Kathy Sierra – Building Badass Users

As a means to help myself learn more about product management I’m going to start creating summaries of material I find online. These are created purely for my own learning, so if they seem totally incoherent, I’m sorry, but tough luck 🙂

Today I’m going to summarize and distill the content provided in this presentation from Kathy Sierra on how to build badass users.

“We’ll fix it in the manual”

Anyone who has worked with user stories before in product management knows that when starting off your user stories describe the most literal interpretation of the user ability you are providing to your users. For example, you may start off with “As a user I can create an project” for you project management software. Building this on the backend using Rails isn’t that difficult to do and very quickly your user can technically create a project in your app. However, it might not be immediately obvious to your user how your UI works. Also, just because your tool allows for all of the functionality that your user needs, doesn’t mean that it helps them within the context that you user cares about. Your user wants to become better at managing their projects. They want to be more organized, and more than anything I bet they just want their projects to be successful and not be messy gong shows. So instead of just making your product more effective at helping your users succeed in their context, you just provide a manual that describes how to use the feature. That is not very helpful.

“Or, We’ll fix it in marketing”

This mindset is what frustrates me most about the “internet marketing” industry. They’re actually very good at selling things. They understand the psychology of why people buy things. They understand the idea that customers desire to be good at the context, and not the tool. The problem is that they emotionally manipulate people to buy a product and then rarely do the work necessary to ensure that their customers adhere to what is necessary for success. They use the cop out that “success is up to the customer”. It is similar to the fitness and weight loss industry which is built upon a foundation of low adherence. The problem isn’t a lack of desire to succeed, or an inability to learn what needs to be done, it’s non-adherence.

“We CAN fix it in the USER.”

This is what is meant by improving adherence. Make it easier for your user/customer to adhere to the program which will result in their success. Give them the ability, give them super powers. Or at the very least don’t make it hard on them, and them blame their failure on their lack of character.

“It is NOT that the PRODUCT is amazing, it’s that the product makes them feel like THEY are amazing.”

“Key attributes of a successful product are in the users’ results. What does this product make your users kick-ass at?”

“We make a tool, customers are interested in the context of what they want to achieve.”

“For example, customers don’t say ‘I’m awesome at using this camera’, they say ‘I take beautiful photos’.”

A great product should be like steroids for you users. It should make them feel like they are better at the context of what they are trying to accomplish. The product doesn’t really matter to them, what matters to them is their success in the context which they are using the product. Sprinters don’t take steroids because they like sticking a needle in their bum, they take them because it helps them become bigger, faster and stronger. It helps them win races, medals and huge endorsement contracts. There are of course products that people use for the sake of the product itself, like drugs. If you give a rat a cocaine pellet dispenser it will keep pressing the button to get more cocaine until it dies. This is where social products differ from B2B SAAS products, and is probably a very important distinction to make. When people use consumer social apps they become addicted to them because they’re seeking that hit of dopamine from getting likes, and comments. This is the digital equivalent of drugs, or junk food.

“We must help our users: 1) build capability (2) stick with it.”

“The user journey: from first time to totally badass –> driven by motivation”

“However, can’t just add more motivation, the challenge is the derailers that pull people off track. Lots of derailers throughout user journey.”

“The user journey take ability and willpower.”

“Adding cognitive friction reduces your will power and ability to complete tasks.”

“Your cognitive resources come from ‘one tank’, meaning if you tire users out in one area, that affects them elsewhere. Using willpower taxes cognitive ability.”

Kathy described an experiment where they split people into two groups. The first group had to remember a two digit number, and the second group had to remember a seven digit number. Then as they thought the experiment had concluded the asked these people if they wanted some fruit, or some cake. The people tasked with remembering 2 digits were more likely to eat the fruit while the people tasked with remembering 7 digits were more likely to eat cake. What they determined was that the use of cognitive resources also taxed their willpower. Essentially they came from the same “tank”. If one was depleted, so was the other.


“Reduce cognitive leaks! This can be anything that taxes cognitive ability.”

“Knowledge in the world vs Knowledge in the head”

“Reduce cognitive leaks with defaults and trusted filters – choices are hugely cognitively taxing”

“Reduce cognitive leaks by eliminating need to use willpower – building habits is very helpful in this regard. Habits are automatic. Help them build habits around the bigger context.”

“Reduce cognitive leaks by letting their brain LET GO. Let your users stop worrying about something.”

We can help our users by making it easier on them. This could include using a more obvious UI that makes it clear how to use the product without needing to guess or refer to a manual. It might not be as pretty and minimalistic, but if it’s obvious it won’t tax your users brains trying to figure it out. Eliminating extraneous design elements could be helpful as well. Flashing GIFs are also probably a bad idea 🙂

Kathy also talks about how building habits is very helpful. When we have habits we have grooved behaviour to the point of becoming automatic. Almost like muscle memory. If I had to look down at the keyboard for every keystroke I would be a much slower typer, but with muscle memory I can move a lot faster. It is the same thing with habits. Also, you can have bad habits and good habits. By helping to train our users to have good habits (or at least habits that we want them to have) then we make it much easier for them to use our products. Nir Ayal’s book “Hooked” as a good example of a framework for why products can be habit forming.

“By pretending like your users shouldn’t have any problems, you’re gaslighting your users, because when they inevitably come up against challenges they’ll feel like THEY are the problem.”

While presenting your customers as uniformly happy and problem free you may see benefits on conversion at the top of your funnel, you will see problems with retention over time. Whereas if you show empathy for them and make them feel as though it is totally normal and understandable for them to be struggling with certain things then they won’t give up when they run up against challenges. It is kind of like if you were to start a marathon race with the expectation that it will be easy as opposed to the expectation that after about 15km you are going to want to collapse. If you expect the run is going to be hard then you won’t give in. It reminds me of a happiness equation someone once told me about. The equation says that your happiness = reality – your expectations. So if your expectations are low and your reality is higher (ie better) then you will be happy. This is obviously a SUPER simplistic framework, but useful to me.

Product Market Fit and Evolution

What do us humans and worms have in common? We are both “Bilateria”:


As such we have a number of similar characteristics, that while sounding pretty obvious aren’t necessarily uniform across all organisms. For example, we have a front and a back, a top and a bottom, and a left and right side. This isn’t the case for all organisms. We also have similarities in our nervous system and digestive system:


This might not sound like it has anything to do with product market fit, but worms and humans both have a mouth at the “top” and an anus at the “bottom” of our digestive tract. We also have a nerve cord with an enlargement (a “ganglion”) for each body segment, with an especially large ganglion at the front, called the “brain” Part of the theory of evolution is that if something is no longer relevant it slowly disappears, like the human appendix and tail. By extension that which sticks around does so because it serves a purpose or provides some evolutionary advantage to that species.

This is important to understand because if we look towards the simplest of bilaterian animals (ie a worm) as compared to one of the most complex (ie a human), the similarities tell us a lot about what is really important. Sure, humans have adapted certain characteristics that have made us superior to the worm, but without that simple bilaterian animal as the evolutionary foundation we wouldn’t exist. I think there is an argument to make that this simple animal achieved a form of “product market fit”. If the most dominant species on the planet stems from it, there must be something to it.

Most people trying to craft product are thinking from a perspective of “intelligent design” rather than “evolution”. They’re always trying to think of what additional feature they could add to help their product dominate the rest, when in the beginning domination doesn’t matter. All that matters is whether you can escape irrelevancy. Using the worm and human analogy they’re thinking about what limbs they can give this creature for advanced locomotion, or to provide an ability to manipulate objects, how to make this thing self aware or intelligent so that it can plan ahead. A worm has a mouth to consume food with, and an anus to dispel waste. A worm has a nerve cord and a brain, and a rudimentary locomotive ability. Those adaptations while seemingly banal were significant enough to be the foundation for the most dominant creatures on the planet.

Messaging apps might be the “worm” equivalent of networked communication, dating back to the early days of the internet with BBSes and the like. Sure that might have been where the internet began, but like the worm it still makes a hell of a lot of sense. I’m not saying that every app needs to start with a messaging app, but really ask yourself what is the core functionality that matters most?. What simple goal are you trying to accomplish for your users? Remember, all bilaterian animals (including humans) share a very small beginning, and yet all big things have small beginnings.


Entrepreneurship and Abstraction

Back before the tech bubble of the 90s burst the vast majority of startups were founded by “business types” as opposed to engineers, or builders. Sarah Lacy has opined that frothy times brought douchebags to the Valley in the late 90s and that frothy times have brought them back.

