How Women Can Navigate Roadblocks to Leadership in Tech: Pitfalls and Practical Tips

Lisa Frusztajer
Investor in Residence
Automatic Summary

Breaking Through Leadership and Technology Roadblocks: Empowering Women in the Tech Industry

Hi there, this is Lisa Frier, an investor in residence at the Capital Network and a certified coach addressing the persistent challenges faced by women in the technology industry.

The Persistent Problems and Practical Solutions

Working in technology brings vast opportunities, and while my career has spanned across various companies, both hard and software, the journey for women to leadership roles has remained fraught with obstacles—a long-standing issue deserving more than just recognition.

Solutions Beyond the Norm

Renowned solutions from authoritative studies like McKinsey offer steps such as mentorship, accelerated promotions, crafting supportive networking groups and equitable training access. Nevertheless, the scenario hasn't radically changed over the years. So, what can be done differently? Here's where our focus shifts to mental preparedness—a profound skill that's seldom taught yet quintessential for resilience, self-deserving belief, and curiosity to discover the mental barriers impeding our progress.

Understanding the 'Big Three' Roadblocks

  1. Impostor Phenomenon: Despite achievements, this crippling self-doubt leaves you feeling fraudulent and unworthy. It's a relentless cycle, magnifying each imperfection into evidence of your inadequacies.
  2. People Pleasing: Rooted in the fear of disapproval, this tendency leads to accommodating others' needs above your own, often sparking resentment from misalignment with personal desires.
  3. Executive Presence: This elusive quality combines gravitas, communication skills, and appearance. It's frequently cited as a promotional barrier, particularly for women and minorities who aren't adequately coached on cultivating it.

How These Roadblocks Manifest in Tech Companies

The rapid pace and ever-evolving structure of tech companies demand constant self-reinvention and the establishment of robust networks, which can be arduous without proper validation mechanisms. Moreover, tech's combative environment and the elusive nature of meritocracy compound the problem, creating a gender double bind where women often face criticism irrespective of their approach.

Making Real Change: Your Formula for Success

To enact meaningful and permanent change, we must first observe and understand our tendencies before envisioning a different future. Here lies your actionable change formula:

  • Observe: Pay close attention next time you feel hesitant or compelled to prove yourself yet again. Awareness is the first step.
  • Set Goals: Pursuing aims, whether successfully or not, empowers you and reinforces the self-confidence necessary to define what you truly desire.
  • Redefine Normal: Accept that feelings of inadequacy are common responses to your environment. Recognizing that can minimize those feelings' impact, helping you grow.

Conclusion: Embrace Challenges and Engage in Self-Discovery

In the tech world, where quick transitions and high expectations are commonplace, it's crucial to realize that your growth lies not in suppressing your worries but in facing and understanding them. If today's exploration resonates with you, remember there's nothing wrong with finding yourself in the midst of these struggles—they're a normal part of the journey towards prosperity in your career and beyond.

Feel free to reach out for more insights or share your own experiences with overcoming these typical leadership roadblocks in technology. Connect with me at [email protected] for any questions or further discussion.

Let's navigate the tough terrain of tech together and uncover the leadership potential within every one of us.

Video Transcription

This is Lisa Frier and I am so excited to talk to you today about roadblocks to leadership and technology. I'm gonna talk about some of the pitfalls and we're gonna get really practical on what you can do. I am my career was in technology.I spent decades um working at hardware companies and software companies. And right now I'm investor in residence at the capital network which educates founders and investors. And I'm also a certified coach with my coaching. I work with founders and executives on leadership goal setting, decision making and on the very topics that I'm going to address today. I need to say I, I loved working in technology companies. It's a fantastic industry, there is huge opportunities. So this is by no means uh anything negative about the technology industry. I think it's just really important to understand how things work. First, I am going to cover leadership pitfalls for women. I, when I start talking about the terms, I know you'll recognize all of them and then I'm going to help you to recognize them when they're happening in general and when they're happening to you, let's think about specific examples and then finally, I'm gonna leave you with a formula for making real change before we dive in though.

What I'm gonna talk about is these are some of the standard solutions that people have come up with on how we can advance more women into leadership roles in technology. It is a long standing problem and one that gets increasing recognition, these solutions are based on a mckenzie study and I think these are great solutions. It it's things like offer more mentors and sponsors accelerate women's promotions, create networking groups. So their support provide equitable access to more training and so on. So there's nothing, absolutely nothing wrong with these solutions. But these solutions too have been around for a while. We keep talking about these next steps and yet things don't change. The obstacles to uh women advancing in technology are so persistent. And so what I'm gonna talk to you about today might sound a little counterintuitive. We're gonna really slow it down. Yes, you can go after getting a mentor and a sponsor. But until you are mentally prepared to take advantage of the opportunities, you are not going to be able to recognize them. So what does that mean? Mental preparedness? It is a skill. It's one that you can learn and we're really not taught this skill. It's about feeling resilient in the face of challenges. It's about feeling deserving and it's about getting really curious about what's going on in your mind. Here's how it's gonna work.

I'm going to start with what I call the big three, these terms, imposter phenomenon or imposter syndrome, people pleasing and executive presence. I'm gonna tell you what these mean. I'm gonna show you how they come up. I'm gonna ask you to think about when you've experienced these.

And, um, I've got a poll that's gonna come up. So I invite you, I really encourage you to think about specific examples and then put them into the pole when that comes up. All right, of the big three. What is the impostor phenomenon? It's when you're convinced you're a phony that anything that good that happens or what you do? Well, is a total fluke. It happens by accident and maybe most pernicious of all is that even when someone thinks well of you, even when you get praise, what your brain tells you is they just don't know what they're talking about no matter what you achieve, it does not change the way that you see yourself, does not change your future expectations when you're experiencing the imposter phenomenon.

And fundamentally, you fear that at some point somebody's gonna discover that you're a fraud and here's how it works in your mind. So you start out with a premise. I'm not good enough. You try to disprove that, you try to reassure yourself by working harder and harder and harder and making things perfect. But the challenge is very little is perfect. So you use the imperfection as evidence that no matter what you do, no matter how hard you try, you'll never be good enough. So you keep climbing and climbing and climbing and trying to scale that wall, but you never reach the top of the hill. Here's an amazing quotation. The seminal study on imposter syndrome was published by two psychologists, Klans and Iams. And this is a quotation from that study. We've been amazed at the self-perpetuating nature of the imposter phenomenon. So you get into this cycle and it goes round and round and round and round. Very difficult to get off of that hamster wheel. This was published in 1978. So we've been talking about this for decades and yet we're still talking about it. We have to ask what is gonna have to happen to change this trend to change this phenomenon. So we talked about what is imposter syndrome. Um What do you do when you're experiencing imposter syndrome? You criticize yourself, you block yourself from praise.

You can't accept good things that people say about you. You focus on meeting an impossible standard that is self imposed and you will never reach that standard. How does it feel when you're experiencing imposter syndrome? You're exhausted. You give in even if you don't wanna do something, you just do it anyway, you force yourself. Oh yes, I can work one more day. I can cancel one more vaca vacation. I can stay up three more hours, et cetera, et cetera, et cetera. And then here's an interesting piece of it, which is this insider outsider mentality. Things are very black or white. You're either you have this perception that everybody else must be in the know and you're on the outside and can't get in. And what does that mean? It means you keep yourself from fully engaging with your colleagues, you keep yourself from fully engaging with your job and you keep yourself from fully engaging with yourself. How can you love your job if you're disengaged and you're using your work as a cudgel to show yourself again and again and again, that you're no good, that's bad enough. It gets even worse. So there are many variations of impostor phenomenon. Um See if any of these ring a bell one is the superperson has to swoop in and take care of everything. If there's a problem anywhere, you're the one who's gonna come and save the day. Uh The next is the perfectionist. Everything has to be perfect.

You'll stay up that additional 45 minutes to make sure there isn't a single typo in the email that you sent. Um A third is the expert, which is that you somehow feel like you need to develop expertise in all areas. And sometimes it's what you do is you end up doing everybody else's job. So I'm gonna give you an example from my own career, which is that I was a product manager at a technology company. Great job. I loved it. Interesting, always learning. And um so I sat on an engineering team and the engineering manager had an employment issue and just one day didn't show up. So, you know, I led the meeting. Ok, that's fine. Next week comes around, he still doesn't show up. So I led the meeting um et cetera, et cetera. So after several weeks, I was chairing the meeting and de facto became the engineering manager. And I only realized that that's how I was seen when I was in a team meeting. And somebody said, oh, yes, Lise is the engineering manager. Well, you know what, I already had a full time job. So I was doing my full time product management job and I was doing another full time engineering manager job. But I think what's really important about this story is how I responded to it. I felt grateful that I had this learning opportunity. I felt grateful that I had a chance to prove that what I was doing and what I was contributing was valuable.

It was not enough to do one full time job. And oh, by the way, I was leading the product line, that was the largest product line in the company. So this wasn't just like, you know, something that was sort of small and on the side, great example of imposter phenomenon. So we talked about impostor phenomenon. Now we're gonna move to number two of the big three people pleasing. So what is people pleasing? Another one of these terms that we hear all the time? Basically, you worry about what other people are gonna think. You have this notion that if you put yourself first, you're being selfish. If you take care of yourself, you're being selfish and your sense of value comes from what others think. It's not generated intrinsically based on what you believe. And what do you do when you people please, you accommodate, you are afraid of confrontation because you imagine that if you state what you want or what you like, somebody is gonna disagree and it's gonna blow up into this cataclysmic disagreement. And in the end, you're blocking yourself from what you want. It can look like spending time with people. You don't enjoy working on things that you don't really value um doing anything you don't wanna do.

When you're people pleasing, you tend to put off decisions because you're concerned that if you make your opinion known, somebody is going to disagree, it's gonna ruffle feathers and that leaves you very often disorganized or messy with a to do list that gets longer and longer and longer.

And in the end, you're ignoring your own desires. By contrast, when you value yourself, you're enjoying the situation, you're enjoying yourself. You think that you're fine, you're worthy just as you are, you're able to listen to what you really want. You're very clear on your own dreams and desires and you don't depend on others to validate those you taking care of yourself in the long run. And that could mean, ok, it's ok if I don't do XYZ today, the end goal is to get to the thing I really desire and I have time to do it. I have the effort to do it. You're working on your own behalf. And when you value yourself, sometimes it means telling the truth and saying no, it's not that you don't care what somebody else thinks. It's that you are really focused on your objectives. So that's what you do when you're people pleasing. What does it feel like? You end up feeling angry and resentful because you're so exhausted and you, you attribute it to things that you have to do when we people please, we experience these depleting emotions. Whereas when we're valuing ourselves, we experience energizing emotions, we experience compassion, generosity.

Those are the emotions that create momentum that inspire us, that keep us going. And I just want to pause here because I think we've all heard that adage um you know, when you can give to yourself, you have more to give to others. And it's a very interesting expression. But what's really going on there is that when you're generating generosity, it pervades everything that you do. Whether you're being, you know how it is. When you do something great for somebody else, you feel really good. And so why can't we learn to generate generosity towards ourselves, compassion towards ourselves? And that gives that to us, it also equips us to give it to others. So why is it so difficult to act on what we want? Why do we fall into this pattern of people pleasing? It's because we worry that others are gonna disagree. Um Others might be inconvenienced and others will disapprove. And in reality, what's going on is that by avoiding the potential short term discomfort, that we think will experience what we're doing is we're taking on longer term exhaustion and resentment. Um I mentioned, I was gonna ask for feedback and um what I would ask is if you can put, if you have access to the Q and A, give me an example of when you have experienced either the imposture phenomenon or people pleasing and how did it make you feel?

So, we talked about two of the three imposter syndrome people pleasing. Now, let's talk about executive presence and this is a very interesting phenomenon. Um In my coaching, I cannot tell you how many people have encountered challenges with executive presence. They're either told that they need to exude more executive presence, but don't really know where to begin. It's frequently in my experience used as a reason. It's sort of a um a very easy thing for people to say to tell women and I was talking to somebody about this just a couple of days ago, why they're not getting it promoted because you don't have senior executive presence was the exact quotation. So it comes up a lot, but we don't really learn how to exude executive presence. So let's first understand what is it? Three main components. One is gravitas which means acting decisively maintaining grace under fire, showing integrity, speaking up about something you believe in, even when that's controversial, maybe, especially when it's unpopular because you're taking a stand. Gravitas has to do with your reputation and your emotional intelligence.

You can burnish your reputation by becoming known as a leader, by becoming known as effective by being one of the quote, good ones. Gravitas also um rests on projecting a vision. So first, you have to think of your vision, articulate it, communicate it effectively and that's a good segue to the second component, which is communication. So communication is key, the good news is communication is something you can be trained on and you can learn, it has to do with having superior speaking skills, having an ability to command the room and being adept at reading the audience and responding to the audience. The final component of executive presence is the first impression you make or your appearance. And this is the tricky one, the other ones are somewhat subjective, but this is very subjective. And on top of that, there's, there are a lot of components you can't do anything about.

Like can you change the way that you look by changing your height or your accent or your gender or your age or your skin color or where you, you know, so there are components of this that you really can't change and yet we're judged on our physical appearance. It's happening in the background, even when people are not aware of it, it's registering all the time. And the fascinating thing about it is that there are studies that show that women and people of color are much more frequently getting judged based on executive presence, but they are infrequently getting coached on executive presence. So that's a challenge whereas white males frequently do get input and guidance on how to exude executive presence. I think this is a third rail topic. People get worried about saying the wrong thing to women and it's a tricky line to walk. So as I said, the good news is that there is something we can do about a lot of what goes into executive presence. Um And also if you can, if there are instances where you've experienced this or you've been told that you need to uh exude more executive presence, put that into the Q and A as well. So what does it feel like when we're experiencing executive presence?

We have a sense of energy, focus, the thoughts are flowing freely. We feel ready to handle any question. We actually welcome the curveballs because we're so engaged, we can improvise. Um We feel very unselfconscious. We're engaged with the audience. We experience a very high level of connection with the people who we're talking to or when we're presenting. So then the question is, how can you create executive presence well, to be effective, it has to be authentic. You really have to show up fully as you. Um I advise women actively to seek feedback on how to have more executive presence. Don't just take a throwaway comment from your manager that, oh you know, you're not getting the promotion because you need more executive presence, seek answers to what that means. What is the person thinking about, seek outside help? Um Either a coach, videotape yourself making a presentation. It's amazing what you can see and not always easy to watch those first few recordings but watch with curiosity and compassion. So seek that feedback again, as I said, it has to be authentic. You really have to show up as exactly who you are and you have to be willing to bring attention to yourself. If you're taking a stand on something, it means fundamentally, you have to speak up about what you believe. Now, look at this paradox though, in order to have executive presence, you need to bring attention to yourself.

And there are a couple of things that are fundamental to the other phenomena that we talked about imposter syndrome and people pleasing, which is the last thing you want to do when you're experiencing those is to bring attention to yourself. So, is this another no win. We'll address that in a second. All right. So we talked about uh imposter syndrome, people pleasing executive presence. How do these issues show up in tech companies? I've got probably 80 ways, but I'm gonna just go over a few. Um The first is that technology companies experience a really rapid rate of change. They tend to have relatively flexible organizational structures very often. They are matrixed reporting relationships and what that means. Things are in flux and things are matrix. So you're reinventing yourself within and among organizations all the time, it means you need allies, you need sp answers. And when you're somebody who tends to look outside of yourself for validation. A this is a lot of work, but it also means you have to prove yourself again and again and again, which reinforces that cycle we were talking about. If baked into the organization is the need to prove yourself. Then if you tend to get onto that wheel of disapproval and lack of self belief, you're going to encounter it every day. So that's one rapid rate of change, flexible organizations. The other is the primacy of engineering.

