Cassius Kiani: Learning How to Learn & the Challenges of Leadership

Cassius and I talk about why it's important to learn how to learn, the challenges of moving into leadership, and why asking questions is key to solving problems.

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Photo of Cassius Kiani

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Product Designer & Entrepreneur

Cassius Kiani

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Website, LinkedIn

Selected links from the episode

Mark Channon – The Memory Workbook

Full transcript

Christian: Welcome to Design Meets Business, a show that inspires designers to think beyond pixels. I’m your host Christian Vasile, and on this podcast, I sit down with creatives to talk about their stories, lessons they’ve learned during their careers, and how you can use design to make a bigger impact in your organisation.

Today we’re talking to Cassius Kiani, a fascinating product designer, entrepreneur, and former lecturer at the Imperial College of London and MIT. In the next hour you’ll hear us talk about why it’s important to learn how to learn, the challenges of moving into leadership, and why asking questions is key to solving problems. 

Cassius, thanks a lot for joining Design Meets Business. Your background in design is very diverse. You’ve got to work with a wealth of companies that everyone has heard about, whether that’s Bumble or GoDaddy, or Facebook, and you also got to lead products in the fields that are a bit more ambiguous, let’s say, like blockchain and emerging technologies. So we’ll talk about what all of those different experiences taught you as a designer. But before that, let’s go a bit into your background and how you started out in Design, and if you remember, what’s the moment that made you want to become a designer?

Cassius: Yes, so that’s a rather interesting question. So I’ve always been interested in technology in general. And I spent a great deal of my time as a teenager and young adult exploring, experimenting with social media. And that could be things such as just creating MySpace themes and hacking around the bits and pieces.

And I wouldn’t necessarily call that design, but it was at say my first soiree into using design tools. And then, from there, I suppose my path is unconventional because I didn’t realise that there was product functions within businesses until I ended up working in a start-up. And I originally worked at a start-up within marketing specifically.

And from there, I then saw different aspects of the product function and realised that some of these skills that I’d spent my time learning as a teenager and hacking around with were actually useful. And from there, I started to essentially do the same thing that I think a lot of people do when they realise that something is interesting, and they start to talk to more people about it, learn more, find out more about it.

Then I met some very talented individuals who, let’s say, acted as my mentors. And then from there managed to scale that into a profession and through the consistent practice of doing good work, managed to, let’s say, move forward from there. So it’s not a very romantic story as much as it’s quite a pragmatic, practical one.

Christian: So, what were some of these skills that you’re mentioning? Because I can relate a bit to that. I started by coding for fun when I was very young, and then suddenly that turned into design. So was coding one of them, or what were some of these other skills?

Cassius: Yes, so I definitely think that programming is something you have exposure to at a younger age than you would, say, design, simply because the idea of making websites and apps comes up a lot. People don’t tend to understand that the difference between design and development is the same as architecture and construction. There’s a fine line. And so I explored programming; I did a lot with WordPress and hacking around with bits and pieces. 

However, I definitely would have considered myself much more of — I think they call them growth hackers in the space; someone who could take different aspects of marketing and a couple that with development. Now, I wouldn’t necessarily say my development skills were rather strong, but they were good enough.

So I suppose that the skills I realised I could apply into design were things such as critical thinking and what people obviously define now as user experience — the idea of how can you help people accomplish their goals or solve their problems through a product specifically. Because you realise quite quickly that — at least I realised that those two things are separate in terms of what people think about as development in a standard sense. So I realised that actually, I enjoyed that side of things much more. And then I’ve managed to find labels from that. 

I mean, when I first started doing this, this would have been around 10 years ago. So the industry itself was, especially if you’re a young person you grew up in the UK, was something which was a little bit more mysterious. User experience existed. Yes, UI/UX was talked about, so was product. However, it was by no means an absolute standard function within businesses, unless you were venture-backed or you’re a booming internet business at the time.

Christian: You’re right. I remember 10 years ago; it was not even product designer. You are a web designer, right? The industry is evolving just as a role if you want, is evolving. Again, with the industry evolving, I guess we as designers need to evolve as well. So throughout your last 10 years, let’s use that as an example, what were some of the things where you can look back and say, “That’s what’s allowed me to get to the point where right now I can build teams, and I worked at all these successful companies?” What’s the thing that made you successful in your career that you’ve managed to develop throughout time?

Cassius: Absolutely. So this is right. This is a rather interesting topic for me, because I have quite a strong opinion on this. So I believe that the majority of leaders in the world are great synthesisers, which means they’re able to find threads between people, business, and technology, and they’re able to pull on them. And typically, to do that, you have to be what some people would call a polymath.

So you have to be someone who is capable of learning, and exploring a number of different areas and understanding how those areas start to fit together and from there, be able to synthesise thoughts based on what you’ve learned. And so for me, I’d say that my unfair advantages is I spent a great deal of time learning how to learn. I surrounded myself with experts within the field. And from there at the same, what I did a lot of was attempt to find my own thoughts and opinions on things, because it’s rather easy to read a textbook. It’s rather easy to listen to what someone says and to say, “Okay, that makes sense.”

However, that isn’t necessarily synthesis. I wanted to understand a little bit more about perhaps why things were the way they are and how I could then apply that into, like I said, these three different fields of people, business, and technology. And so synthesis, I’d say, has been the thing that has been my unfair advantage. And I’d say that any leader in the field or any leader within almost any company is rather good at synthesis. 

Christian: I love this topic of learning how to learn because I think there’s, especially in education today, there’s an emphasis on learning. Here’s the curriculum. Here are the things you need to learn, and by the end of school, you need to pass a test to show that you’ve learned those things, but we’re not really talking in education, whether that’s design education or any other type of education, we’re not really talking about what you mentioned earlier, which is learning how to learn. 

Did that come natural to you, or have you picked it up from somewhere? How did you find this concept, or how did you start thinking even about learning how to learn?

Cassius: For me, what happened was I stumbled across an interesting set of people known as mnemonists — so people who could memorise obscenely long pieces of information. So let’s say 150 words in five minutes or a thousand digits in a short space of time.

And for me, I found that quite fascinating, because I wouldn’t necessarily say I have a good memory by any stretch. And so I was curious to learn more about what these people could do and how they learned to put together these structures in their minds, which allowed them to then absorb copious amounts of information and to do something with them.

And so I actually spent a great deal of time being taught by a previous Grandmaster of memory, who I sought out and asked for some support. And he showed me all of the techniques, tricks, and tips. And from there, I started to ask myself questions around what makes these things work? Why do they work? How does the mind work in relation to these techniques? Why are they so effective and so sticky?

And you quickly realise that actually, this whole process of learning consists of three big blocks, where you have encoding, consolidation, and retrieval. And the memory side of things is the retrieval side, and encoding and consolidation is stuff that we interact with a lot on a daily basis through education and everything else. 

The only downside is that most of that is heavily focused on rote learning and the idea of being able to absorb facts by simply repeating them and expressing them over and over again, rather than understanding them. And from there, I started to dive into the topic and learn more about what is mastery and reading a lot of the literature around that, and at the same time, attempting to apply that as much as possible to some of the things that I’ve learned.

So I’d say that — Oh, how did I learn how to learn? Well, ultimately, I became curious to know how some people can accomplish so much with that time, and why I was accomplishing so little comparatively. And from there, I think I was like everyone else. I was looking for a magic pill, and then what I realised there was there wasn’t one. The closest thing I could find was, let’s say, the equivalent of a protein shake for the mind. 

Christian: Right. So let’s stay on the topic of education and learning. You are self-taught, right? You haven’t gone to design school. If you would have to start all over again today, would you go the same route again, or would you actually try to get get some education? What’s your opinion on that? 

Cassius: So I’d say that design education is fundamentally broken. And I’d say it’s fundamentally broken because it still relies on a huge amount of tacit knowledge in order to get things across. So when I say tacit knowledge, what we can view is we can view — if we view an iceberg, explicit knowledge is the tip of the iceberg, and what sits above the surface of the water and tacit knowledge is everything which sits below the surface. 

So that’s the stuff that we learned from doing, which is rather hard to explain and rather difficult to bring to the surface. Now it’s difficult; it’s not impossible. When we look at fields such as Law, Medicine, or other scientific fields what people have done really well is they found a way to take all of this tacit knowledge and to bring it to the surface and make it explicit, which means we can have a conversation about it and it makes sense. 

If we look at Neuroscience, for example, we no longer need to talk in high level of abstraction around what neurones do and how they interact with each other in terms of, let’s say, neuronal circuits in the mind. We can now have conversations around them and start to understand things. We haven’t done that yet with Design.

Design education is fundamentally, still an incredibly tacit process, which means that you have to have experience. You have to be out into the real world, and you have to interact with these things to get to understand a little bit more about, again, the people, business, and technology of things, and to make it work.

Now, I don’t necessarily believe that that’s how it has to be forever. However, no one has really spent the time to bring all of these tacit and pieces or these tacit subject matters to the surface. They’re not explicit yet. And so if I was to go back in time, I would 100% continue on the path that I continued now, simply because I’ve met and interacted with people who have had a, let’s say, from design education and unfortunately, the curriculum or the system simply hasn’t found a way to take all of that tacit knowledge that you learn and bring it to the surface, not even in a way, which I believe is useful from a fundamental starting point.

Christian: I can relate to that. Just to segway a bit into a story. I do actually have a design education, but as I mentioned in one of the previous podcasts, I haven’t really used it for anything because it was so slow in teaching you what it had to teach you that you could learn it outside of school and get a client or potential client where you could apply that knowledge. So actually, I was always a bit ahead of the school curriculum, if you want. So for me, it was more of a checkbox exercise if you want. 

So because I can relate to that, I fully agree with you that probably because education — design education is broken today, it might not make sense to follow it. But I’m wondering, are there any cases in which actually it would be beneficial to you as someone starting out to go to school to get that knowledge that you’re talking about, even if the system is broken?

Cassius: So my perception here is that when people look at design, they tend to mix design too closely with art. And ultimately, they also seem to mix design very closely with execution. Now, design is ultimately a number of things. It’s a process, which means it can be used for strategy or execution. It does not have to be simply a production skillset. 

Now, when we talk about design education, unless you’re looking at schools which have identified these problems for a long period of time and have done their best to overcome these things, so you have schools such as perhaps Parsons or perhaps Glasgow School of Art, where they have very specific courses where they’ve identified that actually design is a little bit more than simply — I mean, a lot more than simply the case of learning, how to use tools and being a, let’s say, a pixel pusher or production monkey.

So when it comes to design, I find that it depends on your goals, because there definitely are schools which will teach you to produce well. Now in my opinion, production is not a long-term skill. And it’s not a long-term skill which has any longevity, simply for the fact that we have to be quite honest and quite frank here, and the majority of us are going to get old. We’re going to have families, and we’re going to — at the end of the day, end up in a situation where keeping up with the Joneses is far too complex. I realised that at a very young age, when I was messing around with PHP and Java and Javascript, and then all of these new frameworks coming out, and I have friends who are incredibly deep in development who also suffered from the same, let’s say, learning fatigue of having to keep up with all of the modern trends.

Now, you can add huge amounts of value by being someone who can steer the ship rather than the person that builds the ship. And I feel that for a lot of people, if you wanted to just — if you want to do something, which is heavily production-based when you’re younger, by all means, go for it. And I think you put — you rather enjoy it. However, I do feel there comes a time where the majority of designers should consider how much time they want to spend, let’s say, as someone who does pure production versus moving into someone who could move into leadership and management. And I think that that’s a natural transition for a lot of people.

There are some absolute superstars who can, let’s say, go against the grain and be incredible with production late into their 50, 60, 70s, and that’s fine. However, that’s by no means the majority. It’s the minority. It’s the top 1% of producers in the world, let’s say.

