Imposter syndrome can suck the joy out of professional milestones and new career opportunities.
Instead, feelings of self-doubt and lack of confidence and ability swarm the psyche and can paralyze a person’s confidence and development. And while both men and women experience imposter syndrome, research shows that women are much more likely to grapple with it than men.
Tech’s lack of women in leadership positions and presence in fields like engineering means they’re more likely to question their capabilities — and to have them questioned by their colleagues — as they get deeper into their careers.
Imposter syndrome as a concept has existed since the late 1970s and combating it has typically been framed as an individual struggle against a crisis of confidence. After speaking with five women in Boston tech who have dealt with imposter syndrome during their careers, it’s clear that’s no longer the case.
Yes, individual actions still matter, but the senior leaders we spoke with also shared how forming a support network helped beat back unfounded feelings of professional inadequacy along with the responsibility employers have in helping to rid the workplace of the conditions for imposter syndrome in the first place.
Powell has developed her own tactics for fighting imposter syndrome, which include remembering the times she was encouraged to bet on herself and won as well as leaning into self-promotion. However, Powell also noted that her company, Flywire, is doing its part to help fight imposter syndrome and that employers in general have a major role to play in creating an environment where everyone feels respected and recognized as a professional and leader regardless of their background.
How have you experienced imposter syndrome in your career?
Imposter syndrome and I bonded years ago. From the day I walked into the United Nations Consular Corp and Protocol Office for NYC at the age of 24 to the day I left my comfort zone in higher education and entered the technology sector, I have struggled with believing I truly belonged. In the last decade, as a member of a design partnership building out a new student enterprise resource planning system, and implementing the product with some of the very first clients in the country, I am keenly aware that I am highly qualified to do the work but have still been surprised when things went well.
My clients went live successfully, and the people who worked with me excelled and are some of the best consultants in the industry, but these successes changed nothing. Even after years of accepting leadership roles in various professional organizations, becoming a recognized expert in my field and presenting at various conferences, I still struggle with whether I am accomplished enough, educated enough or prepared for the responsibilities I am given.
When frustration and doubts seep in, I remember the people who taught me to take risks.”
How did you deal with your imposter syndrome? Was there a particular situation, quote, idea or person who helped change your perspective?
I don’t think my perspective has changed, but rather my internal monologue is overridden by my curiosity and desire to learn new things and embrace opportunities. This alone does not help when you are the only woman in the room at a product design session or one of only a handful of women in leadership in product and engineering. When frustration and doubts seep in, I remember the people who taught me to take risks.
Maureen McRae Goldberg pushed me to put my hat in the race for the California Association of Student Financial Administrators executive board — which I won — when I was only a year into my career. Kathleen Blackmon gave me a leadership position when I had zero experience in student finance and then trusted me to represent our office during our university’s first ERP replacement since the 1970s. My incredible colleagues in the ERP consulting world modeled what it looked like to excel at discovery, use case design, process improvement, critical thinking when configuring a new generally available product, grace under pressure and empathy for clients. I have all the training and years of experience to be where I am today; if I don’t know something, I will go learn about it.
What advice would you give to other professional women who are dealing with imposter syndrome?
Statistically, the odds are stacked against us. In “The Authority Gap,” Mary Ann Sieghart describes how women get caught in a double bind: “Either they appear as confident as men, running the risk of being disliked, or they do themselves down. Yet modesty too is damaging, for other people are quick to mistake confidence for competence and therefore under-confidence for lack of competence.” After reading this, and the rest of her book, I wondered if it is better to be liked or competent. A harsh reality, right?
For me, what this illustrates is that you need to own your space, self-promote and help to lift others up! We should also meet people where they are and find a company, like Flywire, that is working hard to close the gap for women and other marginalized groups in the workplace. As Ruchika Tulshyan and Jodi-Ann Burey describe in their article for Harvard Business Review: “The answer to overcoming imposter syndrome is not to fix individuals but to create an environment that fosters a variety of leadership styles and in which diverse racial, ethnic and gender identities are seen as just as professional as the current model.”
Chrapaty spent more than 35 years in senior leadership roles before joining Toast as CTO in 2022. In a career that has included stops at Microsoft and Amazon, Chrapaty said she learned one of her most valuable techniques for beating back imposter syndrome at Toast: the importance of forming a group of people who come together for the same purpose, or a “posse.”
How have you experienced imposter syndrome in your career?
