My Myers-Briggs Type Indicator says I’m an ENTP — “The Debator”.
The ENTP personality type is the ultimate devil’s advocate, thriving on the process of shredding arguments and beliefs and letting the ribbons drift in the wind for all to see. Unlike their more determined Judging (J) counterparts, ENTPs don’t do this because they are trying to achieve some deeper purpose or strategic goal, but for the simple reason that it’s fun.
It’s true — I do love (winning) a good, friendly (or contentious) argument.
While I don’t necessarily like to be put in the Myers-Briggs box — nor am I willing to accept that I’m unable to develop attributes outside of my personality type — I do think that the personality types are a really nice narrative to describe one’s cognition. And as they say, I am the ultimate devil’s advocate — I’m good not only at making compelling, deductively valid points on either side of an argument with someone else, but I’m also especially good at doing it with myself.
In a traditional decision-making scenario, I often play point-counterpoint to assess the merits of each option. For “normal people”, I assume this methodology is sufficient — they are able to pick a choice and run with it.
For me, as an ENTP, this methodology can cause paralysis. I’m too good at debating myself — there is no clear winner. It doesn’t help that I’m also a maximizer — I approach decisions with the goal of achieving the best possible outcome (compared to satisficers, who settle for a “good enough” option).
I’ve long thought that I need to find a better framework for making decisions (ironically, I need to make a decision about how to make better decisions) and that my approach to problem-solving and decisionmaking is insufficient given my “natural” tendencies.
In my quest to become a better decision-maker, I’ve learned first and foremost that there is no “right” way to make a decision. And similarly, as we will see, there is no “right” decision, either.
Rather, there are a (non-exhaustive) set of frameworks that can be applied as the situation warrants, either individually or, more likely, in conjunction with each other.
Here are three that I find particularly impactful.
One of my favorite quotes is from the author F. Scott Fitzgerald —
The test of a first-rate intelligence is the ability to hold two opposed ideas in mind at the same time and still retain the ability to function.
Chris Voss, former FBI hostage negotiator and author of Never Split the Difference discusses a concept he calls “tactical empathy” — showing your counterpart in a negotiation that you can see things from their perspective makes it easier to influence them.
I used to think this quote meant a first-rate intelligence meant having tactical empathy; holding two opposing ideas in my mind at the same time in order to best determine which idea, or decision, is best. However, the paralysis caused by my decision-making process only proved that I lack a first-rate intelligence.
Instead, what Fitzgerald is advocating is called integrative thinking —
the ability to face constructively the tension of opposing ideas and, instead of choosing one at the expense of the other, generate a creative resolution of the tension in the form of a new idea that contains elements of the opposing ideas but is superior to each.
In other words, accepting that both (or multiple) contradictory ideas are true at the same time, and allowing this reality (versus “either/or”) to form the basis of a new, superior pathway.
In a recent episode of The Investing City Podcast, investor and entrepreneur Kanyi Maqubela discussed an investment decision-making framework he is trying to make more habitual:
[When making investing decisions] what I constantly have to think about is when I have high conviction about a startup, two things are true. I know, on the basis of statistics that that company is probably going to go out of business. And I also know on the basis of the strength of my convictions that that company is probably going to change the world and become massive, and I have to consider those both as true if I’m going to be a rational steward of capital.
And so, what I’m really trying to do is just develop a better instinct at not getting bounced back and forth between those two things, but rather just having them both be true at the same time… I’m high conviction, even while I accept that it may not work.
What Kanyi is describing here is Fitzgerald’s quote applied — rather than either/or, he must believe in both the inevitability of success and in the statistical probability of failure of a given business and nonetheless make a decision whether or not to invest.
Having high conviction while simultaneously accepting risk impacts how we approach both initial and subsequent decision-making, and is markedly different than making a decision strictly with high conviction or strictly in line with the probability of an outcome.
Psychologist Ellen Langer advises —
Don’t make the right decision. Make the decision right.
Author Steven Johnson recently discussed his new book Farsighted, in a podcast discussion with Malcolm Gladwell. In the discussion, Gladwell asks Johnson if the decision-making process Johnson codifies can apply to something like what college you go to. If the main benefit of college is the people you meet, Gladwell questions, what makes it a useful experience is inherently unpredictable.
Johnson acknowledges — as we must do — that there is a huge amount of uncertainty in any decision with long-term consequences. We cannot account for or reduce uncertainty. When making a decision, the question is not “how can we have absolute certainty”. Rather, we must acknowledge the uncertainty and instead address what is predictable and controllable, and what is unpredictable and out of our control.
When I quit my job to move to South Africa and pursue entrepreneurship, I spent a lot of time reflecting on my decision and question whether or not it was the “right” decision. I’ve come to learn — as Langer says — that there is no such thing as a “right” decision. Rather, it’s a perpetual series of decisions that make the original decision “good” or “bad”.
The initial decision itself, in fact, is not the end but the beginning.
Similarly, when Kanyi chooses to invest in a business that decision is not the end, and it does not make success inevitable. It is the perpetual series of decisions that the business and its advisors make — as well as factors outside of the business’ control (and the business’ preparation and/or reaction to these factors) — that will impact the outcome.
So often, we approach a problem or a decision strictly from a forward-thinking perspective — either in terms of the directional arrow of time or in terms of making the “best” decision (as opposed to avoiding “bad” decisions).
The process of inversion turns the process upside down, allowing us to think backward or in a subtractive manner.
From a timing perspective, one process discussed by Johnson and Gladwell is the pre-mortem (compare to a post-mortem). A pre-mortem is a storytelling exercise, in which a team prophetically tells the story of a failed outcome, in order to plan and avoid the imagined negative scenarios.
Similarly, Amazon is renowned for its product development and innovation process, which they aptly call “working backwards”. During this process, product managers write internal press releases at the beginning of a product development stage —
If the benefits listed don’t sound very interesting or exciting to customers, then perhaps they’re not (and shouldn’t be built). Instead, the product manager should keep iterating on the press release until they’ve come up with benefits that actually sound like benefits. Iterating on a press release is a lot less expensive than iterating on the product itself (and quicker!).
In investing, we can find success by predicting unicorns or merely by avoiding bad (or foolish) losses. As the legendary thinker and Berkshire Hathaway vice chairman Charlie Munger once remarked,
It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent. There must be some wisdom in the folk saying, `It’s the strong swimmers who drown.’
While these processes cannot guarantee certainty — after all, we must acknowledge and embrace uncertainty —
It is important to recognize that one common theme between all of these decision frameworks is that they put an emphasis on process and not on outcomes. In an uncertain and complex world, the best we can do is apply a process in an attempt to uncover “unknown unknowns” and make the “least bad” decision.