Christian: So moving into leadership and steering the ship as you’ve called it also comes with some other challenges that producing the work long-term doesn’t necessarily have — you have to suddenly deal with people. You have to manage people down. You have to manage people up. And every single time you have to deal with people because we are so complex, there are a lot of challenges there. So what are some of these challenges of moving into leadership that you have experienced throughout climbing the career ladder?

Cassius: Absolutely, the two biggest challenges I think most people would face and the ones I certainly faced were the illusion of transparency, which is believing that what you say is what people hear. And that’s an incredibly hard thing to learn and to understand. Because you may have a crystallised idea in your head and an image, your job is to attempt to implant that into someone else’s, and that is — to understand how to do that is it’s an art as well as a science. And it takes a long time and to learn how to use words to — first of all, take what’s inside your head and allow someone else to see and understand that. And then, at the same time, to clarify whether everyone is aligned and on the same page.

So some people call that communication, and I would agree. However, the problem with communication is that we then assume that everything we say is transparent; it’s not. People have different experiences. They come from different backgrounds, and they are likely to interpret what you say differently to the way that you want it interpreted. So creating alignment through communication and, let’s say, bypassing the illusion of transparency is one thing.

And then the other side of the things I say is listening. Leadership is not about telling people what to do by any stretch; it’s about simply making good decisions. And making good decisions requires data and information. Now you may have lots of data and information, and you may already know what you want to do and what to say. However, if you are working with someone or you’re leading someone or managing someone, the first thing that you should ask is what do they think should be done next. Because quite frankly, most of the time, if you ask someone, “Okay, so from here, what do you think we should do?”

Regardless of whether or not you know what to do, that person — one is a useful learning curve for them to attempt to, let’s say, piece together parts of the puzzle, and to then understand where to move forward, which is a good way of creating another leader. I mean, that’s one successful criteria of leadership, good leaders create other good leaders. 

And then the second side of that is, can you then understand and — either what you haven’t seen or perhaps where you fall short, because more often than not, you’d be surprised when you say, “Well, actually I think we should go in this direction.” But you give someone else the platform to speak, and they’ll say something, and you realise, “Wow, that’s interesting. I hadn’t thought of it like that. So maybe we should do that.”

So I find that if I had to summarise those two things, move past the illusion of transparency. Understand that people are complicated and they do not always hear what you are saying as what you wanted to be interpreted as, and on the other side, spend more time listening and asking people what they think you should do and make a decision with that rather than simply being the person who dictates absolutely everything.

Christian: I think that relates really well to what I see the role of a designer and design leader be, which is more of a connector. In a business, you’re the connector between maybe the engineering department and the people who are in sales and marketing and everyone else. But also from the business perspective, you’re the connector between that business and its customers.

So I see communication as — or being good at communication, listening obviously is part of that, as an absolutely fundamental part of being a good design leader. And I’ve heard this quote once, which I think goes like this, ‘Communication is not what you say. Communication is what people understand through the words you’re saying,’ which is basically what you’ve said. 

So when you keep this thing in mind, and when you go into a company where as a design leader you don’t only need to manage down (your design team), but you need to do a lot of managing to the left and to the right and even up. Would those same skills apply, or there’s something else you need here as well? Are there other challenges?

Cassius: Yes. I mean, there’s lots of challenges. And so one of the things that people need to become accustomed to, and I feel that people have a lot of resistance to especially young designers and designers in general. So if we had to look at this from a perspective of personality psychology, we can say that most people who become designers would be rather high in trait openness, which means that we’re rather accepting of a lot of things, we’re open-minded, and we’re interested in exploring things, which means we tend not to like boundaries or hierarchies.

Now the irony here is everything in the world, including your mind and nature is constructed in a hierarchy. And when you hear the word deep, deep is the millennial word for hierarchy. If we say deep learning, it just means hierarchical learning.

So what we have to begin to understand is that all self-organising systems eventually organise themselves in hierarchies, and they do that for a myriad of reasons. The reasons are usually the evil of the hierarchy. Competence is not a reason to be at all for a self-organising system. Competency is great because then people get good results. Now, if something self-organised is in a way where let’s say it’s negative hierarchy based on something arbitrary looks, there’s a problem, because that has no competence, no value. It’s not useful for anyone. 

So when we’re looking at, let’s say a company, and we’re looking at maybe a start-up, or we’re looking at a team that’s growing from 10 to 100 people. You move from a very flat structure because that’s fine. There’s enough nodes in the system that say 10 people that you can share information in a very light, transparent way, and it’s not overwhelming.

Now, if you’re in the middle of that system, let’s say, and it grows from 10 to 100, and now, you’re responsible for the information that flows downwards as well as the information that flows upwards, well, now you become one of these nodes in the network that has to do some level of filtering.

So what you have to realise is that when things start to self-organise into hierarchies, the number one reason for that is to, let’s say, constrain the flow of information. And constraining the flow of information is really important, because if you are overwhelmed by everything that’s going on constantly, you can’t get anything done. And a really simple example of this is to just simply look at the way the brain works. About 99% of our processing is unconscious, which means we don’t really know it’s happening. Our conscious cognition is 1% of all of our total cognition. And that’s simply because if we had to attempt to attend to everything that was going on at the same time, it would be absolutely bloody overwhelming, and it’s the same with an organisation.

Which means if you’re communicating up or down, what you really have to understand is what information has to go where and why. Now there are certain things that I’m completely, let’s say, all for in terms of transparency. By all means, let’s talk about salaries. Let’s talk about what’s going on. Let’s talk about runway, everything else. No problem. 

Now, is it important for, let’s say, management to hear about all of the troubles that happened on the ground if these troubles on the ground are trivial and resolved? No. Is it important for them if these things look like they could bubble over, and let’s say, damage the system in the long term? Yes. And equally, it works both ways. So when you’re working with a company, you have to understand that ultimately, if you’re a leader and there’s someone above you, and there’s someone below you, you have to manage that flow of information. And you simply need to understand what information is relevant, where, when and why, or how to take all of the information that you’ve seen and given and condense it in a way that is useful to that part of the system.

And that’s quite tricky. And I feel that that’s something that people who move into, let’s say a leadership position and design tend to struggle with is the idea of one understanding that the systems form hierarchies for a reason. And two, to understand that actually, the hierarchy is simply to control the flow of information and to ultimately control competence.

Now, if you understand those two things, the world is a lot less mysterious and mystifying. If you become comfortable with that, then you can safely say, “Well, provided I become more competent and I understand how to transmit information in different directions, then I will probably get some social mobility and some upward mobility, that’s fantastic.”

So I’d say that the biggest challenge for people moving into leadership is to attempt to understand how hierarchies work and, at the same time, to understand simply the flow of information. Information theory is really useful here. However, that’s overkill. I mean, the simple answer is know what to say and when to say it.

Christian: And that I assume, or maybe this is the question, that comes with experience, or do you think that’s something that someone can teach someone else?

Cassius: I think you can teach it. I would say that it may feel quite tacit to someone who’s been in that position. And again, if you spend a great deal of time learning from experience and you’re quite pragmatic, it can be quite difficult to pull some of these rules to the surface. However, there certainly are rules where you can say to people, if you do these things, then you’re likely to be more successful, and you can make it rule-based.

What I would say that, here’s the chaotic modifier, if you will, is people are different. And so there are certain people who sit within different positions of these organisations that have different personality types, have different dispositions, and they may want different things from you. And learning to interact as a different node on the network is quite tricky.

So if you are someone who is relatively trusting and the person up top is, let’s say, very skeptical, you have to learn what information they need to hear in order to allow you to move forward in the way that you want to move forward. Especially if, let’s say, you have enough indicators that the team that you’re working with or leading is moving in the right direction. Someone who wants data is not going to be convinced by simply, “Okay, well, these anecdotes make everything okay.”

So to some extent, that’s the modifier. I’d say that if I had to pull out two very — two quick rules, which may be useful here, then I’d say understand who you’re talking to and then understand what they need to hear. And if you can get a sense of that — and that, unfortunately, takes a little bit of time, then usually you’re in a good situation. 

Christian: So it sounds like transitioning from being a designer on the ground, doing the hard work, to a design leader position, that’s a bit of a different type of hard work, takes a lot of experience, a lot of skills, a lot of things that are built over time, but I’m wondering, you as a design leader have probably worked and helped other people become design leaders or at least get closer to it throughout your career. Are there any patterns there? Are there any traits that you know if a designer has this trait they’re much more likely to become a good design leader, or is it down to training and experience?

Cassius: I don’t think it’s done at the training or experience. I think that there’s a number of people who are incredible leaders at the age of 13 and 15, and they do not necessarily need to spend 10, 15 years climbing, say, a corporate hierarchy or even a design hierarchy to get there. I’ve met plenty of people who are serial founders and have exited three companies by the time they’re 25, and they are incredible leaders.

And what I tend to find with these people is that the traits that they show which show that they’re good leaders, is that they can, one listen and two, they can understand where information needs to be channeled more than anything else. Most good leaders are incredibly good at simply finding people to listen to and listening to them and from there, making decisions. It really isn’t a game of becoming better and better at making decisions and understanding when and where you have enough information to make a good judgment call on something.

Now, the more complicated the industry, the more complicated the subject, the harder it is to gain some of that knowledge. If you’re in biotech, for example, there’s a lot of rules and regulations that will dictate how quickly you can move, comparatively to if you’re in a SaaS company and well, let’s say, what is a good and bad move? And even in SaaS, then you have things like FinTech, you have different types of legal tech as well. And they have different hurdles to comparative creating dev tools. 

So I don’t think that you need 10 to 15 years’ experience. And one of the things that I come across when I speak to a lot of young designers is they say, “I don’t have enough experience here.” I think that’s garbage. I feel that, quite frankly, if you wanted to become a design leader, you could do it in six to 12 months, provided you work on the soft skills required to position yourself in a way where one, you learn how to listen, two, you learn how to make good decisions more than anything else. And I think that everything else after that is perhaps superfluous. 

Now maybe you could argue that actually to make good decisions, you need higher IQ, and if you have higher IQ, it becomes easier. However, there’s plenty of people with high IQ that make bad decisions as well. So it’s simply as a case of understanding the frame that you’re working within and the dots that you can join within that frame and to say, “Okay, well, this is a good enough decision right now and here’s how we’ll measure success going forward.”

Christian: So wouldn’t you say — at least I would think, that in order to be able to make good decisions, you need to have a bit of experience in that frame that you’re working in. So how could someone coming in, as you said, six to 12 months, even if that person at a people level is a great leader, how can that person make good decisions considering that person doesn’t necessarily understand and all the complexities of that frame they’re working in?

Cassius: You don’t necessarily need to understand all of the complexities as much as you simply need to understand why? What you find quite quickly is that if you ask someone something and they give you an answer, and you say, “Okay, and why would that work? Or why is that the way it is?” And someone can’t, let’s say, move down one more level of the hierarchy, I mean, usually, the troubling thing that we have here is that if you ask some of the three whys, then they get stuck incredibly quickly.

Now there are certain professions where people do not get stuck at three whys: doctors, neuroscientists, psychologists. Eventually, things — typically, if you ask why enough times, they can still give you a rough answer. What you tend to find is that if someone understands what they’re talking about or the reason why something should be done, then as you question it and you attempt to pull the argument apart, it becomes incredibly difficult to do so.

And then you can start to weight, “Okay. Well, actually, if this person can give me a coherent explanation of this over and over again, and I then have the opinions of five people. And all of those explanations seem coherent, and they’re all roughly in line, well, the question is, “Okay, now I’m going to ask everyone what would happen if we were wrong? What would we do if we’re wrong?” And typically, you then get some more interesting information.

I mean, ultimately to become a good leader, you simply need to — I mean, you don’t need to know everything about industry as much as you simply need to understand how to weight opinions and how to weight information in a way that allows you to say, “Okay, well actually I don’t know anything about, let’s say, human biology. However, you’ve all produced convincing arguments; we’ve now weighed all of that up. Some are false; some are against, some of these ideas have collided and clashed. We’ve now identified what the worst-case scenario is. We’ve identified what the best cases. I think we do this. Can we all agree and commit?” It’s like, sometimes they’ll say, no, we can’t all agree. It’s that fine. Well, can we all disagree and commit? Yes, sure. Fine, but let’s commit.