One way I combat imposter syndrome is by fighting it head-on. I am constantly working to support other women in tech through regular mentorship and by sharing my stories and learnings. I’m part of our amazing ERG, ToastHER, which hosts events and mentorship programs and builds a strong community supporting those identifying as female and allies. During Women’s History Month, we organized several awesome programs and events, including sessions with women customers and networking events. As a senior woman at Toast, I do my best to be visible and support all of our amazing women Toasters, and it’s super energizing to witness these incredible women and all their accomplishments.
Something I learned at Toast is having a group of people who come together for the same purpose — a posse. By finding your posse, you are more likely to succeed.”
How did you deal with your imposter syndrome? Was there a particular situation, quote, idea or person who helped change your perspective?
When I was in my mid-30s, I was offered an opportunity to leave a comfortable job in NYC and move to Palo Alto to be the CIO of a newly public company. It was a pretty big risk to leave everything and everyone I knew and join this bold, innovative company in pursuit of career growth. The company went on to be a true fintech disruptor, and I gained incredible wisdom as a young, woman executive. I am forever grateful for the opportunity.
Fast forward many years later: I attended a CIO conference and sat next to a CIO I knew. He felt the need to tell me: “You know that job? Well, they offered it to me first.” That made me laugh and think, “Sour grapes!” When you are offered an incredible opportunity, don’t be afraid. Take it, have a blast and make the most of it.
Additionally, my customers serve as my greatest inspiration. The power of technology to transform customer experiences has always been the driving force behind my career aspirations, and being rooted in this has helped me overcome challenges and stay focused on my goals.
What advice would you give to other professional women who are dealing with imposter syndrome?
First, always look around corners, anticipate change and stay at the top of your game so that you are delivering value for customers and your industry. Society is changing quickly, and this next wave of technology offers new technical and ethical questions that will be important for up-and-coming leaders to address. I think these issues are much more complex than the ones my generation grappled with and we are looking to you to make smart and right decisions.
Secondly, build support systems. Something I learned at Toast is the concept of having a posse, a group of people who come together for the same purpose. By finding your posse, you are more likely to succeed. Over my career, many things have changed but a lot has stayed the same. I still sit in meeting rooms, boardrooms and at conferences that are largely occupied by men. I am still in meetings discussing the under-representation of women at senior levels. I still mentor young women engineers desperately striving to find their voice and seat at the table. Remember to find your posse, surround one another and support one another as you drive change.
Placais landed her first director role prior to joining Evolv Technology, but rather than being able to completely celebrate her accomplishment she found herself struggling with feelings of self-doubt. Placais took a pragmatic approach to building her confidence back up, one that anyone who has been recently promoted and is struggling with imposter syndrome can easily adopt.
How have you experienced imposter syndrome in your career?
In my previous role, I had a series of successes but then felt stagnant for a couple of years, which put me in a cycle of self-doubt. I was a successful middle manager, but when I inquired about a promotion to a director role, I was given the runaround. I observed several others getting promoted, including my manager, while I was left behind. I eventually left to become a director at another company, but imposter syndrome hit me hard. I started to doubt myself and my abilities, wondering why it was so hard for me to get to this level in my career and if there was a reason I was never promoted at my previous company.
My advice to women dealing with imposter syndrome is to understand that it’s not a lack of confidence but a limit to one’s confidence.”
How did you deal with your imposter syndrome? Was there a particular situation, quote, idea or person who helped change your perspective?
I broke down the things that were limiting my confidence and attempted to conquer them one at a time. I took the time to understand the technology and tools at my new company, seeking out people who could help me and reading books and articles to learn more. Over time my confidence grew, and the ceiling that had limited me before got higher and higher.
What advice would you give to other professional women who are dealing with imposter syndrome?
My advice to women dealing with imposter syndrome is to understand that it’s not a lack of confidence but a limit to one’s confidence. Imposter syndrome can be triggered by drastic changes in your career, like starting a new job with unfamiliar technology and tools. Break down the barriers and take the time to overcome them bit by bit. Imposter syndrome doesn’t fully go away, but understanding what triggers it and conquering those limitations can help you grow and succeed.
Being vulnerable in the workplace is not always seen as “professional,” which can, in turn, make it tough to go to your network for help when dealing with imposter syndrome. While sharing struggles with those you know only in a professional context can be scary, Ramcharran said putting herself out there and asking for help played a key role in helping her feel more comfortable and confident after stepping into the role of director of product design at Crunchtime.
How have you experienced imposter syndrome in your career?
I have been a leader in the product design space for the past eight years, with a collective 15-plus years in the industry. And yet every time I start a new role, doubt creeps in. I am usually the first or second designer on staff at many of the organizations I’ve worked at, in addition to often being the only woman and person of color on a management team. Being the first one in a department, with little support from experts in your space around you, can often be intimidating. Unfortunately, leaving that room for doubt in one’s mind means imposter syndrome can set in.
More recently, I started as director of product design for a B2B SaaS company called Zenput, which was acquired by Crunchtime. When I was brought on, I was the first person in the company’s history to have that role, and there were individual contributing designers in place already looking to me for direction and inspiration. The thought of being the first one in a role with no precedent, along with having people I didn’t want to let down, created a feeling of imposter syndrome.
I dealt with imposter syndrome through a combination of seeking out advice from other powerful women leaders in my product design community and some self-care.”
How did you deal with your imposter syndrome? Was there a particular situation, quote, idea or person who helped change your perspective?
I dealt with imposter syndrome through a combination of seeking out advice from other powerful women leaders in my product design community and some self-care. I belong to a professional community on LinkedIn with other women leaders in product design and know a handful of them personally. A few weeks into my new role, I made a vulnerable post about feeling imposter syndrome and asked for advice. I received an amazing response: It turned out that many of my peers had felt the same at some point in their own careers and had valuable advice to share. I combined this advice with some self-care, which included being gentle in the discovery phase of my job and pacing myself along with recognizing my past accomplishments to boost my self-confidence.
What advice would you give to other professional women who are dealing with imposter syndrome?
Recognize that this feeling is common and you’re not alone in dealing with it. It helps to be vulnerable and reach out to other women professionals who can empathize with what you’re going through and support you along your journey. Giving yourself some self-affirmations, reminders that you were hired into this role for a reason or about some of your past accomplishments, can reinforce the skills and expertise you bring to the table. This boosts self-confidence in executing new things.
Practice some self-compassion. If you need to ask extra questions when starting or learning something new at your job, this does not make you inadequate in any way. Be gentle in allowing yourself to feel doubt, but don’t let it hold you back. Instead of thinking of this doubt as an illusion, recognize that this is a very real thing for women and people of color in the workplace. Encourage others at your workplace, such as senior leaders or those in people operations, to help stop the cycle of imposter syndrome. Voicing concerns to have a more inclusive workplace, plus having a company that takes action on this, can help others feel less alone.
Imposter syndrome makes it incredibly easy to forget how far you’ve come in your career and all that you’ve accomplished. Beaudry, senior product manager at Forward Financing, combats this by making sure to celebrate all of her achievements, which she also writes down to ensure she has an arsenal of affirmations ready when feelings of doubt start to cloud her vision.
How have you experienced imposter syndrome in your career?
Early on in my career, I had the opportunity to join a successful startup as one of its first employees. As the company grew rapidly, my role expanded significantly, requiring me to take on new responsibilities such as managing a team, delivering product demos to large prospects and managing the product roadmap. As I was interacting with executives at Fortune 500 companies, I often doubted my abilities due to my limited experience. It was quite easy to overlook the fact that I was receiving a lot of positive feedback and that my success was in part due to my hard work and initiative to develop my skills through training and education outside of work.
Talking to others and hearing that they are facing a similar challenge gives me the confidence to focus on the problem to be solved without the distraction of any self-deprecating thoughts.”
How did you deal with your imposter syndrome? Was there a particular situation, quote, idea or person who helped change your perspective?
I was not familiar with the term “imposter syndrome” prior to reading Sheryl Sandberg’s book “Lean In.” However, Sandberg’s book helped me view my accomplishments and failures in a new way. Case studies from the book showed how women more frequently doubt their own abilities and attribute their success to luck rather than their hard work. Having this awareness, and then catching myself having these thoughts, was one key component of developing confidence.
The other key component to building increased confidence has been developing a network of peers and mentors I can talk to outside of work. When something is not going well I tend to blame myself, but talking to others and hearing that they are facing a similar challenge gives me the confidence to focus on the problem to be solved without the distraction of any self-deprecating thoughts.
What advice would you give to other professional women who are dealing with imposter syndrome?
Fake it until you make it! Focus on your North Star and all that is within your control on the path to achieving it. Seek out mentors, colleagues and friends who believe in you and offer encouragement, and then celebrate and acknowledge your success. Don’t downplay it! One way that I personally do this is by keeping a list of all of my achievements over the course of the year. Looking back at it can be quite fulfilling and rewarding.
