Joe Cardillo WINS by building diverse teams and new leaders!

You're in for a treat this week! 

An extra ten minutes of WINning! 

Joe Cardillo is the founder of The Early Manager, a coaching firm that supports job seekers and new managers. 

My interview with Joe went long.  Really long.   I learned so much about diversity, power, accountability, transparency and alignment that it was almost impossible to edit it into 20 minutes.  It was almost impossible getting it down to 30 minutes, but it's definitely worth the extra time!

Joe's background is scaling high performing SaaS startups.  They launched their coaching practice in 2020 - a good time to focus on supporting those who found themselves changing industries!

If you're wondering how power and capital - all kinds of each - impacts a business that is trying to create a diverse team (and not just checking boxes), this would be a great episode for you.  Trying to attract and build the next generation of leaders for your business?  Don't miss this one.  If you're looking to change careers, or you're currently unemployed and searching for a new opportunity I encourage you to reach out to Joe to discuss your job search.  If you're wondering how to build teams that are truly inclusive and diverse, a conversation with Joe should be on your to-do list. 

Hosted by Carrie Richardson, partner at Richardson & Richardson Consulting, this is a must-listen episode!

Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now?

Carrie helps businesses improve their sales and marketing teams.

Ian is certified in Eagle Center For Leadership Making A Difference, Paterson StratOp, and LifePlan.

Learn more at www.foxcrowgroup.com

Book time with them here: https://randr.consulting/connect

Be a guest on WIN! We host successful entrepreneurs who share advice with other entrepreneurs on how to build, grow or sell a business using examples from their own experience.

Transcript

 Hi, good afternoon or good morning. My name is Carrie Richardson. I am one half of the consulting duo Richardson and Richardson, and I am today's host for WIN. Today with me is Joe Cardillo.

They are the founder of The Early Manager. And Joe and I were speaking before recording when today we actually connected on LinkedIn through a random post and I really was excited to interview Joe.

Based on the few things that I read on their profile, specifically around one North Star idea, which was listen a hundred times, act 10 times and talk about it one time. And when we spoke about this before we recorded, we went way over time. We spoke a lot about allyship and what that meant to Joe.

And from there we went into all kinds of other interesting places. But today specifically, we're gonna talk about power. And different forms of capital. Joe, thanks so much for joining me twice to record this podcast. I really appreciate your time and your patience, and I'm looking forward to hearing what you've got to tell us today.

So welcome to 

Win. Yes, thank you. I'm so glad to be here. I'm always you, could call me anytime You wanna talk about power and transparency and structure that's I'll live in that world all day long, so I'm glad to be here and excited to, yeah, excited to dig in. 

Wonderful. So Joe is located in Albuquerque and I love all of the Southwest, so I love how beautiful it is there. I love the weather. Tell me how you ended up in Albuquerque. Yeah, Albuquerque 

is, I think I've lived in a few places and Albuquerque is I think one of the most interesting places that I've been.

I grew up in Hawaii. I actually grew up on a very small island called Molokai and I was there from about six months old till about seven years old. Parents moved us to Albuquerque, mainly for financial reasons. It's really expensive to live in Hawaii. It's hard to find work, things like that, especially on a small island.

And yeah. And then I grew up in Albuquerque. Pretty much the, rest of my life I did go to I, had an undergraduate college experience in Wisconsin. I lived there for a couple extra years. I've also lived in San Francisco. I was also in Boulder and Denver for just a little bit. So I've lived in a few different places, but Albuquerque has been home for the better part of 30 years now.

And yeah, and I love it and, I'm glad to be here, wonderful. 

Tell me about the early manager and what's going on with that. It's a fairly new venture 

yeah, I've been running the early manager for about a year and a half. I'm the founder and I am the coach, and  right now it's a team of one.

So I'm also the administrative operations, marketing, sales the person that responds to the emails, pretty much everything. I know that hustle from past experiences. So all things and with the early manager my work really focuses on basically building teams that are ethical and inclusive and that are high performing too.