And it really is just a case of simply being able to pull out the right — pull out information. Sometimes that’s simply a game of asking the right questions. However, if you start with why, most of the time you’ll be able to get past someone that say fake explanation, and a fake explanation is incredibly dangerous, because if someone gives you a fake explanation, well, suddenly you realise that there’s a problem and this is a big thing of design. I mean, if I start to talk to — if someone asks me a question around, let’s say, “What size should fonts be in across, let’s say, hero images?” It’s like, “I don’t know.” 

So there is no right answer, really. It’s like, you can’t make good judgment calls on stuff like that.

I mean, eventually, you’ll get to something which is useful. But as a leader, you don’t necessarily need to know all of these things because they’re superfluous. Most of the stuff that we feel as designers are useful for leaders or not. I mean, I don’t care how big the font is on the homepage. I don’t care what font you use. I equally don’t care the colours or anything else. Provided it sells and provided what we’re doing is putting something together that markets to our target audience. I don’t care if it looks like Airbnb or LinkedIn; it really does not bother me anymore. It mattered a lot more to me when I was younger because that would essentially show how competent I was, how pretty I could make something, but in the future, that no longer matters.

So yes, I suppose if I was to summarise that rather large train of thought, it would simply be a case of, if you can weight decisions and you can ask why, and you can ask the right questions, then suddenly you realise you don’t need to know much about anything. You simply need to be the person that can make the right calls. 

Christian: I want to talk about that transition from a few years ago to today, but before that, you wrote an article which relates to what we just discussed called “Thinking Like an Experience Designer.” And in that article you talk about how thinking like a designer basically means asking questions. Can you talk a bit about that? 

Cassius: Yes. So the fundamental difference between art and design is that design must solve a problem. Art does not need to solve a problem. Art can simply be visually pleasing and appealing. Now, how would you turn art into design? Well, let’s say you create art, which then helps people with depression or helps calm unruly animals. Well, suddenly that’s a design problem, and suddenly, you’ve created a solution for something.

So when we’re looking at what design is really, it’s the case of solving problems. And really, to solve problems, you have to be able to understand what the problems are. It’s really easy to take a top-down approach and to say I’m prescribing solutions to a market rather than understanding the problems. And I’m not necessarily saying that you should take a purely bottom-up approach either of saying, “Well, actually, all of the markets says it wants this. Let’s give it to them.” Because quite frankly, people can’t see what they can’t see, and people don’t know what they want until you show them to some extent, anyway.

So it’s finding that balance between top-down opinions on things, and let’s say, bottom-up support from the people who you want to serve, anyway. However, in order to do that, you have to ask questions. And so when I’ve worked with my own companies’ entrepreneurs that have a track record of success, what I tend to find is that when things go really well is if they have an idea, they first say, “Well, I wonder what problem this solves.”

And once they have that and then go and say, “Well, I wonder if people actually have this problem, people that aren’t simply me.” When a lot of people say, “The reason my company has succeeded is because I built it for myself.” Well, in that case, perhaps after doing a little bit of research, you realise you’re not an anomaly anymore. You realise that the problem that you have everyone shares, and they face, and they experience as well.  

And design really is that process of being able to understand what problems exist, why do they exist, and then to understand a little bit more about, will they exist in the future? E.g., if no one solves this, will there still be a problem tomorrow? And do I need to be build a tool to solve this? Or do I need to simply change the way that someone behaves and their habits, because those are two different things as well.

GitHub, for example, is much more of a behavioural change for people than is an actual useful tool in the sense of what it does. I mean, it does have a fantastic number of things, however, git on a fundamental level. Does all of those things. It simply doesn’t allow people to interact with the system and change their behaviour. And you’d say something such as Asana or a Trello is a good example of this because quite frankly, anyone could pick up some post notes and stick them to a wall. However, that’s not necessarily collaborative, and it doesn’t change behaviour.

So there are some things which we can say will exist forever. I used to, when I was younger, think, well, I can’t start businesses because all the good ideas are taken. Well, turns out that if you want to do something exciting, most of the time you can simply ask questions around the clothes people wear, the food people eat, how people get from A to B, how people collaborate. There’s always a business idea somewhere as long as you can find the problems.

So I guess when I talk about design and being a designer, the idea of asking questions it really comes from taking a problem-solving approach to things and focusing much more on the problem than the solution. And again, we all get caught up, and this is much easier to think about solutions rather than problems and if you can strike that nice balance. This is why I don’t like to label myself as a designer when everyone is really a designer. If you can ask the right questions, then technically you’re using design as a process to solve something as a problem for real people. That’s how I tend to look at these things. 

Christian: If you’d start your career at that lower level, where usually you feel, and the role you take in companies is more of a pixel pusher. Then after a few years of having that experience and understanding what design is, you move a bit more into caring about the experience of the customers, and we call that user experience.

So then after a few more years, you move into the next level, which is, “Well, actually I need to care about the customers, but I also need to care about the business because, without a business there are no customers.” So I know that transition happens over time, but what can you, as a designer, just starting out do to speed up that transition?

Cassius: I mean, this is what’s really interesting to me is that most of the beliefs that people have about what they can or cannot do are self-limiting, they don’t exist. If your dream is to start a start-up, or you dream to be a lead designer or a design leader, then do it. There really is nothing stopping you. The only thing that you have to ask yourself is, let’s say that you right now, you say, “I want to be a thought leader in design.” Okay. That’s fine. What are you going to say or do to add value to the industry? And if you can figure that out, well then go and do it. 

