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Ep. 45: Building Confidence in Female Leadership with Ashley Connell

Being a woman comes with its own challenges, right? Can I get an amen on that? But then add in the weight of having to choose between yourself and your career and your calling and your friends and your family and your [insert whatever in the blank]. There is such a higher calling for women in leadership and the balance that comes with it.

So I’m so excited today to have Ashley Connell. She is the CEO and founder of Prowess Project and has been an unstoppable tech marketer and entrepreneur in both Austin and in London for the last 13 years. Part fearless entrepreneur, part fearless women’s advocate, and she is changing the lives of frustrated managers, women seeking meaningful work, and doing all that she can to close the gender gap. And when she’s not changing the world, she loves yoga, her dogs, and spaghetti and meatballs.

Ashley, welcome to The Gutsy Podcast.

Prowess project

Laura: So Prowess Project, I got on your website and did a little bit of research, but tell me what is that?

Ashley: Yes, yes. So Prowess Project, we help companies find expert talent. The way we do that is we vet and certify accomplished women who took a pause in their career, whether that’s for caretaking a parent or children or just wanting to go from in-person to remote. And then we match them up with businesses based on not only skill and expertise but also emotional intelligence. So behavior type and communication style that then provides the most natural fit possible, all for a lower cost for the company.

how it started

Laura: So take me back to kind of the beginning. How did this come about? What was your calling to start the Prowess Project?

Ashley: So calling to start the Prowess Project. Well, as you said in my intro, I have been a tech marketer basically married to my career for the past 13 years. And I realized before I even graduated college, the anxiety that I was having about how I was going to choose between career and being a mom. Rewind 13 years ago, that conversation was not happening at all. And so I realized 10 years into this that, oh my gosh, there is this weight that has been on me for this past 10 years of, again, where my life is going to go.

So I started a consultancy with two other men and one of our partners, he had his wife come in and help us with some of our operations. So I got to know her. Her name is Leah. She’s phenomenal. She has two degrees in counseling. She did sales for merch, taught herself bookkeeping, taught herself graphic design, and took off three years to raise her children. She was in her third year of just trying to get back into the workforce when she started working with us.

Her and I were chatting and she was like, Ashley, I can’t even get a free internship because I had this three-year gap on my resume and that blew my mind. It was like, this is ridiculous. So me being kind of the nerd that I am, I jumped online to see if there was any data behind this to back it up. Sure enough, according to Harvard Business Review, if a woman is out of the workforce for just three years, she loses 37% of her total compensation power for the rest of her life.

Laura: For the rest of her life. Really? Because, okay, so I’m thinking a resume slides across the desk and they see that through your gap. So you’re penalized forever now.

Ashley: Yes, you’re, well, you’re penalized because you can’t get back in and if you do get back in, you’re not even close to where you are. And then there’s all the unconscious bias that comes with being a mom and taking that time off.

Laura: Wow. Unbelievable. So therein lies the beginning, snowball effect of what should I do? Do I put myself first? So I’d do my family first. Do I have to sacrifice this? I mean it gets really, really stressful for women to make a decision on what to do with their life and their career.

Ashley: Oh my God. Yeah, absolutely. And so when I started talking to Leah about this more and more, her and I were like, we have to do something about this. And I look at starting the Prowess Project as solving my future problem. I don’t have children yet, but I don’t want to be in that situation and I don’t want any woman to be in that situation. So we’re doing something about it.

how it helps

Laura: So tell me a little bit about the women that are working with you. Who are you hiring and how are you helping them get back into the workforce?

Ashley: Yes, so we started in February of this year, so we are pretty new. However, I will say that our job pool, we have a waitlist right now of 40 to get in. I put out one free Facebook post on, Hey, this is what we’re doing. We are looking for talented women who are educated, experienced, took time off the workforce, and want to get back in. I got 60 applicants in two days.

So definitely there is a demand. This problem is a huge one. There are a ton of women who have this. And so before we really kicked off, we did a ton of interviews. I would say hundreds if not thousands of interviews with moms who were in this position. And they said that a lot of the solutions that were out there right now, there are some of them and most of them really are really great, however, they weren’t solving the full problem for them.

And what I mean by that is, from what I’m hearing, when a woman takes time off one of her biggest barriers to reentry into the workforce is confidence. So she can go to one place for a community to talk to other like-minded moms. She has to go somewhere else for certification or resources or education to get back up to speed. And then she has to go somewhere else to get matched up with jobs that she feels empowered and works within her schedule. And so we were like, wow, three different places and you’re kind of daisy-chaining these all together in hopes that it all works out. Why is there not just one place where you can get certification, community, and a job pool all at once?

Laura: I love this concept so much. When you’re like, okay, I’ve got the guts right now, I’m going to get back out there and then you’re faced with all these different avenues. You have to go here, you have to go there, and then you have to re-explain your situation four, five, six different times. So I love that you’ve brought it all under one roof.

So you’re not only helping to get these women back into the workforce and actually obtain work, but you’re helping them with their mindset as well. Is that correct?

Ashley: 100%. So what we do, we have a certification that our talent pool applies for. If they get into the certification there’s then a 16-hour course, I would say 50% of that is competence building. It is goal setting. It is figuring out exactly what your boundaries are, what you will and will not compromise when you go back into the workforce. It also helps you figure out what are my skills, what drains my energy, and what compounds it. And so we spent a ton of time on that. So, our talent pool has a really great and sturdy foundation.

So then on top of that, we can build the skills that are super, super teachable. Like what is the latest technology? What is project management? What are some strategies there? It’s so important to have that foundation before you go into learning the fundamentals if you will.


Laura: What are some commonalities between these ladies that you’re seeing from a confidence standpoint? And this could be just women in general as well, but I’m thinking of working women. They have ambition, they have a drive, they want to do things, but what are some common confidence challenges that you’re working through?

Ashley: So, number one I would say is imposter syndrome. And I would be lying if I didn’t admit to a team earlier today that I was having imposter syndrome. So, it’s definitely a work in progress. But we see that a lot. And it’s interesting because these women assume that everyone who is in the workforce are these experts and masterminds and it’s almost like they think their brain thinks differently — and that’s not the case. Everyone’s just normal kind of faking it until you get to where you want to be.

And one thing that’s really interesting that we did a bit of a study on is confidence, and specifically the difference between men and women with confidence. And we’ve found that there is a different definition for a man and a woman for the word. For a male, it is typically fake it till you make it. And for a woman, it is typically I have all the available information to make an informed decision.

So if you take a step back from there and like, okay, here are the two definitions and you’re going into the workplace and you’re sitting in a meeting, it is not surprising that it’s typically the males who are brainstorming and shooting out answers whether they’re right or wrong, it doesn’t matter. They’re constantly giving input. Whereas typically it’s the woman in the room who may be a bit quieter.

It may seem overlooked really because she’s just gathering all the information then wants to process in, then give her opinion. And so what we’ve seen with that is because of that different dynamic, typically men are getting promoted quicker. And not only quicker but at a more rapid pace because they’re seen as the extrovert with all the ideas. Whereas that may not be the case.

Laura: Interesting. Is there any like science or even just human reason as to why that is? Or just how about like human behaviors. Like why, as women, why do you think we do that and hold back?

Ashley: That’s a good question. I think it goes back to the imposter syndrome. I think it also goes back to the idea that the workplace was built by men for men. And not that they wanted to exclude women, it’s just if you think about the top qualities that are usually associated with being a leader, they’re very masculine traits.

Think about being assertive, being aggressive. A lot of times those are rewarded whereas being quiet or being empathetic, which sometimes seems soft, is not always rewarded.

I’m really excited to see that there is this shift in corporate America moving from this idea that aggression is the best to really focusing on empathy and emotional intelligence. We’ve seen that 70% of Fortune 500 companies are investing in emotional intelligence training. So it’s definitely that shift to the more feminine energy, which I’m so glad to see.

the bitch stigma

Laura: What we’re talking about primarily today is the need for women in leadership. And I think that you hit something on the head a minute ago. Typically, when a man is assertive and states what he wants, it’s rewarded. But then here we come and we’re a bitch, we’re full of ourselves, we’re arrogant. Like who does she think she is? She’s on a power trip or she’s on her high horse.

I’m saying a handful of things that maybe I’ve heard a time or two.

Ashley: Amen, sister. Amen.

Laura: That doesn’t make it any easier when you’re thinking, okay, well I really have something to give here. I really have something to contribute and I’m fairly intelligent in this area. I want to speak up. And then those little voices in the back of our heads are like, mm girl, you’re going to be too much. They’re going to think something of you.

Ashley: Yes. And I think that there is real power in voicing that and having women together talk to each other about those voices and talk to each other about how they’re doing this balancing act between being assertive and being a bitch. But then also bringing males into the conversation.

I feel like if they had a better understanding of all of the tiptoeing that’s going on in our heads, just when we go to a simple status meeting, they would then have a lot more empathy for us.

Laura: I agree with that. I say this all the time, everything would be just so much easier if we just talked more. Like if we just got out of our heads because when it comes out of your mouth, something can be done with it. But when it lands in between your ears and it’s only bouncing around in between your head, that can become a whole galaxy of its own — especially as a woman.

imposter syndrome

Laura: So I can see how also the impostor syndrome really plays in and I’ve bumped into that wall a handful of times. I can see how that would stall a lot of women from either reentering the workforce or going after something that they’re looking for. You’re intimidated by other women just as much as you are everything that’s going on around you.

