The Imposter's Guide to the Job Search

I'm too good at interviewing, and keep getting jobs I don't deserve. Here are my secrets.

Years ago, I was introduced to the concept of “Imposter Syndrome,” while working at a big tech company as a senior account manager. I was assured that everyone at this company felt that they didn’t deserve to work there, because it was just such an amazing opportunity. But I had a feeling that for me, this went a bit deeper. I actually was an imposter. Not that I lied or anything to secure my role—I didn’t. But I had interviewed far too well. My colleagues were much more talented at their roles than I was, or at least way better at appearing competent. All my coworkers who fretted about “Imposter Syndrome” clearly weren’t imposters—they actually had good performance reviews. I, on the other hand, eventually got fired, and even prior to my firing I was known as a problem person around the office. Although these things weren’t the explicit reasons for my firing, they didn’t help: I created a Game of Thrones themed presentation which was apparently put the company at risk of violating IP laws, and I taped up a personal package at my desk using “loud tape.”

It wasn’t my first time being fired. I’ve been fired five times in thirteen years, including layoffs and my role being eliminated. 2-3 of these firings were explicitly for poor performance. I wrote about all of that before. But one thing that multiple subscribers have asked me is how I continue to get jobs despite my track record of being fired so many times.

Let’s assume most people are a 7/10 in job performance and a 5/10 in interview performance. It’s far easier for them to keep a job than get a new job. I’m a bit different. I’m probably a 4/10 in job performance and a 9/10 in interview performance. In fact, even after getting fired, I reliably land new positions that are more senior than my previous job, and pay more. In fact, after the firing I mentioned before, I wound up being hired as a Director of Product—yes, from a Senior Account Manager role—which paid 60% more. I was, of course, eventually laid off from that role as well (although not for performance—more for the fact that my job didn’t need to exist,) and I was unemployed for a few months. But ultimately, I wound up with a better job than that, after a four-month job search.

So, after a thirteen-year career of repeatedly getting fired and failing upward into better jobs. I’m going to share my job search secrets with you. This includes a late-stage interview tip that—I’m not kidding—has a 75% success rate in landing the job offer. I’m going to get into the interview and application process, but also things like how to balance multiple opportunities, how to talk about salary before the offer letter, and even tricky things like figuring out maternity leave policy without scaring employers off.

But first, a few disclaimers:

1.) These tips are things I learned from my career in tech, primarily in sales, account management and product. Some might be a bit specific and would not work for other industries or departments. Others are more universal.

2.) I don’t advocate lying, especially not about the big stuff, like titles or how long you worked at particular places. The good news is that you don’t really have to lie, unless you did something so bad it wound up in the news. Some white lies (or lies by omission) are more or less inevitable, but they’re very common.

3.) I’m sure some naysayers will accuse me of being a “DEI hire” and say that DEI explains why I got these jobs so easily. Allow me to retort: even if you want to assume that all women suck at their jobs, I am so bad at my jobs, specifically compared with other women, that I clearly have a unique talent for getting hired. My illustrious track record of getting fired proves this. Most women are not fired constantly, so cast aside your DEI-related doubts and rest assured that I am uniquely untalented and bad at my jobs (despite actually trying to be a good performer!) that DEI couldn’t possibly explain my incredible good fortune in the hiring process.

So let’s get into it!

1.) It’s almost all about how much they like you.

You might think that the success or lack thereof of your interview is about your experience, your skills, or how relevant a fit you are for the job. Those things are all important, but how much the interviewer likes you is really like…60% of it.

In fact, the Director of Product job I got was more or less sealed after one phone interview with the hiring manager (the VP of Product.) I did have to go through some interviews after that point, but it was clear from that point on that things were going well. He even told the external recruiter that it was the best interview he had ever conducted. We barely spoke about work at all, and we talked for 90 minutes.

In fact, we talked mostly about our personal lives, our attitude about work and family, and our general values. He was a father and felt strongly about work-life balance, so we talked endlessly about his kids, the value of remote work, and the importance of working with people you like on a personal level. I was actually extremely under-qualified for this job, but liking me was enough.

Andy Bernard wasn’t wrong—I happened to have a decent amount in common with this guy (extrovert, family oriented, etc.) but I’ve noticed that it helps to mirror the other person’s general “vibe.” When I’m interviewing with someone who doesn’t have kids, I almost never bring up mine.

You might be like, wait, CHH, I’m not likable at all! And don’t worry, neither am I, at least not innately. But you don’t have to become actual best friends with your interviewer, you just need to be likable enough for a few conversations. Being likable for an interview is very different from being likable on dates or with friends, because the latter two scenarios involve asking a lot of questions about the other person, whereas interviews are all about you. Perhaps I’m naturally gifted at interviews because I’m naturally inclined to talk about myself endlessly.

But anyway, here are some more tips on how to be likable in an interview: