Camilo Oliveira

LLMs as a mirror for what you already know

I’m having fun following the advice of using AI as a thinking partner, not only an operator.

First case: Perplexity, methodologies, and frameworks

Yesterday, while doing personal research for a big purchase, I asked Perplexity about techniques to plan for it without hurting my finances in the future. Its reply gave me a lot of names:

  • Sinking funds
  • Zero-based budgeting
  • Total cost of ownership (TCO)
  • Opportunity cost
  • Discounted cash flow (DCF)
  • Internal rate of return (IRR) and many others

I noticed that out of the ~10 names it brought me, I was already doing 80% of them for years. I didn’t know that they were a part of any frameworks or methodologies, just mere tactics that happen to serve me well.

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“Could have” is dangerous

When using MoSCoW as a prioritization method, two things are obvious:

  • Must have: there is no value without shipping it
  • Won’t have: out of scope

Should have can include some worthy ideas that couldn’t make it into the first launch. It’s also likely that post-launch user feedback will replace most of those ideas as the next priorities.

The last item left, Could have, is pretty vague - and somewhat dangerous. If it doesn’t deliver instant value or can’t bring value anytime soon, should we even bother keeping it around?

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Companies are stuck with their existing products

The Gmail team built a horseless carriage because they set out to add AI to the email client they already had, rather than ask what an email client would look like if it were designed from the ground up with AI.

Their app is a little bit of AI jammed into an interface designed for mundane human labor rather than an interface designed for automating mundane labor.

— Pete Koomen - AI Horseless Carriages

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Talking about your work is how you finish it

Growing up I was taught that self-promotion = bragging, so I avoided it. My father made a living out of being a salesman, but no one at home bragged.

I did the same. Did good work and stayed quiet. It wasn’t modesty, but avoidance dressed as virtue.

Therapy helped me see it differently: talking about what you’ve done isn’t separate from the work. It’s the final step.

  1. Do the thing
  2. Say that you did it

That’s the whole process.

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Designing list - updated 2024

Reffering to Designing list post from January 2020

  1. Designing visuals
  2. Designing interactions
  3. Designing flows
  4. Designing entire product sections
  5. Designing apps/products
  6. Designing teams
  7. Designing businesses
  8. Designing society
  9. Designing nature

Clearly evolved to #6 and #7.

#8 still attracts me a lot with products, companies, inovation and how this should impact public policies so it can impact people, neighborhoods, cities, and even countries.

#9 is just impossible. Nature is perfect. It’s better to think about how not to interfere or even how to stop messing up with this.

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A style of leadership for me

When you share an unfinished product, you give people a chance to engage with you, that is shared enrollment.

– Prasad Narravula

On this day I learned a lesson on altMBA about a style of leadership that worked really well for me.

We were discussing about which idea to pick between two options and while the subject was common, everyone had different definitions and details in their minds.

When I shared the unfinished/half baked work I was doing, everyone could look at one thing and develop from there.

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Soft skills are real

The real (or soft) skills feel as concrete as the hard skills.

You can sense how you are changing because of them, the same way you can see clearly how you have made progress on that design, exercising, or driving skill.

altMBA 45

Adding value by asking questions

There are no consequences here for speaking up, the consequence would be staying quiet and NOT speaking up, not stepping up even if you believe you are not qualified.

I have been telling myself that I would be doing my team a disservice if I did not share my opinions or ask ‘stupid questions’.

I know I am adding value to my team when they explain their thinking.

Teaching is a great way to learn.

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Roadmaps in retrospect

Roadmaps only make sense in retrospect. It’s impossible to predict what a team will do over the course of an entire year.

Plans start as loose for most of the year, but then any changes are met with rigidity from what was arbitrarily planned for a very long time frame, especially in early-stage or early-scale startups.

Take care of my businesses

What else can I do professionally beyond current job and salary?

  • Get better clients no the side?
  • Work part-time to more companies as the number of companies/clients grow so I can do it full time?
  • Work with those companies to create new products and be a partner with them?
  • Advise starting companies in design and product work?
  • Again… what else?

Sam Altman - Hard startups

Part of the magic of Silicon Valley is that people default to taking you seriously if you’re willing to be serious—they’ve learned it’s a very expensive mistake, in aggregate, not to. If you want to start a company working on a better way to build homes, gene editing, artificial general intelligence, a new education system, or carbon sequestration, you may actually be able to get it funded, even if you don’t have a degree or much experience.

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Language auto-fixing

Language has many ways of fixing what has been spoken incorrectly. Some are so subtle that we don’t even notice something was fixed.

In products and systems, small errors are more serious, because the fixes and workarounds are not so obvious, or even planned, by the people who designed them.

Reading: The Design of Everyday Things

What’s ahead

It’s always good to promise a little bit of what’s about to happen so the team can keep engaged and interested in the work.

Depth, process and scope as a designer

These are my notes from a conversation with the gentle brazilian designer Felipe Luize, currently working at YouTube in San Francisco, CA.

Depth

Depth in design and strategy comes from a robust discovery process led by the designer, not just executing well at the tactical level. By the time you’re in tactics, those tasks should be doable with one hand. Most of the energy should be spent understanding what’s behind that request or KPI.

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Many tasks coming up

More and more tasks come up as the work evolves.

When there’s a bunch of things to be done, it’s a sign that the thing might be close to get finished, not started.

It’s probably time to make trade-offs.

(Inspired by Shape Up)

Missing action

In the midst of some anxiety and many thoughts, there is a lack of action to put the planned ideas and ramblings into motion.

Which action is missing?

Michael Jordan - Winning has a price

Winning has a price, and leadership has a price. So I pulled people along when they didn’t want to be pulled. I challenged people when they didn’t want to be challenged.

And I earned that right because teammates came after me. They didn’t endure all the things that I endured.

Once you joined the team, you lived at a certain standard that I played the game, and I wasn’t going to take anything less. Now if that means I had to go in there and get in your ass a little bit, then I did that. …you ask all my teammates, “The one thing about Michael Jordan, he never asked me to do something that he didn’t fucking do.”

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Now you feel it

When you were younger you didn’t know, but now you are an adult and you know because you can feel it.

Self image and the mirror

Not design related:

Isn’t weird how our confidence is often tied with the image we see on the mirror? Who teached us to be like this?

A lovely thought from Daniely Soares, who happens to be my gf.

Improving UX maturity

After a couple of meetings I noticed that I helped raised the company’s level of UX maturity from 5 to 6, considering the framework from NN Group.

The next steps seem to rely on the upcoming launches and the metrics and actions planned.

Next steps seem to depend on releases, monitoring metrics and actions planned based on them.

Seth Godin - Bored

Bored means that you’re paying attention (no one is bored when they’re asleep.)

Being challenged at work is a privilege. It means that you have a chance, on someone else’s nickel, to grow. It means you can choose to matter.

I’m glad you’re feeling bored, and now we’re excited to see what you’re going to go do about it.

— Seth Godin

https://seths.blog/2020/04/thoughts-on-im-bored/

Getting buy in from developers

Start selling ideas to developers using happy paths and good outcomes. From there build off of that with them the other flows and variations, like empty states and technical problems.

Whatever the team can propose and solve on their own, less intervention from leadership is needed.

Mixing geometric and organic elements

Balancing geometric and organic elements in interfaces can help soften the contrast between each one.

This can be applied to typografphy, buttons, illustrations, pictures and every other thing that shows up on screen.

About past decisions

At which time in the project do we stop rethinking and revising what we have already decided?

Not ready yet

While it’s important to ship fast and dont delay, in the beginning, some features ideas are still too young to be discussed with other departments. The product team needs to mature it and be more certain of what they want to present and discuss, as any pushbacks or hard questions would raise red flags that might kill the idea.

Quick mockups and the right set of questions can help to open space for it to get launched at some point.

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Li Jin - 100 True Fans

Rather than viewing one’s fans as a uniform group, the 100 True Fans model calls on creators to distinguish between various subsegments based on affinity and willingness to pay.

The relationship super-fans have with creators is different from regular fans: they become disciples, protégés, co-learners, and co-creators. As such, they require a whole new set of tools and platforms.

— Li Jin

https://a16z.com/2020/02/06/100-true-fans/

What’s the story behind that feature request?

Where is the feature being requested coming from?

Ask the 5 whys to understand it deeply, so it might not have to be compatible to old software that my product aims to replace, not live together and my job is to help kill it and make my product thrive.

Groups blocks with the same size

When the layout is not coming together, it’s better to group elements with the same size - like a sidebar - and fit them into a block.

With that done af ew times, you can redistribute whatever’s left and doesn’t seem to fit this block structure or need to stand out more.

Fillers

Fillers (hmmm, éééééé) are used to keep their turn of speaking and avoid silence between sentences one is still figuring out in their head.

If the one who is talking is still making sounds, no one, in theory, should interrupt.

Information architecture or a user interface problem?

O que estou desenhando resolve um problema visual (de design) ou de arquitetura de informação?

Quando algo está difícil ou incerto de como algo deve aparecer ou funcionar na tela normalmente tem a ver com a hierarquia do conteúdo na tela, melhor dar um passo pra trás, olhar de mais longe, decidir isso ou rabiscar algumas possibilidades diferentes, e daí avançar novamente

Start with an interaction model

You need to have a interaction model before started designing the UI. Without this, it’s impossible to know where to proceed to. Once you have that, it’s easier to see whether the elements on the screen fit that model.

Sure, it’s possible (or even likely) to change the model after starting, but it’s fundamental to start with one.

High fidelity prototypes

Now that I’m on the team, it’s possible to test ideias further through high fidelity prototypes, which was not possible to that team before.

Strong product

“A strong product is easier to sell.”

My job is to turn the product better, better, and better so it’s easier to sell it and help the company grow. Doubling the size is ok, but hyper growth means that you are at least quadrupling your size every year.

Internal layers

Things move slower in deep layers because their impact in both the organization and society is higher. It demands more conversations with non designers, more time used to showing the value of design, and the impact the product will make, beyond understanding the broader questions it demands.

What has been my role in showing the value of research and design for key people that don’t understand it?

How to have more responsibility:

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Jonathan Hsu - Growth accounting

With a 40% gross retention rate, mobile app A churns 60% of its active user base every month. Mobile app A’s quick ratio has been fluctuating between 1 and 1.5, which means that for every three new users the company adds, it is also losing two to three users to churn.

That churn, however, is masked by new users who sign up for the app and show activity in that month.

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Calendar time for feedback

When there are many tasks, it’s useful to have a recurring time in the calendar to give feedback to other designers and developers on their current projects.

Keeping a consistent and somehow short feedback loop will help everyone make decisions or improve what they’re working on.

Cost of delay

Cost of delay https://blackswanfarming.com/cost-of-delay/

  • What is the value missed in each delay in delivery?
  • How is it possible to launch early so the idea is tested in the real world?

If something is taking some time to be delivered, it can have some kind of value (scarcity) attached to this wait, but it’s easy to confuse this perceived value with pure delay.

It’s better to:

  1. Make decisions based on what faster to deliver (and not cheapest to produce)
  2. Prioritize considering cost and duration of delay
  3. Focus on value and speed

Designing list

  1. Designing visuals
  2. Designing interactions
  3. Designing flows
  4. Designing entire product sections
  5. Designing apps/products
  6. Designing teams
  7. Designing businesses
  8. Designing society
  9. Designing nature

Apparently I’ve already done up to number #5 at this point, consolidating myself in this and other aspects of the disciplines, but also thinking about how to grow for the others.

Dominic Price - Scaling organizations become more effective

An org that is truly scaling, however, is becoming more effective as it gets bigger.

The difference is purpose.