And I, worked in marketing and tech and, startup operations for, over a decade. And I took this lesson from my work there that that it is possible to build teams that function at really high levels. And that one of the ways to do that is, is to be transparent and share power and decision making and really create a collective sense of, vision and mission and and reinforce people and, growing within that context.

And so that's really the thesis for the early manager and. I've been doing that for a year and a half. It's been a pretty interesting experience. And, I really learning a lot about building a business on my own as well as the process of coaching and where that fits into the world for people too.

So 

one of the things that I've noticed in the industry that I worked in for the last 10 years, which is technology, is that people very rarely. Make an investment in something like coaching or consulting until they get to the point where they've tried a bunch of other things unsuccessfully. So they've tried to self execute something they read in a book, for example, and it didn't work out that well for them, or they have.

Gotten to almost a, stagnation point in their businesses, and then all of a sudden they become willing to do something differently, which is certainly my experience. I we talked about that a little bit. I, got stuck at a certain spot in my business and it, at that point I was like, all right, if you want something different, you have to do something different.

And at that point, I was willing to go and look for external resources that might be able to support me in getting through that Blockage in my business, and honestly it, worked for me. So tell me a little bit about the, clients that you serve, and then let's talk about how you decided to get into that particular niche.

Yeah, for sure. I have two, two, maybe two and a half primary kind of focus areas. One is, which I, don't even know if I mentioned when we talked last time one is actually coach job seekers, and that's just a passion that I fell into when the pandemic kicked in. So I do that.

And then that actually in some cases leads into working with people who end up in manager, director, senior director roles. That's a, bread and butter is like working with folks who are building teams and doing the day-to-day work of listening and, Putting structure in place and really growing their teams essentially.

So that's a that second constituency and then another constituency that  fits somewhere into that  that same area is, I do end up working with founders a lot who are early and mid-stage. Cuz they're usually running teams that are 3, 4, 5, up to 25 30, 35 people.

And so they're essentially having, in some cases, to learn how to be a manager as they're going through their first or maybe their second startup. They're once you've done it a few times, it gets easier as but in the early going, a lot of founders run into the same kinds of challenges and problems.

And I think a lot of it really does go back to what you were saying. Sometimes it's. There's that scenario where you're like, you tried the same thing a few times and it doesn't work, and you're like, there's gotta be a different way to do this. And I always tell people the way I approach coaching is the way I approached being a manager when I first started doing that back in 2017, which is if you can build for trust, if you can build for alignment then you're automatically building for speed and for making things work smoothly.

And I think a lot of people try to do that last thing first, right? They're like just, I don't have time to listen. Like we need to get things done. We need to get shit done and be be serious about this and grow. And and they forget to do the first two things, which is the trust in the alignment.

And that's where a lot of the Yeah, that's where a lot of the magic happens, right? So tell 

me a little bit about we did talk about this beforehand, but one of the things I want to share with the people that listen to win is this idea of power and transparency and what that means to people who haven't really ever had to consider the fact that they might not have any.

Yeah, and there's, I would never have thought about power as being something that impacted my employment, for example. 

Yeah. It's interesting. So I think I. I'm one of the things that I've learned is there are obviously a lot of forms of capital, right?

And I don't come from wealth capital. Like I'm both my parents. My mom was an immigrant, my dad's family were immigrants from Italy. My mom moved as a child to New York City from Israel, and we didn't have no access to capital. With all of the incumbent challenges that come with that. But I, was blessed with and, have developed a really keen sense of other forms of capital, like social capital, knowledge, capital that sort of thing.

And my my approach to it is to understand that, that everyone has some type of position. So whether you are, and I call it positionality, I didn't come up with that. That relates to intersectionality and other kind of similar comments and, theories and philosophies.

But I think when we understand our positionality and the degree to which we're able to make choices and make changes and also impact other people in that same place of making choices and challenges, then we intrinsically see. Power and capital hopefully in a transparent, in a positive way.

And so a lot of my day-to-day work with coaches is to be like, oh, maybe you didn't think about that, but let's, dig in. Let's reframe it. Let's figure out what's happening in a given scenario, and then let's, rework it. And it may not always be about fixing or solving everything, but in a lot of cases it is.

A about kind of seeing, recognizing, acknowledging, and then reworking what sort of exists in that given moment. And what I found a lot, especially with managers who were earlier in their in their experience, and that goes with founders too, is that we just don't really talk about that, what I just said very out loud, very often it just doesn't come up.

And so people just apply their own individual lens to that, and that usually isn't very effective because other people are not us. 

We talk about listening, we talk about emotional intelligence, we talk about really paying attention to what, where people are coming from, in a lot of cases they're coming with vastly different experiences.

The reality is, I think there's this sort of glorification of let's all be happy and encourage and welcome everyone. But a lot of people who run companies don't, meeting people where they're at is. No, you meet me where I'm at. I'm the c e o.

I'm the founder. I'm the manager. I'm the director.  Here's how we're gonna do it, and so I think the, concept of negotiating the choices more transparently and, in an equitable way is one that is uncomfortable for a lot of people. But I also simultaneously, think there's a desire to do and the example that I often give people is like, how do you handle PT o? And the pain of that all too well. It's like, how do you do scheduling? It's a complicated. Endeavor. And I remember some of my first sort of hiring, hiring and managing experiences. My take is if it's a fairly small team, You should negotiate it, right?

Work through it, figure it out together as a team. Some people did that, made some people very uncomfortable. Other people loved it, right? But at the end of the day the p t o example, just being a small one it's like better in the long term to find a way that works for everyone and is inclusive rather than just trying to like jam something, got people's throats.

Cause then you got turnover issues and, people are just unhappy and not saying anything about it and things like that. So there's a lot of ways that sort of plays out. But I think having an open dialogue and, not just like we're listening, but like we're listening and, we will figure out a way to make changes that work for everyone as needed.

I think that's something that's really valuable and powerful. 

So one of the things that we talked about was an opportunity that you're interested in pursuing right now, and you mentioned that you have recently applied to become a mentor. Can you tell us a little bit about why you chose the organization that you did and what you're hoping to achieve through that 

engagement?

Yep. Yeah. So we talked a little bit about SBA Thrive. They have an emerging leaders program. Essentially the idea is to take businesses that are doing small business leaders who are doing well, they're already growing.

And then just wrapping around some executive level training to help them scale more or less. And so that that really caught my eye because I can relate to that. And I've been in a lot of startups and high growth businesses. And I really do, I appreciate the profile of the, business owner or the founder who has found something that works, they've worked in the business.

And now it's time to work around the business to grow the structural. Opportunities and choices. And so I think that's a always a very interesting sort of time period for, a business to, to grow, whether it's been around a while and finally decided to leap or it's early and it's growing very fast.

Those are two kind of common profiles. So yeah, I I applied to be part of the mentor cohort. And to do coaching. I'm actually waiting to hear back from them, but I'm, excited. I think it was a, sort of a good experience as a lot of things are to help me think about where my zone of genius is and what specific things I can work on in my own community in particular.

Cause it's a regional program yeah, it's a super interesting organizational setup. 

SBA was fundamental to the growth of my business. They introduced us to the Thrive Mentor Program through that SBA Merging Leaders program, and we had access to some fantastic mentors through that program. And I look forward to seeing you move forward as one as well.

Yeah. Is there I can draw on my own experiences as an entrepreneur where I didn't really start a business realizing that three years from that time, I would have 20 people to manage and no idea how to do it. 

Yeah. So no one tells you like, okay, there's gonna be a lot that goes into that.

There's the business mechanics, the model, the finance, the accounting, the forecasting, ugh, sales, marketing, client management. And I haven't even touched on building the team. So it's 

That's, the hard part though, like the team part is ultimately, if I look back on what did I struggle with the most, it was people.

And I think it's like that for a lot of small business owners where we may have a. We are really good at doing something right and we believe that we can do it differently or better than, like the joke was, what do you need to start a business? And it was like, oh, a resentment and a coffee pot. Yeah, 

that's it.

