A 15 Minute Foreplay™ Conversation with Jim O’Shaughnessy

In this conversation, the first episode of the Flux Trends 15 Minute Foreplay series, where we explain the best thinkers’ ideas on how to shape your future with confidence, Bronwyn Williams and Tumelo Mojapelo talk to Jim O’Shaughnessy about the difference between probabilistic and deterministic thinking.

Bronwyn Williams: I’m Bronwyn Williams. This is Tumelo Mojapelo, and we are hosting the Flux Foreplay Conversations. And today our guest is Jim O’Shaughnessy. And we wanna ask Jim one very important question about something that he’s spoken and written quite a lot about, and that is about the difference and the importance of understanding the difference between probabilistic and deterministic thinking. So Jim, what is the difference between these two very different mental models? 

Jim O’Shaughnessy: So I often have a quip that goes, we are deterministic thinkers living in a probabilistic universe, hilarity or tragedy often ensue. What I mean by that is deterministic thinking goes all the way back to Aristotle. And it’s either/or. It’s yes, no, black, white, zero, 100. And that type of thinking within a logical system can make a lot of sense. However, we don’t live inside of a logical system. We live in a highly fluid probabilistic world where the von Neumann distinction, what he calls quantum logic, makes a ton more sense. That’s essentially probabilistic thinking. 

In other words, very few things in the world are yes or no. Most things in the world are maybe. And there’s been an attempt primarily on the side of logicians, but also of scientists dealing with questions that really don’t get answered by a simple yes or no, to think of more multiple variables in these systems. 

So for example, there’s a four-value one that says true, false, indeterminate or meaningless. You can make a lot more sense of the world if you begin to categorise things in this broader context, than in a simple yes or no. Simple yes and no thinking tends to reinforce our priors and close us off to thoughts that would land in that much larger category of maybe or indeterminate. And in fact, Edward De Bono came up with a clever little ditty that went, “People should think yes, no, or po.” And by po, he means what are the possibilities that we could think about here? Po is by its very nature non-linear. It is not deterministic. It’s what if. What if we did this? What might result? It tends to lead toward a far more creative way of looking at potential solutions to problems. And it doesn’t close you off the way deterministic thinking often does. If you’re a deterministic thinker, things get settled really fast, right? Yes or no. And then you basically label it and stop thinking about it. Leads to very suboptimal ways of thinking and more importantly, of taking action against items that you want to achieve.

Tumelo Mojapelo: You know, there’s something that I like that you mentioned, and I think especially about deterministic thinking, and it reminds me of a quote by Albert Einstein about how you cannot use the same thinking to solve a problem that created it, right? So for, like, leaders, for, like, leaders, especially if you’re in leadership, how would they make probabilistic thinking something that they apply to the day-to-day context? Because it seems like basically that’s how we’re wired as humans, right? We always want a solid yes or no answer. So how do we build maybe elements or points or markers or, if I needed like a five-step plan on how to slowly get to a point where I’m not always looking for a black or white or a yes or no answer, especially in leadership because like you just said, we are logical creatures living in a very uncertain world, right? 

How do we now internalise the probabilistic thinking tools or methods in order to be able to respond to the actual environment we’re living in? 

Jim O’Shaughnessy: That’s a great question because part of our human OS is that we are very attracted to people who seem certain. And therefore people in either political or corporate leadership positions often attempt to be just that. We are 100% sure that this is going to work. No, you’re not. But people love to hear that sense of assurance, that sense of certainty. And in the real world, only, like, people who are pretty crazy are absolutely sure about anything other than maybe death. And with everything that’s going on, we might even have to get uncertain about that at some point in our future. I think the way that you can internalise a more probabilistic form of thought is to think in terms of bets. 

My friend, Annie Duke, wrote several books on this. And one way to really get yourself in the habit of thinking more probabilistically is to mentally think, how much would I bet on this? You know, statement A, statement B, the sun will rise tomorrow. Well, I probably bet a lot on that. Even though it is not an absolute certainty, the probabilities of that bet are very much in your favour. And so I probably bet quite a bit on that. The idea from quantum physics: is Schrodinger’s cat alive or dead? Well, if I know about that, I think, well, according to him, we don’t know until we look, right? And then we collapse that quantum wave and it is one way or the other. But that’s at best a 50/50, even under standard logic, that’s a 50/50 proposition. So I’d probably want to arrange my bet in a way that took advantage of those odds. 

And then thirdly, I would suggest thinking in terms of, what’s the batting average or base of something occurring? You know, base rates are incredibly useful information. And yet we tend to dismiss them when there is stereotypical information available. And a classic goes, if you put a bunch of people to a test and you tell them just one thing, you say, there’s 100,000 people in this town. And I can tell you 70,000 of them are lawyers and 30,000 are engineers. When you ask them to guess what a randomly picked name, Tom, Mary, Frank, is, and it’s just the name, guess what? They pay attention to the batting average or base rate. And if they’re trying to get the highest number right, the easiest answer is, I’m going to guess they’re all lawyers because my chances are 70% in my favour that it’s a lawyer. When you add meaningless but descriptive information, like Tom is 33 years old and has dark hair, people begin to ignore the underlying base rate and they start thinking in terms of, does Tom sound more like a lawyer or an engineer?

Well, then finally, when you add stereotypical information, Frank is 43 years old, shy, likes mathematical puzzles, and has his glasses taped at the bridge. Everyone says, I don’t care, you could say there were 99,000 lawyers, Frank’s an engineer. Well, that’s not true, right? The likelihood that given the base rate that he is a lawyer is much, much higher. But when you start thinking in terms of those underlying base rates and remind yourself constantly of them, that automatically puts you into a far more probabilistic way of approaching a thought or an outcome and gives you the ability to think, okay, well, how much, again, back to bets, how much would I bet that Frank is a lawyer or an engineer? You just follow the odds. 

Tumelo Mojapelo: Thank you. I mean, you mentioned that we are wired to be deterministic, right? But then as a leader, how do you then move your team or individuals that you’re leading, right? ‘Cause now you’ve determined that this is how I’m gonna think, I’m gonna approach decision-making, I’m actually gonna place my bets on this side, right? How would you then move or mobilise people or conscientise them? ‘Cause I don’t know if it mobilises the trajectory but conscientises them to also move along in that way of thinking and feeling. I mean, I can’t believe I’m saying this, but certain in the uncertainty. So feeling comfortable with the discomfort enough to be open, to actually explore a different way of thinking and trusting that this leader’s not literally just making us walk off the cliff because they’re betting on something that doesn’t make any sense. Because, like, I think that’s the thing with humans. We want security in some way. And I think that’s why we always fall back into the deterministic thinking. So like, now I’m a leader, I’ve trained myself in thinking in a certain way. How do I get my team on board? How do I get buy-in from my customers, shareholders, stakeholders? Like, how do I get everyone on board so that when we move towards exploring various options, we’re all, not on the same page, but similar wavelength. 

Jim O’Shaughnessy: Great question. I would start from the smallest group and then expand like when you throw a rock in a pond and the ripples go out. So I would start with your core group that you are leading. And with them, I would encourage, kind of almost a socratic method of looking at talking about whatever the subject of the matter is. Well, what do you think about trying this policy? And why are you in favour? What are some of the good reasons that you might be against this type of policy? And getting that discussion gets buy-in from your closest associates. And it creates an environment in which they understand it’s okay to say, you know, I don’t think that policy is gonna work, but here are the reasons why. If you can get a conversation going with your inner group of people, leadership team, you’re going to create an environment where that type of thinking is rewarded rather than punished and where it is encouraged rather than discouraged. 

Once that happens and the team starts vibing together that way with one another, then they will naturally appear that way to people that you’re trying to influence outside of the team. And people rather than hearing, you know, a canned, this is the way it’s going to happen. This is the way we’re gonna do it. This is the only way. They’re gonna hear a much more nuanced and interesting conversation that importantly invites them to contribute their own thoughts to the process. And once you get that ability to include the people you’re trying to convince of a particular policy or a particular path, if you’re in a corporation, that is going to not only invite their buy-in. So in other words, they’re not being sold to, they’re actually buying in, which is really important. And the only way that they can do that is to feel they have the freedom to listen to the leadership team and think, “Wow, they really seem to have discussed and really thought about all of the various ways of where this could be,” right? Or all of the potential ways that things could go wrong. That type of conversation really invites people’s participation. And once you get participation, everybody’s rowing in the same direction. Even if they have different ideas, that’s critical. 

It also often will lead to a change being made, particularly when you’re having and encouraging that type of conversation with your core leadership team. In an environment where probabilistic thinking is dominant, people feel quite free to add things to the conversation that might in fact change the ultimate decision that’s taken. And once something like that happens, and it happens a couple of times, you get into a much better communication space with your team, and then ultimately with the people you’re trying to convince of a particular policy or path. 

Tumelo Mojapelo: Thank you so much. So in a nutshell, I’m just summing all the ideas as you shared. The benefits of probabilistic thinking is that they bring everyone on board, right? They prepare leaders for an uncertain environment. We’ve always lived in uncertainty. We’ve just not acknowledged it and actually internalised it. And unfortunately, in today’s day and age right now, we need that kind of thinking  – that is open to input, because that’s basically what it is, right? Another benefit is that it allows you to open decision-making, but also agency, up not just to your core group, but it creates a ripple of change and action in the right direction. 

And there’s a point that you highlighted that I really liked. It’s about not agreeing. So it’s not, like, groupthink, we agree or nod, just because when I keep the peace. But it’s having different perspectives, right? And going in a direction where there is more authentic change and transformation, right? Because I think that’s basically the point. It’s not to stay in the same place. It’s not to repeat the mistakes that a deterministic thinking pattern has repeated over and over again. It’s to explore different options and new horizons, right? And ask the questions like you say, what if? What if we consider this? What if we bring these people on board that might have not had a voice? I hope I’m summing it up in the best way for our listeners. 

Jim O’Shaughnessy: I think that’s an excellent summation of it. So you’ve done a great job for your listeners. 

Tumelo Mojapelo: Thank you so much, Jim, for your time. And just making, helping our listeners and our viewers to understand the difference between probabilistic and deterministic thinking. And thank you, those who are watching, for joining us for our foreplay conversations. I hope you stay tuned and subscribe and join us for more conversations. Thank you. 

Jim O’Shaughnessy: Thanks very much for having me.

By Flux Trends 

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Image credit: Flux Trends Analysis