The Modern Headcount

I can’t help but look back on my article highlighting how it feels to look for a job these days and consider what things look like from the other side of the interview table. 

Broken Metaphors

The biggest flaw in the dating metaphor is that the candidate is not dealing with a single entity. It may feel like interacting with Company A is like dealing with a single person – a living, breathing, single-minded business. However, it is made up of fractured and ultimately busy individuals. When that recruiter doesn’t message you a rejection letter, he isn’t being rude; he is simply going home to his family. Those second dates that don’t reach out are busy dealing with a change in headcount and priorities. And those third dates are simply a fraction of a workday that has to be dedicated to finding yet another plate spinner in the middle of a one hundred plate performance. 

“Startup A* is interested in you!”

* Read – Either some recruiter or some hiring manager thought your resume looked neat. The corporate entity known as Startup A has no legal opinion of you at all.  

If the modern job search is like online dating that is ends in career engagement, then the modern head count is trying to find that marriage partner through speed-dating by committee. I get 30 minutes on the phone with you and ten other candidates to decide if someone else should invest even more time into the relationship. My entire team rotates through an interview room to get to know and quiz everyone. All told, we get 3-4 hours tops to hone in on whether you are more capable for the job, a best fit for the team and company culture, and ultimately, the best person to work alongside. If a job offer is professional marriage, then you are telling me that a team of people has to decide matrimony after only a whirlwind afternoon romance with a small handful of people. Running with the metaphor, the honeymoon phase must be over after week one.

1st Phone Screens (AKA First Dates)

First dates are necessary. They are the level-set before either party continues to invest more time. We are checking if basic wants and needs align. What if there isn’t mutual attraction? What if there is a red-flag – like he still lives with his parents? What if you don’t want to move to San Francisco? Or, your salary expectations are extreme? First round phone screens with the hiring team are the level-set that speeds everything up down the line. You want to find the job of your dreams; we want to fill a position while also keeping the trains running on time. A first date buffer helps accomplish that for everyone. 

Are the questions and topics a little superficial? Sure. But, at this point all you know about the role, job, and company is what you’ve read from the hiring page, some Google searches and a glance at Glassdoor. You may think this is your dream job, but how do you know until you ask a human being some legitimate questions? They don’t have to be complex questions, but at this point, isn’t more data better than less to test your theory?

The problem with wanting to cut the line and chat with someone in the role is simply scale. You are one of many. You may think you are Gate’s gift to programming, a Rembrandt of branding, and a strageic Stradivarius. Statistically though, that is unlikely. (Yet another fitting SMBC Comic.) And 30 minute calls with everyone for screening can take a lot of time. Can we get more in depth? More intimate? Sure. But this is simply untenable at any sort of realistic scale unless we dedicate a full-time person to it – one called a recruiter.

2nd/3rd Phone Screens (AKA Second Dates)

Second dates are great. The basics are out of the way. There is mutual attraction, and we can really get into the nuts and bolts of compatibility. However, I think the dating metaphor breaks down again at this point. Why? Because I have seen success before. I’ve seen people kick ass in this position. I’ve built an image of who we should hire based on this past experience. Barring plural marriages and multiple divorcees, this doesn’t quite fit the dating metaphor where both sides walk in with a lot more questions than answers.

Dating and a relationships have a lot more ambiguity, and hence, complexity in their courtship. Dating is about two imperfect humans beings projecting their wants, needs and vulnerabilities on one another. The job search is about a team of people mapping a job description and known successes against your background experience, personality type, and general capability. It doesn’t require the flirtation, awkwardness, compromise or intimacy of real dating – hence it just doesn’t quite fit the analogy. 

But, at least there is a spot of agreement between my older and younger self, we’d both prefer knowing earlier than later if you’d be unhappy or ill-fit for the role. This is more time for my team to interview other candidates and spin other plates. If anything, this conceit is even more evidence for the importance of a first phone screen/date and validated learning on both sides. 

In-Person Interviews (AKA Third Dates)

Once again, the metaphor benefits from a limited perspective. A full day of interviews to a single candidate is a bunch of fractured spots in the workdays of 5-6 other people. The interview was likely already a masterpiece of coordination and planning among multiple, very full calendars (Thank you recruiting teams everywhere). And as much as we may try to share notes and feedback, the interview itself was not planned to such utter perfection that we’d repeat absolutely nothing for validated learning purposes.

You (and your fellow candidates) invested an entire day interviewing. That is great, and we appreciate the time. But, are you hoping for a scorecard? A grade? An essay? For each of you? I’m a huge fan of feedback, but again, we hit the issue of scale. When you go speed-dating, is there an expectation that each person will hand you a handwritten, heartfelt,  personalized rejection letter? Even with advanced candidate tracking software, this would be a complete nightmare. And hence, you’ll probably get a canned rejection letter. Its nothing personal; its just dating at scale. 

As a thought experiment, say we didn’t move forward with an offer. However, you had drunk the kool-aid and were extremely passionate about the company and the role. What would happen? You would work for free. You would email people. You would try to learn. You wouldn’t wait for feedback; you would pry it from every email and contact possible. You would be the driver and motivator. Which is easier? Diverting your passion because I didn’t offer you any generic feedback, or proving your commitment by asking it from me outside of the hiring process? Establishing a relationship with me and others on my team until you finally get that position you so desperately desired?

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


Oi, another feedback complaint. You can really tell I was just out of a school system.

Applicant homework is our chance to see if you can really handle the job in even a small, single-serving way. However, I would disagree that it is like a favor. This isn’t dog-sitting or moving unless you want to become a dog-sitter or mover for the rest of your life.  Unlike small social favors, there is an expected return from your efforts – a job. Outside of that, the company owes you nothing to better yourself as a human being or future applicant. We are trying to assess your skills and nothing more. 

Powerpoints, excel sheets, and coding exercises are all attempts at affirming what you have on your resume and have espoused on your dates. And by ‘you’, I mean all of the candidates in our pipeline. So, once again, scale is the enemy preventing us from consistently grading and providing feedback for these homeworks even if we wanted. Keeping all the plates spinning does not normally require a written report on why all but one of the prospective plate spinners was asked to stop spinning paper practice plates (Say that one three times fast.) Ultimately,  it would be great if could provide that feedback, but it simply becomes impossible. 

The Pipeline

Dating pipelines. Candidate pipelines. Sales pipelines. Application pipelines. Marketing Pipelines. Pipelines are everywhere. Recognizing that your life tends to work in funnels and reward persistence, discipline, and sheer quantity isn’t very tricky. I would still agree with this entire section, but with some added advice.

I enjoyed a snippet of advice from the book “How Google Works.” It flips the concept of role-first hunting on its head with a surfing metaphor. The general practice when building pipeline is to prioritize company, then role, and finally industry. But, in the same way that a hostess at a five star French restaurant and a hostess at Hooters have very different day-to-day tasks, you’ll find a PM or SE (Solutions/Support/Sales/Sexy Engineer) can be extremely varied depending on the company, culture, and industry.

I agree with building a new career-pipeline by focusing on industry first since you’ll switch companies and advance in roles throughout your career. Industries that are on the rise allow to you specialize in an ever expanding pool of success. Starting at the company can pigeon-hole your dreams from the very beginning, and a role can vary so much between companies. 

Second, after you’ve confirmed you enjoy the industry and it’s direction, you can look for a company that you can grow within. You want to find the biggest opportunity, and at this stage you should have developed a unique skillset to your industry. The niche and general experience you’ve built up within your career can now be put to work in a great company.

Lastly, find your role. 

Personally, I started in computer science – an industry that definitely wasn’t shrinking. This led me into web development work for big data and entity analysis. I doubled down on big data and tech after my MBA, and ended up moving to California to work in internet performance and security with a great, growing company. Overall, I have enjoyed a nice and continued rise into industries and sub-industries that can offer me massive opportunity – assuming the internet never ends.

The Internet will never stop growing.

Best Practices

Make my job easy.

Come prepared to every interview with stories of past success and failure. Don’t make me pry it out of you with twenty questions. These stories should supplement your resume; so there is new information at play. I tend to enjoy walking away from interviews that are more dynamic and conversational. The ideal interview isn’t adversarial. We both have the same goal, and it is mostly down to you to prove that you are the best way towards that goal.

Know what we do.

You think this one would be self-explanatory. I don’t expect 100% knowledge or understanding. I always leave time for questions so you can learn more about the internal processes and culture of the company. However, I shouldn’t have to explain what our company does or what market it is in. A dead giveaway of a candidate failing this is when they just rattle off buzzwords from our website. Saying the word security ten times doesn’t really make the case for how we help customers. It is pretty simple, and an aspect of making my job easy – know what the company does.

When I was interviewing at smaller places, I googled the crap out of them. I found Youtube videos of current employees explaining the company to strangers. I even used the exact same explanation when interviewing. I read the blog and watched introduction videos. Anything to help me learn so I could spend the interview getting more detail and asking better questions. There really is no excuse for not doing things beyond a basic Google search.

Bring your own motivation.

Now, I’ll be the last person who thinks you need to have “drank the Kool-Aid” before joining a company, but I do expect you should bring your own water. When you are a full-time employee, I won’t have the bandwidth to motivate you. During the interviews, it should be very obvious that you are already motivated to do great work whether it be the aspects of the role, the aspects of the product, or the potentially awesome Kool-Aid mix.

Ask for feedback right in the interview.

  • “What do you see as success for this role?”
  • “Are there any concerns you have for me being a good fit?”

Layers of a Relationship

Many of our modern relationships are completely managed online, but recruiting is much more like Tinder than it is Okcupid. This isn’t burgeoning love, it is speed-date swiping by committee. A pile of resume’s get left- and right-swiped and only a few get funneled up to a brief chat. This perspective seems to be lacking from some job candidates. 

From the moment we have a first date, you should ask great questions and really learn if this is the right fit. All you have is an assumption that this is the correct industry, company, and role. Validate that assumption. Don’t just write off a conversation as some random first date that lacks intimacy. 

After one or two phone calls or in-person interviews, you are still a professional stranger. Sure, we’ve invested more time into screening and determining your fit, but that doesn’t suddenly warrant that we should update you when things change. I’m sure we will try, at least with a token email. But, remember, you are not cavorting with a single entity. You are not the only candidate in the pipeline. So, you may not always get to a rejection email. 

After we ask you to invest some time and effort into your application, you are still a professional stranger. We’ve asked a favor of you, sure. In the same way, we ask a favor when we require a resume to inspect, or details about past experiences. This is not a trade, or date, between equals. This is a daily double challenge between Alex Trebek and a random contestant. It is a very asymmetrical exchange. To expect any enhancement in the relationship just because we asked for a new challenge is pretty extreme. And as always, feedback simply doesn’t scale. 

From the moment you have an in-person interview, you are still a professional stranger. Only now, during the marathon of interviews, are we actually determining your fit as a future colleague.  At this step, we would likely keep you up to date on if you don’t make it, but you are far from a fiance – even my older self realized the metaphor started to break down around this point. 

From the moment we extend you an offer, we are professionally engaged.


My Happy Ongoing

Oddly enough, it feels wonderful to revisit this topic and this perspective from another angle. I always enjoy questioning my initial assumptions and positions. This was a fun diatribe against my younger self. 

Oh, and yea, I still work at company called CloudFlare. And guess what, we’re hiring in San Francisco, London, and Singapore. Come check us out.



Banner Image By Jerzy Strzelecki (Own work) [GFDL ( or CC BY 3.0 (], via Wikimedia Commons


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