Notes from the AI Underground, Prompt #9: Get a Job!

Wherein we discuss Artificial Intelligence, Oscar Wilde, job searches, LinkedIn, funding startups, HR, ATS, Human vs Machine, Leonard Cohen, the rise of bureaucracy, love letters to hiring managers, playing operator with goldfish, finding the right words, Gen AI, Glassdoor, Rocky III, and the future of talent and recruiting.

“A career is born in public – talent in privacy.” – Marilyn Monroe

I’m currently on my second startup. There are so many metaphors one could use to try and explain how vast a founder’s perspective changes between their first and second go around. I’m sure you can scroll down your LinkedIn feed and find at least two or three listicles or infographics about the subject.

I’ve done a lot of things twice – had two kids, wrote two books, released two albums. I’m a Gemini, so technically, I’ve done all those things four times. Regardless, I’ve never learned so much or had such a wildly different mindset shift upon doing something for a second time.

One of the key takeaways of founderdom is that unless one is funded to the gills in their new venture, or independently wealthy, you should probably keep your day job. You are inspired by your idea, and while others might be inspired too, most of them need to get paid. You, as a founder, are the one who ends up doing that.

So obvious in hindsight. Investors and advisors may warn that they expect the founder to be committed full time, but that doesn’t mean they will pay you to do that. ?

“Going to work for a large company is like getting on a train. Are you going sixty miles an hour or is the train going sixty miles an hour and you’re just sitting still?” – J. Paul Getty

So, I now find myself in a position I have not experienced in 30 years: looking for a job without technically being in one. At least not a job at a big company that makes it easy for a recruiter, or hiring manager, to find me and my applicable skill sets and easily match that to the role for which they are hiring.

Like many of you who have worked in large organizations, I have found myself being recruited on LinkedIn throughout my career. It’s the first place recruiters go. Find someone currently in a role at a big company and put them into a similar role at another big company. I was recruited into Ogilvy from HFI, from there I was recruited into Accenture. I wanted to work in a unicorn product company, so I leveraged my relationship with Prezi while at Accenture to get a job there. It's a corporate cadence that retrospectively seems like a conveyor belt.

It's a different world when you don't have that F100 address that makes it easy to find you. Upon reconnecting with the process of trying to find a great job, I’ve reached out to my network over the last set of weeks. For many of you that I have talked to you know what it’s like out there right now. For those who don’t, let me be blunt: The current state of the hiring apparatus is an excruciatingly-difficult and mind-numbing process that could make a lesser person shrivel up and pray for a natural disaster.

At the same time - because, remember, I’m a Gemini – it’s not without its positives.

But let’s talk about the shitty part first.

“The best way to enjoy your job is to imagine yourself without one.” – Oscar Wilde?

This may not be news to a lot of you, but the application and hiring system is in its darkest days. Three little menacing words ring through the sleepless, addled minds of every job seeker on the market right now: Application Tracking System.

Not unlike Voldemort, no one calls it by that name, unless they are trying to sell it. Most refer to it as ATS. It’s an AI-led, algorithmic system that relies on keywords and witchcraft to adjudicate whether an applicant’s resume is right for the role to which they are applying.

A recent study by Jobscan revealed that 70% of resumes get filtered out before they even reach human eyes, which means ATS has an outsized impact on who gets remembered and who gets lost in the digital ether.

On one hand, a company having to deal with 1,800 applicants for a single role is a massive problem. But lopping off 70% of your candidates in a somewhat arbitrary manner is an even bigger problem. One with far-reaching implications. More often than not it results in employers missing out on top talent. Instead they get a pool of candidates who were really good at getting the exact key words right.

This is not only frustrating many potential, high-caliber candidates, but it's also damaging brand reputations that many companies worked very hard to build. Armies of disgruntled applicants are currently railing on the process, leaving horrible reviews on Glassdoor, et al, cratering the scores of once popular organizations. One might think this doesn’t really matter. But talent is still one of the top battles these companies are fighting. 85% of job applicants research companies on these sites in order to decide where they should bring their talents.

In an artful display of irony, all of you who were worried AI was going to take your job are wrong. It won’t take your job. It will just keep you from getting hired. - Chris Cole

Obviously, AI can and will be of immense help in the hiring and selection process. Eventually, it will be effective in helping solve things like: how does one sift for gold amongst the mile-high heap of resumes HR receives for a given role. However, like a lot of instantiations of AI at this current point in history, ATS is best used as a co-pilot not an auto-pilot.

Perhaps we have become so awestruck by Gen AI that we believe one can materialize a candidate by putting the right prompt into ChatGPT. But, no, we can't Midjourney our way into this yet. The right candidate won't materialize in the same way a LinkedIn head shot of you in the style of Wes Anderson will. That expectation is not fair to the candidate, the hiring manager, or the HR professional.

Trying to convey the essence of what a hiring manager is looking for in a rock star BizDev exec, or a marketing guru, or an operations leader in a few key words is an unnecessary and fruitless effort. Especially since the same role may require vastly different personalities and cultural fits, depending on company, geo-location, industry, etc.

Besides, how are candidates supposed to cram the sum total of their experiences, stories, anecdotes and achievements into single keyword phrases that miraculously match what a hiring manager, HR professional, or algorithm might have meant by their keywords?

Companies are not trying to hire someone with ESP. They are not trying to hire resume-building professionals. They are trying to find a competent Partnership Lead, or GTM Strategist. Some of the best hiring managers might not recognize exactly what they need until they actually meet and talk with a candidate. Needs vary, contexts shift, cultural fits and personalities matter.

Worse still, HR, Talent and recruiting professionals get caught in the middle. They are some of the most highly skilled and honed listeners we have in the business world. They go through years of training and then marry that with hard-won expertise. All to arrive at a place where even they have to meet and interrogate a candidate before truly feeling that there might be a fit. Now they don’t even get to see a resume until 70% of candidates are jettisoned.

Who is to say the 30% who did make it through ATS screening are even good at the job to which they are applying? Perhaps they’re just really good at filling out forms and gaming the system. And, hey, if you’re in the market for an army of bureaucrats, maybe it’s the right system for you.

This whole ATS process, in its current state, is about as effective as playing operator with a goldfish. Yet, the business world saw fit to employ - almost overnight - this blunt force weapon that scythes off 7 out of 10 of the people who were interested enough in their company to take a couple hours and go through the application process. That’s a pretty barbaric and cynical way to claw back costs.

Just because something is efficient, doesn’t mean it’s effective.

“If opportunity doesn’t knock, build a door.” – Milton Berle?

So what’s the good part, you may ask?

The resistance I have felt getting back in the ring over the last few weeks has been unexpectedly inspirational. Getting pissed off, confronting my ego, getting knocked down - it's made me feel like I'm in the third Rocky movie (the one with Mr. T). For those who need a refresher: by the third movie Rocky had gotten complacent and was starting to punch below his weight class. He needed to get back in touch with what got him where he was. He started training with Apollo, running in the sand, doing sit ups while hanging from rafters. He got back to the fundamentals. In touch with the drive and ambition and alertness that made him successful in the first place. I’m not sure I’ve seen the movie since I was a little kid. But I can remember the essence and I hear the message: I’m a fighter.

I have done some cool shit over the last decade. Over the last year. Stuff that happens to be very valuable for where we are now, and where we are going. Having to really activate those things, having to tie them together so they are contextual to a particular role I want... well, it's work. But work is what I am seeking.

All of us are more likely to enjoy and be successful at what we do, if we have to seek it out. If we have to really examine how our skills and passions best activate, rather than resting on the laurels of being in the right company, in the right role, so that we are easy to recruit.

Like most problems and obstacles, the workarounds often lead to unintended but beneficial consequences. That’s what I’m finding. This sometimes torturous process has brought me so much, if I look at it from a clinical pov.

1.???? Reconnecting with people I haven’t talked to in years

2.???? Enlivening dormant swaths of my network

3.???? Making new connections and strengthening my already valuable network

4.???? Re-enlivening muscles and skills that I haven’t had to use over the last decade

The entire process, as broken as it may be, is already making me better suited for whatever role I end up falling in love with over the next month or so. By understanding how rough this process is, I have gained empathy with the people I might be hiring one day soon, or the people I work with in HR and recruiting. Hell, this may even be the impetus for startup number three.

In fact, as I was polishing the last section here, I got a call from one of the long lost re-connections I made in the last week. He has an amazing opportunity that may work out. One that I didn't apply for, but that nonetheless found me. Because I went looking.

"It's not so much that I got what I was looking for, but the search itself dissolved" - Leonard Cohen

At least half the people I’ve reached out to, over the last few weeks, have recently lost their job, or accepted a gold-plated parachute, and find themselves in a similar position of searching LinkedIn and their soul. Obviously, seeing smart people getting jettisoned bums me out. But we’ve traded stories, reciprocated on recommendations, promised to look out for one another. We have deepened our connection to each other. In the midst of fighting a war with a broken and battered system, we have found each other. Again.

And even if we can’t find the exact words, we know how valuable we are.