstock:

What do you see as the biggest, the biggest challenges people? I imagine that’s one of them. But what are some of the biggest challenges that you’ve helped your clients through?

Alyson Caffrey:

Yeah, I mean, listen, it’s first and foremost that mindset piece, right? Having the confidence and the clarity to be able to confidently tell team, clients, investors, partners, whomever, hey, this is what I really want in this season. So just having a sounding board that isn’t somebody on your team who can support and really getting clear on what you want from the business, from your family life, you know, your personal life, you know, whatever that looks like for you. The second is really getting clear on this, the systems that are making folks successful. I actually believe that businesses only really need 4, 4 key systems in order to be wildly successful. And that’s a lead getting system, a conversion system, a fulfillment system, and an improvement system. That’s it. And I think further complicating past those four, even those high-level operating systems like scaling up and EOs, they often all fit under those four categories. And I think complicating your operating model is something that is really, really, I guess, popular because folks want to seem smart, or they want to cover all the bases or all the things.

Alyson Caffrey:

And I actually believe that simplicity scales farther and faster than anything else we could ever imagine. So, first is confidence. Second is establishing Those systems that actually work. And third is just knowing our numbers. Right. How can we take a look at something, and it’ll tell us how it’s performing? So those are the three big things that typically folks will come to me wondering is like, how do I get the confidence to even voice this? What systems do I even need? Because I just don’t even know what I don’t know, or I don’t know if this thing is working. And then the third is the data picture that supports it all. Because I think if we have those three things in place, we’ve got the confidence, we’ve got the systems, we’ve got the numbers.

Alyson Caffrey:

We can take a look at a dashboard and know what the next move might be in our business from a, you know, we might know what the next move in our business is from a decision-making perspective. And then from there it’s just got.

Melinda Wittstock:

Yeah, I think that’s really important. The know your numbers. Talk about that on this show a lot. It’s amazing to me how many entrepreneurs don’t really know or afraid to look, you know, exactly.

Alyson Caffrey:

One or the other or both.

Melinda Wittstock:

Right. But it definitely tells a story. Okay, so all that’s complicated enough and then we’ll go back to. Okay, so you’re balancing kids, babies, toddlers, teenager. I mean, you know, know, they’re, they’re all different. They, they require you at every step.

Melinda Wittstock:

One of the things that I took away from that is allowing my kids to see me fail and pick up, like, see me have a crisis and figure it out was actually really good for them. They’re both very resilient.

Melinda Wittstock:

Right. Because they’re probably better at dealing with change and uncertainty, the things that come with entrepreneurship. Because I was in no position, I guess, to really, I don’t know, helicopter parent. Like, I didn’t have time to helicopter parent.

Alyson Caffrey:

Yeah.

Melinda Wittstock:

You know what I mean? They both kind of grew up like oh, well, when things go wrong, you can figure it out. Like, because we’ve seen mom do that. It just sort of like this is my epiphany looking back on it now.

Alyson Caffrey:

So honestly, that’s wisdom, right?

Melinda Wittstock:

Because. Yeah, because our nature as moms, we really want to protect our kids. Right. I want everything to be again, it’s this perfectionism thing. It should be an AA for perfectionists. Right. You can’t be, we’ll call it PA, right.

Melinda Wittstock:

Perfectionist Anonymous. And, as someone who hires, you know, young people and their parents have sort of done everything for them or protected them from things, so they actually don’t know how to be resilient because no one’s shown them or let them be. Right?

Alyson Caffrey:

Yeah. I’ll say this, I am super early in my parenthood journey. So, my older son is 4 and my younger son is 3. And we have a lot of fun over here. And Steve, my husband and I, we always joke that we’ll know if we’re doing a good job, but we’ll know late, so it’ll be too late. We’ll know it when they’re 18 or 25, whatever that number is. And we’ll get the include link. But I’ll say this about I think demonstration because I think kids are incredible sponges.

Alyson Caffrey:

I mean, my 4- and 3-year-old, they pick up things that I never would have imagined in my wildest dreams. Sometimes it’s confronting, I’ll be honest, and sometimes it’s actually really impressive. And I get really proud about how we, my husband and I are being as parents. So I think the thing I constantly think about in terms of, you know, a lasting lesson and this could change as I learn more about motherhood and business ownership and how to be around my kids and what type of influence I’d like to have over their life and skill building and decision making and all those things is I believe that they see their parents as lifelong learners. And I think that to me is my North Star, where I think failure is part of that. I think what you’ve touched on is a super important piece of that. But I don’t want my kids to think that I know everything, and I don’t want my kids to think that they know everything. I don’t want our kids to see us, you know, not trying because we’re beginners or not learning because we know nothing or saying that we know something that we don’t know.

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Melinda Wittstock:

And we’re back with Alyson Caffrey, Operations Strategist, Bestselling Author and founder of two businesses, Master Maternity Leave, and the consultancy Operations Agency known for the Operations Simplified™ framework to unleash the power of small teams.

[INTERVIEW CONTINUES]

Alyson Caffrey:

I think a lot of specialization comes with this natural, like, I know everything about this subject or any of those things. I really do enjoy learning about new things. I enjoy the opportunity to hone a different skill set. And I think business ownership is one of the most wonderful breeding grounds for something like that. So, I hope right now, as of this recording, that my kiddos can see my business as me being a lifelong learner and observe me trying and failing. Observe me trying and winning. Observe me taking a risk on myself because I believe in something. You know, see me learning a different way of doing something so that I can go out on a limb and help somebody who’s less fortunate than our family.

Alyson Caffrey:

And so those are the types of things I really do believe will ring into hopefully really sweet personalities for my voice.

Melinda Wittstock:

You know, beautifully said. Your kids, they are sponges. And, I remember, I think, when Sydney, my daughter, was 10, and I was having, like, sort of a difficult day, and she just wrote on this giant post it notes and posted it up in my, like, home office, and she just wrote, mom, ‘you’re enough’.

Alyson Caffrey:

Oh, my God.

Melinda Wittstock:

Like, you know, like, you’ll figure it out. You, you, you know, you always do. Do you know what I mean?

Alyson Caffrey:

And because that is so sweet, right?

Melinda Wittstock:

And they learn these things. Or like, the other times, you know, she invited me to her, like, class, give a talk on entrepreneurship, and she said, “now, mom, you got to tell it to, you know, all my friends think it’s really easy, do you know what I mean? To just make millions of dollars and entrepreneurs go in there and she did this thing, like, motion with her arm. like the hockey stick sort of, you know, I’m great. And then this kind of wave. And I want you to tell her what it really is, right? She did this kind of wave motion with her arm, and I think she was like, 13.

Alyson Caffrey:

Oh, my gosh. That is the coolest thing.

Melinda Wittstock:

And so, it does kind of teach them a passion, I think, because to succeed as an entrepreneur, just like you said, you have to be curious. You have to be coachable. You have to be like a lifetime learner. So, when your kids see you doing that, that’s good. So, there’s nothing to feel guilty about.

Alyson Caffrey:

Yeah, 100%. I remember there’s a. Recently we joined a gym in town. We just moved from Pennsylvania to Colorado, and we love Colorado. Steve and me, we lived here early in our marriage, and we’ve always wanted to come back. And so, we joined this gym and my older son Frank, he’s four, he, we go to the gym, and they play in like the little kids area while I go up and do yoga class or workout or something. And the first two days were pretty rough on him. He definitely is Type A.

Alyson Caffrey:

He wants to know what’s happening, he wants to know the schedule. And there was quite a bit of free play from what I understand, which is great. I think it’s really great for him. So, we’re taking a bath like two days after and we, we do a lot of our chit chatting in the bath because there’s no distractions. You know, we’re all kind of in there together. And he’s like, you know, going to lifetime is hard. And I was like, oh yeah? How come? And he said, well, you know, I never know who’s going to be there and I don’t know what the kids are going to say, and I don’t know how they’re going to treat me. And I remember thinking to myself that I as a mom in that moment recognized that he needed more information rather than less.

