#hiring #product-management

The Experience Trap

I don’t know about you but I think we may be optimizing for the wrong things when hiring.

The pattern

You’ve seen the posting: “Senior Software Engineer — must have 5+ years in [insurance billing systems / healthcare patient technical support / logistics for emotionally stunted fathers / crypto for tigers at the zoo].”

And it’s obvious why we do this right? We know what we do today, the most valuable person that we could find is someone that’s done exaxtly that before. Right? Right?????

How does a person become a job?

So let’s start with a question:

How did that “experienced” person get that experience in the first place?

There’s a few potential answers here:

  • The one we all assume - They had a genuine passion/interest in the subject and are truly above average. This led them to get promoted and accumulate direct experience.
  • The sadder answer - They don’t really have a passion, and they aren’t above average. They’ve managed to be just good enough not to get fired, didn’t have any better options to jump ship, and were willing to kiss just enough ass to get promoted. So they persisted.
  • The real one - Completely arbitrary. They are average and due to some luck, have perissted.

So when we select on experience, we’re selecting for “this person has done a thing before”. I once went skiing. Was I good at it? No…

Domain knowledge is learnable — critical thinking is not

Ok I mean critical thinking is definitely learnable. But its much harder. Learning how to analyze a situation, distill its workings and priotize actions takes years to learn. Its the real reason why a STEM background is so valuable. What you learn in engineering school (or any other technical or scientific discpline) is how to think critically. And that is very much, NOT EASY.

On the other hand, learning exactly how something works in a small amount of time is much more achievable. The mental models transfer: data flows, system boundaries, regulatory constraints, edge cases. The specifics change; the patterns don’t. At the end of the day, the difference between an insurance company and a retail outlet is a matter of degrees. How critical is X vs. Y?

The real cost

So clearly we’re overvaluing experience in many cases (to be clear, there are many exceptions to this like being a doctor or a carpenter or any number of other hands on disciplines). But that’s not the only cost we’re incurring. We’re filtering out a differnt kind of person who can actually bring even more to the table.

Traditionally, jumping from job to job or industry to industry is a red flag. It signals “You don’t know what you want” or “You couldn’t hack it where you were”. And while in some caes that is true, there’s an alternative explanation that I think is underappreciated: The person excelled at their role but ran up against either boredom, or they weren’t able to grow at their current company (or more likely, weren’t willing to kiss enough ass or make enough bad decisions). But these individuals may have proven an important skill: the ability to apply their cirtical thinking to ANY business context and quickly add value.

Furthermore, their breadth of experience might be a distinct advantage. The best ideas often come from adjacent industries solving analogous problems. It’s tought to recognize those opportuniites when you’ve been in the same space for 10 years.

The uncomfortable truth

The industry experience requirement often isn’t really about the candidate. It’s about the hiring manager’s comfort level. It’s easier to evaluate someone whose resume looks like yours. It’s easier to justify the hire to your boss. It’s easier to imagine the onboarding.

But easier isn’t better. The best teams are built from people who’ve seen different problems, worked in different constraints, and learned to learn quickly. That’s the skill that compounds.

So what do?

I think there’s a few practical steps to take if you’re someone hiring:

  1. Don’t discount (and maybe even seek out) someone who has a variety of meaninful experiences (more than 6 months). You can always talk to their references to see if this is a good or bad thing.
  2. Use a skills based interview process. Dont waste time on behavior questions. Give them a live problem and ask them to explain their thinking process. For the true critical thinkers: this is a piece of cake. For the process followers: it can be impossible.