The portfolio theory of hiring
Eight. That’s how much is enough.
When I was a kid, we swam in a pool with Dick Van Patten. Okay, that sounds weird. All of it.
The then aging star from the hit TV show “Eight is Enough” was at a resort hotel at Disney World. He was there with his grandchildren. Round, tan, and happy. Golden fat looks a lot better than a paler form of obesity.
My mom was really excited. Van Patten was famous, and his fictional character had only narrowly bested her in the dubious contest of bulk child-rearing.
This lead role was based in large part on the life of Thomas Braden (journalist, CIA officer) whose book of the same title was the foundation for the “Eight is Enough” TV show. Just like Van Patten’s depiction, Braden had eight children in real life. Anyone who’s a parent knows how crazy that number is. So by “enough,” I wonder if Braden meant:
“I couldn’t possibly be happier than I am with eight children.”
“The stresses and costs of a ninth child would be too much to bear.”
Put another way, did Braden mean “enough good” or “enough bad”?
Or, more likely, was he saying both? As in, “I’ve done the cost-benefit analysis, guys, and there is just no break-even on a ninth kid.”
You can have enough aspirin. You can also have enough pizza and morphine. It’s hard to have enough sushi.
Part of growing up is realizing when you have (had) enough. Enough material things, enough IPA, enough love, enough shit from your boss. Some handle parts of this equation better and earlier in life than others.
When you are evaluating qualities in other people, the problem gets even tougher. Perhaps this is why hiring processes tend to be like cold brew: slow, inefficient, unreliable, and frustrating for everyone.
Perhaps this is why hiring processes tend to be like cold brew: slow, inefficient, unreliable, and frustrating for everyone.
Most military and company values (and forms of evaluation) get three big things wrong:
(1) Value Differs: All traits are not of equal importance, but most organizations are not explicit about about this.
(2) Interplay Matters: There should exist a framework for how different mixes of strengths and weaknesses combine with varying degrees of effectiveness and desirability.
(3) Structure is Critical: Each of a company’s values has its own particular range of possible and ideal quantities.
Classes of Traits
It’s tempting to say that one can never have enough character. But it is relatively easy to define a notion of perfect honesty. Of course, no one actually wants someone around them who is perfectly honest. The ideal might be something like 96% honesty. It’s like that green tea you’re supposed to steep at a couple degrees below boiling. One can understand the urge of Sunday schools to just round up.
Frugality is an Amazon leadership principle for which there is universal acceptance within the company of ever diminishing marginal returns.
Depending on the job, there are some things you can never have enough of (practically speaking anyway). Creativity and the ability to build relationships are good examples.
Employee review systems are often detrimental to unbounded traits. The existence of a maximum rating can deemphasize continual improvement and mastery of craft.
When I started with as a PM in the operations org at Amazon, they gave me a set of cards with the company’s “leadership principles” and operations values on them. Each card had a Goldilocks structure. Too much “Bias for Action” is bad and looks like ‘x.’ But too little is also no bueno and looks like ‘y.’ And if Bias for Action were a latte, the perfect temperature would be ‘z.’ 
Many people are familiar with how this operates for the quality of ownership. Ambitious businesses need people to point fingers less and take responsibility more. But (and I speak from experience) project managers who overexert their ownership can destroy relationships.
“I met this designer the other day that we should totally bring onboard! She’s super creative, insanely data-driven, thinks strategically, loves diving into the details, she’s a super prudent risk taker, and she’s really funny and assertive without being overbearing. Oh yeah, and she makes the best cortados!”
First of all, Alexa, what the fuck is a cortado?
Secondly, everyone would hate this person if she existed. Thank goodness she doesn’t.
But because organizations often produce irrational outcomes, companies rarely pick and choose the one or two traits they want to emphasize. Rather, they look at a broad set of skills and figure they’ll hire someone who is “just” mildly imperfect at everything. This is not only suboptimal in many cases but remains a near impossible bar for applicants to achieve.
And interview questions — to the same candidate — often oscillate between pairs of diametrically opposed extremes. For example:
- When is a time you made a lightning-fast, life-or-death decision with limited information? Like… picture a desert where it doesn’t rain and where the Romans have salted the “fields” just in case a storm comes once a millenium. That’s the barrenness of information we’re talking about at your disposal!
- When is a time where you dove really deep, asked five hundred and five Why’s, and didn’t rest until you had thoroughly mapped the nanoscopic universe that constituted the problem at hand?! (5 Whys)
No one can be good at everything. And you don’t want someone who is good at everything. You want someone who is insanely great at one or two things you need — and merely acceptable at everything else. 
Organizations should embrace the varied nature of humanity and the exponential returns to mastery of one or two areas. This requires viewing a person’s set of skills as a portfolio of assets and risks, each component of which has its own probability distribution of value for a given situation.
But what we see is a tacit beauty-by-beholder approach that ironically rewards gray suits with zero defects instead of flawed beauty.
The point of ‘data points’
“Ah!” exclaimed Honest Old Abe, “you surprise me, gentlemen. But can you tell me where he gets his whiskey?”
“We cannot, Mr. President. But why do you desire to know?”
“Because, if I can only find out, I will send a barrel of this wonderful whiskey to every general in the army.” 
Imagine you’re hiring a data analyst. You interview someone who rocks at SQL and is sophisticated in thinking about probabilities and your industry.
They also ‘kick ass’ at thinking big, which sounds impressive and gives them the edge on paper from other candidates. But you know what, you don’t actually like them. More than that, you dislike them. They have a tick that’s annoying, and you can’t connect with them in conversation.
While more subjective “data points” like actually liking the person may make you feel — or appear — like a terrible person, what’s more important? 
Do you really need a data analyst who has big ideas? Why not get one you actually like?
Who knows, she might even make cortados.
About the author: Sri hosts The Warrior Poet podcast, a show on the philosophy of leadership based on his experience in the SEAL Teams, at Harvard Business School, on Wall Street, and in tech. Shows every Monday. Follow him on Instagram @sri_the_warrior_poet and @sri_actually.
All the way wet (aka footnotes)
 There are lots of possible nuances and objections to my definitions, though I don’t think these detract from the high-level point above. Some examples: Are we measuring the value of increasing amounts of the trait? Or are we measuring whether it is physically or psychologically possible to max out? Meanwhile, if the trait is one where “world-record style” examples exist (think Bill Clinton for charisma), how do we classify it if we can always expect a new gifted outlier to surpass the previous world-record holder, however rarely that might happen?
 If you’ve bought a house before, think about the options you had and the decision-making process you went through. Chances are that each top contender was great in a couple ways and crappy in at least one way. You didn’t have the luxury of choosing one that was a B+ in everything. Even if you did, there is no reason to be convinced that this option is better than the house that has an A+ in one thing and B-’s in everything else.
Of course, it helps that it’s difficult and illegal for houses to lie about their qualities, so you have much better information than the market for talented people. Also, while your process was probably much less methodical than corporate hiring, you also were able to avoid corporate pressures, groupthink, CYA rationalization, etc.
 Abraham Lincoln on the drunkenness of Ulysses S. Grant
(1963 New York Herald account)
 Group debriefs tend to downplay these sorts of things, because the hiring manager wants to appear cold and calculating, while the other folks (especially at large companies) often take the attitude that as long as the hiring manager can work with the candidate, then it’s not their place to exert a strong “dislike” opinion.
The reputable “How to Start a Startup” video series emphasizes liking the person you’re hiring as the number one consideration.
Not sure I care about that article, Sri. I’m just here for the cortado: