Female Empowerment and Leadership Strategies from Me in This Podcast for Women
I recently discussed how women can break barriers, embrace their full potential, and lead confidently in their personal and professional lives as a guest on the Lead Fearlessly podcast.
Here is the full audio and a transcript of my inspiring conversation with host Katie Winchenbach.
Katie Winchenbach, Host: Hey there, welcome to Lead fearlessly: Strategies of Confident Women Leaders—the podcast that will empower you to unleash your inner strength and embrace leadership with confidence.
I'm your host, Katie Winchenbach, and I'm excited to have you join us as we dive into the experiences of extraordinary women, who’ve shattered glass ceilings and redefined success on their own terms.
Get ready to be motivated, challenged and equipped with the tools and strategies to lead fearlessly in your own life and career.
We are joined today by Lisa M. Masiello. Lisa is an author, an entrepreneur, and she is a champion of women's advancement and their entrepreneurship. Welcome, Lisa. Thank you so much for joining us today.
Lisa M. Masiello: Thank you, Katie. I’m so excited to be with you. Thank you for inviting me.
Host: Of course. So, I'm going to jump right in and have you introduce yourself a little bit to our audience and briefly describe your career journey so far.
Lisa M. Masiello: Well, so, my career journey started in the technology industry. I've been in the tech industry my whole career.
Started out working in and then running corporate marketing departments for some small startup tech companies and some very large technology companies that you would know the names of.
And, you know, all along the way, I had, really I had that entrepreneurial drive and I really wanted to get out there and start my own business. But, you know, throughout my career journey, it wasn't the right time. It wasn't the right time personally or professionally or financially.
And, you know, the tech industry, if you've ever been involved with it, it's very volatile.
You can have some really wonderful, exciting years and you can have some horrible downturns where you get laid off from a company and it's not a fun experience, but I actually like that volatility. I thrive on that.
But you know, over the years companies that I've worked for, they've been acquired or they've dissolved or they've merged with other businesses. So finally, I got to the point, in 2014, I think it was, where I decided this is it. I'm going out on my own. I'm going to start my own business and what's the worst that can happen? If I fail, then I go and I get another job.
But what could be worse than that?
And what was worse than that was getting to the end of my life, at some point, and looking back and saying, “what would have happened if I had tried?” And so not trying was worse to me than failing.
And so I did it. I took the leap and I started my own business and because I had been in the industry a long time, there was a lot of people I knew. And a lot of people came out of the woodwork and said we'd like you to do some work for us.
So ultimately, it has been a great success and I've enjoyed every minute of it. But it really took me a number of years to get up the courage to take that leap and really say what's worse, taking the leap and failing or not trying at all?
And so that's where I am today.
What was your biggest challenge as a business owner? How did you overcome it?
Host: That's wonderful. And I know so many of our listeners are in that spot where they're balancing chasing dreams and making those kinds of changes. So, tell me a little bit about what was the most significant challenge that you faced when going out on your own. And how did you overcome it? Because you obviously did.
Lisa M. Masiello: I did. You know, I was pushed into a corner. As I said, I had been in the industry for a number of years so I knew a lot of people. And so when they found out that I wanted to start my own business, a lot of people came to me initially and said we'd like you to do work for us.
So, I’d say for about the first two years, 2 1/2 years I had a customer base and so I had money coming in. You know, I had bootstrapped to my business. That was my goal. That I would have enough money to initially start and grow my business on my own without seeking any external funding. And so I thought, I have enough money in the bank for probably two to 2 1/2 years to be able to survive. And I had enough customers but, you know, at a certain point you have to go out and you have to get new customers. And, when you start a business, you think you have all your ducks in a row and you think you know everything. And the second day of your business being open, you realize you don't know everything that you thought you knew. And so I was forced to…
You know, I'm very much of an introvert. And so, you know, I don't like going out and asking people for help or for advice or those sorts of things. But I found that that was something I absolutely had to do.
I only had a certain runway of clients and of money. And so eventually I had to sort of suck up my pride and suck up my fear of going out and asking for help. And just do it.
And you would be surprised when you open yourself to that and you ask for help, or you ask for advice, the entrepreneurship community, those men and women who have already started their business and they're already on that path, you know further down that business owner path than you are, they are so open and so helpful to sharing their insights and their knowledge and their resources with those of us who were not as far down that road as they were. And so that's really what I learned, that if you get out there and you open yourself and you become a bit more vulnerable as a business owner, there are so many people out there willing and waiting to help you if you just ask for that help.
Women’s networking
Host: That's wonderful. And I think especially for women who are starting out and who want to be entrepreneurs, finding that network and that group of people is so, so important. So, I really love that you touched on that and that that was a significant part of your journey.
Lisa M. Masiello: Absolutely. Because, you know, so often… I think small business owners in general, but especially us women, you know, we traditionally tend to start jobs that we can do out of our homes.
And so while that's a great opportunity, we're very isolated at times and we run up against problems and we think that we are the only one in the world with this problem. But there are so many other women and other men and women.
Who are new business owners and we all have the same challenges and same problems.
So, if we can find networking communities of other women, they are so willing to share their knowledge and their expertise.
Women and Self-Advocacy
Host: And going back to something you mentioned—the importance of for you putting yourself out there and getting over being a little bit more introverted. I know that women tend to struggle with what we like to call self-promotion or self-advocacy. How did you become comfortable putting yourself out there and soliciting new clients?
Lisa M. Masiello: Oh, you know, like I said, I had... my initial way I overcame that was because I had a specific runway of money and clients and once that was starting to run out, I thought, you know, either this business is going to end or I need to do something.
And the second way you know, as an introvert, one of the great things that I find is a great way to get new business is to speak. Speak at events. Speak at conferences. Put yourself out there as an expert in your industry, in your business and the things that you know, especially if you have had a long career. And now you're going out and you're starting your own business. You know a lot of things that you can share with other people.
My challenge was that I didn't really have a problem with going out and speaking per se, in front of other people. But my feeling was, well, you know, what do I have to share that… these people know what I know and they know more than I know. What could I possibly share with them that would be helpful to them?
And I had been invited to different industry conferences and things to speak and I had always said, “Oh no, I'm too busy. I can't do it right now.” And finally, someone said to me, “Lisa, you have to join me in in this presentation that I'm giving. You have so much experience and so much knowledge. I’d love for you to participate with me.”
And I said, oh, okay, I'll do it.
And we gave our presentation, and you know after the presentation some attendees sometimes come up and they want to chat further about what you've spoken about or their specific business situation.
And that's when it dawned on me.
A couple of people came up to me and said your presentation was so wonderful. Thank you so much for sharing your expertise. There were so many different things that I didn't know. You provided such valuable information. And that's when the light turned on for me. I thought, you know, again, people are at different places on their journey, whether it's their career journey, their business ownership journey, their experience, whatever it might be. And so me sharing the information I have, while I may think everybody knows it, not everybody knows it. And so speaking was another way that I got out there and was able to share what I know, help other people and then, besides that, gain business from that as well.
Host: That's a great tip, and that's actually a tip I’m surprised I haven't really heard before, getting out there and finding those speaking engagements, and I think that's a really creative way to play into your strengths. And turn business development into something a little bit different.
Lisa M. Masiello: Absolutely. Because first of all, you're educating. You're not selling. And that's so important. You're establishing credibility for your business and for yourself. And so someone who sees you at a presentation—they want to do business with you. They say, “Well, she knows what she's talking about. And I'm going to do business with her.”
Building leadership in a male dominated industry
Host: Let's pivot a little back to your career in tech, which I think not only can be a little volatile, but also is a bit of a male dominated industry. How did you navigate, you know, the challenges of being a woman in that field and being able to build up your leadership?
Lisa M. Masiello: Well, it’s interesting. It wasn't really a challenge for me until I got into more senior management positions. You know, initially when I was a much more junior marketing professional, you know people in different departments, and the men, the engineers that I worked with and things like that, they would say, “Oh, Lisa's wonderful. We love working with her. She takes our technical messaging and our technical products and she makes them really easy for people to understand. And she's great to work with.”
But then when I got up into the more senior management positions, I did come up against some men who felt that I was going to take their position. I was a threat to them. I was competition. And so one way I got around that was that I am very collaborative. I have never said it's not my job or it's not my department. I have always worked closely with the teams and the heads of other departments, whether it's the engineering department or customer service department or the sales department or the finance department, whatever it might be.
So people really got to know me on a professional level, but also on a on a friendly level.
You know, we got to know each other personally. And so, when there was a person who felt threatened, and they might go and have conversations with their boss or with another person that there's a there's an open position here and I don't think Lisa should have that position because of these things.
Well, those other people that this person is talking to, they already know me. Interacted with me.
I have presented myself to them as opposed to someone else trying to position me to those people.
And so, I think being very collaborative and open to working together with others has positioned me in a good way because I'm presenting myself as opposed to allowing someone else to present me in a way that's not right.
Embracing change in the workplace
Host: And aside from collaboration, which I think is so important for really anybody in the business sense who's looking to advance, what are some of the other qualities or strategies that you feel have really contributed to your success?
Lisa M. Masiello: I think that the biggest one is really the idea of embracing change. Be adaptable in whatever you do, whether you have a staff position or you have a management position. Certainly in a management or leadership position, you must be adaptable and embrace change.
So, if you're an employee, the take away for more of a junior level person is that if you are asked to participate in a new project or take on new responsibilities, you may not like that change at first.
But everything that you experience is something that you can put in your back pocket and you can take it with you and grow with that knowledge. Every piece of knowledge that you gain from something new that you do will help you expand.
Host: I think for a lot of folks, myself included, change can be a little scary.
As you're going through it, you kind of get comfortable where you're at and as you start to pivot, I think it takes a lot of confidence in yourself and in your skills to be able to have that adaptability that you mentioned, Lisa. How have you built that confidence in yourself and what’s some advice you have to women who may be struggling feeling confident in their skills and how they can adapt those.
Lisa M. Masiello: Oh, I didn't always embrace change. Absolutely. And, as I had said before, I'm very much of an introvert. So, when I was early in my career, I didn’t ask a lot of questions. I tried to figure things out on my own because I figure, well, if I ask questions, then I'm going to be seen as not knowing the answer. Not intelligent. If I asked too many questions, maybe I won't get the next position or something like that. And you know what I really realized was that it is WHEN you ask he questions, again when you open yourself up, That's when you learn and you become much more knowledgeable and people see that you have an interest In what you are doing. So if you are put on a new team, new project team or you are asked to take on new responsibilities, ask questions. Don't be afraid to ask those questions so that you can understand. You can learn more quickly. And you can be successful more quickly.
The people who have put you in that position want you to succeed. And so, when I learned finally, that asking questions was not a detriment but a benefit, because I'm actually going to be more successful more quickly, if I do ask those questions, then it became much more easy to embrace change because I was asked to take on more responsibilities, I asked a lot of questions. I understood what I was supposed to do and what was expected of me, and then I moved forward learning new things and enjoying what I was learning and enjoying the new tasks that I was taking on.
Host: I really love that you said that the people who have put you in that position are rooting for your success. Because I think that's something that we forget a lot of times as we're trying to be perfect in a role and not ask those questions.
A rising tide lifts all boats
Lisa M. Masiello: Absolutely. At the end of the day, whether you are two team members in the same department or different people in different departments, you know, I'm sure you've heard the saying, “A rising tide lifts all boats.”
If we work together…you know, I am happy to share with you. You are happy to share with me. We work together and we are successful together. We shouldn't see this as a competition. If we work together and our team is successful then all of the departments are successful and the business is successful and ultimately at the end of the day, that's what you want. If the business isn't successful and the business closes, well, that’s it. We’re all out of a job.
But if we were, if we work together and we share our knowledge, we share our expertise, we help each other, we don't say that's not my job, then everybody benefits.
What one piece of advice would you give your younger self?
Host: It's true. And to close us out, I love to ask this one question to everyone. This is my favorite question. If you could give one piece of advice to your younger self, what would it be?
Lisa M. Masiello: It would probably be about, you know, asking questions. Open yourself to vulnerability. It’s not as bad out there as you think it is. And people are there to help you. As I said, they want you to succeed and they will help you. You just have to ask for it.
Host: I love that. Thank you so much Lisa, for joining us today.
Lisa M. Masiello: Thank you, Katie. It was a pleasure.
Host: To learn more about Lisa, visit her website lisamasiello.com, and you can find her book, Trade Show 411: The Essential Guide to Exhibiting Like a Pro, on Amazon and on our free book list.
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