Getting Your Team Unstuck

Hosted By Lauren Conaway

InnovateHER KC

See All Episodes With Lauren Conaway

Maura Charles

Today's Guest: Maura Charles

CEO and Digital Product Consultant - Keep It Human

New York, NY

Ep. #987 - Getting Your Team Unstuck

In today’s episode of Startup Hustle, we’re focused on getting your team unstuck from those sticky situations startups can oftentimes find themselves in. Lauren Conaway welcomes Maura Charles, CEO and digital product consultant of Keep It Human, to the podcast. Let’s learn how to create highly functional and diverse teams and unlock their potential.

Covered In This Episode

Want to know a little secret? A healthy, diverse work culture creates improved team performance and engagement.

Hear about getting your team unstuck from Lauren and Maura. Also, uncover the value of work-rest boundaries, aligning personal values to work, and more.

Get Started with Full Scale

So let’s go take your team’s performance to the next level! Listen to this Startup Hustle episode now.

Check Out Our Startup Hustle Podcast


  • Maura Charles shares her journey (02:45)
  • On being creative and building a company (06:28)
  • Going back to your core values when you feel stuck (07:56)
  • Prioritizing balance (10:20)
  • How to prioritize the things that need to be done (11:14)
  • Taking the time to rest to get more work done (14:19)
  • Setting boundaries between work and rest (17:01)
  • Aligning personal values to your work (18:08)
  • Building a healthy work culture and team (19:47)
  • How did Maura build her team? (22:52)
  • On getting support from your employees (25:26)
  • About making valuable connections outside workplaces (28:11)
  • On being part of a women founders group (29:30)
  • How to activate your teams and unlock their potential (32:03)
  • Creating the human connection and balance (34:50)
  • On hiring more women and building diverse teams (36:55)
  • A case study on diversity and how it affects technology (39:34)

Key Quotes

Creativity is obviously an important part of problem-solving. But what I felt was that I was solving a lot of the same problems over and over. And that’s when I thought, oh, this isn’t terribly creative anymore, and I want to do more.

– Maura Charles

Balance is important. It’s a value that you hold. It’s something that you prioritize, but it’s not something that you can always have.

– Lauren Conaway

A lot of times, it’s like the team doesn’t really have a playbook, or they don’t have a working agreement. Honestly, if they just had a working agreement and got to know each other a little bit better, maybe they would be able to get where you’re trying to drive.

– Maura Charles

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Rough Transcript

Following is an auto-generated text transcript of this episode. Apologies for any errors!

Lauren Conaway 00:02
And we are back! Thank you for joining us for yet another episode of the Startup Hustle podcast. I’m your host, Lauren Conaway, founder and CEO of InnovateHER KC. And I got to tell you, today, friends, our episode is sponsored by Double, a flexible assistant service for busy executives that matches you with an experienced assistant. And I know that we can all use assistants, every last one of us. Some of us could probably use three or four. But with Double, it’s easier than ever to hire a virtual assistant online. No solution is better than Double. They are a flexible assistant service built for busy founders, executives, and anyone who is looking to save time and focus on what matters most, which is probably most of us. If you want to take control of your business and unlock a more productive version of yourself, go to today. You can get $300 off your first month when you sign up with the code HUSTLE22. That is Use code HUSTLE22, and save $300. I mean, come on. That sounds like a pretty great deal. Now friends, today we have fabulous experts with us. I love our Startup Hustle producers. They do such an amazing job of identifying fantastic leaders and experts in a space. And today, we’re joined by Maura Charles. Maura is the founder and digital product consultant for Keep It Human. Thank you so much for taking the time to chat with us on the show.

Maura Charles 01:27
Yeah, thanks for having me. I’m happy to be here.

Lauren Conaway 01:29
Yeah, we’re gonna have a lot of fun. We have some fun in pre-show prep. So I always feel really good. Like, once we hit that record button, when I know that somebody is willing to have a little fun with us, we get good energy going. Oh, yeah, we’re like five in. It’s amazing. I’m doing a little dance right here. Y’all can’t see me, but I’m doing a little dance. So let’s go ahead and kick it off. Now that I actually know what . . . Do you want to do a little dance for us? Sure. All right. We’re about dancing right now, friends, and I hope that you’re dancing at home. So let’s go ahead and kick it off. I’m just gonna say more. Tell us about your journey.

Maura Charles 02:05
Oh, sure. Well, so I’ve been working in digital since before I graduated from college. I’m not going to tell you what year it was. But what I can tell you that might give you some idea is that it was a CD-ROM project.

Lauren Conaway 02:22
That means something to me. I’m an older millennial. Yeah.