Alyson Caffrey:

And when we were going to Lifetime, I was trying to kind of prepare him for what would happen. And so, in that moment I stopped because I realized it was actually feeding his anxiety about what was going to happen. Because if mom said it was going to happen and it didn’t, then he got all dropped, jostled and it was going to be funky. So now he really enjoys going. And my sentiment when we are in the car is, hey, we don’t know what’s going to happen, but it’s going to be fun, right? And it’s just a totally different shift. And he’s been a totally different kid.

Melinda Wittstock:

Isn’t that interesting? I love that because this is where I go back to being a mom made me a better entrepreneur, and being an entrepreneur made me a better mom.

Alyson Caffrey:

Yes.

Melinda Wittstock:

Comes down to right in the end. So, you know, summer’s approaching. Everybody’s got, you know, like, trying to figure out, I don’t know, do their kids go to camp? Are you going on big vacation? Like, what are you going to do? How are you going to balance it all? What are your top tips for just how to navigate the next few months?

Alyson Caffrey:

Yeah, totally. And I think it’s. It’s the three things, right? Get really clear on what you want. So be confident to tell your team, your clients, your partners, your investors. What exactly is the priority for the season? To set up your systems in a way that you really feel like you understand that they’re high performing and they’re moving your business forward, not just a drain. And the third is, of course, make sure you have a really clear data picture so that if you do decide to take some time off and you want to just check in and make that time really efficient, you know exactly where to look, what numbers to look at, and how to address them really quick, quickly. I break a lot of this down, actually. I have a totally free resource.

Alyson Caffrey:

It’s on AlysonCaffrey.com it’s called the remove yourself from your business handbook. And it’s a 37 page, really, no fluff field guide to how I would do this. So, if you’re coming into the summer and you’re like, I need to put my kids in camp, or I can’t possibly take a few weeks off to just go and be with them, but you want to build in that time. I would take a look before you make any major decisions about what to enroll kiddos in or how to get a additional support, because you might be in a position where you can start to weave yourself out of some of those things that feel really important but might not necessarily be a priority in the season.

Melinda Wittstock:

Amazing. Well, Alyson, thank you. It was great talking to you and thank you for doing the work you’re doing, because I think we all need it. Record numbers of women are going into entrepreneurship and all sorts of types of business, and we all do better when we support each other. You mentioned the handbook. What’s the best way to find you, to work with you?

Alyson Caffrey:

I’m super active on the socials. I. I answer all my DMs, so at Aly Caffrey A L Y is the perfect place to get in touch with me. My website, AlysonCaffrey.com also has all the ways you can work with me. So, if you’re a business owner and you’re like, hey, I’ve got a big team, and I really want some consulting, you know, we do that every day, all day at operations agency. And if you’re currently expecting or trying to conceive and you’re just wondering how the heck you’re going to do the business and motherhood transition, just know that I’ve created a little special corner of the world for moms just like you at Master Maternity Leave. So, all the information’s there, there, and I am, again, super accessible.

Alyson Caffrey:

So, if you’re struggling with something, if you particularly took something away that resonated, I would love to hear from everybody. I love chatting in the DMs.

Melinda Wittstock:

Amazing. Well, thank you so much for putting on your wings and flying with us today.

Alyson Caffrey:

Thanks, Melinda. I had a blast.

[INTERVIEW ENDS]

Melinda Wittstock:

Alyson Caffrey is an Operations Strategist, Bestselling Author and founder of two businesses, Master Maternity Leave, and the consultancy Operations Agency known for the Operations Simplified™ framework to unleash the power of small teams.

Melinda Wittstock:

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Melinda Wittstock:

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