thinking on thinking · S2E2

Thinking on decision making when you lack certainty

January 11, 202336 min designbehaviorcreative

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notable moments

The hardest decisions are the ones where no amount of information will make you certain. At some point, you have to act on incomplete knowledge and trust your ability to adapt.

We often delay decisions waiting for certainty that will never arrive. The cost of waiting is usually higher than the cost of being slightly wrong.

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Hi, I'm Kahran. Hi, I'm Divya. And this is episode 12 of Thinking on Thinking. This week we talk about decision making. We start from including potato as a mascot for Joyce, but from there we move into thinking

about how do we make decisions, how, what are the things that stop us, what are the things that help us and how we can build systems that can help us into making better decisions, faster decisions. We hope you enjoy. Coming up with branding is hard.

Coming up with branding that will resonate with a firm early company is hard. And like being like, oh guys, I really think like I see resonance in a potato would just be like, it'd be a hard conversation. What would you look for to make that kind of decision? I don't know.

It feels a little bit weird. And then I guess like in this case, I would think, oh, does it feel quirky? Like because that's the key thing that I think about when someone says potato is like a part of our branding. Right?

And so I'm like, huh, what is the sort of standout quality of this decision? Like almost like a meta analysis of the decision itself. Like potato is a bland thing if you just look at a potato. But like what made you choose a bland thing seems like a quirky decision. So I would think about like, what does it represent?

Like what does it mean? Well, and it almost sounded like you were saying not just that, but what was the emotion that drove you to making to to wing the factors in this way? Like why were you looking for a quirky decision right now? As we have discussed, like we are going to probably try and be much more flexible with

our branding. We don't want to do just one logo and then it's done for the next five years. But at the same time, we don't want to do, oh, we are doing our branding exercise. Well, that is how it has happened that it has dragged on for a long time. But like we would ideally not want to get in that space.

So I think that like that also makes the decision a little bit easier because there is sort of the decision does not feel like, oh, I can never change it. It becomes easier to make it. Like, otherwise, I would be trying to evaluate as quirkiness the right feeling. But here it's like, huh, okay, it might be.

What makes something the right feeling or not? In case of most of the brands that I've worked with, generally it comes from like a lot of discussion about what they're doing, why they are doing it, what feelings do they want the audience to have? Is this the right, like does it feel resonant with what their brand wants to stand for like

five years from the line, 10 years from the line? And like that's a very hard question to answer. Okay. Because I feel like you can gather data to answer some parts of that question, right? Like you could be able to figure out, okay, here's the 20 different adjectives we're

thinking about for this brand, right? And then being able to find some prioritization method or something, right? At least you'd have like some sense of the landscape. And then if you can't prioritize between them, then that means that you have equal kind of feelings towards them, which then why would one be right or wrong, right?

As long as it's within the realm of possibility. Hmm. How should I put it? Because I think this is part of the bigger idea that we were planning to talk about today, right?

But there is this way that people have been selling and way that people have been kind of operating in corporations and in business that is very like just confidence and like certainty driven, right? And it's like this notion that like you, we have to make these decisions now with the information we have, even though it may be incomplete.

And I feel like we've kind of been coming from this notion of saying, well, maybe that's not true, right? Like maybe it is okay to keep decisions open longer and make things that are imperfect decisions. To kind of like break that down further, you have to figure out like what is it like something's

driving you to make the right decision or to make a decision now. And then I think of obviously like certainty can be a driver, which is what keeps us from making a decision and pushes us to make only the right decision. But I think that there's something about like understanding it's how people are engaging more with their emotions in the interim, if that makes sense.

That's so interesting because as you were saying, I realized that I did that as well. Like I said that, oh, I can sort of trade off uncertainty because I know that this is a changeable decision. Otherwise, like despite the fact that we have discussed this multiple times, my brain still wanted to go in the space of no, but I want to be certain that this is the

quote unquote right decision to make or right choice to make for us. And it's like, huh? I think that I mean, even from childhood, right? Like when you're younger and you like, you know, someone asks you, oh, beta, what do you want to be when you grow up?

And you know, you say some really stupid stuff like I want to be an ice cream seller because then I love infinite ice cream to eat. And they're like, no, no, beta, that's not the right decision to make because that doesn't give you enough money and ice cream seller doesn't. And like you start hearing that there is like a right answer and a wrong answer.