Maura Charles 02:29
I’m technically a Gen X-er, I believe. But, um, but yeah, so I, you know, I really was, my background was in writing and music. So, you know, I studied, I kind of studied humanistic studies in college, which was like a big broad thing that basically said, Take whatever classes you want. And then, I ended up concentrating on writing, which is one of my passions, and music, which is my other. And I got a, I was able to get a work-study job on campus that actually was designed to they were essentially building a CD-ROM, and this was literally this is like the early days of CD-ROM, and so there weren’t actually even that many out their models of how to do that kind of software development. And I was on a very small, cross-functional team, and my responsibility was mostly editorial. So getting you to know, figuring out what the right content was doing all the research, we were, we were teaching, it was a CD ROM designed to teach digital drama, to teach drama, you know, drama to students and on a digital platform. And so the thing I loved about it, though, and it’s funny because I recently found, you know, a news clip of when I had an interview that I did after the CD came out, and what I had raved about was the experience of working on a cross-functional team, and about how we each brought, you know, different kinds of expertise to that team and how that was really the coolest part of the project was seeing how a designer and an engineer and you know, a graph, like our sponsor, or faculty sponsor, look at how everybody brought different skills and different kind of points of view to the work. And as it turns out, you know, 20, something years later, that’s still the thing that I’m really excited about in work. And so when I started keeping him and it was really to take all the years that were in between that and, you know, two years ago when I started this business, was to really take all the experiences that I learned from working in product management, which is really the path I ended up taking for most of my career. And to really go back to like those cross-functional teams and how can I help those teams because that was the sweet spot, the part of my work that I was the most passionate about, and the part that I enjoyed the most. So I think it’s funny that that was my origin story. You know, that’s how that started. And that’s still the thing today. So right now, I do a lot of coaching. In my consulting practice, I do also consult, but a lot of that is just setting up for things like what kinds of team coaching or individual coaching A business might need at any given time. So I think that kind of gives a big broad picture of my journey as well.

Lauren Conaway 05:08
So I’m curious. One of the things that kind of sticks out for me is, you know, you started as a creative, like, that’s where your journey began. And so I’m really curious, you know, one of the things that we talk a lot about is that entrepreneurial mindset, the entrepreneur, which you very clearly are, and you work with entrepreneurs, I’m sure, and, you know, but you have that creative, start onto the entrepreneurial mindset is creative, resourceful. And so I want to ask you, the first question I’m gonna ask you is how, how has that creative mindset helped you in your business, as you’ve been building your brand and building, building your company?

Maura Charles 05:48
Well, it helps that. I mean, it’s kind of the easy part of the work, I guess, what I would say. So coming up with ideas is not a problem. It’s, you know, finding the time to execute them and figuring out which one to execute first. You know, as a team is something that all teams struggle with.

Lauren Conaway 06:06
So it’s all you know. We’re gonna drill down on that. Well, I mean, it’s so often like drinking from the fire hose, it’s like, you’re a visionary, you have all these amazing ideas, but it’s like, I can’t, you can’t do all of them. Well, so you’re gonna have to pick one, maybe two.

Maura Charles 06:21
Yeah, totally. And but I think what happens when you’re in these, you know, kind of whether it’s an individual contributor role, or even as you become, you know, a leader, in, you know, in within a corporation, let’s say, or within a startup, that you, you have the kind of necessary constraints of day to day work. And so, even when you have lots of creative ideas, you don’t always get to use them. Because sometimes you’re just like, they’re, you know, there are certain foundational things that need to get done.

Lauren Conaway 06:48
And so you’re really keen on that because you have to close the books for the month or something like that. Exactly.

Maura Charles 06:53
And so you, you end up focusing a lot on problem-solving and on Discovery and trying to figure out, and so yes, you are being creative in your day-to-day, and creative creativity is obviously an important part of problem-solving. And what I felt was that I was solving a lot of the same problems over and over. And that’s when I thought, Oh, this isn’t terribly creative anymore. And I want to do more. And I think one of my values has always been that right, like learning more. If I’m not learning, I feel like I’m a little stuck.

Lauren Conaway 07:22
Yeah, I love that. So I did a workshop recently where I was asked to think about my core values, like, what are the things not my company? Not like me more? What do I value? And one of the things that came out was curiosity. Like I always, I always want to know more, I always want to, you know, I want the context. I want the info because it helps me make better decisions. But I love curious people.

Maura Charles 07:51
And I think it tends to show a growth mindset, too, right? Like, if you’re curious, it means you want to, you know, you want to either do better or, or know, you know what’s possible.

Lauren Conaway 08:01
Yeah. Well, that is super cool. So just out of curiosity, haha, see what I did there? I’m gonna ask you, what are some of the things that you’re most curious about? And I mean, I know, I know that we, you know, you’re, you’re definitely very focused on that human connection. I’ve seen that we kind of talked about that creativity piece, but what are some of the other values that you hold?

