Remember email? It’s still a thing

Earlier this year, I was one of the many designers at our company that participated in a an in-depth study about small business owners to determine how we might build our products to serve them better. We kicked things off with a segmentation study that helped us break down and prioritize the vast landscape of small businesses into more discernible groups. This was followed by an intense qualitative study where we spoke with a number of small business owners from across the United States. Our team wrapped things up by meeting in San Diego to comb through the data we collected and synthesized it into actionable insights for the company.

Looking back at the findings, I am grateful for the opportunity of taking part in a study like this because it reminded me, among other things, that we are not the people we design for. A lot of tech folks I know, myself included, have an aversion to email and as a result feel really annoyed when they get emails from companies. The business owners we spoke to on the other hand felt very differently — they love email!

On the go, or in the office, they check their mail a million times a day and use it stay connected with their clients. They also use it to learn new skills, stay up to date with industry news, and keep in the know about networking events and conferences. Hearing business owners talk about email that way really stuck with me really left an impression on me and changed the way I think about it. It is a tried and tested communication tool that still holds value for lots of people out there and should therefore be considered as an integral part of any complete experience.

Starting with curiosity to make the difference

Before getting into my design career almost 15 years ago, I was an art student for an even longer time. At school, I was trained to be curious and produce creative work. We were taught how to explore the unknown, try things that hadn’t been done before, and seek out different approaches. Those skills carried over well for me when I entered the design world and worked for various agencies producing websites, digital products, and print pieces for their clients. Our first step was always to gather information about our clients and their needs. Then it was up to me, and my colleagues, to explore different ways of delivering quality work that represented them well.

A couple years passed before I started working at product companies, then a couple more years passed until today where things are very different thanks to Steve Jobs. He showed us how thinking different could change the world and having a deep understanding of your customers can lead to innovative products. I’m seeing that impact right at the company I work Automattic as we undergo a transformative process into becoming a design led company.

A couple of months ago, I participated in a foundational research study in which our goal was to better understand one of our target customers: the small business owner. We conducted a ton of interviews with people from all walks of life and visited them in their homes and offices via video chat. Throughout the interviews we recorded our sessions, took notes, and added our takeaways as stickies onto a digital Mural board.

The amount of data we collected was intimidating at first but then we found different ways of synthesizing it into actionable insights. We’re just getting back into a regular groove of producing new work and thanks to being inquisitive and doing our research, I can already tell the difference in the type of work we’re coming up with. The future for looks very bright.

Unboxing Gutenberg for WordPress

There has been a lot of excitement building in the WordPress community about a plugin called Gutenberg. The plugin offers a new publishing experience that promises to transform the way people create content and build websites. With the first official release around the corner, a challenge was issued for all the designers at Automattic to try it out and share their thoughts. As part of the challenge, we were asked to replicate any post featured on the Editor’s Picks of the Discover Blog with Gutenberg. I picked Evergreen Ideas and Rethinking the Meaning of Content by Maria Popova because I liked its featured image.

First impressions

Eager to get started, I installed the plugin on one of my existing sites thanks to the WordPress mobile app. The Gutenberg editor wasn’t available in the app yet so I had to switch over to the browser on my phone to create my first post. Having worked with lots of different content management systems, I immediately noticed how simple Gutenberg looked. Most other editors bombard you  with palettes, buttons, or fields when you open them up. Gutenberg on the other hand greets you with a friendly prompt to “Write your story”.


Poking around

I typed two paragraphs and then wanted to add an image but it wasn’t immediately clear to me how to do that. Nothing changed in the interface after I started typing so I then tried to press the big plus button at the top left of the screen but that didn’t do anything either. My next guess was to tap one of the paragraphs and when I did, a new set of controls appeared. In addition to some text formatting options there were also buttons to move, edit, delete, or add new content.

After I pressed the add button, a modal filled the screen and presented me with a group of suggested blocks. Some of the choices included a heading, paragraph, image, quote, and gallery. I tapped the image and a new block was added to my editor with options to add an image from the media gallery or upload a new one  The process felt seamless and I was happy to see that I could upload my own image because it wasn’t very long ago that you couldn’t do that from a browser on a phone.

The image pulsed until it was fully loaded and it offered me a space to write a caption. I was curious to see if I could add some “alt” text and reached over for the settings button but accidentally pressed the delete button. I looked around to see if there was a way to undo what I just did but couldn’t find anything so I took it as a sign to get started on my challenge and created a new post.

Completing the challenge

I visited my post on the Discover blog and copied and pasted it right into Gutenberg. To my surprise everything made it over just like in the original post. I checked the preview and confirmed that all the images and text formatting remained intact — it was like magic. With the post looking good on my phone, I wanted to see what it looked on a bigger screen and switched over to my computer.

Looking at the two posts side by side, I noticed some minor formatting discrepancies that needed to be fixed up so I hopped into Gutenberg on my computer. I needed to center align the headers but couldn’t find any text alignment options in the formatting options for the Header Block. After a little poking around I eventually found what I needed in the side bar settings and centered my headings. With the titles centered, I had completed my challenge and began writing about it in a new post.


Writing this post

The block concept in Gutenberg took some getting used to when I began actually writing the content for this post. I have been typing on computers for most of my life but never really learned how to type “properly”. Over the years, I have developed all kinds of weird and quirky habits. In most editors, these habits aren’t an issue because all the text fits into a single container but with these blocks, I ran into some hiccups because they’re all separate from each other.

The first one I encountered was when I tried to use the “command + A” keyboard shortcut. Rather than selecting all the text in the post, it only selected the paragraph I was working on. The other issue popped up when I tried to select text from two paragraphs. Starting with with my keyboard, I wanted to select the last sentence from one paragraph along with the first sentence of the next but ended up selecting both paragraphs the instant I transversed out of the first paragraph. I then tried with my mouse which yielded the same results. With a little extra effort I did what I needed to do so it didn’t bother me too much.

And that’s a wrap

Considering Gutenberg is still under development, my experience using it for the first time got me very excited for the future of WordPress. The long term vision for Gutenberg is for it to become more than just an editor. The Gutenberg team is already exploring different ways of using it to fully power site customization in themes. From what I’ve seen, there’s a lot of potential for it to grow and I can’t wait to see where it goes.

X graphic rising to the next level

Leveling up at customer research

We just wrapped up a week of usability testing for a new design I’ve been working on and thanks to Lynne Polischuik, a new researcher at Automattic, it went off without a hitch. She worked with another colleague, Lilibet Greig, to recruit, screen, and schedule all the participants and even helped me out with my script — all I had to do was show up with my prototype. In a little over a week, we knocked out eight one hour sessions as well as an initial synthesis of the key take aways. Who knew conducting research could be so easy?

The interviews

Our quick recruit yielded some folks that were a bit more advanced than we initially wanted, but that still helped give us insights into our developer and client services audiences. We started our interviews with a set of contextual questions that shed light on the different types of customers we serve, the problems they face, and their preferences — gold for our product and marketing teams!

Then we walked through the prototype which if it were up to me, we would have only tested two screens. Thanks to Lynne we ended up testing the entire sign-up funnel which gave us a ton of insight into the work we’ve been doing over the last year. We walked our participants through the prototype asking them to describe what they were seeing and the actions they would take. I was surprised by how much value we could from such a basic prototype.

Summarizing our findings


After our last interview, we organized our research, documented our findings, and then met to discuss our take aways. The discussion went really smooth thanks to a handy Mural board provided by Lynne. She created it before we started our interviews and asked us to add our insights as they came up. With everybody’s findings all in one place it was easy for us to group people’s insights into similar themes and have a productive conversation about our next steps.