Now along the way you’re going to learn, anyway. If you say, I want to be a leader in interaction design. Well, you’re going to have to talk about and create things which are used by lots of people in that process. And simply by doing that, you’re going to learn more. I mean, depending on how much time, energy, and effort you want to commit to this, you could in six months achieve what some people achieve in six years. And it really is that process of saying, “Look, if you want to fast track something, the honest answer is simply to go out there and do it.” If you want to be the founder of a start-up, the only thing that’s holding you back is self-confidence, because quite frankly, if you want to raise money, then what you do is you put together an idea, and then you go and talk to some investors, and the investors will hate it.

And then you go and talk to the customers again. And the customer say, “I don’t know why the hell you put this together. This idea is rubbish. These are my problems.” And then you say, “Okay.” And then you put together another idea, and you’d go back to the investors, and the investors will hate it. And you do that a few times, and suddenly you realise, “Oh, wow. Someone’s willing to invest. Let’s say a small seed into this, and I can get somewhere.” You simply have to be comfortable with failure because it’s the only way to learn. 

So my concern here is that most people take a really safe path into moving forward because they’re worried about arbitrary limitations around failure or all of the things they need to learn. And nine out of 10 times, it comes back to this idea of information theory. Is you don’t need to know that much; you simply need to know enough about the problems that you care about and the direction that you want to go in, and that’s enough. And if you go out there and you flounder around and fail, that’s absolutely fine because if you’re able to listen to this, then you’re in a privileged position in the world where failure is not going to be the be-all and end-all of your life right now. It’s a very different position if you come from different backgrounds, but if you are part of the 10% of people in the world that can listen to this, it’s like, “Well, count your lucky stars that you could go out and fail and there would be no problem here.”

And most of the time, if you want to keep your day job, which is still very safe and spend 6:00 PM to 12:00 PM every night, working on wherever you want your future to go where you can, and that will happen. So I find that it’s so arbitrary when someone says, “What can I do to speed things up?” Is that do what you want to do or do the things that you feel are going to be useful for you. And ironically, provided it’s overwhelming, and this is my only criteria: if you’re moving in the right direction, it should feel overwhelming. Nothing that’s easy or nothing that makes your heart sing is really ever, “Oh, this is easy,” etc.

I mean, there’s a reason that people talk about creative distress and things like that. It’s because when you’re putting yourself on the line, it hurts, and so to some extent, if you’re feeling a little bit overwhelmed with where your life is going, but then hopefully provided you’re taking action, which is moving you in the right direction. And you’ll be able to tell by giving yourself some arbitrary markers, “I want to be a design leader in six months. What does that look like?” Pick any arbitrary measure. I don’t care if it’s followers on Instagram, Twitter, or anything else, just pick something and measure it. 

Now, if you’re measuring it and it’s not going up, it’s like, “Okay, well now you know what to change.” If there was no measurement, then that is a bit tricky because you don’t know if you’re just being unusually stupid or if you’re actually moving in a positive direction. I suppose if I had to summarise this, it’s the shortcut for anyone that wants to do anything is simply to go and do it.

And, quite frankly, I sat there idolising the idea of running my own start-up and raising money at a very young age. And I realised that actually, the difference between the person who raised money and run a start-up was, quite frankly, nothing other than I was willing to go and do it. The trending right now is the fact that the founder of Gymshark is a billionaire at 28. And what’s the difference between me, you and him is simple: he started Gymshark. There really is no difference at the end of the day. I have two arms, two legs, and so does he.

Christian: Nice. So you told about just go there and do it. I liked that mantra. I think Gary Vaynerchuk talks about this a lot. He says, just start. That’s his thing. When people come to him and ask, “How do I start a business? How do I do this?” He says, “Just start.” Just start and then you’ll — as you go on that road, you’re going to see there’s a way to the left, there’s a way to the right and then that’s kind of going to guide you, but if you don’t start and you’re stagnant, how are you going to go? Which direction to go into the next? So I love that.

I want to talk a bit about, you’ve built a few product teams in your career and the things that you’re looking for when building teams, the things that you’re looking for when you’re interviewing designers, when you look at their portfolios when you try to build a high performing team, what are some of those?

Cassius: Most of it comes down to hard work and work ethic, and ultimately it comes down to someone’s ability to realise that they can do more. I would say that I don’t care necessarily too much for someone who has — it depends. It depends on the project. So if I’m hiring freelancers, I need someone who can come in quickly and get things done. So in that case, I’ll look at your portfolio and say, “Well, you have what I need right now. I don’t need to nurture you, and equally, I don’t see us as long-term investment. I need you to come in, do your work, and you want to leave anyway.” So that’s a valuable exchange. We shake hands, and everyone wins, done.

And so if you’re a freelance, you really should simply be able to show some level of competence to the person that you’re pitching to around what you want to do. So if you’re a web designer or you are a UI/UX designer, you’re product designer, a design strategist, anything to do with design regardless of where you are in the value chain. Provided you can show and convince someone else that you are capable of doing what you do and that you are able to deliver and other people can vouch for your delivery, and sometimes that’s really as simple as putting some logos on a page. That’s enough. 

Now, if you’re building a design team and you plan to scale something. Well, if you’re hiring — it depends how high you’re hiring to some extent. Even then, if you’re hiring for junior to mid-weight designers, 90% of the battle is their work ethic and how much they’re willing to learn and improve and just take on feedback. Most of the time, if you have people that tick those boxes, then they’re the right people. And I don’t want to get into this weird, aggressive work culture where people suggest that you should work 20 hours a day.

However, if someone comes to me and they are slightly below what I believe they need to be, and they work 20 hours a day, I sure as hell would give up person priority over someone who won’t. And the fact is that you can technically, to some extent, outwork the competition at that level. It becomes a bit trickier later on in life. I mean, quite frankly, I can’t outwork Bill Gates, because Bill Gates is much more efficient than I am. He has a myriad of things and a cumulative advantage that I do not have. So I can work 24 hours a day and still lose. However, when you’re starting out, that does work, and it does work relatively well to a point. So for junior and midway, work ethic is something that I would definitely hire for. And I think that 90% of design leaders will take work ethic and someone’s ability to take on information and feedback on board as a positive indicator of joining a team. 