I don’t disagree with her arguments, but I also don’t think that all “business types” are douchebags. Maybe I say this simply because I don’t want to be seen myself as a douchebag, but I don’t think all tech company founders have to have engineering or strong technical backgrounds.

The way I view entrepreneurship is that you build a business, much like an engineer builds software. An application is a system that follows certain rules when it’s told to do certain things. A business operates in much the same way. With that in mind I can certainly see how having an engineer’s mind would be helpful in building a business, but being a trained engineer, not necessary.

Some programmers deal with things at a very low level of abstraction that requires knowledge of the computer hardware and where the program is run, whereas some programmers are working with frameworks like Ruby on Rails where the framework does a lot of “magic” that “abstracts” away a lot of the stuff that is happening in the background. Of course if you know what is happening underneath the hood there is a benefit, but at some point there are diminishing marginal returns if your function within a team doesn’t need to dive that deep.

The way I see it there is a minimum threshold that you need to understand at each level of abstraction above and below where you’re working, and the further down or up you go the lower that threshold is. So if I’m a Ruby on Rails programmer I need to know a lot about that framework and everything that it can do, but I don’t need to know much of anything about circuit design (down) or much of anything about venture capital (up).

If your goal is to start your own tech company you don’t need to be a strong programmer yourself, there are no doubt some benefits to this, but the more time you’ve spent becoming a programmer the less time you’ve spent learning about the breadth of things you’ll need to know about as a CEO. Do you think Mark Zuckerberg spends much time programming anymore, if any? If you’re starting an internet software company you need to know a fair bit about programming, design, finance, recruiting, communications, sales/marketing etc, but you don’t need to be capable of being full time in any one of those roles.

I don’t think you need to be a programmer to build an internet software company, but you do need to have a builder’s mind. I think this is where the Sarah Lacy’s of the world get so annoyed with the douchebags that have gone to the Valley at different times. The douchebags aren’t builders. They are vultures, hyenas, scavengers. They’re the same breed of creatures that caused the sub-prime mortgage crisis, and the accounting scandals of Enron. They’re looking for arbitrage opportunities. Buy a struggling company, tear it apart and sell off the pieces for a profit. They’re the ones that saw during the 90s that you could just hype the hell out of a startup, raise more and more money, have an IPO and get the hell out. They don’t care who gets left holding the bag, as long as it’s not them.

So while I think the fear of the douchebags is justified, it doesn’t mean that all business types are douchebags, some of us are builders too. We just work at a different level of abstraction than a programmer or designer does. Instead of spending my days in Sublime Text and the Terminal, or drawing wire frames and Photoshop mockups, I strive to serve those that do.

The Stalking Horse

The Stalking Horse or Why Tech Giants Don’t Innovate More

Why is it that after tech companies reach a certain size they seem to stop innovating as much? Well it should first be pointed out that this question is flawed. It isn’t that they stop innovating, it’s that their innovation shifts from product innovation to platform innovation. All truly giant tech companies operate platforms of some sort, and their innovation needs to be around supporting that platform. That includes infrastructure innovation, and integration innovation. Both Facebook and Google for example have made incredible innovations around servers and other major infrastructure projects, some of which have been open sourced, and others which have been kept proprietary. Regardless, they continue to innovate in truly impressive ways that just aren’t as obvious to the average consumer.

Now, with that out of the way we can address the intention of the original question, namely why do tech giants stop innovating on products once they get huge? To understand why let’s take a look at something called “The Stalking Horse”. The following comes from Wikipedia:

A stalking horse is a figure that tests a concept with someone or mounts a challenge against someone on behalf of an anonymous third party If the idea proves viable or popular the anonymous figure can then declare its interest and advance the concept with little risk of failure If the concept fails the anonymous party will not be tainted by association with the failed concept and can either drop the idea completely or bide its time and wait until a better moment for launching an attack

This is basically what a startup is. A stalking horse. When you’re a team of 4 or 5 college kids trying out some new app idea, it doesn’t really matter if you fail, at least the stakes aren’t nearly as high for you as it is for someone like Google. When Google puts something new out into the world the expectations are very high, and the costs of failure are much higher as well. So what do giants like Google and Facebook do? They sit back and watch the startups, or stalking horses, making their way in the market. Then, once the risk level passes an acceptable threshold they swoop in an make an acquisition. Where that threshold is varies by industry, for example enterprise companies have lower risk tolerance and therefore make acquisitions once a startup has reached even higher levels of certain success.