Yeah. You need a chip on your shoulder and a little bit of morphine. 

Yep. F this. I can do this better than for me it was more of a, oh wow, my current career path isn't working out for me  

and I can look back on that now and a hundred percent admit, like a little bit of education or coaching or consulting or something to just, I. Teach me the basics would've been helpful. Like I can't even, like we had a seven, we had 70% turnover year over year, and that's fairly common in the call center industry.

But we were able to get that down significantly once we started looking at the business through the eyes of our employees. Yeah. Like why are people coming to work here? Nobody wants to be a telemarketer and we know that. 

Yeah. So you have to find some other connection. That's relevant.

And the other thing too is so I I worked in startups, went through startup accelerators and incubators. So I've been through that road of the wraparound services. And the thing I always tell folks, which I think touches on what you were saying too, is like in that first year, 1, 2, 3, even five years is like, And I have a lot of intro calls as a coach.

It's part of the culture and I always tell people, I'm like, look, I don't, I'm not attached. If we should work together, great. Let's look for that alignment, seek that alignment if it makes sense. But it doesn't  even without that. The one thing I always want every manager, director, senior director, founder to know is you need proper resources and support and you need to keep trying things because if you don't have therapy to, to work through your own life so that you don't, you know where the boundaries are between what you do in your life and what you bring to work.

That's very complicated, right? Everybody's different. You gotta have a therapist. If you're gonna be running a business I recommend a coach, but you don't have to have one, and not everybody needs one. And, sometimes it's a timing issue. You here's a must. You have to have a set of peers.

If you don't know and have a regular set of folks who are experiencing what you're experiencing and going through it at the same time, it's very hard to do your work. Mentors, sponsors there's a lot of different definitions out there in the world, but you need a good set of resources that do different things for your intellectual and emotional growth, as well as the growth of your business, because at the end of the day so it's like you'd probably experienced you don't know what you don't know, and then you get there and you're like, wow, I've gotta figure this out right now.

This is pretty hard to do. And certain things where there's a lot of relationship mechanics and like trust being built. Like you can't do that in 20 minutes, you know that the team building part of it takes time. It takes what I call long listening. It takes this real kind of evolution.

And so you have to have enough supports and resources in place. Otherwise, it's very, hard to, not just validate the business and the product and the customer set, but actually build it in a way which it's repeatable and, doesn't harm people, including yourself as well as your employees, customers, stakeholders, et cetera.

No. 

Can you dig into long lead listening? I've never heard that phrase before. 

Yeah. I think it's more important now than it's been in a long time. And it's just the way I, this is the sort of short definition is, stuff that you keep returning to. And people probably have other phrases and words for this, but I think I'll give the classical example, like when you work.

With folks, whether you're a founder or a manager or director, whatever the case might be, if you have folks on your team that report to you, your job is to understand what's important to them. But you, don't necessarily get an answer to that in the here and now. You get that answer over time.

And so I always encourage one of the core EQ skills that I, teach managers and founders is. You need to keep coming back to and folding in what you know about that person. So if somebody says something to you in your one-on-one or you problem solve a, an issue, and then you move on, you need to make a note of that and you need to practice the habit of coming back to it.

In 2, 3, 4, 6 weeks and say, Hey Carrie, I wanted to ask you about you said something a while back. I think it was when we were in a one-on-one or we were dealing with X, y, Z problem. And I was thinking more about that and I wanted to, just mention it cause I'm curious to see if you thought about that more.

Or I have a thing that I think you might find interesting. You might read or, whatever, very basic example. But what happens when you practice that type of long lead listening is a. First of all, you get buy-in, right? People. You create a trusted relationship where people are like, oh wow, My manager or my founder's actually paying attention to what's happening in my life. They're, thinking about what's important, and you get a chance to check that with them, right? Because you might be wrong. You might be making an assumption. Most of us do. But you, create this relationship that is where there's this trust and this medium and long term kind of evolution and loop.

