Why heuristics can be your biggest technological blocker

Former professional baseball player and current COO Alex Feinberg explained why mental shortcuts can stymie your company's digital transformation process.

Why heuristics can be your biggest technological blocker

TechRepublic's Dan Patterson talked with Alex Feinberg, COO of Petram Security, about his journey from professional baseball player to a career in finance and tech, and why the two required different mentalities.

Watch the video, or read part of their conversation below:

Patterson: The idea of a mental heuristic or A, not a shortcut in the way we typically think of shortcuts as a way of getting around the hard work, but a way to really understand, like a mental macro, a way to understand A, B, C, and D, can be useful, but as you said a moment ago, it can hold people back. Can it hold you back? Especially when you made that transition from baseball to managing a hedge fund to Google, is it possible to apply the same heuristics to yourself and prevent upward mobility?

Feinberg: Yeah, I mean, there's no free lunch, right? The heuristics that you develop in one facet of life don't actually fully translate to the next facet, and that can be really challenging. I think that's sort of why people say, 'You can't teach old dogs new tricks." So one interesting mental model that I took from baseball that I struggled with as I transitioned to finance and then as I transitioned to Google is, baseball scouts always look for very confident players, because they somewhat falsely equate confidence for competence. But I didn't realize that this wasn't 100% of people at the time. You know, when I'm 19, 20, 21, 22 years old, I just think, 'Okay, this is how most people understand their world. If you want people to perceive you as being competent you should project confidence,' because that's how the scouts that I was familiar with evaluated people.

What happens is, if you take that exact framework and pivot it into a corporate environment, you will come off as too aggressive, you will come off as over-confident, because the level of confidence and the level of charisma that a professional athlete exudes is actually too much for a mid- or junior-level position within a company. It'll come off the wrong way. It's really interesting to think the same professional athletes that you see on TV are like 25 years old. People look at them and they don't think of them in the framework that these people are 25 years old. But all of a sudden if you take that same 25 year old and put that person in a corporate hierarchy, even if that person's just as smart as people higher up than him, those people higher up will be threatened by that same person because they'll think, Oh, he's only 25 years old, why is he acting like this?'

So I think part of making that transition, is having the tolerance to hit your head against the wall a few times and think, 'Why is my framework not working here? What could work from that?' Because it's not 100% inaccurate either. There are certainly elements that translate, but when they don't fully translate, as they won't when you switch environments, it's important to kind of think back and reflect and try to understand, 'Okay, why is this working? Why is this not working? What commonalities exist between the two environments? How do people succeed within each environment?' Because that's also very important too.

This is my hypothesis. If you look at industries that have very strong metrics around performance, whether it's trading financial assets or professional sports, the people within those industries are very, very aggressive because they don't necessarily need to be able to get along with large groups of other people in order to be positive contributors to their team.

SEE: Digital transformation: An IT pro's guide (TechRepublic)

So what happens is, when I go hang out with my baseball friends, some of whom are still playing in the major leagues, as I juxtapose that to, say, my friends at Google, it is very, very, very apparent that my baseball friends are so much more aggressive than the typical person working in Silicon Valley. It's almost by necessity. It's because the light at the end of the tunnel is so bright as a professional athlete, and the most, most, most important thing is that you're good, and if you're good you don't really need to be the friendliest person if you're really good. That's not true at Google. You can be a tremendously competent partnerships or BD person, but if the people who are around you don't really like your presence, then it's actually better for that organization to swap you out for somebody who's even slightly less competent but just friendlier to others.

So, yeah, you'll see a lot of different personality differences across domains, but a lot of the same competitive underpinnings are there. It's a different environment, so different skills will be rewarded, and hopefully you can take in enough information to figure out, 'Okay, these skills are rewarded in this environment. These are kind of the skills that I perceive the people near the top of the organization have compared to my former organization. So let me develop some hypotheses to figure out why, and let me just mentally test it against what I see on a daily basis.' You'll find that you can develop a reasonably consistent mental model so long as you're honest with yourself.

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