It’s this concept that insulates many small startups from ever having to worry about direct competition from the likes of Google, Facebook or others. If what you’re doing is big enough that those companies are immediately interested, it means you’re too late to the party already, and the market is fully validated and mature enough for their interest. The best startup ideas need to be contrarian or risky enough that these guys just aren’t willing to do it yet, or the market is still too small to be worth their time.

Obviously this line of thinking doesn’t apply to more niche, bootstrappable businesses. In those cases you absolutely don’t want to go after the high risk, unvalidated ideas. You want to find a sliver of a market and then slowly expand your market share. This is more or less what Basecamp has done, and has done so exceedingly well.

You Are What You Repeatedly Do

You are what you repeatedly do. So ask yourself what are you? The answer is easy, look at what you REPEATEDLY DO. Titles don’t matter, actions matter.

It isn’t enough to have warm thoughts and good intentions if your actions don’t stand up to scrutiny. It’s very easy to congratulate ourselves for our future successes, as though they are inevitable, or to feel as though we are “good people” because of our political leanings or our outrage at videos we see online. What do you repeatedly do? The actions we take matter. The processes we run matter.

Our world is made up of a series of processes, and the more consistent they are, the more we can rely on them, and the more valuable they are to us. Making the right choices is important, but doing the right thing poorly can be worse than doing nothing at all. This is why making choices, and taking action when you’re emotional is a BAD IDEA. Even if you make the right decision, your execution will be impaired.

This view of the world can be incredibly valuable in a variety of different fields. Medicine. Aviation. Engineering. Commerce.

Ask yourself two questions:

1) What process should you run?

2) How do you run that process as reliably as possible?

As an entrepreneur it isn’t only about your ideas, it’s about your process for working through, vetting, and executing on those ideas. Entrepreneurship is about what you do, the actions you take, over and over. You identify a course of action you wish to take, or a process you wish to run, and then you seek to run that process as well as possible. As you’re running the process you need feedback loops in place to track the efficacy of that process (is it producing the results that I want?), and the consistency (how often does it produce the result I want?).

It’s the same in medicine:

1) What is wrong with this patient or what process should I run to deal with their situation?

2) How can I run this process as reliably as possible?

The Hippocratic Oath that physicians take states “First do no harm”. Much like in entrepreneurship it is important to have feedback loops in place in order to track the efficacy of your actions (do patients have positive outcomes?), and the consistency (how often do patients have negative outcomes?).

Your Mom and Dad might love you for the goodness in your heart, but the world needs value from you. The value you provide is based on what actions you decide to take, and how well you execute on those choices. Think long and hard on what you want to do, and be disciplined in how you do it.

The Importance of Sequencing in Startups

Over the last few years as I’ve worked my way down the path of learning about startups there is no other lesson that sticks out in my mind more clearly than sequencing. What is sequencing you ask? Well I might be the only one who uses the term in this context, but what I mean is the order in which you do things. Allow me to provide an analogy to help explain.

Imagine you’re a 15 year old boy aspiring to be a pro-hockey player in the NHL. It’s fair to assume that for you to have any hope of making it pro at this age that you’re already an amazing hockey player and on the radar of scouts, nobody starts playing hockey at 15 and ends up going pro. If you live in Western Canada your first big step is getting drafted into the WHL. From there you have a few years to develop as a player before you’ll try get drafted into the NHL. If you’re lucky enough to get drafted into the NHL then you’ll probably play a couple years in the farm system via the AHL. Then after a couple years in the AHL you’ll finally get called up to the NHL. This is of course a simplistic view of how to become a pro player, but what I’m trying to illustrate is that there is a clear path that a large proportion of people take. There are outliers who find their own way in, but don’t ever bank on being an outlier. Mark Zuckerberg is probably a lot like Sidney Crosby in that people were likely noticing his brilliance very early on.

So, taking this analogy and applying it back to startups, what sort of sequencing can one expect if they’re hope to achieve startup success? Well luckily for you there are many pathways, and I actually can’t really prescribe an exact path for you because it will always be different for everyone. That being said, what always remains constant is the steps you take always need to scale up, and taking big leaps generally doesn’t work. What do I mean by that? Well let me provide some examples from my own experience.