Now, as you move up and you start to move away from production, what I really care about is, are you going to listen to other people? Are you able to communicate? And if you’re able to communicate, are you then able to make good decisions based on the information that you receive? And are you able to put out fires before they start? And are you able to identify some markers of performance going forward that makes it easy for you to do your job and easy for me to do my job.

And if you can take all of those boxes, then as far as I’m concerned, you’re a good designer. And I would certainly say that a portfolio is important if you’re earlier on in your career than later, because as you move later on into your career, will people realise quite quickly that the way that you speak and the way you interact with the world is much more important. Whereas, if you’re junior to mid-weight, you’re going to have to prove to someone that you can — you can create and commit. 

And nine out of 10 times the portfolio is — it’s an arbitrary checkbox exercise. It’s simply needs to show that you understand what design is and if you can do so in a way that says, you kind of understand the job you were applying for, because that’s a problem in itself and you know how to solve that, then I’m fine with that. It doesn’t need to be especially aesthetic. It doesn’t need to be anything else. All of that can be tweaked and changed. Someone can say, “Reduce the padding on these buttons, space this out there, don’t use these colours, don’t do that.” It’s arbitrary comparatively to someone who can work and learn in the process. 

Christian: I’ve always looked at portfolios, especially for more junior people as — or I’ve only said the portfolio is what actually has to get you through the door. It’s the interview where you’re actually making the impression, because you’re talking about hard work, for example. Hard work is difficult to show in a portfolio. How do I show in a portfolio that I’m working hard? However, if I’m front of you at an interview, and we tackle that topic, then that’s what I would bring that up. So with that in mind, how do you, how would you split the two — if you would have to create a portfolio for a junior, what are the things you’d focus on, and then what are the things that you would focus on in the interview process? 

Cassius: So for a portfolio for a junior, I’d simply talk to someone about why you did what you did. Okay, so you decided to do this. Why? Okay. For this reason. Okay. What made you think that was a good idea? These things. Okay. And what were the results of doing this? So if you’re really junior, you may have only arbitrary projects for show, and that’s fine. However, we live in a world where there’s no code tools right now, and there’s a few things that you could do. 

And even honestly, if someone gave me a portfolio and they said, look, “I put together this distributor website, and I wanted to sell sponges, but I didn’t really want to build it. So what I did is I went to a market, and I tried to sell sponges using this messaging and everything else. And say, “Okay, that’s interesting. So you’re testing an MVP. What happened? What did you learn? How would you move forward?” It’s not clear-cut. It really is a case of, “Can you show that you understand the process and that you will do, let’s say 1% more than another candidate would.” And that really is the seeding deal when you’re hiring anyone. And then moving forward is, can you show that you are willing to do that little bit extra? 

So in terms of portfolio, how you’d show hard work is, are you — how different is your portfolio in terms of what have you done that I haven’t seen before that shows hard work? What have you done that shows you know some semblance about the job or me? And I’m not — I mean, this isn’t too complicated. For example, you could scrape LinkedIn, you could use Zapier and Google slides to then take all of those tokens and create — you can have one template presentation. You could use Zapier to then take information from a CSV and update all the name tokens within the presentation. You could send it to me, and it could simply say, “Hey, Cassius, I’m this designer applying for this position.” 

And you could have already automated this whole goddamn process. I’ll never know. However that’s enough that most other candidates wouldn’t have done that, and you have my attention. So I’m willing to have a conversation with you. Now in the conversation, what would you have to prove? Well, typically, the conversation is a gauge of how well does someone fit for a role based on their character? And it’s really unfair.

A conversation is a really unfair way to understand how well someone would do at a job because we’re really biased. I mean, the human mind is subject to contamination from everything. And then when people say this stuff doesn’t matter, it really does. The way someone looks, the way someone sounds, the way someone does XYZ, it all matters. It all makes a difference. And simply because you are not conscious that you’re making decisions based on these arbitrary factors. Well, you kind of are. So someone does have to go out of the way to attempt to be their best self in an interview. And if you feel that you’re not getting — and my honest answer here is if someone feels they’re not getting an interview for a very specific reason, then that’s probably true. And so you should ask yourself, how do I change this thing to stop it biasing someone else? Obviously, I don’t want to get in to a PC argument about XYZ. Honestly, the problem here is that humans are really biased. They’re subject to contamination. 

Now in that interview, if you want to show someone that you’re good at — that you’re willing to work hard and that there’s a bar that you need to reach, well, you’re going to have to tell me things that form an impression in my mind that you will do those things, or you have done those things, or there’s some type of character reference that suggests you would. 

Now you might say, I train as a martial artist, I do CrossFit, I spent the last six months learning how to use Framer. I did this; I did this; I did this. Oh, on the weekends I take care of my sick parents. I don’t know, but there’s something somewhere that has to suggest that actually you are not like everyone else, because you are willing to do these things, and that’s interesting for me, and quite frankly, it depends. If you’re a junior, I’ll take a big risk, because one, you’re probably not — you’re going to have to work hard. However, you’re easily replaceable, and at the same time, to some extent, as a junior, my expectation of you is lower than probably what I expect you to do anyway. I’m going to want you to reach for the stars, but I’m going to underestimate you slightly, and your job really is to impress me. 

Now, if you’re mid-weight and the more senior you get, the more I overexpect you to deliver. And so in those situations, it’s a completely different paradigm. Saying that I’m going to learn, etc, etc. That’s why being able to read a conversation and understand the flow of information is more important. So for junior and mid-weight, again, there’s probably — there’s a bit of advice I’d give specifically around the portfolio and the interview is show that you in a portfolio do 1% more than someone else would. And then, and as far as the interview goes, simply give me indicators or give someone else indicators that if there’s a bar and you’re going to reach here, and you’re going to go beyond that.

Christian: The reason I love the answer around the portfolio is because you’re — it’s a thesis that I really believe in, which is,you can –there are some things you cannot control, so don’t worry about those. There are some things you can control, and that’s what you want to focus your energy on. And what you’re talking about is as a junior, I can’t control how much — how many projects I get, or I can’t control whether I’m self-taught or educated, but what I can control is the work I put in in creating that portfolio or anything around it. 