And actually one right answer and many wrong answers to these questions which in reality do not have any definitive answers. But we price that sense of security like as a society too much. Yeah, I'm wondering about is it that people start to feel more like people like us only do a few things, you know, and those things that might be on the edge of what people

like that. That kind of tribal group that I belong to. So things that may or may not be done by that group. Like I get more and more wary about doing those things on the edge as you get older, frankly, mentally or like starting to learn that not doing the things that the tribe

approves as consequences. Yeah, has consequences. That's funny. Yeah. That's funny.

Yeah. And in a lot of ways, I think even when you thought that they didn't have consequences, the consequences sometimes surprise you. Yeah. It's also really.

So we had thought that we would discuss like how confidence is probably not needed in like, you know, how you're thinking about things and how you're making decisions and like I always find like, I'm just pointing out something which is like slightly meta, but I always find it interesting that the moment we start thinking about thing while recording an episode, we arrive at something different.

I mean, I don't think this is necessarily different. It feels to me like it's the same notion, but from a slightly different lens or angle. Yeah, but like it is an angle that we were not thinking about from before. Yeah. Like even when we were just before recording, having a chat about like, you know,

different decision making styles and oh, how your style is like different from how I make decisions or how I think about things. It's still just. Neither of us had connected it to that's how we are like cultured from the beginning. Like preadulter like we were thinking majorly in context of work.

Well, I was I mean, I think I was thinking about it from the perspective of like, I think data has driven this certainty based selling, particularly within marketing and product where it's like, oh, you know, I have the metrics I can figure out who the audience is. I can I can tell you with certainty that, you know, you are touching the right people

for for you right now. Right. And I think that that that there's there's it's not really true. Right. And as anyone who kind of has spent more and more time deep into data has realized

that whatever question you're trying to answer, you will find an answer for that. But if you're asking the right question or not, is the whole problem. And it's very easy to kind of not realize the questions are changing as your product is progressing. Yeah.

And also like data is only a like data driven decision making. Is a little bit iffy concept in itself, because it's only it's trying to say that inductive reasoning is the same as deductive reasoning. Like X, Y, Z has happened before. So we can just draw extrapolate the line further up ahead.

And like, that's not how most that's not how most technology works. Like even if you think about people's behavior over the last like 20 years, 15 years, right? Like how they have kids who are born today versus kids who were born 15 years ago versus like kids who were born 30 years ago.

So much difference in how lifestyle is and how people are cultured and how people are socialized and how people behave and how people think. And like data could not have led you here. Unless you now with hindsight bias, cherry pick the right information. I mean, even just like, even in like the progression and like like queer queer rights

across the world, right? You wouldn't have been able to have guessed what's happened in the last 20 years from the 20 years before. Yeah. I hear what you're saying about how I think, yes, the way that we culturally grow up,

it does kind of push you into thinking that like, yes, people like us make these kinds of decisions, but I feel like that macro trend of having grown up in this kind of like world of data has really, um, cause I think even stuff like Instagram has made it so everyone thinks at a data level a little bit, right? Like you can see your likes, you can see comparative posts, you can see how many,

how people are engaging. Like I think even if you have us, how many followers you have versus how many followers your friend has, right? And you can see the difference in the kind of content your friends post versus what you post, right?

So I feel like that to me, that has driven more of this like surety mindset, right? Where people are always just looking for like, like I remember I have a really good friend who has I think like 10,000 followers and she's like, yes, you know, whenever I post skin, like my follower account goes up and every post I do where I'm fully covered, my follower account goes down.

Wow. She might be right, right? But I feel like everyone's looking for these kind of rules that you can establish models really, right? And saying, okay, yes, you know, this is the, this is the thing I can plug in.

And then I know I'll get this output when I, when I plug in these input variables. Yeah. And I guess, no, I definitely see this. It's almost like we're living in an increasingly complex world. So the need for maps, which correspond to that complexity is also increasing.

And like the current quote unquote map making model is just using data. Everything can be measured. How strong are your friendships? Are you healthy? How healthy are you?

Like, you know, how's your sleep? How is everything? Like, I mean, both of us use sleep factors and both of us are like, hey, how did I sleep? Not like I check it the first day in the morning and it's literally how did I

sleep? And it's like, well, you could just ask yourself, do I have a good sleep? Do I feel rested or you could look at it and feel happy about the fact that wow, today I got 80 score. Have you gotten an 80 score?

My goodness, my sleep scores have been today. Well, and I mean, it's not completely useless. It's pretty useful to have this information. But at the same time, I think that like it can be pretty tempting to substitute it. So I think I don't even remember where I read it.

But like, when you can't measure what matters, what you can measure becomes what matters somewhere. And like, I feel like I've always had an inherent discomfort with that, especially as someone who works with both products and gains. And there's always this like angle of vision, like creative vision when you're

making a game. Like, sure, you know what sells like, for example, in India right now, if I made a card game, like some version of a poker, people would love it. And those are the games that make the most money. But like, do I want to do that?

And like, that's a question that you often ask yourself and much more strongly than most people who are building products to. And that philosophical difference has always interested me. Okay, given all that, like, do you feel like it's possible to be building a company that is trying to sell something other than certainty right now?

Because I mean, as we're talking about, this is the age of certainty, right? Like this is the age of data. And sure, maybe there is kind of a growing awareness that like data doesn't predict everything accurately. But, you know, that's still, it's where we are standing right there here today.

Is there's data for everything, right? And people are looking for predictions. I mean, I wonder if that dichotomy is as strong as it appears to be on the surface. Okay, say more. You mentioned it earlier in our chat today, but like, sometimes you don't

need to take certain decisions and you're forcing yourself to take those decisions. And there's this conversation I was having with Charu where she talked about how often she would try to hide behind action so that she doesn't have to take certain decisions, whereas like an imperfect decision would be way better in that same situation.

And both of those things are basically talking about like lack of certainties. Okay. And I think that those problems plague everyone from personal life to companies. Like oftentimes I would consult with companies. There are two co-founders in the team.

There are like a bunch of team members and everyone has a different thought. But because nobody can say with 100% surety that we should definitely go in this direction, nobody takes a call. And it's often like the decision call is also. I don't know very contingent upon how brave are you to take that call.

Do you feel like you need to draw the box smaller? So the decision feels like either that means that like, like reducing maybe the impact of the decision. So making it into a smaller decision or reducing the. So I guess the first one is a kind of prescri perceived scope.

And then I guess the second one would be like the, the, the like permanence of the decision, right? So making it feel like it's not as either by deciding less of it or by deciding it in a way that feels like it's an easy to undo decision. Huh.

If we were to think about like what we were talking about last time in our podcast episode, and we were to think about end times for things. Okay. Like as one is making decisions, one can also think about what is the lifetime of this decision.

Like how long do I expect this to be valid for? That's exactly, that's a great way of phrasing it. Yeah. That's what I was trying to get at exactly. Yeah.

So for example, when, where do you want to go for college and what do you want to study is such a massive question for like a large part of humanity. Right. And it's because we think that it's a 60 year long decision. Instead, if we think that it's a four year long decision, suddenly the, not that

it isn't a four year long decision. It is definitely a four year long decision, but it's not a 60 year long decision. Like neither you nor I are working in the domains that we did our undergraduate degrees. That's true.

Right. And like if I knew it when I was choosing it, I would probably have been a lot more freer with the choice. And so I just wonder if like just introducing a model of, okay, so how long do we expect this decision to be valid?

That to you feels like it's a scary reduce the, the, I don't know, weight of it. Yes. Yeah. I mean, going back to the potato example, if I have to think that like, you know, Joyce might be about a potato for the next six months, I'm like, I'm okay with

that. For the next 10 years, I would be way more skeptical of it. Interesting. But how do you feel about it? But how do you feel about this?

Like how do you think about, I guess, like permanence or impermanence or perceived permanence of decisions and how that impacts like what choices you make? Well, I mean, I'm trying to think about it from the perspective of a company, I guess I would say, and how companies would, would think about choosing their vendors or choosing who you're hiring or who you're trusting.

Like how, where is that? What creates, I don't know, confidence, I guess. So maybe I don't want to use that word confident. What gives, what, what gives the weights that you use to value the pieces of information, right?

Because we're all going to put different weights on the different inputs that we're getting. Um, so if I was talking to a vendor, right, and a vendor was saying, Hey, you know, let's, let's carve these decisions to be smaller, like smaller length decisions, right?

Um, I think that makes a lot of sense to me, right? I think that a lot of the conversations I have with vendors are not like that, right? There, there's this like degree of indefinite, sorry, there's, there's a degree of, um, indefinite interval, uh, to the, to the way that those people present,

you know, the way the relationship they're, they're expecting to have with you or the value they're going to bring. There's no, it's very hard to push people on saying, okay, you know, what are you going to deliver in what period, especially when you get into these kind of more retainery, uh, sort of engagements.

Hmm. I wonder if that also contradicts with this idea of finite game and infinite game. Yeah. Because if I think about it in that way and think about some of the engagements that I was part of, especially when I was consulting, um, you know, full in my

previous career before, before, but the next, the people that did draw the, the boxes really tightly, sometimes it's very hard to even just have enough room to operate, right? Like when people are looking to say, okay, you know, we are looking for what we can achieve in six months or nine months, that can be a very small window.

Uh, and then you have fallen to the classic problems where sometimes it's very easy to measure what's easy to measure. And so you're not, you're, you're not being able to go out and get a good, accurate read on what's the execution of this idea bad. Did we just not build it long enough?

Does it need more commitment? Um, very easy to end up in a confounded place when you, when you've drawn the box too small. Interesting.

So it's almost like there is a drawback in the current way when people think about not like bounding your decision making it's within certain confidence intervals, right? Um, like it's the term that statisticians use, but I'm using here like slightly more loosely.

Um, but like, I wonder if there is this, uh, this is a pitfall that your brain would instantly go into finite game mindset and you want to get the quote unquote, your money's worth and you want to do the best by yourself, like, you know, undercut the other person if you can. Like how do you not fall into that pitfall while also recognizing that no

decision is going to be forever and you don't need for the decision to be forever, to be able to make movement on the path that you're going. Yeah, I know what you're getting at. I mean, I think it's something to do with how, you know, future you is going to be making decisions, right?

And if you're thinking about it from that perspective of like saying, okay, what is future current need to be able to make a good decision in this area? I feel like that can help you draw at least, right? Then you can start to draw boxes and be like, okay, you know, here's my places of uncertainty.

Here's the places where I'd like to be more certain or at least like convert some of my unknown unknowns into known unknowns, right? No, I really like that. Like just this idea of I need to do enough so that future me can make a better decision or being a better space to make a better decision.

I mean, if like theoretically that's how most of science. Operates, we have a theory that presents a better understanding of the universe. It's not a perfect understanding. And eventually there will come a theory that you'll smash this one to pieces and replace it.

But until we get there, we use this one. Hey, that makes sense. I mean, I also think that when you're struggling with a decision, right? Whether it's kind of a personal decision, or, you know, maybe it's a direction for taking your product, or maybe it's like a problem you're trying

to solve, right? With your product or with your onboarding or with your friends. There's usually some reason why the decision hasn't been solved. You know, like it's there's some reason why you haven't been able to make the decision.

And I think oftentimes we don't look at that aspect as carefully, right? And saying, okay, you know, what would make Futurecard more confident about making this decision? And because I think that that requires more saying, okay, what is it that's stopping me from making this and trying to understand those components?

And then saying, okay, which of these components can be solved in which ways? Versus trying to focus on the decision itself and saying, you know, oh yeah, I just need to make a decision here. It's like, well, it's like, well, do you? Huh.

It's also making me think about this idea that I think we have discussed in the past. I'm not sure if you've discussed on podcast, but it's almost like you, the you're describing it feels like you're improving the quality of network connections rather than focusing on individual nodes.

Like you're improving the efficiency of how your brain moves from node to node and makes like, you know, connect like decisions that affect each other and how you can quickly and efficiently navigate that map rather than thinking or rather fussing over each individual node. That's the picture that it painted in my mind.

