I can't get a job because I can't get a job

It's really hard to get entry level PM jobs, and I think it's representative of a broader issue in how software companies hire.

The situation

I’ve been interviewing for Product roles around New York City, and I keep getting turned down for them because I don’t have enough experience. I’m sure this has happened to you before at some point, and it’s unbelievably frustrating. If entry level jobs require 2-3 years of work in that field, how the heck are you supposed to get one in the first place?

This isn’t an issue just for Product Managers. Entry level Data Scientists are supposed to have 2+ years of experience working with data. Designers are supposed to already have UX/UI portfolios. Why will startups hire Software Engineers out of college, but rarely anyone else?

The abstraction

There are three broader ideas at play here:

  1. Experience vs. skills – what role does experience play in successful work products?

  2. Appetite for risk – is a company willing to hire someone that hasn’t done this exact type of work before?

  3. Nature of the position – how straightforward is the end product of your job?

They all rely on the relationship between skills and success. In theory, we assume that the right skills and the right context (culture fit, savvy, interpersonal stuff, pace) lead to being successful at a job. The problem is that the world is random, so this connection isn’t always 100% accurate. Experience bridges the gap.

Experience helps beef up your skills, but what it does the most is prove the relationship you have between your skills and your success. With that in mind, let’s break down these abstractions one by one.

Experience vs. skills

The tech industry as a whole assumes that experience is a crucial part of being successful at a new role or venture. In theory, experience should ensure that you can pattern match: when an issue comes up, you will have seen it before (or something similar to it) and will consequently be able to effectively solve it.

I’m not so sure. The nature of reality and the complex corporate system means that new experiences will rarely resemble old ones, and even if you think they do that may not be the case. As human beings, I’m not sure that we get that much better at knowledge-based tasks over time if we already have the skills to do them well, aside from concrete / basic stuff.

In general, it seems silly to assume that experience is required to complete most tasks successfully. That’s why this ends up being a risk vs. return decision.

Appetite for risk

Startups aren’t stupid, and they know that some of their best hires will be the riskiest, least experienced ones. But interviewing is a numbers game, and companies can’t afford to interview every candidate that just might be a 10x opportunity. Experience is a filter, because startups assume that the following asymmetry exists in hiring:

  • Some people without experience will be great, and some people without experience will stink

  • Most people with experience will be great, and nobody with experience will stink

This is exactly the same trend as VC funds only hiring MBAs and Investment Banks only hiring kids from Harvard. It’s risk mitigation. As frustrating as it might be for candidates, it’s just a calculated filter.

The problem is that this asymmetry doesn’t actually hold as cleanly as companies think it does. Given the subjective and random nature of hiring, plenty of people with experience will end up stinking – that’s why they sometimes get fired too. Companies at the earlier stages tend to align with this sort of thinking, but get more conservative over time (until they can afford to explicitly hire junior people).

Nature of the position

Some jobs are more straightforward than others, which means companies can draw more direct lines from skills and context to success without experience in between. There are two broad types of jobs in this domain:

  1. Straightforward connection between practical skills and end product – e.g. Software Engineer, Graphic Designer, Salesperson

  2. Nebulous connection between practical skills and end product – e.g. Product Manager, Growth, Management

For the first category, something catastrophic needs to happen for someone skilled and contextual to fail. For the second category, it can happen all the time. Accordingly, if you’ve proved that your skills and context connect to success, you make the hire more straightforward for the recruiter. Recall that their incentives aren’t excellence: they’re lack of failure.

Here again I suspect there’s more nuance than companies allow for. Jobs that seem straightforward are often not really that simple (we don’t really have good ways of measuring engineering output / success, but that’s for a different time). And perhaps most importantly, experience doesn’t prove that you made a connection between skills and output – it just means someone trusted you to do so.

The fact that you worked at Facebook for 3 years doesn’t mean you did a great job, it just means you didn’t get fired.

This is why the way reference checks are done makes no sense to me. Most companies will only do it once they make you a job offer (?), and even then many employers only do verification. Why do we assume that working somewhere means you were successful there?

(Wait, there’s no conclusion! That’s intentional.)