Maura Charles 08:25
Hmm, I think there will be a lot, right. But I think the basic ones are about, you know, just kind of balance keeping, like a level head. So. So there’s, like, two different things, but they’re kind of two parts of the same hole, right, like, so yeah, I have a lot of passion, you can tell probably from the way I’m talking here, right now that I, you know, I have a lot of energy and creative energy, but I don’t, it is also really important to kind of like, keep to, like, have an even keel. And that’s, I would say, that’s a value, even if it’s not something that I’m always good at, right. So like, kind of user data, like using inputs and logic, and also all the, you know, variables that are around you and figuring out what you’re going to do with that. I mean, I think that’s part of the human side, right? Because that’s the emotional intelligence stuff. I think that that, that all different kinds of components of emotional intelligence are important to me because it’s just a lot of it’s about knowing yourself and knowing your limits and understanding a situation that you’re in, right, like, situational awareness is so important for all kinds of business folks, but especially, you know, technology and product management, folks.

Lauren Conaway 09:42
Yeah. Well, so that’s, that’s super cool. I, one of the things I think we don’t talk about often enough, and you just made a really profound point in there, you know, like balance isn’t high value. It’s something that you prioritize, but it’s not Something that you can always be. Okay? You know, like, I’m not always curious, sometimes I’m tired sometimes. Sometimes I just want coffee, and I want to curl up in a ball. You know, and because I’m an entrepreneur, sometimes curling up in a ball means that I cry. But you know, we can’t, we can’t be all of the things all the time. And so I love that you’re able to acknowledge that, you know, I can value something without having it be everything that I am all the time, 24/7.

Maura Charles 10:36
It’s good to have guiding principles. But it’s the mark of a well-integrated personality, like understanding that, hey, you know, I have limits, and it’s okay to honor that.

Lauren Conaway 10:39
Well, so I do want to ask you because this has come up a couple of times now. But I want to talk to you, how do you prioritize, you know, the things that you value and the projects that you’re excited about? And, you know, your life? I mean, we talk about things like work-life balance, you know, that phrase, but how do you prioritize all the things that you want to do?

Maura Charles 11:07
Poorly, but I just almost spit out my dream. But, you know, I, it’s, uh, I’ll just say it’s a work in progress. But I will say I legitimately have a lot of systems that I use. So I’m a, I’m a passionate user of Trello, which if, you know, people in that project management platform, it’s a project management platform, but it’s essentially just like a lot of different columns with like, little cards. And so you can take, you can put everything on, instead of lists, it’s like lists of lists, and then you can just move things around, it’s for visually oriented people, it can be really useful to be able to put things in different kinds of categories, right. And so, so I tend to use, I tend to use that. And then what I’ve gotten really good at is using some of the principles of agile and things that I you know, different different frameworks that I’ve used over the years in my, in my product management work, to kind of treat my work and myself as like a product. And so this is something that is very hard to do, by the way, if you’re if this is something that you do professionally, and then you try to do it on yourself. It’s like, you know, the cobbler’s children have no shoes.

Lauren Conaway 12:16
Do not do this kind of thing. Yeah. Yeah. That kind of stuff pops up all the time. Like, I’m so much better at solving other people’s problems.

Maura Charles 12:26
So it took a lot of it took a long time for me to get to a point where I knew what the those categories were, for example, but then what I also had was this, I used to, you know, I had so many things on these in these boards that I couldn’t ever possibly get through them. And so before I kind of like, let me come back to that for a second. But the other thing I was going to tell you is that I just read this book, which I’m passionately recommending to everybody who comes into my Zoom my world, which is fear of influence, my sphere of influence, and it’s called 4000 weeks time management for mortals written by a journalist named Oliver Berkman. And what, you know, in the first, I was listening to it on audiobook, but I have since bought the hardcover too, so I can mark it up. But what I saw really helped me see was that there will always be more things to put on that list. And on that, it could literally be never-ending and that productivity is kind of a trap.

Lauren Conaway 13:26
And they rarely do. I need you to drill down on that a little bit.

Maura Charles 13:29
Yeah. So I mean, basically, if you get if you’re really productive, and you get a lot done, what’s your reward? Yeah, you get more stuff to do, right? It’s the same thing. In most businesses, if you’re really good at what you do, your bosses will give you more to do. And it’s the same if you’re, you know, a productive personality, if you value productivity. Yeah, that becomes all you do. And then you do things like, you know, one of the things he talks about in the book is this idea that, you know, rest has become a thing that we do, because it makes us more productive. How backwards is that?

Lauren Conaway 14:06
Yeah. It’s kind of like you, there’s that saying where it’s like you’re you’re working to live not to work and it’s kind of like you’re you’re resting to do rather than doing to rest I don’t know, right.

Maura Charles 14:20
And we used to, I mean, I know, I think Lauren you’re of an age where you might remember this but we used to just watch TV and not do anything else.

Lauren Conaway 14:29
Yeah, that’s true. I don’t know about your personal break sometimes. Yeah, like what happens if you want to go get a snack man right, but I just see so many people who are like they need to keep their hands busy.

Maura Charles 14:40
They need to enter the ship to feel like they’re doing something or accomplishing something. Yeah, and so I think that the thing that and that kind of to bring that back to how I prioritize I think in the past I’ve just been like, okay, you know, you have your you kind of aligned things to value so my aunt Sure, if you’d asked me this question three weeks ago, my answer would have been, I prioritize based on my values. So I, you know, try to keep up, you know, a running check in with myself about what my core values are. So if it’s, you know, family and always being learning, and I don’t know, whatever, I’ll say, whatever else is my value this year, so, so you take those kinds of core values. And, and you really just make sure that the work you’re doing is aligned to them, right. And so if you can, if you’re in a position to do that, which I feel that I am right now, which is that I, you know, I’m able to kind of make, you know, make the income that I need to be to, you know, to live my life, and then I can figure out what to do with the other time. So, I’m, you know, I’m already making a compromise there by saying, like, Yes, I have to do, I’m not, I’m not, I’m working to live and living to work at the same time. But, um, anyway, back to this. So back to this idea of changing this notion of time, I think what I’m starting to realize is I’ve been trying to do everything, or at least as much as, pick off as much of those to do lists, and like, and it’s just never-ending. And then you don’t get a rest, and then you do burnout. And what I think I’m learning is that you need to have those boundaries with yourself even to say, you know, what, if you could only do one thing today, what would that one thing be?

Lauren Conaway 16:23
Yeah. Well, I mean, like, even now we have this, this sea change in society where people keep up, keep on talking to me about quiet quitting. And I actually hate that phrase. I don’t I don’t like that phrase. Because in most instances, instances, like when I asked people like, well, what does quiet quitting quitting mean to you? The response is something along the lines of, well, you know, I turn off my phone when I’m at home, or, you know, I might actually take a lunch break instead of eating at my desk, or what have you in the fact is like, that’s, that’s quitting, that’s not quitting it. Boundaries, you know, set it, it’s setting boundaries. So you know, we have to be careful with our word choice there. Yeah. Because I think quiet quitting sounds a lot worse than it actually is. It’s really been quiet.

Maura Charles 17:11
No, no, that’s true. Because I’ve seen quiet quitting, that has not worked by quitting. Really, why quit?

Lauren Conaway 17:17
You clock in and check out light?

Maura Charles 17:19
And you’re like, in your honor, performance plan, and you don’t even care? Yeah, whatever, you know, keep the keep the paycheck coming.

Lauren Conaway 17:23
So I’m really curious, because you kind of touched on this a little bit. And we heard about your, you know, your origin story. And just, you know, like, when we get to the human question later, you said, you use the phrase origin story, which means you might get a superhero question. I was throwing that out there. We’ll see. But I’m really curious, like, how do you feel about your personal values, and you as a founder, how are those aligning with your work with Keep It Human?

Maura Charles 17:57
Well, the clients, first of all, the clients that I choose to work with, all are looking for this kind of connection on their teams. So I think, you know, the, I always make sure to tell people the reason that I named my business what I did, because I don’t want them to have any assumptions about what it might mean, but for me, Keep It Human is about a couple of things. It’s about keeping the teams that build technology, like letting them be the human beings they are. So the king of the things, we were just talking about having boundaries and having a life and being able to get a you know, to take a nap whenever you you know, Sunday or to be able to take a day off when you need a, you know, a refreshed and really enjoying that kind of balance, whatever that balance looks like for you. But there’s also the interaction, the human interactions and the collaboration that happens as part of working in a company, right, and there’s so there’s so many of those different kinds of dynamics. And so you know, I think that the people aspect of that has to be important. It’s funny, because I remember when I first started the business, I thought, How am I going to convince people that they need to pay attention to this thing, they need to pay attention to those dynamics. And then what I realized is there’s plenty of people who already think it’s important, and the company doesn’t maybe or the other way around, the company thinks in support, but they don’t know how to do it. And so I think the trick has been figuring out which of those are the ones you really know, where you can actually bring the most value and might enjoy the experience. So sometimes that means I embed with an organization for a longer period of time. I’m doing a product transformation for a company right now. And I’ve been there for almost a year, and it’s not full time. It’s not full time, but it’s like but you do get quite embedded during, you know, during that length of an engagement and that flow allows you to form those relationships into real, really build trust and kind of build your brand even within that company, right? Which is kind of funny. Yeah. But it’s very different from having, you know, an engagement where you kind of dip in do a quick evaluation of, of what’s happening and say, you know, here’s where I think I can help you and do some quick workshops where maybe you do one on one coaching with somebody on the team to help them level up or get where they need to be. Or maybe you suggest, a playbook a lot of times, it’s like, the team doesn’t really have a playbook or they don’t have a working agreement. Honestly, if they just had a working agreement and got to know each other a little bit better. Maybe they would be able to get where they’re where you’re trying to drive. And so those are the ones you know, that’s so I kind of I would say I pick more the engagements than the but the people sent tend to kind of pick me because they are like, oh, I want that value in my company.