When I was getting started I had this notion that all I needed to do was convince some VCs of how great my idea was and then I’d be on my way. They’d invest a bunch of money and then all of my problems would be solved. I’d hire a team to build my software and then we’d be on our way to success. I even managed to get intros to some VCs and sent off copies of my business plan to various other VCs. Of course I only sent the business plans to the top VCs, because they’d certainly get it right?

You wanna know what’s the biggest dead giveaway that an entrepreneur is inexperienced and naive? They think their idea is so special that it holds any value within itself. If all you have is an idea, you’re not really worth much of anything to the business. You have no leverage, because you cannot execute the idea, or participate in the execution of the idea.

Executing as a startup CEO is very similar to a sport. The execution is ongoing. The preparation is ongoing. You’re always looking to improve yourself. It’s incredibly competitive. Perhaps most similar is that over time the superstars become apparent through their execution.

I grew up playing badminton competitively. I spent years building relationships in that community locally, nationally, even internationally. I know a LOT of people in that community, and while I’m not as good as I used to be people in that community give me respect because I’ve spent time in the community. They know my approximate level, what to expect from me. Sure I might be capable of playing beyond their expectations, or below, but for the most part they know what to expect from me based on previous execution.

This is what investors are looking for, but it’s incredibly difficult to find this in startups, especially when the founders are first timers. There is no data to judge them on. The best way to provide them data is to get involved in your local startup community. Help with local meetups, become a familiar face in the community. Give them some data on which to judge you, even if it is pretty basic. This also serves to teach you more about startups.

Okay, so you’ve started hanging out within the startup community, congratulations you’re now a startup groupie. Don’t fret though, this is a necessary step in the right direction. The next step is you actually need to build some relevant skills.


Jack White On “Inspiration”

A few years ago I was watching MuchMusic (okay, it was a lot of years ago), and Jack White of the White Stripes was being interviewed.  Jack was talking about the power of using constraints to drive his creativity.  I couldn’t find the MuchMusic interview, but I was able to find this video on YouTube.

I really identify with this mindset.  When you have limitless options you get distracted, and spend so much of your mental energy just wrestling with those options.  When you have only a few tools to work with you really need to get creative in how you use those tools.

Why Are The Tech Zeitgeist So “Meh” on Enterprise?

Over the last few months the tech press and venture community have begun to take note of enterprise software, as though it were somehow something new and special.  However, it has recently been revealed in a report on private tech companies with valuations over $100 million that around 80% of them are “enterprise” tech companies.

When we look back at the last 10 years or so of tech startups the vast majority of them have been focused on consumers, in spite of the fact that more returns are being provided by the enterprise.  Part of this is because the nature of consumer startups is that they tend to be fairly binary outcomes (ie they’re either huge or they fail).  This binary nature could very well be why venture capital follows them more closely as the mandate of venture investment is basically to get binary outcomes.

Putting the venture side of things to the side, why is it that the entrepreneurs go after the consumer side of things?  Why are so many of our smartest engineers, designers etc putting their considerable brain power towards solving problems relating to photo sharing?  When I think about the types of problems that are being solved on the consumer side compared to the enterprise side the conclusion I come to is consumer is the lower hanging fruit.  I don’t mean that in terms of making money, I mean that in terms of creating a product that people will use.

Creating a product that a consumer will use, and that will spread widely among people is way easier to do than an enterprise product.  The enterprise is harder, even if it is more rewarding financially.  You have to deal with more issues that can stifle adoption of your product.  In the enterprise you have to take security and privacy compliance much more seriously.  It’s also much more challenging to convince someone to pay you for your software, although when they do pay they’re sure worth a lot more to your company.

Yes, enterprise software continues to be “consumerized” in terms of how the products are developed as well as the sales models to a degree, and this makes things much better, but that still doesn’t change the fact that the product creation process is much more complex.

Perhaps the most intimidating part of the enterprise software industry is the fact that the incumbents are so much more entrenched than the consumer side of the industry.  There’s an expression that “nobody ever got fired for going with IBM” that should help illustrate this point well.  However, this also means that the enterprise software industry has much more room for disruption as they have been resting on their laurels longer.  Cloud software has eroded much of the stranglehold that Microsoft once had on consumers, and it will eventually do the same for the stranglehold they have on the enterprise.

