The Modern Job Hunt

So, I’ve been meaning to write this post for a very long time. I have been searching for a job for roughly a year. I thought about doing the post in parts and pieces as I interviewed with companies like Facebook, Dropbox, and Palantir, but I never had a solid ending until now. And what is a story without a good ending?

Modern Metaphors

First off, I dislike how much modern job hunting is similar to online dating. It is no longer a job hunt where I’m slowly stalking my prey in a tailored suit armed with a degree in one hand and a handshake in the other trying to separate the eager and looking from the herd to pick off a healthy piece of personal income and profit sharing.

It is now an entire courting process filled with winks, pokes, subtle flirting, and wasted time. The experience of searching hundreds of online profiles for open positions, sending your initial, tentative application message and hoping for a response will be déjà vu for any modern online dater. Sites like LinkedIn, AngelList and Monster are simply cousins to OkCupid, and E-Harmony, and they are not even distant cousins. AngelList uses similar methods and language to pair candidates and companies:

“StartUp A is interested in you!”

So, you finally get a response. They like you, your profile, and want to learn more. So, after a few awkward scheduling emails, you finally have a first date and the relationship begins.

First Dates

In the dating world, this ends up at some local watering hole. In the career world, this is normally a phone call with HR or the hiring manager. Regardless, the little white lies, exaggerations and superficiality seem to be exactly the same. (A fitting SMBC comic.)

So, typically this is where you learn about the role (assuming you couldn’t read the job description), you learn about the company (assuming you didn’t research anything about them), and you learn about how great the culture is (assuming they’d tell you if it was bad). Very little new information comes from these phone calls in my experience.

This is also your chance to “Tell-Them-About-Yourself” – your hopes, dreams, and career goals. At least, all of the ones that align with the current position. At this point, you don’t want to deviate too far from the pitch that this is the company of your dreams, and you will be together forever. When HR is deciding to move forward, they already have an image in their head of how you’ll fit within the company. The first date is not the time to ruin that image.

So, like any first dates, both parties are trying to put on their best face. Honesty and complexity seem to take a back seat. Many companies do not want to acknowledge that the career market no longer includes pensions, 40-hour weeks, and 40-year loyalty. Because of these shifts, many companies want to hear that you’ve already drank the Kool-Aid and believe in their mission statement and values before you’ve even experienced them. Now, I agree you should at least know their values, and be intrinsically motivated and attracted to the role and the business, but in my opinion, these first dates felt like a relic of a previous time, and they need to change.

In my experience, the best first dates I had were second dates. They immediately connected me with people in the position – no call with the recruiter or HR. They allowed me to learn about the role from someone doing it every day. I learned more directly about the culture, and the greater level of intimacy just allowed things to flow more easily.

Multiple Second Dates

As I mentioned above, the rest of the interview process was typically with potential colleagues and bosses. This allowed a much greater level of matching. Both parties could really learn about role capability and cultural fit. Additionally, I think there was more room for complexity in these conversations. One of my favorite questions concerned the challenges of the role, or what the interviewer would fix at the company if he could. The predefined image in the interviewer’s mind was a bit more blurry and free form than HR’s connect-the-dots picture.

Often, these were the interviews where it became obvious that I just didn’t belong. The role demanded something of me that I was lacking. I am no longer as much of an engineer as some positions required. Or, I lacked in-depth experience in X, Y, or Z. And, honestly, I’m perfectly understanding of these conclusions. If I would be unhappy or ill-equipped for the role, I would rather find out earlier than later.

The Third Date

(In the world of Tinder, are third dates still significant? Is it still a relevant marker in pop culture or am I getting too old already? )

So, I’m going to mark third dates as in-person interviews. These varied from half-day to whole-day marathons and were pretty different between the companies. The best ones had me perform a task similar to one I would do on the job or test my presentation ability. Often, there was repetition from my second-date experiences, which to some degree is okay. However, I like to think that interviewing is an exercise in validated learning, and repetition shouldn’t be necessary if the process is planned correctly. If the goal is to learn about the candidate, then steps should be in place to learn the correct things only once to save time and resources.

One of the weaknesses of final interviews was the lack of insight after a rejection. After an entire day invested, it was hard to pinpoint where third dates went wrong and why were you not invited in for a night cap. I have my general theories and was able to pick out key weaknesses (such as not wanting to work in a SCIF after biking around Google), but additional feedback beyond the generic ones about fit and experience would be great.

As a thought experiment, what if I had drunk the kool-aid and was extremely passionate about the company. Heck, lets pretend I would work there for free. I interview and things end at final rounds. Ideally, I would apply again and again until I worked there because it is my passion. However, I’d have no data to learn from and no way to grow from my failure. I may keep making the same mistakes or whole new ones without any awareness. Now, if the end goal of the company is to get talented, passionate people, wouldn’t feedback help this eager employee who will likely get a job at your place eventually or potentially divert their passion elsewhere?

“One person with passion is better than forty people merely interested.”- E.M. Forster


Now, on the note of feedback, I don’t quite know how to include the recent rise in applicant homework to the dating world. Maybe it is similar to providing a favor to a friend, like dog-sitting, where you are proving to be a fitting friend with little expectation of a return.

For the most part, I didn’t really mind the requests made of me. They ranged from Powerpoint presentations, to distilling an Excel sheet, to specification documents. Heck, I’ll even count coding interviews where I had to open up a Google Doc, Collabedit, or similar tool and type out an algorithm over the phone. I understand the purpose of these assignments, and I believe they are very helpful from the standpoints of validated learning and a minimum viable employee. Am I capable of doing a small fraction of the necessary work in an acceptable manner? It makes perfect sense, and I think more companies should use homework as an additional data point.

However, I had one major complaint as time went on, and I was investing more and more time to these assignments.

Feedback is non-existent!
Companies – this is not all right. You shouldn’t ask a candidate to invest hours of their time and expect nothing in return. Even if I did really well on an assignment, there were likely weaknesses that I could improve. And if I did poorly, I want to learn from my investment of time and effort and do better in the future. Both scenarios would benefit from feedback. It reached a point that when I learned there was homework involved I would ask about feedback from the start.

I understand most companies do not want to enter the legal murky ground that feedback could become. However, I think even sanitized and general feedback that passed through legal would be better than nothing. Give me a score on a few categories or something. Try to keep it objective. There has to be a middle ground of feedback that is less legally risky and helpful to the candidate.

Now, maybe I’m especially sensitive to this issue since I just left graduate school. Life was built around performing a task and getting evaluated. To do the former without the later just seems like I’ve been cheated. This just insults an internal measure of fairness in my mind. If I invest a few hours of research, time and effort into a company for them to better evaluate me as a candidate, then I expect at a minimum an acknowledgement of strengths and weaknesses and ways to improve. This way, both parties can value from the homework experience instead of it being completely one-sided.

The Pipeline

So, like anyone on the dating circuit will realize pretty quickly, you can send plenty of highly-personalized and in-depth messages to a dozen profiles and never hear a thing. Or, you can send 100 copy-paste messages and get replies from 10 of them. Many times, it seemed like an expansive pipeline was a much more important aspect than a pristine and passionate cover letter.

Additionally, an interview process could range from 3 months to 2 weeks depending on the company. Interviews seemed to come in waves, and a rejection email could happen at any point. Just like dating, after a few lovely dinners and drinks, your prospective love can stop replying to your calls, your texts, and just break all contact with you at any moment. (The nicest ones will at least email you when it didn’t work out.)

Now and then I think of when we were together
Like when you said I was so perfect you could hire
Told myself that you were right for me
That I’d be happy with your company
But that was hope and it’s an ache I still remember
You can get addicted to a certain kind of call back
Like optimism to the end, always the end
So when you found that I could not move on
Well you said that we would stay in touch
But I’ll admit that I am sure you were lying
But you didn’t have to cut me off
Make out like it never happened and that we were nothing
And I don’t even need your offer
But you treat me like a stranger and that feels so rough
No you didn’t have to stoop so low
Ignore my emails, skip my calls, and then change your headcount
I guess that I don’t need that though
Now you’re just a recruiter that I used to know
Now you’re just a recruiter that I used to know
Now you’re just a recruiter that I used to know

Gotye Parody – ‘Recruiter That I Used to Know’

In terms of pipeline, I applied over 100 times at different companies in a variety of roles that leveraged my Computer Science and MBA backgrounds to varying degrees. Between Jobvite, Jobscore, AngelList and others, I tried to keep the pipeline alive at all times. Now, as you can see, I did lean towards smaller, private technology companies with a few of the big names sprinkled in. My starting guide was actually The Big Data Landscape with some Crunchbase and Forbes lists to round things out.

Below is a list of all the companies I spoke with in some form (some even twice or thrice for different roles). This list doesn’t include all of the companies that I applied to that declined to go on a first date. That one obviously is a bit longer.

My Wall of Learning

  • Amazon
  • BlueKai
  • Booz-Allen-Hamilton
  • CloudFlare
  • Dropbox
  • Egnyte
  • Evolv
  • Facebook
  • Google
  • LiveRamp
  • Localytics
  • Medallia
  • Mixpanel
  • Opower
  • Palantir
  • Pivotal
  • RelateIQ
  • RocketFuel
  • SalesForce
  • ShareThis
  • Socrata
  • SocialCode
  • Sumo Logic
  • Yelp

Now, I have individual notes and opinions on each interview process. Aside from simple things like what Facebook asks during a programming interview, some experiences strongly painted my image of the companies both positively and negatively. Maybe I’ll share them someday anonymously on Glassdoor, but to remain diplomatic, I’ve tried to aggregate the bests and the worsts in my conclusion.

Best Practices

So, given this new metaphor that the job hunt is akin to trying to find a relationship with someone, it only makes sense that the best interviews were with companies that were open, communicative, and efficient. They treated me like a person and not simply an online profile or resume. Time was considered valuable on both ends.

Efficient Scheduling

The best companies I worked with had online systems for scheduling an interview. Some were homemade during hackathons; others simply leveraged Google. They made their calenders transparent to immediately set up a phone call. This little tool saved time and 2-3 emails covering the question of open time slots and availability. It is grease on the wheels of the interview process, and I immediately gave mental brownie points to the companies and recruiting teams that used it. It is the little things, ya’know?


The worst companies I interviewed with required me to ping them every week or two just to keep things moving. It felt like the onus was on me to crack the whip and get my own job. This was typically after a few great interviews and positive feedback. The world would just slow to a crawl with no message or update at all. I’ve had scenarios where it took a month to hear back after a first and second date despite me contacting them in between for a pulse.

Communication is easy these days. With candidate tracking systems like Jobvite, you’d think it be a joke to keep candidates in the loop. The best companies kept me aware as much as possible. They informed me about the process and any snags it may have hit in terms of vacation days, paternity leave, and conferences. I can understand these reasons for delays in the interview process, just let me know so I don’t assume you are one of the bad companies that don’t communicate at all.

Now, many companies (most not on the list) simply refused to communicate at all. A token rejection email is better than nothing. It is at least a data point. A fun trick I noticed was when my Jobvite status was updated, but I never got an email from the company saying good-bye. I was simply “Not Selected” or the position was closed without any actual external acknowledgement. In all honesty, I would’ve preferred the token email. Oddly enough, there are still a few companies ‘In Process’ that have yet to respond to my pings for information after some nice second dates.

The Layers of a Relationship

Many of our modern relationships are completely managed online. From tertiary Facebook connections to burgeoning love and friendship at OkCupid, we are much more comfortable with building, managing, and expressing our relationships online. This mindset seems to be lacking from many recruiting offices.

From the moment we have a first date, we are professional strangers. Expectations at this point are minimal, and I’m perfectly content with things ending quickly and quietly. Heck, I went on so many first dates when I first joined OkCupid, yet very few second dates. If things simply will not work out, I would rather know early than waste more time for either of us.

From the moment we have a few second dates, I think we are professional acquaintances. My expectations are a bit higher in terms of communication and trust. If something changes or things simply aren’t working, I would rather know than not. Send me that rejection text or email. I understand that better than radio silence.

From the moment you ask me to do homework, I think we are professional friends. You’ve asked a favor of me, like dog sitting or helping you move, and I expect a something in return. It doesn’t have to be a job, but something akin to pizza and beer would be great. I think feedback is reasonably similar in that it helps the relationship grow positively. Same communication rules apply for friends and acquaintances, simply tell me if you don’t want to hang out anymore.

From the moment I have an in person interview, I think we are professionally engaged. Now, the metaphor breaks down a little, but hear me out. We’ve both potentially invested a month or two into the process with a handful of phone calls and one or two favors. At this point, we are determining whether I can really cut it as a future colleague with more in depth conversations and testing. At this step, I would love to hear about rejection or an offer as soon as possible. You would not inform your fiance that things are over by ignoring them or lying to them. Communication should be as open as possible at this stage because the next step would be equivalent to marriage with an offer and a commitment from both parties.

Weeks without communication with many of our friends would feel so foreign to us these days, yet it seems to be the norm at many recruiting offices despite the ease of email and candidate tracking systems. I think our comfort with building, managing, and expressing our relationships online needs to be explored better in the interview process. The current steps that exist seem a little counter-productive if the end goal for both parties is a happy professional marriage with a passionate and capable employee.

My Happy Ending

Oh, and yea, I got a job at CloudFlare, Inc. in San Francisco as a Solutions Engineer. I’m looking forward to being back on the West coast and starting a new adventure with a great company. CloudFlare, Inc.


  1. I’m amazed, I must say. Rarely do I encounter a blog that’s equally educative
    and entertaining, and let me tell you, you have hit the nail on the
    head. The problem is an issue that not enough men and women are speaking intelligently about.
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  2. Loved your piece Dan. I find this quite fascinating and I especially liked the online dating metaphor. Congrats on your nuptials 🙂

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