Overcoming imposter syndrome: How to get that job you’re terrified to apply for (and make sure it’s right for you) by Cat Fletcher

Automatic Summary

Overcoming Imposter Syndrome: A Guide to Thriving in the Tech Industry

Throughout my two-decade career in the tech industry, currently serving as the VP of Engineering at the cybersecurity startup Exel, I've experienced and seen various colleagues wrestle with the persistent self-doubt known as "imposter syndrome", which often afflicts women and underrepresented groups due to longstanding systemic biases. Today, I'll share my strategies for overcoming imposter syndrome, particularly in the high-stakes context of interviewing for a challenging new job you might initially feel unqualified for.

Understanding Imposter Syndrome in the Tech Industry

Imposter syndrome arises from the fear that you are underqualified compared to others' perceptions of you. Even when you've attained significant skill and self-confidence, the experience of marginalization can fuel self-doubt. This can inhibit you from pursuing long-shot opportunities or fully showcasing your abilities, thereby dampening your professional advancement.

Four Key Steps to Overcome Imposter Syndrome

Through the lens of my personal experience, I will walk you through four key steps that have helped me manage this anxiety, hopefully helping you to professionally thrive even in the face of imposter syndrome. Remember: the objective is to discover if the job is not just right for you, but can foster your growth without reinforcing imposter syndrome.

  1. Map Your Experience: Carefully map your prior experience against the job's responsibilities to prepare for potential interview questions. This retrospective exercise can also serve as a confidence booster. For areas where you lack relevant experience, you now have a list of specific skills to grow in future.
  2. Practice a Pretend Interview: Practice answering questions about your past experience and skills. The goal is not to memorise a script, but to become familiar with having a natural conversation about your experience.
  3. Research the Interviewers: Show your interest by researching the interviewers beforehand using LinkedIn. This can provide conversation openers and help set a positive tone for the interview.
  4. Remember You're Also Interviewing Them: Approach the interview from the perspective that you're also assessing the company and people there. Ask targeted questions to discover if the company lives up to its stated values and commitments. Always remember: you need to find a place that not only rewards your experience but also fosters your growth.


With a few hours of upfront preparation and self-reflection, you can face even the most daunting job postings or interview questions with renewed confidence. By focusing on your skills and experience, you can present your best authentic self during an interview. And who knows, perhaps you'll eventually find that perfect place where you can shake off imposter syndrome for good, or at least most of the time.

Remember, although imposter syndrome can be a challenge, it doesn't have to define your career or potential. You can overcome it and thrive in the tech industry.

Video Transcription

Um I'm gonna go ahead and try to leave time for questions at the end, but um in case I don't have time or um you know, if there's anything else you wanna follow up on it, just pop the link to my linkedin in the chat.Um You feel free to connect with me there. So, um Hi, I'm cat. Um I'm currently the VP of engineering at expel a pretty mature uh cybersecurity start up of about 400 employees. Um I've been in the tech industry for some 20 years now. Um And today I'm gonna talk about how I've been able to overcome imposter syndrome. Um specifically as it relates to getting a job that you are terrified of. Um And just as importantly, making sure that that job is right for you. Imposter syndrome is the persistent self doubt that comes from feeling like you don't live up to others perception of you. It can affect anyone. Uh It often affects women or other underrepresented groups in the workplace. Um because of the systemic bias that has been in place for basically forever. Um So after repeatedly experiencing bias, it gets much harder to trust in our success or even in people's praise. And even when we have a ton of skill and self-confidence, that is the weirdest part about it.

I think that combination of self-confidence and self doubt, um or rather doubt in the systems that we live and work in, we succeed, but we continue to question ourselves and our abilities because we've experienced being marginalized regardless. So this can hold us back in many ways.

Um including keeping us from going for opportunities that are a long shot or keeping us from putting our best self forward when we do. Um So we end up in situation after situation where we either don't advance, we don't get credit for it or we do finally get that promotion after we've been actually doing the job for a few years. So taking a leap, feels impossible when you think you need to already be an expert in every aspect of a job before you're qualified. I've been in the tech world, like I said, for the last 20 some years and I have absolutely experienced it myself. Um And I've seen it in my colleagues from all walks of life. Um And while I'm talking, if, if you all wanna go ahead and talk on the chat about experiences you've had, then that would be great. Um I'm gonna walk through a personal story. Um And it will immediately become clear, I think that I am an expert in impostor syndrome. So when the pandemic first hit. Uh I was working in a small company as an engineering director. I had been there for four years at the time with a ton of experience as an engineer, an architect and a technical leader. I was already getting restless there feeling like I'd grown out of it and wanting that next challenge.

Um My career actually seems to have been defined by taking on one challenge after another and I've objectively been successful and yet at that time, especially after the pandemic hit, and I was really strapped with supporting my Children and maintaining my job respon demanding job responsibilities.

I felt defeated before even starting a job search. I had a few of those half hearted discussions with recruiters where I didn't feel good enough and didn't feel energized even a coding challenge. I buried embarrassingly bombed um because I went in assuming I'd fail and then I just, I just gave up um until locally recruiter reached out to me with a job uh with spoiler alert. Uh my current employer um for a position as a VP of engineering at a fast growing start up. The recruiter said in her message that she about fell out of her chair when she came across my linkedin profile. I had the technical depth missed, mixed with the leadership experience they were looking for, but I still couldn't quite uh couldn't get the narrative in my head. I I can't do this. I'd be crazy to go for this, right, especially now, right? But this place sounds really special and the opportunity sounds amazing. So I looked carefully at each of the responsibilities listed out in that job posting, build and execute a strategy that promotes ever increasing customer happiness. Ensure we understand the technology landscape and our path through it, wield your experience to see the future and anticipate business needs, develop a strategic financial plan and deliver against it. I can't do this. I've not mastered every single one of these requirements.

I am never going to get another job. I will be stuck here forever. If I'm lucky where everyone will figure out that I'm the worst person who ever worked in this industry. I've tricked every manager and every coworker I've ever met over 20 years. This has all been a scam and my kids and I are gonna be living under a bridge by the end of this year. Ok. Deep breaths, maybe this has resonated with some of you. If so you are not alone in these feelings, I'm gonna walk you through how I have learned to cope with this anxiety and hopefully it helps some of you all too for me. What helps is recognizing the absolute ridiculousness of that catastrophizing anxiety that I just talked about for what it is that is imposter syndrome and then I get organized and really prepared. That's a form of taking control, right? So we're going to review four steps of preparation to nail that interview. And just as importantly, find out if the place is a good fit for you where you will be in an in an environment where you can flourish, not somewhere that's going to reinforce that imposter syndrome. So first, let's go back to that job description I talked about. Um So, you know, they're gonna be asking you questions to determine if you can do those things. So I thought, let's figure out how to map your experience to the specifics of this role.

So if you go into an interview cold and they hit you with those, like, tell me about a time when you did such and such type questions. If you're like me, you probably have trouble remembering last week, let alone five years ago. When you experienced a conflict, you could have handled better. So we're gonna build a case and revisit all of those past experiences. So they're fresh in your mind, an added benefit. Um is that this exercise can be a great confidence booster. In fact, there are two potential good outcomes from this exercise. You feel confident and prepared and ready to go for it or you realize that maybe you're not quite ready and in that case, all is not lost those requirements where you're missing relevant experience. Well, now you have a list of specific skills you need to grow in order to get a similar position. If it's still one you want so to get started, you're gonna bust out linkedin and we're gonna be using that a lot in this plan. So as a side note here, remember to keep linkedin up to date, maybe even set a recurring calendar reminder. Um Even just taking a minute to add titles and projects and stuff, can jog your memory later on when it's time to review. So we start going back through all those old jobs and remember what you worked on who you worked with problems you solved and match those up with the responsibilities in the job posting. I personally like to handwrite it out, it sticks in my mind better.

You could also type it up or record it. Uh But keep in mind, we are not writing a script to be read during an interview. So let's take a specific example from the job posting that I uh mentioned earlier. So if you recall, um I started to have a breakdown around when I got to um develop a strategic financial plan and deliver against it. My first reaction was I've never done that before. But then as I'm going through my job history, I get to this bit where I pulled together infrastructure planning for my company and that included cost analysis and projections and I delivered on it. So there is my relevant experience. I may not have done strategic financial planning at the org level before, but I have shown the aptitude for something similar So as I'm building out this mapping, I'm realizing I, I do in fact, have a lot of relevant experience. I have actually done a lot of cool things and I'm actually really good at a lot of these things and maybe I wasn't actually tricking every person I worked with over the last 20 years into thinking that I was valuable. So I've got some more confidence and I'm ready with a lot of examples from my past to refer to during the interview. So what's next? We're gonna build a pretend interview. So I'm sure most hiring managers will agree.

Rarely are interview plans prepared without the use of either what we've been asked before or what we uh find with a good old fashioned internet search. So, are you going to be able to guess exactly what you'll be asked? Certainly not. Um But this is all about practicing and building confidence around your experience and skill so you can present yourself in the best, most accurate way again. I wrote mine out because this works for me personally just to implant things into my brain. Um You could practice a few answers out loud in front of your pets or your stuffed animals. Um You could get a friend to do a mock interview with you, whatever works for you to feel familiar with that conversation you're about to have but not sound too rehearsed. It is a conversation, not a presentation. So let's walk through one of mine here. You can see the Google search, right? First one on the list. How would you describe your management style? So the key thing here is to find compelling examples, anyone can prattle on about management best practices and that's fine. But what really demonstrates your skills and experience is specific examples from your past. So I've just gone through that exercise of going back over my career.