I definitely have my fair share of “consumer” software ideas that I’d love to make if things don’t pan out with CareNetwork, but frankly I like the idea of tackling a complex problem that has an actual business model from the get go.  Hoping to be acquired by one of the existing tech juggernauts isn’t a business model, even if it does happen to lots of companies every year.

What If We Banned Cars From Cities?

Perhaps the title of this post presents a somewhat ridiculous thought, but allowing ourselves ridiculous thoughts often yields the most interesting results in my opinion.

I was thinking about the ridiculousness of cars today.  When I think long and hard about it, the fact that we each need our own automobile to get ourselves around a city is quite absurd.  It would be like Fedex having an individual courier or delivery truck for each letter they carry.  It doesn’t scale very well.  With our world bumping up against the limitations of our petroleum infrastructure I wonder how much further we can continue down our current path.

A much better path in my opinion is to do away with cars, at least in urban centers.  Sure electric cars get rid of a great deal of the carbon emissions, but you still need to have an electric grid that is not connected to a carbon source (ie coal powered electricity).  If we had amazing public transportation options we shouldn’t need cars.  Much of our infrastructure that we currently have in place is legacy from past eras, so it’s very hard to start fresh, perhaps impossible.

The times where I have been most happy have been living in cities where I didn’t need to drive on a daily basis to get around.  I currently live in Edmonton, Canada.  In this city it is not practical to use public transit.  I have lived in and traveled to a number of cities where public transit was amazing.  Places I lived include:

  • Vancouver
  • Toronto
  • New York City
  • Copenhagen

All of these cities I didn’t need a car.  I had a car in Vancouver, but put on about 10% of the KM that I do living in Edmonton (over the course of 1 year I drove around 2,000 KM in Vancouver).

What if we started a city and banned cars?  What if on the outskirts of the city there were parking lots where you had to store your car, and then you would take a subway of some sort into the city?  The city would be designed for walking, and for public transit.  Buildings wouldn’t need to be nearly as tall since their footprint could be bigger because there would be no roads.  There would be way more green space.

I think that living in an urban center would be so much better if cars were removed from the equation.  I like cars, especially sports cars, but I hate driving in cities, it sucks and it’s stressful.  Someday I’ll build a city from scratch that doesn’t even have roads.

Why Microsoft Is Poised For A Comeback

Microsoft missed the boat (at least the first boat) on smartphones.  They were the leader before, but those phones weren’t really smart.  They were just phones that had PDAs attached to them.

So Apple came in and totally changed the game by giving our phones a beautiful and easy way to access the internet. BOOM.  Suddenly everyone wants a smartphone, and then Android comes along and offers essentially the same thing for OEMs to be able to make their own iPhone copycats.  Android essentially is to iOS what Windows was to Mac OS in the 80s/90s.  Now Android is killing it in smartphones, and you’d think that there would be a pretty easy transition from smartphones to tablets, but it hasn’t turned out that way and nobody seems to know why.

This brings me to why I think Microsoft is poised for a comeback.  In a word, tablets.  You see tablets are NOT big smartphones.  This is why Apple has done well with the iPad while RIM has struggled with the Playbook.  Playbook is a BIG smartphone.  iPad is a touch screen tablet COMPUTER.  Sure it utilizes the interface that iOS provides, but it’s success is dependent on BOTH iOS and Mac OS X. Case in point, iPads are cannibalizing laptop sales, NOT iPhone sales.

Android doesn’t have the desktop OS to support it’s efforts in the tablet arena.  THIS is why Microsoft will succeed in tablets, while Android hasn’t.  Microsoft has a HUGE number of developers who make productivity and work related applications for the Windows platform, and most importantly with Windows 8 coming in the near future these apps will be easily ported to the tablet form factor.  Microsoft essentially baked this into the new OS.  So this means that OEMs will have a platform that they can license that will help them sell tablets, LOTS AND LOTS of them.

Then once they have tablets kicking butt they will be able to support their smartphone OS because it will be a smaller jump for developers to make, and OEMs will have more faith in the platform.  If I had some money to spare, I’d start buying Microsoft stock, and this is coming from one of the biggest Apple fans you’ll meet.