Yeah. I'm thinking about that. I guess so. I mean, I think that makes sense to me because especially when you think about complex systems, like whether you're building a product or even just like

interacting with people, there are a lot of parts, right? And it's very easy to kind of reach conclusions from the, you know, the side of the elephant you can see, right? And be like, oh, you know, if someone is acting in this way because of me and not because of their circumstance, because the circumstance is so much harder to

understand than, oh, they're upset with me. Right. And I think in a business context, I get so hard sometimes to uncover what are the confounding variables and what are the primary variables, right? And you're so often chasing the wrong input or output variables.

And it's like, well, you know, you have to look at it more holistically, um, whether it's, you know, an onboarding experience or maybe your purchase flow or whatever, right? Like you have to look at it holistically and say, okay, you know, where are the places that, that we are uncertain about and what would drive more certainty about

it? It's really interesting that I feel like I've come kind of back to this notion of certainty in the end, right? That it is kind of a question of like, how do you break things down into what you think it's a different? I feel like it's a different kind of certainty though.

Like it's not the same thing. So earlier when we were talking about certainty, there was like certainties, a binary thing. You're not allowed to go back on your idea of like, you know, like you just have to stand with it.

You have to be confident about it and you have to be like, yes, this is how it is. This is where I'm coming from. But now it almost feels like you're saying there are degrees of certainty. There are shades within certainty. And can I arrive closer and closer to it?

Almost like this idea of like knowledge is infinite, but we can always keep gaining more knowledge. Like while we're using the same words, I don't think that they mean the same thing. That's usually a sign you should be using different words. It's...

Right? Like, I mean, certainty and confidence in the colloquial sense mean a certain thing, but I don't think now what you are trying to say, where it's like, it's more increasing amount of clarity that you can get with things. And that can help you make better decisions rather than being certain.

And I think in this conversation in some ways, it's actually even helped me find a little bit more clarity because I feel like now I could go have a conversation with someone about that and be like, Hey, you know, why haven't you been able to make this decision or solve this problem today? What are the things holding you back?

And I think that's the right place to be able to then go and say, okay, you know, how can we help you drive more certainty around these kind of components of the decision that are big unknowns for you today? I think those kinds of conversations are not so much what I see happening in corporate. If I say corporate America, but we could just say the corporate world.

But right, people are not saying, they're not saying asking people to acknowledge that they have not made a decision. Right. And there's some reason why they haven't made that decision. And then trying to unpack and drive more, more clarity or certainty around those.

That's not because that requires a certain kind of buyer as well. Who's willing to acknowledge that? It also, it's also, it also requires on a social level, a certain amount of accountability and ownership of your own thinking. Like the kind of self-awareness that can be a little bit painful.

If you look closely at it. It's the same thing, right? It's much easier to point it ever and say, they're the problem. Instead of looking and saying, what is, what is my role in this? Interesting.

Yeah. I also feel like a lot of times when people are trying to sell or when people are trying to buy from someone, they are trying to buy certainty. And so like, for example, at least like my friends who have worked with the big three strategy consulting firms, they always say this, that yeah, all you're

often the CEO's person, when the CEO wants something implemented and they don't think that the internal team is going to buy it, they just bring, you know, BCG or Mackenzie in and they come and they sell the idea. And because these are big shot consultants who are telling this big shot idea, and suddenly everyone in the company has to use it.

And it's a very different kind of social thing that's being sold rather than, you know, solution to a problem. That's not what is being sold. And I'm not sure if like, you know, the C level executives are even interested in thinking about that in many places.

But I think there's a shift, right? And I think the shift we're seeing is as kind of our generation is coming into, you know, more senior roles and starting their own companies. Because I think it almost, it feels like hubris to me, right? To like, to even think that you could be feeling so responsible or thinking

that all of these decisions are really being made by you. It's just like, no, right? Like that's, there is so much of chance. There is so much of the circumstances and so much how much did you use to perceive even what all the options were?

A lot of times, you know, you can't even realize all the options in front of you because you have a set sort of understanding of this is what these are the kinds of decisions I can make. So I don't know. I feel like there's more awareness of that, right?

There's more people who are kind of seeing that crazy decisions are happening. We live through crazy times and you can do, you know, you can start a business without an office. Even 10 years ago, that seemed insane. And now it's just like, all over the place.

Hmm. This is reminding me of something, but this can be a little bit of a side too. But yesterday I was watching a video on philosophy to you and she was talking about the concept of identity. Yeah.

And like, she was talking in context of being a trans person, but she was talking in context of being a trans person. But the way she introduced it was really interesting because she contrasted Renee Descartes idea of identity, where he starts from, I think, therefore I am. Right.

What an individualistic way of looking at yourself and the world around you that I can only be certain of my own existence. Right. Like, and there was this other philosopher whose work she was referring to. I'm sorry, I've forgotten the person's name, but she was a lesbian, black

communist philosopher in the 1920s or 30s, something like that. So it's like, you know, that's some confluence of identities. And this person was basically talking about how Descartes can say that he thinks therefore he is because he hasn't seen his identity reflected back on to him by the world, like the world is not trying to control who he is.

And so he can think that, oh, I could just be a brain in the jar because nobody else is trying to influence his identity. Right. And an interesting thing that now, like, as you were speaking, somehow it just connected for me is I think that as more and more people who are conventionally

in the minorities who have conventionally been much more socially tightly bound as they come into possessions of power, they might not feel as OK with just saying, yes, my way or the highway. They might not feel OK with just projecting infinite confidence that they might just be like, no, things are complicated.

They're not as simple as whatever I said or whatever I came to. Yeah. I guess that part I feel like is like, yes, because we are seeing more of a diversity of viewpoints in positions of power, we will see that happen. But I think the notion that we kind of like struck upon a few minutes ago, I

feel like feels more insightful to me in some ways. There's a reason why you haven't made a decision and looking to how you can make the future you feel more confident about the decision making. I feel like it's just it's such an interesting notion. It's it's I don't know.

People don't talk about it in that way. Like what? Yeah. People often talk about who this will be future the best problem. The future currents problem.

Yeah. I almost wonder if it would be like useful to start to help us have like decision making points that you know are coming. Like one of the things that I think you and I have talked a lot about is when we first started to work together, we had this rhythm of speaking every day.

And I found that it just meant that I was less stressed about remembering to tell you things because I knew that I would always speak to you the next day. And I wonder a little bit about that, that if you were able to kind of build into your mind or have a model where you knew decision days are like coming, maybe it's every third Friday or something, right?

You're going to make these decisions. And because you know, first of all, that it's on a schedule, so you know that, you know, you're going to make another one three weeks later. And also, you know that it's coming. So you know, like, oh, when on this day, I'm going to have to make this decision.

What information am I going to need in order to be the most prepared that I can be? It just gives you an interesting way to think and think about like, what do I do right now in order to help myself be the best I can be when that point comes? Wow, I really like that.

Like that feels so implementable and it feels so valuable. I really like it. We should do this. We should definitely do this. Okay, we'll make it into an offering and we'll go out and sell it to businesses.

And we shouldn't turn the lights. I think you're right. I think we can internally do it. I think it'll be a great place to start. I feel like it's very easy to think about like decision making and be like,

oh, just decide. But it's often not that like you need certain heuristics on how you're going to make decisions and then you're going to make decisions and all of those things help a lot. And just having like, you know, just like, you know, you're going to have to

think more. And just having, like, you know, just building this structure or even talking about the nature of decision making can be really valuable thing. Especially when, when there are undone and unsaid things, which are like, okay, things are not working, but then we also don't know how to make them work.

It's a good way to just transition into a space of, okay, this is how we can make it And not to say that product development has solutions for everything, but I think in some ways, like this happened, right? 10, 15 years ago when like we went from waterfall, sort of product development methodologies to more agile methodologies. It was about saying,

how do we make decisions smaller? How do we make them more regular? How do we get in the habit of making them regularly so that, you know, as circumstances change, we're able to keep making decisions quickly and regularly. Yeah, better. Yeah. Yeah. Good talking. I feel like we should explore this a little more. Yeah. Like in some time when we have actually had time to implement this thing and to see like how has it worked for us? If it has or if it has? Well, and I think

because this is going to be one of our areas of focus in the new year. So really kind of, we should be able to have a few podcasts, I think, underneath it. And then also, yeah, maybe talk about our, how it's going for us in our, in our blog. It'd be cool. Yeah. Okay. Bye. Good. Awesome. Good chat. Bye. Thanks for listening to this episode of Thinking on Thinking. Our theme music is by Steve Gomes

and you can find a link to it in the show notes.

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