So it's all pretty fresh in my brain. And now I'm thinking about examples of my management style. I have a few from being a manager that are fairly run of the mill. But I'm also thinking about how I developed my management style. I spent many years as an architect and with nobody reporting to me and I couldn't just tell people what to do. I had to develop the skill of driving change through influence so I can tell a story there. Now, about a time I got to engineering teams going productively in the same direction by organizing a plan to finding a process and getting buy in from individuals. So the more I'm thinking through this and writing down about it, the more it comes back to me. And now I have a really valuable example that could be applied to a number of possible questions. Speaking of questions, it's important to ask really good questions even in the part of the interviews where they are asking you the questions. Um It's likely that they are asking you a specific question because they currently have that problem. So ask for more detail, for example, uh something from, from my experience, how do you feel about outsourcing? So you can talk to your relevant experience there, but then ask about the team structure about past experiences that may have been a problem about what their internal concerns are.

This demonstrates your interest in working with others and solving problems, your curiosity about the company and the people in it. Uh Plus, it keeps the interview more conversational and collaborative, which is more engaging for everyone. And if the interviewers react poorly to this, then that gives you some information about the culture there and could be a red flag. So remember you wanna find a place that's going to support your curiosity and growth. So now I have thought about my experience as it relates to the job posting and I have some examples at the ready for possible questions. So what else can we do? We're gonna research the interviewers. So uh first you're gonna get a list of interviewers from the recruiter. This is a totally OK thing to ask for. If they don't give it to you up front, why are we doing this to help drive conversation primarily in your question time at the end? Um But it also can come in handy in those first few awkward minutes of hi, how are you while you're waiting for everyone to join the Zoom link and fix their audio. Um The first few minutes can help set up the whole conversation. So confidence and that ease of conversation up front just makes everybody feel more comfortable and sets the tone for the whole interview and it shows you've done your homework, but you're serious about this and you're seriously interested. So, uh what do we do back to linkedin?

People expect you to look at linkedin for this kind of thing. It is not creepy though. Anything further than linkedin is creepy, don't do it. Um So what are you looking for? Um Are they connected to anyone? You are? This is a great conversation opener. If it's someone you know, well, you can reach out to them and get some tips or feedback. Remember you are also interviewing the company and its people. Where else have they worked or what else have they worked on? Maybe you have something in common, maybe they had a really unique role somewhere or worked on something really interesting. That's all good opener content. What roles have they had at the company? And for how long this shows you their path and a bit about how the company has evolved and that's really good for questions. Like why did you decide to move into this role? What are the most significant changes of the company since you started five years ago? Why did you join as an architect? Similarly? Uh You can look at a company blog, if they have one or their social media or you can familiarize yourself with the company and the product and the culture. So now we're ready with our opening small talk. We're ready with examples of our experience and we've got some questions for our interview interviewers um which brings us to the last step finally. And just as importantly, let's remember again that you are interviewing them just as much as they are interviewing you.

Again, this mindset helps with confidence and it ensures that you don't end up in a job you don't actually want in the first place. So how do we figure this out? What did they, what did they say they have that you think sounds awesome. Maybe even too good to be true, either in the job hosting or in the company marketing or blog content. That's what we're going to try to hone in on to make sure it really is true by asking some targeted questions of all the people in the panel. So for my last interview, I noticed the company on the company blog that um they had a manager program that included coaching for every level of manager in the company that sounded really unique. And I wondered, is it really for all employees, is it really as rich a program as they say? So I asked each of the people in my interview panel, uh what they got out of the program and how they sought benefit managers on their teams. Each person had an enthusiastic and unique perspective which told me they weren't merely robotically repeating some line from the company values. So it's some generic questions that can usually provide insight, especially if you ask across a number of people on the panel. Uh If you could wave a magic wand and fix one thing, what would it be? Every company has challenges. It would be boring if they didn't. Are they the type of challenges that you want to be solving? And if they don't say anything?

So no, nothing's nothing's wrong here, then maybe, maybe question their transparency. Um Honesty with this question is a good thing. Even if they're talking about a pain point, how are you gonna help me be successful in this role? This will get at what they need the role for how much they've thought it through and how invested in it and you, they will be. If you're worried that this is off putting, would you want to work somewhere where you can't ask a question like this? That goes for any question? Really? What another one is? What have you and your company done to create a more inclusive environment at work? Asking what have you done? Gets them to speak to specifics rather than asking something like do you have an inclusive workplace or how many women work there where they can just then just respond with the run of the mill stats or hit Oh yeah, we totally are inclusive answers. So just to reiterate, it does help to ask the same questions to multiple interviewers. It can help you get a more well rounded perspective of the company and the culture and that's it. It's a few hours of upfront work. But hopefully it leaves you pre prepare, feeling prepared, confident and in control.

This is especially important if you are moving from a position or a company where you don't necessarily feel supported or valued, that kind of environment is fuel for the imposter syndrome and you will have to make a real effort to find confidence from within. So by focusing on your experience, you can defeat the feelings of paralysis that can come from daunting job postings or interview questions. You can authentically put your best self forward and remember an interview is about finding a good match between you and a company that is going to value your experience and support your growth and who knows? Maybe you will get to a place where you can finally shake that imposter syndrome for good or at least most of the time. Thank you so much. Um Maybe have like one minute to answer questions, but um I really appreciate you all attending. Um Yes, I can, I can figure out how to share um the the deck with everyone. Um um Thank you again so much attending. Enjoy the conference, take care of everyone and good luck.