Lauren Conaway 20:53
Yeah. Well, so I love that. And I love the fact that we’re talking about building teams and integrating into teams. And I do have to tell you, friends, one of the most impactful things that a founder can do, particularly in the early stages, is start building that team. So when people ask me what my best advice for building a business is, most of the time, it actually involves the team. And you have to know, you know, you have to put the right people around you and you have to know when to delegate. So, today, I just want to add that knowing when to hire an assistant is really key too. It’s usually the hardest thing for a startup founder to do, because they want to feel so close to everything. Finding an assistant is hard. Well, it doesn’t have to be when you connect with our friends over at Double, they are experts in pairing founders with remote executive assistants you can trust, Double will match you with experienced US based assistants and arm them with tools and training to ensure you are always getting the best of the best Startup Hustle listeners can go to Use code HUSTLE22 and save $300 Right off the bat. That is using code HUSTLE22 to save $300 Alright, so Maura, I need to know, how have you built your team?

Maura Charles 22:12
I haven’t. I haven’t. It’s just really me and it’s a challenge. And kind of back to your question earlier about how do I prioritize? I do think a lot about that. Do I want a team? And I think I do. But I also think it’s a lot of mental, like, labor to figure out like what, where you would want to do that, right? A lot of people will say, and I talked to other other people, especially women, I think who work as solopreneurs. And people are always saying that well, how are you going to scale? How are you going to scale? And sometimes, you know, the answer is, well, I’m not going to. And so I think there’s a difference between growing and scaling. And for me, I’m more interested in growing my business in directions that I might want to go than in scaling to like a, you know, even a three or four-person company like I’m at a point now right now, you know, I’m I’m a nearing a certain age, and I’m at a point where I’m thinking, you know, I don’t know that I really want a big team, or even a small team, I had an idea this year for some a solution, or, you know, a problem that I that I wanted to solve in, in the space that I work in. And I kept thinking like, I have an idea that it could be it, maybe it’s software, maybe it’s a software platform, and I you know, I had some pretty, pretty good ideas, and I started to test them out. And then I thought, oh my god, you know what, I want this product to exist, but I don’t actually want to build it. Right. And so I think that was a big wake up for me. And when I started the business, I never really envisioned it being, you know, a consulting practice. Although I do think of what I do as like a practice, I think that I don’t, I don’t think I have any ambitions right now to build it beyond myself. And so I do try to get help where I can and I do hire, hire out help for especially for you know, for specific things that that were, maybe you know, I don’t work so efficiently at it. So I can use a canceling place like it can be so transformative for a business.

Lauren Conaway 24:19
So we talked about this on the show, or at least I talked about it on the show, but the fact is, like a lot of startup founders, they have to you we have to be generalists because we are the only person who is responsible in the beginning for doing all of the things and the fact is like when we’re doing things that we’re not good at, not only is it unfulfilling personally and professionally, but it’s also really shitty for your business.

Maura Charles 24:47
Yeah, and it’s a bad use of your time right from always taking no much longer. Yeah, I think that was a big wake up for me. I think I used to feel guilty about even being in your Personal life, like, you know, getting help for certain things, right? Because there are things where you’re like, Well, I know how to do that I could, why would I hire somebody to do that? And then you realize, oh, I’m actually first of all, either I’m not that good at it, or I hate it or, or, you know what, it’s not that expensive to pay somebody to help me with that piece of my life, you know, let me maybe I should maybe I should get some help.

Lauren Conaway 25:21
You can put that time to better use, empowering you to like the thing that you hate? And then focus on the thing that you love. Yes. So I’m a work in progress there for sure.

Maura Charles 25:31
But I do ask for help. And I’m trying to get better at it as part of my new vision of working smarter.

Lauren Conaway 25:39
Yeah, well, and I think like when I said, like, how do you build your team, like, one of the things that I’m getting at is like, sometimes your team is not your employees, or your staff, like the team, your team is the people that you surround yourself with the people that are in to help you and support you, whether that’s through mentorship, or contracting, or, you know, whatever it is.

Maura Charles 26:06
So, I mean, it sounds like you’re, you don’t necessarily have that traditional, like, WTO team, but you’ve gotten, like you, I’ve got a lot of really, first of all, I have been so grateful that a lot of the people that I had worked with over the years, you know, reached out and said, Well, how can I help like I want, you know, or, you know, what are you doing, they all just, so I’ve been, you know, I’ve tried to keep people up to date on LinkedIn about, like, the kinds of things that I was interested in, and really, you know, put that brand out there of, you know, the kind of work I want to do, because, because I wanted to make sure that I did a certain kind of work, what I didn’t want to do was be like a fractional chief product officer, or, you know, just dip into teams and do product consulting, that wasn’t really what I wanted to do, what I wanted to do is the specifics, you know, aspects of helping teams perform better. And so back to kind of like the, the, what does that look like then, I had, so I had all these wonderful colleagues, some of who ended up hiring, you know, former colleagues that ended up hiring me on consulting gigs, which was wonderful. But I also just feel like I have this wonderful network of people that either whether they’re, whether they’re out on their own now, or they’re, you know, running a business unit in a corporation, they’re people that I can bounce things off of. And so that’s been really wonderful. And I’ve also found a lot of that in my local community. So I live in the suburbs of New York, on Long Island. And what I’m finding is that even in you know, just than the mom groups, I have a, I have a seven year old daughter and I in, you know, in her school out meet other parents and, and have lots of kind of professional things in common with them, even if they’re in a completely different industry, I’m finding that that’s a really wonderful way to make those kinds of connections in a way that we couldn’t before COVID Because everybody was commuting. And so that’s been a huge win is finding people locally, because then you feel like you’re not, you’re like, you’re literally not alone. Because if you work in your home, you’re in the suburbs. For a lot of zoom calls, you’re not in person a lot. So when you do, it’s nice to have people that you can connect with that way. And the other thing is that I, you know, I have a lot of really strong, wonderful women who are also, you know, independent consultants that I, you know, I really connect with on a pretty regular basis. Some of them are people I partner with on engagements, sometimes it’s just folks that I know, through different connections. And then the other thing is I belong to a couple of networking organizations that are private networks that I think are, have been really instrumental in helping me kind of find my values, but also to really understand my value in the marketplace, which I think is incredibly important, particularly again, for women. We tend to undersell ourselves, this was this is the kind of these are the people who will kind of say to me, like you were you know, if you’re like things like if you’re too busy, if you’re not busy, if you’re so busy, if you’re too busy, then you’re not charging enough, like people who say things like that those are the people you want to stay close to because they’re the ones who help you see, like stand in your power, right? This is something that you’re really good at, make sure that you’re getting what you’re worth. And, and so I’ve been really fortunate to have that.

Lauren Conaway 29:24
It’s like x executives and CEOs. I think I’ve been invited.

Maura Charles 29:28
It’s not it’s not just executives and CEOs.

Lauren Conaway 29:32
I mean, there’s a lot of well, so that’s what their marketing and messaging is, that is what their marketing goal was.

Maura Charles 29:34
And it’s funny because I wonder if it’s changed a little bit over the years since they started, but I was a founding member, maybe three or four. And so there were only 200 of us back then. And we were in New York City. There was a clubhouse there and we would actually have meetings and dinners in person and it was a little a lot different than I would say it is today just because of the nature of what happened during COVID. But yeah, have, you have these core groups that you get. So you get assigned a group of peers that you meet with on a regular basis, usually once a month, and then you have an executive coach who facilitates, and that was, I think, that was, like a big pivot for me joining that joining chief was a big change in was when I my life, I would say took a turn for the for the better because of the because of those ideals of a really understanding what my worth was, I think for a long time, I just took whatever our company offered me and you know, accepted salaries and didn’t negotiate that. And it took a long time to realize that if somebody says no, it’s not that, you know, it’s not the end of the world, or maybe that job wasn’t really for you. Yeah. And I think that that’s something that as founders, we need to remember to write, like, you asked me before about, like, how I, how I engage or how, you know, how, what kinds of companies I work with, a lot of it is, you know, if I don’t enjoy, if I don’t think I’m gonna enjoy working with somebody, I probably won’t take the contract.

Lauren Conaway 31:06
Yeah, well, good for you. I think that firing clients and being able to be more discriminating and discerning as a, as a business owner, I think we need to talk about that more, because the fact is, the customer isn’t always right. And more importantly, the customer isn’t always right. For you. Yeah, so yeah, well, so let’s I want to take a moment I do I want to get tactical with you, because we’ve talked a lot about your journey and kind of, you know, your your methods and processes, but what I really, your focus is on humans, human beings, teams, how to help them perform better, you know, working through things like organizational structure, you know, leadership tactics, you know, highly functional teams are really, really difficult to come by. And they take work, they take culture setting, they take a strong leader, they take a strong leadership team. So talk to us a little bit about your work there, like some of the things that you’ve seen. And really, what I love to do on the show is offer our friends at home who are listening, you know, what are some ways that they can activate their teams, you know, unlock a low performing team or, you know, practices to to bring up that engagement in that performance in productive, healthy ways?

Maura Charles 32:24
Well, a lot of, you know, there’s been so much research on a lot of these things. And so a lot of what I’m going to refer to is not stuff that your audience won’t have heard of will have heard before, right? So things like psychological safety, right, like Google did a big study a few years back, I think was called Project Aristotle. And what they found was that the teams that are the most successful are the ones that have psychological safety.

Lauren Conaway 32:47
That was like the number one thing is psychological safety for the folks who don’t know, and I’m going to take a stab at it here more, but feel free to correct me wrong. Psychological safety means that your team feels comfortable voicing concerns, and you know that they feel safe and supported when they are able to give feedback and receive feedback. And so creating an environment where your team feels empowered to make decisions, ask questions, and do exploratory discovery work to make your company better. How was that?

