The Worst Interviewing Experience I've Ever Encountered (part 1)

Though I'm currently not on the market for a new opportunity, I like to keep my eyes and ears open if I hear of anything interesting.  In the past quarter, I came across an interesting opportunity on AngelList, and decided to apply for the position.  The rest of this blog post is a funny little story of the unexpected turn of events.  My next post will reflect on lessons learned. For the sake of confidentiality, I left company and names anonymous. Anyway, this position I found on AngelList sounded extremely suiting: not only was it in a field that personally represented me well, but it was also a rising, profitable, up and coming company with a strong brand.  To top it off, the company had big lofty hiring goals, three separate offices and currently did not have anyone in the HR/Recruiting function. It was a big opportunity for me to step it up and help be part of rising company. I was excited about the opportunity to establish the framework for future hiring practices and to spearhead the organizational development/structure of the company. Sounded pretty "dream job" to me. I sent my resume in on May 21.

A week later, the CEO of the company reached out to me for an initial conversation. I was ecstatic! I spent about a week researching about the company and brainstorming new ideas that I could share.  In my head, I nailed it already.

First Phone Interview: When it was time for the call with the CEO,  I was super excited and had all my notes ready. To my disappointment, after about 5 minutes of introductions and learning, the CEO cuts the conversation short.  "Unfortunately, it doesn't look like you are a good fit for the company. We want someone with a retail background, and yours seems too technical."  I fought back, saying how I could adjust to the role, and how I was adaptable (don't give up on the initial rejection!).  That's what a good start-up recruiter does anyway; you need to be flexible with whatever the company needs.  He responded "I know that you'd be perfectly capable, but we prefer to have someone with a retail background. I have a friend at Company X that is looking for a technical recruiter and can refer you over there if you're looking."  Ouch. I tried another rebuttal, but at the end, I left it with "if anything changes on your end, please don't hesitate to reach out to me."

After getting off the phone with him, I was naturally pretty upset. What does it mean that I am "too technical" anyway?I cant believe he tried to pawn me off to another company (that company, by the way, has the same engineering chops as my current start-up, and we often compete for the same talent pool -- aka we try stealing each others engineers. Company X is well aware of our recruiting team, as my colleague received an offer from them before deciding to join us. They also reached out to me for an opportunity about a month ago). I eventually got over it. After all, it was probably the universe telling me that it wasn't meant to be.

The Boomerang A few weeks later -- surprise, surprise.  It was a Sunday evening, and I receive an email from the CEO.

Hmm.. Okay that's nice. I guess I can give it another shot. I mean, it's still an interesting opportunity so let's continue conversations. To be honest, at this point, I felt victorious, like heh heh, I knew you'd come back.

I ended up speaking the the Head of People on the phone the following week. She was fresh into the job, as the day I spoke to her was her first day at the company. Overall a smooth conversation, and we decided to move things forward with a coffee date.

Hmm.. Interesting.. It was Friday, 3 days before I was schedule to meet with the Head of People. In the afternoon, I get an email from the CEO, telling me how the Head of People had left.

Er.. okay, well that's weird. Whatever, I'll roll with it; I get to meet the CEO, so that's cool, and I like meeting entrepreneurs.

Coffee went well.  I learned that the Head of People worked at the company for maybe a couple of weeks (days?) before leaving for a full time role. That should have been a huge red flag for me, but nonetheless, I was still excited. Later that day, the CEO emailed saying he wanted me to meet more members of the team. Sure, I'm game.

The onsite interview, finally! I took the day off to meet with the company.  There was no doubt that the management team was a smart group. They all attended graduate school together, and seemed like they knew their stuff. Overall the onsite interviews went smoothly (I was impressed too, given their lack of having a centralized recruiting or HR team).

However, I do recall having a strange interview -- probably one of the toughest interviewers I've had by far.  He basically came into the room, looked at my resume, and off the bat said "you're going to leave us in a year."   I was a bit confused, and asked him what he meant. "You've job hopped around and switched jobs pretty much every year" (valid point -- be sure to know how to answer this if you're like me).  I justified myself, but he threw me another weird question: "why do you think you're so good?"  That was another question that threw me on edge, but lol, I'm confident enough in my abilities to justify that, so I gave him some examples.

At the end of the interview, the CEO synced up with me, and asked me the typical concluding questions, like "when can I start" and "what are my salary expectations."  I told him I was available as soon as September, and that my salary expectations fall in line with the range provided on their AngelList profile.  He responded with "I don't even know what we listed for our current range; it was a huge range we wrote." Another red flag to me, as you cannot just bullshit your numbers publicly like that! We wrapped things up, and the CEO told me he'd have an update for me by the end of the week.

Oh yeah, before walking me out, he asked if I could do some "homework" (aka free labor) and send him some profiles I thought that would be good for the Program Marketing position. I was happy to do it because I wanted to show them my interest level, and my ability to source non-technical roles.  I spent the rest of my evening sourcing and finding several top notch candidates, and emailed them over promptly.

Sitting, waiting, wishing.. Given that the CEO is a busy man, I gave him some extra time before following up with him on feedback. He originally promised to get back to me by the end of the week (which was 2 business days), but I gave him a full week. After nervously following up, I receive an encouraging email from him saying that feedback was positive and that they wanted to move forward with next steps.

OMG -- AWESOME! I was really happy, because those are typically good words, and things you want to hear. It's been a 2.5 month goose chase, and the end looked like it was drawing near.

Bait and Switch We hopped on the phone later that week, and I left the conversation really confused. He told me that they liked me and that feedback was all positive; yet at the same time, they were not sure of my interest level and were continuing to interview other candidates? Er.. okay. He also asked me if I'd be negotiable on my compensation (clearly, it looked like they were not really ready to provide those salaries listed on their AngelList and fudged the numbers). I told him my ultimate decision would be based on the whole compensation package -- equity, flexibility, benefits, bonuses along with base pay.

Given there were a couple other candidates in their interviewing pipeline that he "wanted to give them a shot." I complied and agreed to give them another week and a half to get back to me. Granted, it's already been 2 weeks since my onsite interview with them; I was not going to let myself be dragged along in the process.

The strangest last week ever My patience was running thin (and I'm sure yours is too, don't worry, I'm almost done with the story). In my head, I'd give them ONE LAST WEEK to get back to me, otherwise I would withdraw from the process. Everything up to this point has been unnecessarily drawn out: my feedback was positive and they were interested, yet they were still interviewing other candidates.  Reject me or move things forward; don't keep me in limbo. We've been talking since early June, and it's already mid-August!

Anyway, on the week of August 11,  I had the strangest emails. First, an external, third-party agency recruiter messages me telling me about the opportunity.

I thought this was hilarious, yet at the same time, I didn't know how to feel.  Was it a compliment that an external recruiter thought I'd be a good fit? Or a slap to the face because this clearly indicated to me that they were still looking around?

The next day, I get an even stranger email from the CEO asking about my relationship with my coworker, including in a LinkedIn profile to my coworker.

When I got this email, for lack of better words, I WAS PISSED. What does this even have to do with my candidacy? Why bring this up now, after we've been talking for 2 months? Plus, if he was paying attention to my resume or interviews, he'd already know the answer. Most importantly, is he breaching interviewee confidentiality?! Not cool, man. After debating in my head how to respond, I decided to drop it and just let it go. I'll give a couple days to cool off and decide what to do from there.

Ending the chase This past Monday, I emailed the CEO letting them know that my circumstances have changed and I wanted to stay put. It was a nicer way of saying that I was no longer interested in the opportunity and chose to withdraw. I felt completely liberated, because this whole process has been a complete (emotional) roller coaster, when it shouldn't have. To this day, still have not received any message back from the CEO, not even an email of acknowledgement.

The process took almost 3 months (applied on May 21 and ended things on August 18). For a fast moving start-up with a high caliber management team, it was a disorganized and disappointing interviewing process.  There were multiple hiccups in the process, with the initial rejection, the boomerang, and the Head of People turnover, false promises, and strange unprofessional emails.  Overall, interesting experience, but I have absolutely no regrets for withdrawing.

Stay tuned for an even more exciting Part 2 sequel, about Lessons Learned.

Have you ever experienced a difficult interview or interviewing process before? I'd love to hear about your story!