Lynne’s help on this project was invaluable. She showed me how quick and easy it is to do research. I learned more about our sign-up process in this past week than I did all year looking at our data and funnels. It was also validating to see that some of my hunches about the gaps in our sign-up were correct but at the same time I learned my priorities were a little mixed up. These sessions brought more clarity to the problems in our sign-up flow and inspired me to think of different ways of solving them.

Inviting customers to an interview

You’ll often hear that quantitative data tells you what’s going on but if you want to understand why it’s happening then you need to collect qualitative data. I have found this to be true and also believe that a balanced diet of qualitative and quantitative data is the key to a healthy design process.

We recently launched a new feature on and now I’m in the process of understanding how well it’s doing. It’s still early to get excited but we can already see patterns emerge from the quantitative data coming in. On the qualitative side, I started recruiting people for customer interviews this week and it’s going really well thanks to the approach I outlined in this older post. Just as I was about to send out the email to qualified participants, I thought I’d share it here:

Subject:  📣 Tell us about your experience with

Hello, my name is Filippo and I’m a researcher at I’m reaching out to you because you left us your email while trying our new site checklist feature. We’re constantly working on it to make it better and can only do that by talking with people like you.

Can you spare an hour of your time next week to talk about your experiences with so far? You can participate from the comfort of your own home or office and we’ll give you a $50 Amazon gift card to compensate you for your time.

If you’re interested in participating, please book a time that works for you on my Calendly account.

Find a time

Filippo Di Trapani

At the very least, this will make it easier for me to find in the future but I also hope that it’s useful for you should you need to write an email like this. Until next time!

Driving more traffic to my blog

I have been running my blog for a little over a year now and after getting over the fear of writing content, the next biggest challenge I ran into was driving traffic to it. It seems I did something right with one of my posts that brings in one or two organic visitors a day but I’m not entirely sure what I did to achieve that. For the rest of my content, I noticed the amount of traffic coming in is equal to the amount of effort I put into promoting it. I wanted to see if there was a more sustainable way of growing traffic for my blog so I reached out to some experts in the field to see what they had to say.

Luca Sartoni

Luca is a Growth Engineer at Automattic, he’s my go-to reference for everything a/b test related and as of now also SEO/SEM. When I asked Luca what I should do to get more traffic to my site he responded with the advice he gives everyone that asks the same question:

It’s all about consistency, differentiation of channels, and concertation.

Consistency: A piece of content should be consistently promoted across all your channels. Images and headlines are important for grabbing attention so make sure to use something that works well everywhere keeping in mind that images still need to be formatted appropriately for each channel. Luca suggests that you can’t go wrong with a title under 120 characters.

Differentiation of channels: For maximum impact, a piece of content should be distributed on all channels. Every channel has a different cost and reach so your overall distribution will be impacted by the amount of money or time you spend on it.

Luca finds that paid channels always out perform organic ones. Although organic channels are free, they end up being more expensive when you look at the time and resources you put into getting it right. It’s is hard to measure your efforts and can take a long time to see the results come through. Alternatively, with paid channels you can buy traffic and optimize your output in real time.

Concertation: Channels are not only interdependent on each other but also complimentary. It’s important to keep in mind how they all play off each other. Social media channels like Facebook also operate as search engines. For this reason, your efforts for picking the best keywords are not only important for search engines but also on social media channels. Another good example is how traffic coming to your site through an organic search can drive traffic to your social channels which would increase your ability to engage with these people.

Luca stresses that focusing on a single channel won’t get you the results you need. You shouldn’t be thinking of search engine optimization OR search engine advertising, it should be search engine optimization AND search engine advertising.

Simon Heaton

Simon is a Growth Marketing Manager at Shopify, we worked together for a couple years on the same team and saw some incredible growth on the Shopify Partners Blog thanks to Simon’s efforts. He believes that search engine optimization is a key contributor to sustainable growth. It can be hard to compete on keywords depending on your subject matter so Simon suggests going with a long-tail approach where you optimize for a bunch of small, more relevant keywords where the aggregate volume has potential to be larger than those whales.