So I really love that. And I think this is really useful and helpful advice for anyone who’s sitting out there wondering, “How do I get myself out there? How do I make people see me?” And I think doing, as you said, 1% more than everyone else does is probably the best way of doing it. So I really love that. 

We’re running out of time. I just got a couple more questions. The questions that I ask everyone at the end of the show. First one is, what’s the one thing you wish more designers would know?

Cassius: That’s a good question. And if — one thing is quite difficult because I’m going to paraphrase it as one thing I wish that designers would know and then one thing I think that the industry wishes that designers would know. 

And so the first thing I think that the industry wishes that designers would know is that the way things look is arbitrary. I care about how much revenue you can generate for this project because revenue gives my company energy and that energy I can use to then do, let’s say, more good in the world.

So provided that you believe you’re working for a company that’s generating wealth, which means that they’re, let’s say, taking money, using it as energy to create physical transformations in the world for the good, then that’s fantastic, and that’s what companies care about. How can you help me generate wealth?

Now, what I think — or what I would really like more designers to know is how to learn. And I think that if people would simply understand the, let’s say, process of encoding, consolidation, retrieval, and they could simply repeat those loops over and over again. They could do so efficiently. Well, suddenly, you realise the world is not such a scary place, and you realise that actually, if you’re concerned about the threat of artificial intelligence or machine learning or anything else, well, design is fundamentally a process and a mindset.

And that can translate anyway if you decide that you want to move away from design and move into finance or anything else is like, those processes would still apply. They wouldn’t disappear. There’s a reason why most industries have product teams, and there’s a reason why design thinking and design, let’s say architecture and execution, are becoming much more of a talking point, especially design strategy actually, while I’m on the topic.

So if you know how to learn, well, suddenly you’re very dangerous, because you don’t necessarily have to fear change. And I feel that that’s something that I wish most designers knew. Is that your job is as far as I’m concerned, you’re in a privileged position because you can move and transform as you need to, provided you rely on the principles that you help other — you use for other companies to help transform, if you will.

Christian: Are there any resources, while we’re on this topic of helping, that can help people learn how to learn, any books, any podcasts, anything that you’ve discovered out there? 

Cassius: So I was originally taught by Mark Shannon, who was a Grandmaster of memory. And he has a book which is — I can’t pull it out. I’ll link it to you so you can put it in the show notes, but it’s incredibly simple. I think it’s called The Memory Work Book or something.

And that comes with a series of really simple exercises where you can prime and gauge yourself and how to learn. And it’s some of it’s really, really trivial as much as learning the phonetic alphabet or learning what, Alpha, Bravo, Charlie, Sierra, blah, blah, blah, that kind of stuff. But it allows you to understand the process of that over and over again. And all you have to do is then transform that process into things you actually care about and things that you want to learn. It makes it a bit different. So that is a — I think it’s about $10 and that’s a really bloody useful resource.

And I think that if someone started with that and they persevere because quite frankly, it’s the new skill and the way that you’ve thought for the last 25 years or 30 years, it’s going to be hard to overwrite and persevere with it, practice with it. There’s a task in there a day. That’s what originally helped me a lot to improve my skills exponentially, and then I just kept investing resources to improve from there. So that’s a very nice starting point. 

Christian: Okay. We’ll put that in the show notes so everyone can find it. Cassius, last question for you. How do you reckon the future of design as an industry looks like?

Cassius: I feel that the future of designers and industry it’s interesting because I don’t know if design will be an industry anymore. Because one of the things that we have to bear in mind is that because design is a process and a mindset and a series of, let’s say, a series of understanding how to solve problems, it’s a little like saying, “Well, it’s critical thinking and industry.” No, it’s a soft skill. It’s everywhere. It’s university applied. So product, I believe, will still exist. I think that one of the things we start to realise quite quickly is that design begin to, let’s say, transition away from simply being an industry, unless, of course, we’re relating to design in the most literal kind of sense of graphic design and everything else. That’s relatively timeless.

However, I feel that to look at something and say the design industry is – well, if we say design industry, we’re literally talking about producers. We’re not talking about design thinkers; we’re not talking about design strategists; we’re talking about producers.

So I really do feel that if the design industry still exists in 20 years, it will exist in the same way that it exist in 20 years prior, where we’re talking about producers. I think design thinking and design strategy and everything which surrounds that will be incredibly commonplace, because there’s a really big movement in design education right now. And the ability to democratise design as a process, and companies are switching on to how useful that is, and at the same time, why they should use design as a strategy and as a long-term investment in terms of people people’s mindset and performance, rather than simply an arbitrary production function.

Christian: Awesome. This was a learning experience, a learning show for me, and hopefully also for everyone listening. Where can people find out more about you? Where can they find you? Where can they get in touch with you? 

Cassius: I mean, they can — if you go to www.cassiuskiani.com, at some point that will link to more than my LinkedIn profile, go to a website or something else, because I have a few interesting projects in the work, specifically around learning that I’d like to share with people. I’ve just finished doing a set of them user interviews, and I’m running a short beta test in the next – in the coming weeks. So I’d suggest that anyone who wants to keep up with me, by all means, just go to www.cassiuskiani.com and if it’s LinkedIn feel free to connect and if it’s anything else, then let’s see what the future holds. 

Christian: Cool. We’re going to put all of these in the show notes so people can easily find you.

Thank you so much for being part of Design Meets Business. Really appreciate you. This has been very inspirational for me and again, hopefully, for everyone else listening. Thank you so much one more time, and hopefully we’ll catch up soon. 

Cassius: Privilege. Thank you very much. 

Christian: That’s it for today. Thank you so much for listening to the show. Since you’ve made it this far, I hope you found this useful, and if you did, you should know there’s much more content just like this on the way. So if you want to learn more about how designers can impact businesses, please consider subscribing and maybe sharing the episode with others. And before I say goodbye, remember that you can find show notes and links for this episode and others on our website, designmeetsbusiness.co. Catch you in the next one.