Maura Charles 33:22
Yeah, I think that’s really accurate. I think the other thing I would add to the mix is how they also need to feel safe with their peers, right? And they need to feel kind of accepted, or you know, that there’s this openness to diversity, right? So one thing, so you know, that could be cognitive diversity, it could be the diversity in the kind of definition. It could also be, you know, different cultures. One thing that I was not particularly sensitive to, although I should have been earlier in my career, was that not everybody wants to go out and get drinks after work, right? And so, you know, there are people who, for various reasons, don’t drink and you need to be sensitive to that. And then obviously, when I became a parent, I suddenly realized, oh, my gosh, like, nobody, I don’t have time to go for drinks anyway, I would love to go for drinks, but I didn’t have time.

Lauren Conaway 34:13
That’s something that we talk a lot about around innovator late from a cultural perspective, you know, at least here in the States, the expectation is still that women still tend to take on the bulk of child rearing duties, household labor, the mental and emotional labor that comes from running, making sure the trains run on time within your household. And so we have to be, we have to be really, really conscious and cognizant of that. And so that is a cultural value that you hold. Like, we’re sure if you’re having a ton of meetings, you know, or coffees or whatever, you know, you’re networking events and it during times when people are expected to be parents, you’re creating hardship for your team and you’re kind of blocking that that connection that you’re at actually trying to create, right?

Maura Charles 35:02
I think so. And I think, you know, one of the companies that I worked at before I went out on my own was really good at kind of doing a mix of those things, right? So they would sometimes do something at night, but they often tried to do team building things during the work day, so that people didn’t feel left out. And they didn’t always, you know, they didn’t always involve alcohol. So if, you know, if you were a non drinker, you didn’t feel you didn’t feel pressured to, to, you know, be participating in something that made you uncomfortable, or even just to be, you know, to be present for any of that. But I think it’s related to that idea of like, the time of day, and like all those kinds of things, I think there’s also just this idea of the way that you hire when you’re hiring this. So they all have this kind of psychological safety and like this team, diversity and the kind of accepting of all those things. And so that leads to psychological safety kind of starts when you’re hiring. And so, it really, you know, I hear a lot of people say, you know, I didn’t get to hire this team. And now I’m trying to figure out how to make it, you know, how to make them all work better together. And that’s a lot harder to do, obviously, than if you can start from the beginning and build a balance as you go. And the kind of biases that come up when you’re interviewing people, you know, we’ve all heard that there’s all these studies that say that a lot of tech jobs in particular, are really the way they’re written is very gendered, right? So there’s, like, we’re looking for a rockstar we’re looking for, you know, somebody who can just use all those terms that are very kind.

Lauren Conaway 36:45
Because that’s like, 90% of my consulting work, like, tech companies reach out to me and be like, hey, Lauren, how can women not apply for jobs? And I’m like, Are you really ready for that answer?

Maura Charles 36:55
Because the analysis, unbelievable, right, like the word the word. And so a lot of times they don’t even realize they’re doing it. And you know, sometimes I’ll see, you know, I’ll even see like, the icons that they’re using in a presentation to represent, you know, a specific role. And you’re like, Oh, God, do you not even realize that you just put a bunch of like, male icons on that, and some female icons on like marketing, one of the first things that I always look at is the website, because most of the websites like the, the designers are pulling stock photos.

Lauren Conaway 37:18
And I’m just like, hey, so are you aware that like 95% of the people depicted on your website are dudes that could see him on I know that that’s not your intent. But that could certainly seem unwelcoming to someone who was not a dude.

Maura Charles 37:40
And I hear and I talk to women all the time in my consulting who say that, like they’re, you know, they were hired, and somebody told them after they got hired that they were a diversity hire. And you’re like, what?

Lauren Conaway 37:51
Yeah, yeah. Oh, man.

Maura Charles 37:55
But I do think it’s important to think about that stuff. As you’re forming a team, whether you’re new to a company, or if you’re a founder, thinking about like, what are those? You know, going back to what we were talking about? What about values? Like, what are your values? Like? Do you want that kind of diversity, because the truth is, like cognitively diverse teams, diverse teams in general, culturally, cognitively, gender, culture, all those different things will make a team perform better. Because you’ll have different points of view kind of baked into the team, it’s a lot harder if you have, you know, 10 people on an agile team who all think the same way. Yeah, you’re not going to be able to get creative, because you’re going to assume you know the answers a lot of the time.

Lauren Conaway 38:39
Well, I mean, you’re, you’re a product person, like, like your product suffers as well, no matter what it is. So really, it’s if people are like, Well, why? Why should I care about diversity? It’s well, because it’s gonna make your business better, it’s gonna make your product better. It’s gonna attract customers. One of the kinds of case studies that I always use is actually very product-driven. But, you know, there’s, there’s a major tech conglomerate, and I’m not going to name them. But, you know, they had some controversy around their AI interfacing. Their AI was having difficulty recognizing people of color, because when they were developing the product, they were using their team, their staff, they were the easiest test subjects. And so all of their test subjects were white. And so their end product was very frustrating for a large portion of their users. It was a huge controversy, like you can I’m sure you can Google it.

