How painful is your app?

A couple of weeks ago I was listening to the Tim Ferris podcast. His guest during this episode was Tony Robbins.

A funny side note: I typically listen to podcasts at 2x speed, but I had to slow this episode down, due to the rate at which Tony speaks. Another confession: I’ve always dismissed Tony as a bit of a self help snake oil salesman. I feel bad for judging him. Turns out, he’s actually a pretty amazing individual.

As a result of this interview, I decided to read his book, “Awaken the Giant Within“. I don’t typically read self help books, but I have to say that I really enjoyed this book.

One of the underlying premises in this book is that all of our actions are ultimately driven by either:

  • A) how painful something is, or
  • B) how pleasurable something is

The goal of the book is to get individuals to change their behaviors. That said, it actually got me thinking about how these same principles apply to web and mobile applications. One line in the book stood out in particular:

Link pleasure to any behavior you want someone to repeat.

With this as a filter, it’s interesting to think about which apps you use repeatedly, and why. What have those apps done to create pleasure for you?

If you have an app of your own, it’s also interesting to think about how painful, or pleasurable of an experience you’ve created for your users, especially within your onboarding experience.

Questions to consider

  • When is the last time you did a pain/pleasure audit on your app?
  • What specific things create the most pleasure for your users?
  • How long does it take for a new user to find pleasure in your app?
  • What can you do to reduce the painful elements in your app and in your new user experience (NUX) flow?
  • Are there things you can do to make pleasure more immediate? How might you reduce the time to pleasure (TTP) in your NUX? Could you reduce your NUX TTP from minutes to a matter of seconds?

My Dream Job

I work out of a 10×12 ft room in my backyard.

I wouldn’t change it for anything.

It’s my dream job.

Reflecting on how blessed I am

A couple of things this month have caused me to pause and reflect on how fortunate I feel to be able to work at Automattic.

First, my sister Lisa asked to interview me for her local college paper.

Second, Matt shared that Automattic just celebrated it’s tenth birthday.

Third, was a random thought tweeted by @bryce which turned into an epic thread. Bryce asked:

what message does early stage startup culture send to parents with kids? honest question for those wearing both hats.

This last one stood out the most. Mind you, it’s been a long time since Automattic was considered an early stage startup, but reading through that thread sort of re-confirmed that what we have at Automattic is something that’s unique, and special.

What makes Automattic so unique?

Before Automattic, I had never stayed at a job for more than 2 years. In September, I will have been at Automattic for 5 years.

I thought I might take a few minutes and share a list of the reasons why Automattic continues to shine (at least in my eyes) as an amazing place to work.

Our mission – (and the mission of WordPress core) is to “democratize publishing”. WordPress now hosts 24.1% of all websites on the Internet. That’s a sizable dent, but to be honest, we’ve only just started…
Our values – our company creed and designers creed though short, speak volumes about the types of things we care about.
I get to work with wicked smart people from around the globe.
We believe strongly in open source, which means a great deal to me personally.
We care about our users. No matter which role you’re hired for, your first 3 weeks at Automattic are spend doing support (a happiness rotation as we call it). Teams are also encouraged to continue to do 1 week happiness rotations once a year.
Our company is 100% distributed. We all work from wherever we live. I’m able to work out of a small town in North Carolina vs. needing to relocate to the Bay area just for a job.
I get to work from home. That picture of the shed-looking building at the top of this post is the backyard office I work out of most days. I’m able to work from home, and make my own hours.
Automattic trusts us to get the job done. I don’t clock in or out. If my daughter has a swim practice during the day, I can take her. I don’t have to ask anyone, or clear it with anyone, I just go. No one keeps track of the hours I’m online or off. All that matters is output.
– We’re paid a good salary.
– My family is expecting our third child any day now. As such, I’m about to head on paternity leave. At Automattic we are encouraged to take the time that we need for both Maternity and Paternity. That’s our official policy. No questions asked. I plan to take 4-5 weeks. Some people take 12 weeks. Some people take less. Some people take more. If you’ve been with Automattic for 12 months, your leave is fully paid.
– We have an open vacation policy. If I want time off, I take it. Again, fully paid, no questions asked.
We cover all costs of company travel. We all get together once a year for a Grand meetup. Then throughout the year, each team is encouraged to pick a location and meet together in person for a week. Earlier this month I was in Copenhagen with half of our designers. Last month I was in Atlanta with the other half.
– We have a generous home office setup stipend
– We have a monthly co-working allowance (if working from home is not your thing).
– You can replace your work machine once every 18-24 months.
Devices, hardware, and software are all 100% paid for.
– We have company-sponsored life insurance.
– You can snag a WordPress branded laptop at your four-year anniversary (Yes, the WP logo actually replaces the Apple logo!)
– Every 5 years we’re encouraged to take a 2-3 month paid sabbatical.
– We’re encouraged to swap around to different teams. In the ~5 years I’ve been here I’ve been on 6 different teams. Some people choose to stick to a team a lot longer. It’s almost entirely driven by you.
– We’re encouraged to continue learning by attending conferences, and by purchasing books, and can expense every bit of it.
– We have access to unlimited WP swag, more than most of us know what to do with.
– When you first become an Automattician, you get a free Timbuk2 bag of your choice with a WP logo embroidered on the back.
– Other benefits which are country-specific include health, vision, and dental insurance; matching retirement/pension contributions; childcare vouchers; income protection, and travel insurance.

I’m sure there are more, but I’ll stop there…

Needless to say, I love my job. I feel blessed to work for such a generous and trusting company who’s mission is to legitimately change the world by further democratizing publishing. Each day I’m grateful to work with such brilliant, and amazing co-workers. The way that we run the business (with a focus on long-term impact over short term gains) is something that I admire and respect. We’re not in this to sell out, or to cash out in a quick IPO. We’re in this together to try and make a dent in the world, so far a pretty sizable one. In the end, I can say without a doubt that after 5 years, I’m still really proud to call myself an Automattician, and that Automattic is still my dream job.


The designer sweet spot: Gut driven design that’s data informed

Gut Driven vs Data Driven

Very few organizations exist that are primarily data driven when it comes to design. These organizations allow data to call the shots. They’ll head whichever direction the data points them.

Most organizations these days seem to skew heavily to the other side of the spectrum. They rely almost exclusively on their gut (plus experience) to make design decisions.

Where do you stand?

It’s natural to feel polarized toward one side or the other. Many organizations are either all in on data driven design, or zealots about listening to their gut.

You already know from the title of this post where I stand. I believe pretty strongly that there’s a sweet spot, and I don’t think it lies at either end of the spectrum.

In my experience, the sweet spot comes when a designer primarily trusts their gut to design, but also allocates some time to collect data, and to do some testing. These last two things are key, because they help you validate your assumptions, and they add clarity to your design process.

Trusting your gut is paramount

Great design comes primarily from a combination of experience, and from a designers gut intuition. That said, at what point do you know (not think, but really truly know) whether a design is great?

Truthfully, many designers and organization never take the time to find out. They’re content to ship whatever design they think is best. End of story. But that’s a shame. Launching designs without testing is just ignorant, lazy, or both.

Think about it. You’d never intentionally launch a design that stinks (at least I hope you never would). But chances are that some of the designs you launch — even though you may feel they are great — may actually stink. If you aren’t testing your designs, you’ll never really know which of your designs are the great ones, and which ones could still use some love. Without testing your design or looking at any data, all you really have is a hypothesis that the design you’ve created is great.

Clarity comes via data & testing

Just mentioning the word “data” can brings a sour look to some designers faces. But it shouldn’t. Data in and of itself isn’t bad. Data when leveraged properly can lead to insights and clarity.

It’s worth noting that there’s a huge difference between being data informed, and data driven. Data’s only role should be to inform – never to drive design decisions.

So far, I’ve been ranting about incorporating some “data” and “testing” into your design process, but what does that really mean?

Let’s look at a few examples

Here’s a list of things that you can do throughout your design cycle to add clarity, and gather insights about your design:

  • You can dig into analytics to try and discover existing insights.
  • You can use Qualaroo, or SquareInsights to ask users questions inside your app.
  • You can chat with happiness/support folks to help determine what the most common complaints, and user pain points are. You could also do support regularly yourself.
  • You can ask other designers for feedback.
  • You can ask your partner/spouse/relative/friend to try your interactive prototype while you watch.
  • You can run some quick usability tests on
  • You can approach strangers to help you out for 5 min in exchange for a $10 Starbucks gift card.
  • You can ping people in your company that have never seen whatever it is that you’re building, and request 5 minutes of their time, watching them attempt to use your design.
  • You can run a user report in KISSMetrics or MixPanel (or whatever app you use to track users), get a list of actual users, and email them requesting feedback.
  • You can run an A/B test on your design to make sure that it isn’t sinking the ship.

This is by no means an exhaustive list.

Each of these activities will help you validate the hypothesis that’s in your head, and either A) confirm your assumptions, or B) give you insight into how you might tweak your design to make it even better.

Feel free to pick and choose. If you try one of these things a couple of times, and it doesn’t work for you. No worries. The important thing is to try a bunch of them, especially early in your design process. The earlier you incorporate these activities, the quicker you’ll know whether the design you’ve come up with is a great one, or whether it’s a dud.

I’ll repeat this one more time, because I think it’s important:

The sweet spot comes when you A) primarily trust your gut, but also B) use data, and testing to validate your assumptions, and add clarity.

Thoughts? Ping me on Twitter, or shoot me an email:

A big thanks to @hnshah, @melchoyce, and @folletto for reading, and providing feedback for this post.


Rest in peace “growth hacking”


“Growth Hacking”: Can we lay this term to rest? It just feels… tainted.

To be clear, growth in and of itself isn’t a bad thing. But somehow “growth hacking” has earned itself a bad reputation. Why is that?

To figure this out, let’s journey back to the very beginning.

Doomed by definition

When Sean Ellis coined the term growth hacker in 2010, he stated that:

A growth hacker is a person whose true north is growth.

And therein lies the problem…

Growth for the sake of growth has never been a good LONG-TERM business strategy. Growth for the sake of growth may appear to work wonders in the short-term, but long-term it’s a wolf in sheep’s clothing. Long-term, growth should be centered around people not numbers or percentages.

Everything that a “growth hacker” fights tooth and nail to optimize can be improved across the board by focusing on one thing:

Just focus on making your users lives better

Instead of having your north star be growth, what if instead you focused on the success of your users as your primary objective? Once your primary focus shifts to making your users lives better, everything else that you used to wrestle with as a “growth hacker” will begin to fall into place:

  • Activation – By focusing on your users, and their needs, you’ll have less friction in your new user flow, so more people will stick around.
  • Revenue – With more people sticking around, chances are you’ll make more money.
  • Retention – By definition, if more people stick around, your churn decreases.
  • Referrals – If people find your app remarkable, they’ll spread the word.
  • Acquisition – As people tell others, you’ll acquire more users.

By focusing 100% on users you likely won’t see as many short-term benefits as you would if you continued growth hacking. Unfortunately, one side effect of aggressively optimized short-term growth is that it often comes at the expense of long-term losses. Only, you won’t see the long-term effects for years to come, and by then it’s often too late to do anything about it.

At Automattic our growth explorers are embedded in our design team. Their job is to understand our users (better than anyone else), and to help our users reach their goals, faster (whatever they may be). We’re actively hiring for growth explorers. If this sort of stuff interests you, I’d love to hear from you.

I don’t do comments, but feel free to reach out to me via Twitter or email: