No Apologies: On Going All In As A Female Founder With Leadership Coach Laura Westman

Leadership Coach Laura Westman

As part of our mission to support founder development throughout every stage of the startup journey, FounderTherapy recognizes that women encounter distinct challenges in building their businesses. When leadership coach Laura Westman, PCC, approached us about using FounderTherapy as a backdrop for her monthly meetup dedicated to helping women overcome these obstacles, we eagerly signed up to be part of it.

Creative Female Founders helps women build powerful businesses, express authentic leadership, and make glass ceilings a thing of the past. The group’s events focus on forging powerful bonds between founders, creating an empowering peer network, and honing and developing the creative leadership skills within each member.

Westman, an accomplished coach and self-professed “creative weirdo,” is both a coach in private practice and a trainer of coaching and ontological leadership at Accomplishment Coaching. Through her background as an artist and an improv teacher, she cultivates an approach that involves harnessing the power of humor and power together, leading to breakthroughs in interpersonal dynamics and making even the toughest conversations seem simple.

Inspired by the group’s purpose, FounderTherapy talked to Westman about the unique challenges female founders face and discussed what they can do to overcome them.

Interview by Whitney Meers

FounderTherapy: Let’s start by addressing why it’s so necessary to build the CFF community in the first place. What are the unique challenges female founders face relative to their male peers?

Laura Westman: One of the biggest challenges is that we’re always working on a higher gradient. Most of our society is actually conditioned to believe men more, and men also have less to prove. I’ve been reading a lot about Hillary Clinton’s new book that just came out, and one of the things I’ve been acutely aware of is how women leaders have a really bizarre standard to meet. The expectation is that they will be able to create sufficient relationships with the people that they lead, and be authentic, and be engaging, and be there 100%, and bring their power, which is really challenging. I’ve been in ontological leadership for five years now, and I still have conversations with my mentors about “How do I bring my love?” and “How do I bring my power?” It’s not a natural thing that people always know how to do, and it’s not a challenge that men face.

Every once in awhile, someone will criticize a male leader for not being engaging enough. But for the most part, the challenges that women founders and women leaders tend to face are mostly about how people interpret everything except for their power and their talent. How do they present? How engaging are they? Do people believe them and want to trust them? These are all relationship questions that most men actually don’t encounter.

FT: To dig a little bit deeper with that, how are these leadership challenges compounded when a female founder identifies as LGBTQ+ or PoC or some other group with less visibility in the tech industry?

LW: I can’t speak on behalf of leaders of color and other groups, but the coaching term for this would be “the gradient.” Because what people the typical white, male audience are used to and typically engage with and have no questions about is whatever they also see in themselves. So white women face a very specific type of listening where they have a certain element where they have to prove themselves and they have to behave a certain way. But women of color, gender nonconforming people, and anyone who presents as anything other than straight is going to have similar challenges.

The gradient for persons of color, gender nonconforming individuals, or LGBTQ leaders can be even higher. Our society requires an unhealthy and unjust amount of work in order for them to be “heard.” I coach many of these people and the hoops they have to jump through for a “normal” level of respect and airtime given to a white male is appalling.

Because they’re different than the white, male audience, these people often have to compensate or overcompensate. One of the things we always say is that’s “in your space.” If I, for example, walk in your space and I’m white, and I’m female, and I’m a lot younger than most of the people in any workplace that I’m entering if I think that’s a problem, or if I think they’re going to have ideas about me or something that I have to overcome, it’s going to be in my space and I’m going to have to respond accordingly.

A lot of training and leadership is actually supporting leaders to get all of that stuff out of their way. So if it’s not actually in their space, other people are less likely to care. I’m not saying that solves all the problems, because it really doesn’t, but that’s one thing we can actually be responsible for shifting.

FT: So it becomes an internal focus, which actually leads into my next question. Internally and externally, what are the main things that are holding women leaders back from reaching their full potential?

LW: At the last Creative Female Founders meetup, we had a smattering of people across the spectrum of founding their companies and moving their ideas forward and being leaders in their companies. One of the common problems that came up in the course of the discussion was this idea of “How do I stand for what I think is the best and what I know, and also keep people happy?” That’s a compelling need.

If we think about traditional masculine and feminine energy, masculine energy tends to say, “Here’s the truth. Here’s the knowledge. Here’s what we know. Therefore, this is what we will do.” Feminine energy is much more about consensus-building, keeping people happy, and from there creating the best result. I think one of the main questions from women leaders and women founders is “How do I get guidance from the people I need and also bring everything I know to be right?”

We have these external forces we just talked about some of them like other people’s perceptions, how other people are going to be toward us, what it is that we have to actually speak toward when we’re working with other people, and understanding the filter that other people are going to have. Those are some of the external things people have to fight against. But internally, it’s all about how you’re willing to see yourself.

There are some people who refer to themselves innately in terms of, “Well, I have a great vision, and I trust that I’m going to get there.” They have no drama internally about how it’s going to go externally. And then we have people like I was just describing where there’s this tension with being able to be powerful but also this innate need to consensus build or people please or whatever. It’s a common thing, especially among women. But it can also create a cage, if you will, of what we think we can and can’t do. We create these barriers that aren’t real. They’re completely made up. But that’s often a way we limit our own power.

FT: The tech industry is a notoriously rough space for women founders in particular. Only 17% of startup founders are women, for some of the reasons we just talked about but also some broader reasons as well. What do you do in that situation when you’re up against people who just don’t believe you have what it takes to run a company and scale it to a multi-million dollar business?

LW: There are a lot of different answers to that question. I know for me as a leadership coach, the answer would actually depend a lot on what’s authentic to the person. That being said, it’s such an interesting question because I remember when I was a brand new coach, I was living in D.C. and doing a lot of networking. Internally, I was in some space of needing to prove that I was good enough and that I was able to run my own business. There was a lot of hungry energy on my part. I felt like I could energetically pick up on people who didn’t totally buy into what I was doing. And I would get drawn to that, if that makes sense. I would kind of pick up on it and say, “Oh, that’s a good place for me to prove myself! If I can win that person over, I can do anything!”

Some of us actually have that innate need that we tend to operate from. But in the industry, what you’re describing is a real experience for many people. And it matters. You need people to believe in you so you get funding to build your product and build your company. One of the most important things that I would tell anybody is that you have to not care. You have to be completely on board with your own idea and your own vision, and be willing to do whatever you need to do to get the team that you need. There’s always going to be somebody who doesn’t believe that you can.

But, that being said, one of the most powerful tools that anybody has as the leader of a company or as a new founder is the ability to learn and grow. Your commitment to what you’re doing has to outweigh your ego conversation about your own limitations and your own abilities. I also think that, if you come back to this idea of masculine energy and feminine energy, in that situation, masculine energy would be like, “I don’t care. I’ll just go find someone else.” Feminine energy would likely take it to heart, make it mean something, and so on. The way I see it is, there’s always going to be somebody that says no or doesn’t believe it, and I would say, don’t make that mean anything.

It’s a little tough, because usually that kind of feedback or that kind of a “no” is from a masculine state. A lot of the conflict I’ve observed, especially in tech, is the difference in communication and how people communicate. Often, people are in the same conversation but they’ll come at it from a masculine energy and a feminine energy, and they don’t mesh. In the business world, it’s a lot of masculine energy and a lot of very direct communication. In more feminine energy, there’re more warmth and more relationship. But that also makes us susceptible to reading into what other people are communicating or saying when there’s usually not anything to read into.

FT: You started to talk about this a little bit, but you yourself are a female founder. I wanted to know how your experiences have shaped your thoughts about female leadership over the past five years.

LW: I shared a minute ago about where I started, which was from a place of a lot of fear. Excitement and possibility, but also a ton of fear… “Can I actually do it?” and “Will anybody let me?” which gave itself to a lot of feeling the need to prove myself. From that place, I was building my business with a lot of, “Well, I’ll see if I can!” and secretly holding a really high bar.

But what’s really changed and a lot of what I’ve learned is that I thought it was about people outside of me saying yes to what I’m up to. And what actually makes the difference is my holding myself as someone who can run her own business. With that choice, instead of having it be about everything outside of me saying yes to me, and showing me, “Yes, you can run your own business, Laura!” it actually became about, “How would I approach this if this were my own business? As a businesswoman, how would I be in this conversation? How would I get hired by this person?” It’s a really different way to think about what you’re up to.