That's really important. But the other thing is that when, the shit goes down, which it does when things get stressful or heavy, you have a context with that person and with that multiple people on your team already, so that you can sit down and, basically say look, we're gonna get through X, Y, z I, know it's gonna be different for each person.

We'll figure it out. But, you have set a stage for sort of the, ups and the downs already where there's, a sense of trust and also, and I think this goes back to the, transparency and the kind of the talk about power and, being open about it is if, you're also practicing those two things concurrently, then you're not necessarily in charge of making all the decisions as the manager or the founder.

You, keep opening that door and going I, we talked about this a while back. This is a very complicated situation. I actually don't have the answers to this one, but I think we should talk more about it and figure it out. And that, of course takes time to do.

And I think especially in our super fragmented eco attention economy, app economy world it's even more important to practice long  listening in that fashion. Whether you call it that or something else is, not important. 

Do you think there's a big difference between the way software companies build their teams and the way services, or like small business owners build their teams?

I'm seeing a lot of small businesses modeling what they're doing after, let's call it very successful. Staff startups kinda like they, they innovate in some way and then smaller businesses watch and try to adapt. Are you seeing? 

I think there's a couple of inputs and so this definitely goes to having worked in startups and also working in journalism a little bit, like understanding the, landscapes.

I think there is a modeling that happens. I think it's in some ways it's tied into conceptions of, traditional conceptions of what to do with capital and that it's possible to build things really fast. And I'll give you an example. 10 years ago if you said we, one of our most important teams is our customer success team, most people would be like, I don't even know what you're talking about.

Because customer success is a new newly minted thing that Google and other it actually. I remember when that term first got used or started being used regularly. Startups were using it and then big Tech picked it up and turned it into a really big function. As customer success is really just some combo of support and account management, right?

At the end of the day, it's just a phrase for that. I think a lot of like early stage founders as well as long-term small business owners do look to that model. And I, think it's, you can have the fanciest tech stack in the world and be using all the things and you can still be missing some of what I was just describing, where you don't really have a real connectional relationship to your to your team.

And like in a retail environment, for example, scheduling's very different than you can't have the same. Flexibility or freedom that you might have at a tech startup where there's a lot more design knowledge, work, communications things, engineering, things like that. But you can still have the same style of, working and the same cooperative and collective approach.

And it actually one of the reasons that I always talk about it when people were in both of those verticals is I think it actually de-risks your business in a lot of ways. It, creates less stress on the people at the top to make all the decisions about all the things, and it gets buy-in.

It creates trust and belonging, all those kinds of things. But it also means that there's a deeper and more consistent listening to the rhythms of the business, which again, you know a ton about having built some businesses, the rhythm. Is really important. And that's I think that's something that's applicable for both of those profiles.

Is there anyone 

in the market that you think is doing an exceptionally good job of creating teams where the power is balanced and capital is attainable by teams at the people coming into the business, the people that have been with the business for a while. Who should we be looking to as examples right now?

It's 

a good question. I don't think it's, I think there's some movement in that direction at Microsoft especially. There's certain teams and units that I pay sort of close attention to that are really interesting. So I see a little bit of that in that stack. I think a lot of the big tech companies are not they're struggling with what I'm describing, which is the degree to which  we're, leaving an era. In which, talking about inclusivity, talking about welcoming people, talking about diversity really taking all of , that stuff is now like being critiqued in a different way as this era shifts and it's being critiqued, especially by millennial folks, gen Z and then Jen Alpha, of course is on the horizon too.

And I think the, general sort of philosophy there is, yeah, we see you, you're just talking a bunch of game about being a place that actually cares about its employees and, is in a trusted relationship. But your, structural norms are not set up for that. So I don't see a lot of it, unfortunately in, and I think that's a  reality of executive management and cuz I just to use an example, I'm not against I don't, when people talk about kind of work flexibility, I'm like, cool every.