Ashley: 100% and we have got to get out of this scarcity mentality. And this is for women specifically. There is an abundance of leadership roles for women, especially right now where we have this spotlight on it where we want to have more women. We know that more diversity in the workforce equals more productivity, which equals more profitability. That has been proven with data. So let’s bring up our fellow female leaders with us.

And I think that is so important and I think we now have that opportunity to do so.

Laura: Agreed. I absolutely agree. So when you’re working with women on imposter syndrome, what are some tips and tricks you give them to help overcome that?

Ashley: Great question. First and foremost, I feel like that is being vulnerable. And what I mean by that is naming it — naming what it is you feel insecure about. And one thing that I do all the time, I have a little sister, she is 12 years younger than me, and I do a bit of role-playing. And I say, what if Avery (that’s her name), what if Avery came to me with this concern that she wasn’t good enough? What would I tell her? And then I’m like, I would say all these amazing things about her and why she’s so qualified in that. So silly. Why am I not saying that to myself?

Laura: It’s true. We are our own worst enemy and we will throw ourselves under the bus quicker than anybody else.

Ashley: Yes. And I see it time and time again and I do it time and time again. It’s not like I have all the answers. I mean, it’s definitely an ongoing, I won’t call it a struggle, but an ongoing process to really come out of being in this imposter syndrome kind of shitstorm drought storm. Like we have to on purpose, get out of it and shift our thinking.

confidence challenges

Laura: What other confidence challenges are you seeing patterns in these women that are coming to you?

Ashley: So, one that I find fascinating is I will have women who come to me who have two or three degrees, worked in the workforce for 10 15 years, have a humongous network, and let’s say that they were out for a year, year and a half. They’ll come to me and they’re like, Ashley, I have absolutely no skills. No one will want to hire me. It blows my mind.

I look at them and I am like, that is bullshit. If anything, you have been project managing a family of five or six for the past year, year and a half on top of all of the skills that you have been harnessing when you were in the workforce. And when they sit and think about it like that, they’re like, Oh yeah, I guess you’re right. I was, you know, running the family budget and Oh yeah, I guess I was volunteering and helping my daughter’s school fundraiser. I guess that kind of is like sales.

And so we sit down and have this conversation about how all of these skills that were done recently easily transfer over into the quote-unquote workplace.

emotional intelligence

Laura: So I love the phrase emotional intelligence. I want to dig into that a little bit, if you don’t mind. What does that mean to you and how are you working with women through this?

Ashley: So to me, emotional intelligence is being self-aware of the people in situation around you. To me it means noticing other people’s reactions, what they say, what they don’t say, and what is that really telling us. And I think that having that, harnessing that, and using that is so incredibly valuable; especially when working with a team.

And let’s be honest, when you’re at work, 99% of the time you’re working with other people or you’re working with a team. And so it is so critical to have this emotional intelligence. And I think a lot of women do this naturally. We’ve actually found that women are 45% more likely to show emotional intelligence in the workforce on a consistent basis than men. So we know that women have these innate skills and traits.

And so what we spend a lot of time doing with Prowess Project is showing these women how valuable those traits are and sifting them out and making sure that they know to use them in the workplace.

women supporting women

Laura: I think there’s also power in strong female leaders supporting other strong female leaders because it can get really competitive very quickly. But when you bring powerful women together, really incredible things can happen.

So I’m curious how that’s played into, any of the experiences you’ve had about women supporting women?

Ashley: Yes, I have had great experiences with this. It has blown my mind how supportive my fellow female leaders have been.

For example, and this is one I think you know too, there are companies that do things very similar to what Prowess Project does. I was worried coming into the market that a lot of these other companies would see us as competitors. I could not be more wrong. I have had women leaders of these companies welcome me with open arms, getting on phone calls with me, and walking me through do’s and don’ts. Don’t make this mistake that I did and heads up and be aware, but definitely do this.

I’m just so grateful for that and I was not expecting it. And so now I want to return that favor.

I mean, you could say that a recruiter could be a competitor of ours. And my answer to that is absolutely not — that’s our collaborator. This problem that we’re solving of gender equality and getting women back into the workforce and then on the company side of finding expert fractional talent, those are such huge problems. It’s going to take so many of us to solve them. I mean, we’re all on one team and I think that’s critical.

everyone can win

Laura: Comparison is the thief of joy, right? We get on the internet, we open up Instagram, and we’re like, Oh crap, somebody’s already doing that. My idea’s stupid. We see one person in one state or three states over doing it and we’re like, well fuck it. That’s it. I’m done. Screw everything that I’ve ever thought in my entire life.

But there’s such magic when people do what they are called to do because not only do they do it really well, but they literally have the opportunity to shift something in the world. So if there’s one of you doing it or 500 of you doing it — you’re all pushing to change something. And I think that’s really beautiful.

Ashley: I do too. And so one thing I didn’t know, becoming an entrepreneur, is you nailed it. We have this business idea and you go onto Google and you check it out and Oh my God, there’s three people already doing that. I almost packed it up and I was like, no, Prowess Project isn’t going to work. Someone else has it.

Then I started talking to other entrepreneurs and their answer to that was actually no, you want competition because that proves that there is a problem out there and that proves that the solution you have in mind is working. And that completely changed my mindset.

And it goes back to kind of what you were saying about this is a big ass world and the flavor that I have — my solution — may be very different than someone else’s. But we have an audience for each. And that’s so, so key.

Laura: That’s exactly what I was just thinking. Like literally just pulled the words out of my mouth. Yeah, there may be other people doing what you do in your industry, but no one will ever do it the way you do it because you’re the only you.

If you think, McDonald’s launched the hamburger, you know, a hundred years ago or however long that’s been. If every restaurant in America was like, wow, McDonald’s did the hamburger. So now it’s off the table. People innovate hamburgers and you can go anywhere and there’s artisan hamburgers and there’s organic hamburgers. I mean you can have whatever you want, but it’s serving different markets across the world. And that’s the beautiful thing.

the choice to be an entrepreneur

Ashley: Deciding that you’re going to be an entrepreneur is fucking scary.

Laura: It’s pretty awful.

Ashley: Oh, hey, I’m going to give up this really decent paying job that I know I’m going to get a paycheck from every two weeks to put myself out there, make $0, and hope that my solution is what other people want. Like what is scarier than that? I really don’t know. And I saw it in the early days. I felt like the universe wouldn’t let me give up on this idea.

Laura: It will continue to present itself until you do something with it. Until you literally like check yourself out and say no I’m not. And then you shut it down or you start feeding into it. Like one of the two will happen.

And then I’m even going to throw out there that even when you say no, unless it’s like coming from the depths of your soul, it’s still kind of an open window in a winter house. Like there’s still a little bit of a breeze that comes in. So it will get louder and it will talk to you more and it will present itself and all of a sudden you’re going to start hearing.

It will get louder and stronger until you do something with it and until then — it gets painful. Like it wants to like hit you in the face. You’re like, I just want to love you, but why do you want to hurt me?

Ashley: What I find is really interesting, too, is when I’m having one of those really bad days and I feel like, Oh my God, I got to give this up. Oh my God, is this stupid? I’m never going to make any money out of it. Or all of these crazy things. Remember that imposter syndrome? Yeah. All of that swirling around in my head. I feel like every time the universe swoops in and gives me just a little bit of hope. Just like a little wink that, Oh, you’re doing the right thing, you’re doing what you’re supposed to do.

And I swear that little wink is what makes me wake up the next day. And I was like, all right, 16-hour workday. Yup, let’s do it. Okay. Haven’t seen my friends in quite a while. My poor husband who’s that? But Hey, let’s do this again.

career or children

Laura: There’s one last part. I love this concept and this phrase that you have and you call it the mommy penalty. So as women, we’re often pressured to choose between our careers and our children. So tell me about the ladies that are coming to you are facing that battle because that can be very real and very deep.

Ashley: Yes. We talk about this a lot and the statistic that I brought up at the beginning, how you lose 37% of your compensation power — that is the mommy penalty in a nutshell. It’s also the unconscious bias that you get at work where, Oh, she’s a mom now. She’s not going to be as dedicated. She’s not going to stay long hours. She’s distracted because there’s all these other things she’s dealing with at home.

We don’t realize that we’re taking those biases and making very important decisions because of it. And that has a huge part in the gender gap because again, we’re like, Oh she’s a mom of three, she has her hands full. She probably can’t take on this promotion. She probably doesn’t even want it. Like I kind of feel bad even asking her to take on this project. And so we hear that a lot from really all sides cause we do a lot of conversations about gender equality in the workforce because we want to help our talent pool understand what they’re getting their themselves into.

I think instead of hiding the fact that you’re a mom, be proud of it. I think again, it’s going into naming it. I think there is a huge power in setting those boundaries. Maybe you have to leave every day at 4:30 because you have to pick up your kids. That’s a boundary. So if you have to leave at 4:30 to pick up your child, stay firm on that boundary because it shows people you respect yourself and your family and that you’re going to be 110% dedicated while you’re at work. Because you have a finite amount of time to get work done and so you’re going to be super efficient in it.

It is very interesting how many people will respect you more because you stay true to those boundaries.

What Does Gutsy Mean to You?

Ashley: This is such a great question. Gutsy means to me that I’m going to put myself in uncomfortable positions and scenarios and be the voice for other women who can’t.

connect with ashley

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