Maura Charles 39:33
I remember this. I remember that, and, you know, the product suffered because there was a lack of intentional diversity in its creation.

Lauren Conaway 39:37
It wasn’t baked in.

Maura Charles 39:43
Well, and so what’s happening now, so not to like, go off on a little go on a little tangent, which is that with generative AI, which is this new field, folks are not familiar with it is really about kind of using all kinds of data inputs to it. Do things like generate an image. So you could write a bunch of text to say, like, I want to see a picture of a pink airplane with flowers on it on a green background. And literally, it would just, like, come up, right. And my daughter is having a blast with this. She’s got, we’ve got an app on my phone, and she’s just making crazy images all the time. So there’s a lot of those. And then there’s also text version text ones, where it actually like writes for you, you know, rights and what what you know, so things like even the things that all of our auto-suggests on our phones and, you know, software like Grammarly, and things that will like to help you kind of with predictive text, they’re all biased. And the reason that they’re biased is not just because of the teams that are building them but because the inputs are already biased, right? So if you, you know, I know somebody who is writing a lot about, specifically about this topic and about how the, you know, when you if you write the word CEO, and one of these software’s, it’s all men like, yeah, it’s nothing percent of the time, like, you can’t and so even so it’s misrepresented, because so much of the history of a term may be in one direction. And so we have to think about that, as teams are building new technologies, whether it’s AI or something like, I don’t know, like a home assistant, right, like the way people use your technology is going to be impacted by what you put into it. And so, you know, there’s just so much risk there. And I think there’s a lot of responsibility for companies to have ethics that guide those products, right? So like, one of the questions you hear all the time is, we could build it, but should we? Yeah. And so, yeah, so back to the diversity thing. That’s it. It’s a huge input into that it’s both, both on the team side, and on the, you know, how you’re what kind of data you’re selecting?

Lauren Conaway 41:57
Yeah. Well, so. So, to sum up, and I absolutely cannot believe it, we are actually about to head into the human question. This time has just flown by. I’m kind of. Oh, I know. But I do say. So to sum up, you know, one of the things that we can do to create really, really highly functional teams, healthy teams, is to intentionally create that environment of psychological safety, to support the diversity of thought, diversity of background diversity of circumstance on your within your teams, and then creating an environment where those individuals, those very different divergent individuals can feel heard and supported. Yeah. Obviously, there’s a lot more to it than that, obviously.

Maura Charles 42:41
But yeah, I mean, I think getting the leaders in place that can support that, and that is and setting them up for success and actually make Yeah, I think is another piece.

Lauren Conaway 42:50
Absolutely. The last thing you want to do is bring someone onto your team that checks the box but then sets them up for failure from the outset because you’re not ready to welcome them into your environment. All right. So I got to ask the human question. This is actually one of the more frustrating episodes that I have recorded recently because I wanted to continue the conversation. But the question, I’m going to go back to superheroes, and I’m going to ask. If you could be any superhero, who do you think you’d want to be?

Maura Charles 43:23
Right. Oh, well, that’s easy. That’s Wonder Woman.

Lauren Conaway 43:26
Okay, I was hoping that you weren’t eating. Surprising. Absolutely.

Maura Charles 43:34
No one lasso of truth, friends, Linda Carter.

Lauren Conaway 43:37
Such a badass too. Alright, so there’s this game, and I cannot. It’s kind of like Mortal Kombat. I can’t remember the name of it. But they use Marvel characters, DC versus Marvel. And I’m always Wonder Woman because she kicks total assets.

Maura Charles 43:53
Yeah, I just bought a pair of Wonder Woman sneakers, and they’ve got clear. I’m gonna send you a picture. If they’re relevant.

Lauren Conaway 43:58
I need to see that because I actually have a pair of Wonder Woman Converse. Yeah, wonderful.

Maura Charles 44:03

Lauren Conaway 44:04
I’m doing this. All right. Well, yes. You have to send me that picture. And I’m going to tell our listeners at home. Hey, definitely, check out more on Keep It Human. You know, if you want to elevate your team experience, we definitely want to put the people in front of you that can help you do that. And clearly, Maura is one of those individuals. Thank you so much for taking the time to chat with us today. This is fun.

Maura Charles 44:32
Yeah, this was a lot of fun for me too. Thank you so much.

Lauren Conaway 44:35
Good. Well, I’ll tell you what else is fun. Do you know what else is fun? Having extra free time or even extra time to just devote to the things that you actually like doing. Once again, today’s episode of Startup Hustle was sponsored by Double. Double’s remote executive assistants can help you with everything, from email and calendar organization to expense reporting and database management. That is, the gift of time, my friends, is the best gift. Find your perfect assistant today. Head over to Use code HUSTLE22 to get $300 off. Even easier, click on the link in the show notes. And while you’re there, make sure you hit that subscribe button so you can always be sure to get your daily dose of Startup Hustle. Thanks so much for joining us, friends, and we will catch you on the flip side.