Business should be thinking and talking about remote work. It should be thinking, talking about hybrid work. It should be thinking and talking about when and where it makes sense to be in person. So a lot of these sort of Big narratives that are trying to make the decision about what is the future of work gonna look like?

It's gonna look collective is my personal opinion, but I don't think a lot of people are prepared for that. So I, don't think there are a lot of examples right now, but I think there is a growing set of cooperative startups especially that are thinking about and doing it a little bit differently.

Do you see the 

most opportunity being available at that kind of emerging stage where you can almost impact the way a business is going to be built versus coming in and trying to rip and replace? Would it have been installed previously? 

Yeah it's a good question. A lot of the big companies are.

Salivating over AI and the opportunity to automate things and I think some of them, I'm not gonna go down the path too much, but I think some of them would love to automate the customer and the employee. Wouldn't it be easier if we could just ex have the, capital exchange without any of people, which you can tell by sounds like the promised land.

Yeah. You can tell about one my voice. I'm not into that dystopia personally. I and I don't think it's gonna come to fruition in the way that they maybe think on that side of the house. But I think I, think that there is a very interesting opportunity and I think because when you think about that adoption, Cycle of technology, which is faster than it has ever been, and it's getting faster, right?

And I, I can't remember the chart. You probably can remember it. The one that's like, how long does it take for a business to become, come to market and then become the dominant and then maybe become decay, right? There's that loop that cycle's getting faster. So I think there's a lot more room in the sort of, I guess I would call it like like mid-stage startup to mid-market companies to impact that.

And I think from a talent retention perspective, it's only gonna get harder from the things that I see with clients and, companies that I work with. So, 

we're not gonna see AI coaching coming out of the early manager anytime soon. 

No I know it's happening. I know people are like, let's let's totally automate that.

I think AI has a lot of potential to increase eq, but I doubt the strategy is there for a lot of these companies. They're for just as an example, like the fact that Google rolled out a half formed product because it was so freaked out about. Open AI and Microsoft getting ahead of their these are bi billion, almost trillion dollar in some cases, trillion dollar market cap companies.

And they're so freaked out that they're launching a product in six weeks that is, has no guardrails or few guardrails. That does not, speak well. And so I think that is in some ironic ways that says how open they are to being disrupted by some of these other mid-market and smaller, faster companies.



Fast forward a year into the future. You're mentoring for Thrive or maybe several other business organizations, is there a something you wanna manifest today, like a business that you think would truly benefit from engaging with the early manager? Like where are the places that you wanna be a year from now?

Yeah. 

I think put it out there. Yeah. Yeah. No, it always, it never hurts to say it out loud. I think that's, useful. I I think that sort of the place where I like to work the most and where I'm most effective, which is the two things I think about a lot like, anybody that's paying attention to purpose is I think really working with Companies that are in that kind of small to mid-sized realm.

And I think especially companies that are interested in building more, either more cooperative models for the business overall, cuz there is, there's actually a growing set of. Startups and companies that, that literally in their legal and financial structure are creating ownership shares, equity these cooperative structures have been around.

But they're becoming coming back and being thought about in a lot of ways too. So my hope is to be working with more kind of cooperative oriented startups or larger businesses that want to take that and, come back and do what they do, right? The innovation arm or whatever, where they're trying to infuse that.

That section because I think honestly at the end of the day we're, coming to better and Closer understanding that social impact and E S G and CSR and a lot of these traditional terms like these. My belief is these things become incumbent if you have a structure where you're responsible to your stakeholders already.

And so working with businesses that are that are really in that place of being serious not just like we put a press release out or we do some cool social media content that says we love or we care about it's May so Asian American and Pacific Islander Heritage Month.

I'm, a believer in in having companies that are trying to build. Cooperatively. And so my hope is yeah, is just do, did you do more of that? 

I can't think of a better place to leave off today than that. Thank you so much for joining us today. I appreciated learning from you and I know that the WIN listeners will as well.

I look forward to following up with you to see where you are a year from now, and wish you all the best. Thanks for joining us on WIN Today, Joe. 

Yeah, thank you. Thanks for having me.