There's always a new project, there's always a new deliverable within the project. You could have a monthly deliverable, a weekly deliverable, a daily deliverable if you're in an agile environment. So again, you have to prove yourself again and again and again, and there is that scorecard against which to be measured. Did the code work? Yes or no. Did it pass the test? Yes or no. And I'm not saying this is a bad thing. I mean, obviously we all want to aspire to quality, but you really need to be aware that this is very fundamental to cultures in technology companies. A lot of the companies that I've worked in have been highly combative. So people are fighting over funding. I'm not saying this is a bad thing. It is ostensibly to create discipline about resource allocation, but it means that there are winners and losers. So when it's a combative environment, what does that do for women in that environment? Well, you can fight the fight, you can be combative, you can be aggressive. But culturally that makes you a bad woman. If you don't fight the fight, if you are not assertive, then you're weak. This is called the gender double bind. Sort of women can't win. If you're strong and forceful, then you're not complying with the stereotype of a woman. If you're weak, well, then you're, you're weak.

And an example for me was I was working on a, a project um that had gotten funded and it was somebody who was two levels above me who had gotten the funding. This is a long time ago in my career and I realized, as I looked at the product and the uh researched what the market thought of it and the likelihood of its success, it really was, I, I felt it was, I had a lot of evidence, a lot of data and a lot of feedback that was not gonna hit its targets.

So I proposed canceling the project. And what I didn't realize I was very naive about this. This was really egg on the face of the person who had won the battle to get funding. So it was worse for him to be perceived as going back on his word or getting the resources and then losing out on it than it was to bring the wrong product to market. And this goes to another point which is that at least nominally, another aspect of tech is that it's at least nominally based on meritocracy. But in reality, is it a meritocracy when these ways of working are prevalent, when the person who's judged to have executive presence, is somebody measured against a standard that is primarily focused and primarily prizes more assertiveness, more aggressiveness. So I would really question whether it's a true meritocracy.

Um Two more things I'll cite one is that tech tends to have more men than women. And there is a severe lack of female role models, a severe lack of female standard setters particularly at the top rungs of management. So these cultural phenomena tend to perpetuate themselves.

And finally, something I'm sure all of you have been aware of and this is why we're here today, many women, there, there are a lot of women coming into uh engineering in educational institutions and taking those jobs. But there's a lot of drop off. A lot of drop off. In fact, more than half of women leave their technology careers at midst stage. That is a critical inflection point. That's where you're gonna be at the fork in the road. Are you gonna continue into senior management or you gonna stay where you are? You're gonna try something else. So, more than half of women are leaving their technology careers when they're at mid career, that's more than double the quit rate for men. And what's also interesting is that more than half of those women who quit are abandoning their technical training altogether.

So it says a lot about tech work environments, looking ahead, women are tending to decide that they don't think they'll succeed or maybe they just don't want to play the game the way it's played. But basically you have all this training and preparation and you're not reaping the benefits you've invested in yourself, you've invested in your education, you've invested in your career. So, have you ever had thoughts like this? Have you ever grappled with whether, whether to continue or whether to leave?

So, we looked at some of the problems, but here's the key question, what if nothing's gone wrong? This is sort of the ultimate perspective shift. Why do we pathologize these phenomena? And oh, by the way, the way that we portray them is as though there is a problem with the person experiencing them. So it's on the uh on women to go and do something to work even harder to get a network to fight for training, et cetera, et cetera. What if instead of beating ourselves up about this? We just say this is all normal. Of course, we're experiencing imposter syndrome. Of course, we're people pleasing because this is how we're socialized. This is what happens in the environments that we're in and this is how we're trained. Does it help to conclude that there's something wrong with you? If you're experiencing these things, I uh would propose that the answer is no. What if instead we just get curious about what's going on and if any of what I mentioned in the last few minutes resonates and feels familiar and is something that you've experienced, pay close attention to that you have spent your entire life honing the habits that you have and that you bring into your work environment.

It takes time if you spent, let's say you're 25 if you, you know, you've spent 25 years developing these habits, does it take 25 years to break them? No, that's the really good news. And I'm gonna tell you how you make change and then I'm gonna leave you with a few concrete suggestions about what you can do right now to start the momentum to break these habits because it does take time and when you're in it, you're not really aware a lot of the time. That's that it's happening. So here's a breakdown of how meaningful change happens. The first of course, you have to be aware of what's going on. So, observe what's happening, observe yourself next time, you're in a meeting, observe if you really want to say something, but you're worried about what others will think or you're waiting for the more senior person to go or you're afraid it's right or wrong or that kind of a thing.

Observe when you're feeling exhausted and uh you know, you just kind of keep plowing through anyway, or when you're not excited about where your career is going, where it doesn't align with what you truly want or when you feel confused about what it is that you want to begin with.

So again, observe the current state and be compassionate with yourself. When you're doing that, don't look at it as a problem. Be kind of a scientist about it, gather the data. Then in order to really make change, you have to start believing that something could change. Then the third step is picture what could be different, how it could change that in itself is often enough to make a change. Just seeing things differently, seeing yourself differently is a change. So don't underestimate that and being able to picture a future with you in it, that is a huge, huge leap forward as soon as you can imagine yourself in something that you want or something that's possible. You're halfway there in getting to the new state. So that's how change happens. And here is my formula for change. I pick these things because they are small steps that you can do today this week, next week, but they're really, really meaningful ones and I'll explain why. So first, as I described before, watch what's going on, observe when these phenomena are coming up even, you know, think about um where you're sitting in a room or where you are on the agenda and how that makes you feel. Do you want it to be different or are you hesitating? Are you holding yourself back? Are you feeling confused about what you want in the direction that you want to go in? Do you have this perception that you'd really like to talk to a person? XYZ?

But they wouldn't want to talk to you um Or that, you know, you're overworking consistently or um you know, you're rushing around like a crazy person or you're um missing out on the things in your life that you really want to do. So start observing when these phenomena are coming up and try to link them to the frameworks that I just talked about and remember there's nothing wrong with this. This is you're just gathering data. Second, I talked about a lot of these things, the skills that you have to learn that were not taught. Going after a goal is something that takes practice. You get better at it, whether you succeed or fail, you get better, better at it when you practice. So just pick a goal, pick anything. Could be something big. It could be something small, whether you get there or whether you don't get there. It doesn't matter. It's more tapping into what you want and what you like that creates more self-confidence. It creates these neural pathways where you start thinking about. Well, what do I want? What do I think is important? It's incredibly empowering. And then the final piece of advice is redefine what is normal. So by that, I mean, two things, one, there is nothing wrong with you.

If you experience imposter syndrome or if you're people pleasing, it's normal. No wonder you experience these things as we talked about, the way that they work in general and the way that these come up in technology companies in particular is very normal. And the reason why this is important is if you try to suppress these phenomena, then they actually get worse. If you can face that feeling of discomfort or feeling like there's, you know, like you'll, you'll never be good enough if you can just acknowledge that and face it, it really minimizes those feelings. And the degree to which you can sit with the negative emotions is directly correlated with your ability to develop. And grow. So I wanna thank you very much for being here. Feel free to be in touch with me. If you have any questions, I'm just gonna check the chat and the Q and A. But if there's anything here that struck a chord, you'd like more information on, by all means, feel free to be in touch with me. This is the best email to use Lisa at get on stuck dot.