When you know why you’re doing what you’re doing, you make better choices about allocating resources and saying “yes” vs. saying “no”. Scaling enables you to stop doing one thing so you can start doing something new.

— Dominic Price

https://www.atlassian.com/blog/teamwork/unlearn-five-fallacies-innovation

Ryan Singer - How I wrote Shape Up

After the workshop, I emailed every attendee and asked if I could interview them by phone. The interview wasn’t about the workshop — it was about what was going on in their company when they decided to apply. I had a lot to say about product development, but I didn’t know which specific things actually mattered to people. I didn’t know what they were struggling with. The interviews gave me a way to learn what was going wrong in their teams, how they made the decision to attend the workshop, and what they hoped to get out of it.

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Jeff Glueck - Start charging early

First, Foursquare decided to start treating its data like the valuable property it is. It asked those big companies to start paying for its API.

The developers on the other end of the line basically laughed and said, “Yeah, we were wondering when you were going to start charging.” Crowley was amazed. “I had never had that experience in extracting dollars from big enterprise customers, but thankfully we had people here who knew how to do that.”

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John Biggs - Time constrain your work sessions

How well is your company doing? How many users do you have? How fast are you growing? How much revenue are you generating?

If your numbers are good, chances are that the investors will pay attention, even if they’re not immediately interested in your space.

If someone is pitching something that is consistently growing at 50 percent per week, I’m reaching for my checkbook, and you can explain to me what it is later. It’s that simple.

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Andrew Chen - Growth hackers

Growth hackers are a hybrid of marketer and coder, one who looks at the traditional question of “How do I get customers for my product?” and answers with A/B tests, landing pages, viral factor, email deliverability, and Open Graph. On top of this, they layer the discipline of direct marketing, with its emphasis on quantitative measurement, scenario modeling via spreadsheets, and a lot of database queries. If a startup is pre-product/market fit, growth hackers can make sure virality is embedded at the core of a product. After product/market fit, they can help run up the score on what’s already working.

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Rise Vision - How we are using Jobs to be Done

When outlining a project we specify The Problem To Be Solved and How We Measure Success. The Measure of Success is typically defined as one of our key performance indicators such as improvements in new user acquisition, retention, store sales, or cost reduction, etc. If solving the problem that the Job To Be Done requires isn’t expected to move a key performance indicator then it is very likely that this isn’t a high priority project and there are others that will have a bigger impact and should come first.

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Miguel Ángel Ortiz - Football is being sold

Eduardo Galeano se lamentaba de la venta del fútbol, «en cuerpo, alma y ropa», a las pantallas chinas.

Y añadía: «Es más importante la publicidad en el pecho que el número en la espalda».

En los 70, apareció en la camiseta del Eintracht-Braunsckweig y, desde entonces, las marcas se han apoderado de todo, incluso de los nombre de los estadios. Han comprado el fútbol, transformándolo en un deporte con un 2% de ganadores y un 98% de perdedores. Ganadores que, curiosamente, defraudan fuera del campo.

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Tom Foster - Reimagine the entire industry

But perhaps the most important thing in this building is on Arison’s computer. It’s a document that lists everything he learned from his experience with Taxi Magic, which he’s now applying to Shift.

This might be the biggest Uber lesson of all, and one that Arison hasn’t yet internalized: If you want to build a transformative company, you have to reimagine an industry, or create a new one, not buff up an old one. That’s why Uber succeeded where Taxi Magic failed. It didn’t try to improve taxis; it replaced them.

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Aaron Levie - Business structures

There are a lot of people around the world that actually want to do awesome things. They want to do their best work, but they’re not recognized by the organization. Their ideas don’t bubble up to the top, because of the complex and archaic way that we built businesses. I think that some people will lose in this future — the people that got ahead hoarding information and working in a way that was very specific to that model of an organization. You’ll have a new era of people that are able to win on their ideas, and able to win on what maybe we would consider to be actually better reasons, that open up opportunity for a lot of people that previously their voices were not necessarily heard.

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Naval Ravikant - Lessons learned

What used to cost $1M-$2M to set up, now costs $10K. What used to cost $5M to build, now costs $250K. What used to cost $20M to go to market now costs $1M.

But the upside hasn’t gone down. It has gone up. The 3 billionth person will be online shortly. They can all use the product. Network effects are stronger than ever, and some businesses become natural monopolies very quickly. Most web products have no marginal cost of replication, so adding a new customer is pure profit.

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Scott Belski - First mile of a product experience

The first mile of a user’s experience is the top of your funnel for new users and needs to be the most thought-out part of your product, not an after-though.

For any product with aggressive growth aspirations, I’d argue that 30%+ of your energy should always be allocated to the first mile of your product.

Even if your user experience for new users is performing well, don’t forget that new types of new users are the real source of growth.

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Yaakov Karda - Lessons learned

In many ways, Getwear’s story was an attempt to revive a golem. Most people, whatever their social group or сlass, don’t see the need to design their own clothes. Getwear was doomed from day one.

We started listening to user feedback only when we were already up and running, and acting on it didn’t change much. What sense would adding color and fabric options make if people simply are not interested in purchasing custom jeans online?

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Jason Tanz - Trust in the share economy

Much as the traditional Internet helped strangers meet and communicate online, they say, the modern Internet can link individuals and communities in the physical world. “The extent to which people are connected to each other is lower than what humans need”

So over several years, Chesnut’s team built its own trust infrastructure. It began monitoring the activity across the eBay marketplace, flagging potentially problematic sellers or buyers, providing its own payment options, and eventually guaranteeing every purchase. In so doing, eBay evolved from a passive host to an active participant in every transaction.

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Michael Bierut - Massimo Vignelli was very enthusiastic

Massimo cared deeply and obsessively about typefaces, kerning, and the space between objects.

Every time he sat down to make a three-and-a-half by two-inch business card, it was like no one had ever made one before. He worked it out so carefully and came up with something that he hadn’t quite done before.

Then he’d exclaim, “Ahh! Isn’t this great?!” He was so enthusiastic and uncynical and ready to be surprised.

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Dan Martell - Time constrain your work sessions

That’s it. Most of the time, we don’t fail to achieve our goals because of lack of knowledge and how-to, it’s because we haven’t associated the right level of motivation to the outcome.

It’s a powerful story to help remind you that anything is possible when our backs are against the wall.

Crating time constraint work sessions either personally enforced, or by not bringing your power cable on a work session will have a huge impact on your output. It also gets you into flow a lot faster.

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James Altucher - Dig far enough to find love

Every single one of us, without a single exception, has gone through a period of enormous stress and sadness in our lives. This is the knife that shapes our futures. Without understanding these moments, we miss the entire picture, we miss the subtleties of the work of art that each one of us uniquely is.

An archaeological dig can take years. So can a friendship. So can a love. So can a business or a work of art. The secret origins of the people all around you are like these archaeological digs.

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Robert Williams - People need to believe in your punchline

To make you laugh, a comedian has to convince you into believing their punchline. Jerry Seinfeld is a comedy master. His observational humor is not only hilarious, it’s caused millions of people to say “the way he explained that is exactly how it actually feels!”

This is what our websites don’t do. They don’t setup the punchline. Instead they just go straight to “we’re the best, laugh at all of our jokes.”

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Ben Horowitz - Lead bullets

“There are no silver bullets for this, only lead bullets.”

They did not want to hear that, but it made things clear: we had to build a better product. There was no other way out. No window, no hole, no escape hatch, no backdoor. We had to go through the front door and deal with the big, ugly guy blocking it. Lead bullets.

— Ben Horowitz

https://a16z.com/2011/11/13/lead-bullets/

Michael Lopp - Stables and volatiles

Stables - appreciate direction, happy to work with a plan - they appreciate it. Order is good. dot the i’s and cross the t’s. Play nice with others and are carefully work to mitigate failure make good & predictable decisions.

Volatiles - define strategy rather than follow it; failure is not interesting to them. Risk gives a thrill. Code volume over quality. Reliable when it’s in their best interest. Tell them what to do and they’ll say ‘fuck you’. Allow them to choose by proposing you have a hard problem and ask if they can help or give you their advice and they’ll jump right in (a bit like a 5 year old!)

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Ryan Luedecke - Ideas from past experiences

Determined to turn this rejection into a learning experience, I probed Logan for details. He didn’t want to make his office manager split the snack budget just for some jerky.

I framed Sumo Jerky as a healthy & productivity enhancing office snack and he seemed much more excited.

Logan’s office never ended up becoming a customer, but his excitement would eventually help me sign up hundreds of customers.

Lesson: Always politely ask “why” when people reject your sales pitch.

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James Victore - How to get hired

[…] Your next employer (if they’re worth their salt) is going to want you because you have a particular brand of awesome and vision. The next time you go into an interview, or send an email, or ship a box of goodies to that company you love, make damn sure that you represent YOU at your best.

A monkey might be able to do the skills required for your job, but it’s going to take your own special blend of kindness, honesty, enthusiasm, ingenuity, humor, and gusto to make that job YOURS, and to make it sing.

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Oliver Reichenstein - Thinking is stressful

Quality — as in “fitness for purpose” — lives in the structure of a product. A lack of quality is a lack of structure, and a lack of structure is, ultimately, a lack of thought. One does not find a solid structure by following some simple method. We deepen the structure by deepening our thought on the product. Our role as designers is to put thought into things. And that’s why most websites, clients, and jobs suck, and will always suck. Everybody hates to think, because everybody hates to listen, everybody hates to reflect, and we all hate to use our imagination.

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Justin Kan - B2B Customers will actually pay

B2B Customers will actually pay for your products.

B2C is way harder to monetize unless you’re at massive scale because no one wants to pay.

When asked how much people would pay for Facebook, it’s a fraction of what Facebook actually makes from ad revenue. Consumers are price sensitive, so you often need other models that rely on some other element, like data, to make sufficient money off consumers.

In B2B you can just charge a price and the company will pay if the product is worth that much to them. Then, over time you can improve it and charge more. Also, it turns out that most everyone in B2B is charging too little.

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Derek Sivers - Generosity and abundance

All great service comes from this feeling of generosity and abundance.

Think of all the examples of great service you’ve encountered. Free refills of coffee. Letting you use the toilets even if you’re not a customer. Extra milk and sugar if you need it. A rep that spends a whole hour with you to help answer all your naive questions.

Contrast it with all of the bad experiences you’ve had. Not letting you use the toilets without making a purchase. Charging an additional 50 cents for extra sauce. Salespeople who don’t give you a minute of their time because you don’t look like big money yet.

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Dan Wieden - Chaos challenge authority

Chaos does this amazing thing that order can’t: it engages you.

It gets right in your face and with freakish breath issues a challenge. It asks stuff of you, order never will. And it shows you stuff, all the weird shit, that order tries to hide.

Chaos is the only thing that honestly wants you to grow. The only friend who really helps you be creative. Demands that you be creative.

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John Maeda - Business models that pay for the design

My interest is not the physical design. It’s the fact that there are two things. There’s the iTunes ecosystem, which allows people to pay for downloaded music. And number two, there were all kinds of business models built around the iPod.

For instance, there was a 34-cent chip that you had to buy if you wanted to connect your box to the iPod. The cable had a chip inside it, so you had to have a chip inside the cable for it to talk to the iPod.

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Seth Godin - Pick yourself

Are you satisfied creatively? Not even close. That’s a very dangerous place to be and it would truly depress me if that happened and I would get very scared as well. I think if your goal is for everything to be okay, that’s a mistake. To achieve that goal, the only obstacle you’d have to face tomorrow is to eliminate all risk so that everything would be okay. I’ve made the decision that I’m never trying to make everything okay. I’m trying for there to be more loose ends, not fewer loose ends.

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