FT: So it’s no longer about, “Do these people think I can do it?” It’s now, internally, “I’m going to do this regardless, but I have to do it my way.”

LW: Exactly. And then all of the discovery and experimentation and beautiful failure that comes with that conversation.

FT: Do you think that’s something that’s more common for female founders to experience? Or is that a challenge a lot of founders face across the spectrum?

LW: It’s a funny question, because I think there are many answers to it. I’m not going to talk about the Fyre Festival, but I think one of the things that women face that men often don’t is that question about, “Can I?” and waiting for confirmation from the world. I don’t think it’s a personality flaw. I think it’s just innately how we tend to operate. It’s part of that feminine energy of needing consensus and needing to feel creatively safe to do what it is that we want to do. And, from that place of security, safety and confirmation, we can generate anything. There’s so much creative potential.

Masculine energy, male leadership styles, and men in general tend to be less freaked out about the question of “Can I?” and more interested in “How do I?”

FT: You’ve sort of touched on this, but I wanted to make it very, very clear. What should women who are founders or even women who are interested in becoming leaders within their organizations… what are the core things that they should focus on improving if they’re trying to take it to the next level and raise the bar on what it is they’re trying to accomplish?

LW: Such a great question. The first place I would have people look is, what’s their vision? For themselves, for their company, where do they actually want to go? And from there, I would actually want to ask, so what’s your relationship to that vision? Does it feel close? Does it feel attainable? Does it feel like it would be a stretch? It’s so easy for people to say, “This is the thing that I want!” without actually putting anything under it. It’s so much more comfortable to talk about the stuff we want without actually doing anything about it. For many of us, when looking at what we really want, especially if it’s like, moving up to CEO, something that’s like a quantum leap from where we are, it can be really confronting to think about, “Well, what would it be like for me to actually get there?” So I’d want to know what their relationship is to it.

I have a new client who’s a screenwriter, and he has this thing where he’s like, “Here’s all the stuff I want to produce. And here are all the reasons why I don’t.” A pretty normal coaching conversation. What do you want? What’s in the way? And he revealed that he has a lot of judgment about people who do the thing he does.

You can hear innately that doesn’t work. Or it could work, but it’s going to be really painful. To be up to something that you’re totally judging the entire way. That’s just extra energy. And then you also kind of hate what you come up with a little bit. So it’s just total energy blocks. There’s no way to actually create it.

I say this because the last piece of the puzzle, if part one is the vision and the second part is how connected are you to this vision, I would also challenge women to be willing to fall completely in love with the thing that they’re up to.

No apologies. No freaking out about what people think. Everything else is able to fall to the wayside. Because when you can actually be 100% in, for upward movement or wherever it is that you think you’re going, it creates so much possibility for things to actually work out for you. When your apology is gone, that’s when the magic happens.

FT: What’s the one strategy that female founders should apply to their lives?

LW: My first instinct is to say that hiring a coach is the best thing you can do, because all of that will be tailored specifically to you.

I think in terms of strategies, one of the most useful things that anybody could do is to practice being more interested in what they’re building and less interested in what people are thinking. Really get connected to the strengths that you have and start trusting those a lot more. I know that for my clients, we’ve designed their leadership teams, or if they run a company or an agency, we’ve designed what they’re up to in their companies, based on their highest and best. What support would they need under that? If you can actually design structures around you that pull forward your highest and best, you start showing up that way.

FT: Last question. What can male allies also do to support women leaders?

LW: They can listen. Listen, listen, listen, listen. That’s probably the most important one.

This interview has been edited for clarity.

Are you an NYC-based female founder? Join us on Tuesday, Oct. 2, at FounderTherapy for the next Creative Female Founders. This month’s meetup will help women leaders build the vision that will allow them anchor their leadership. More details here.

This story originally appeared on Medium.

Whitney Meers is Director of Marketing at FounderTherapy. With a specialization in digital strategy, she has been credited with adding millions of dollars to clients’ and employers’ bottom lines. Whitney has contributed to marketing projects for NBC Universal, Samsung, HuffPost, ID Channel, Nerdist and more. Follow her on Twitter at @whitneymeers.