According to long-tail keywords are:

Long-tail keywords are longer and more specific keyword phrases that visitors are more likely to use when they’re closer to a point-of-purchase or when they’re using voice search. They’re a little bit counter-intuitive, at first, but they can be hugely valuable if you know how to use them.

Take this example: if you’re a company that sells classic furniture, the chances are that your pages are never going to appear near the top of an organic search for “furniture” because there’s too much competition (this is particularly true if you’re a smaller company or a startup). But if you specialize in, say, contemporary art-deco furniture, then keywords like “contemporary Art Deco-influenced semi-circle lounge” are going to reliably find those consumers looking for exactly that product.

Managing long-tail keywords is simply a matter of establishing better lines of communication between your business and the customers who are already out there, actively shopping for what you provide.

Obviously, you’re going to draw less traffic with a long-tail keyword than you would with a more common one, but the traffic you do draw will be better: more focused, more committed, and more desirous of your services.

Alex Hosselet

Alex is Digital & Marketing Strategist for United Way Ottawa, we worked together a number of years where Alex was a marketing manager on a product I designed for. I always admired Alex’s passion for connecting with people and measuring results.

Alex’s advice was to make sure you have a good combination of content strategy and search engine optimization. Content strategy is all about making the right content that attracts people. That involves taking the time to understand your audience and developing a plan with clear goals that can be measured. Search engine optimization is a combination of writing, research, and coding best practices.


My biggest take away is there’s no silver bullet to getting more traffic — it’s a lot of hard work. If you want people to visit your site, you need to pay with your time or money. Based on these conversations, here are some of the tactics I’ll employ to increase traffic to my blog:

  • Share content on as many channels as possible,
  • Try paid advertising,
  • Optimize posts for long-tail keywords and SEO best practices, and
  • Improve visibility of my social media channels on my website.

Crossing the digital divide

Taxiing home after my first Automattic Grand Meetup in Whistler, I was happy to get to know my driver Mohamed. He has been running his family business for over 20 years and also drives a taxi to help make ends meet. Like me, he has three kids and we spoke about them at length. We also spoke about work and got excited when he heard that I’m designer at He pulled out his phone right away and told me that he downloaded the app with the intention of starting a new site but didn’t have the time to get to it.

We’re often encouraged to work with people that use our products because it helps us see our product through their eyes. This seemed like the perfect opportunity so I offered to build Mohamed his site on He was really grateful and humbled me with his response. We exchanged contact info and agreed to meet after I recovered from my trip.

Going into this I thought I was just going to build a site but while prepping for our first meeting I realized it could be a lot more. I had been working on a new post-signup checklist to help new site owners get their site ready to launch. Most of the details were figured out except the checklist tasks which I was still in the process of finalizing. My epiphany led to me drafting up an agenda which basically included latest version of my checklist — what a great way to test it out I thought.

We met at Starbucks, my usual out-of-office meeting place, and he brought a friend along. Mohamed confessed he wasn’t very good with computers and needed someone to help him out with the “technical stuff”. His friend was also a small business owner and managed multiple businesses so he was very interested to learn more about WordPress. After some personal introductions, I asked Mohamed to tell me more about his business and what he was hoping his website would do for him. Within a couple of minutes, I had enough information to start working through my checklist.

Through multiple experiences of my own and hearing about others, I would have to say generating content is the hardest part of building a site. We can help you create a site in seconds and give it a professional look, but without the content, it isn’t very useful. I tried to be resourceful and started by asking if they had any existing social accounts or websites. My thinking was that I could maybe get a logo, a colour pallet, some images perhaps, and if I am really lucky some writing too — but no, they didn’t have any accounts. This reminded me of a poll we once ran where almost 60% of 4400 people signing up said they didn’t have an existing online presence. It was also something really important to keep in mind so we can think of other ways to help people generate content for their sites.

As I went down my list, I would explain why the task was important and how I was executing it. They couldn’t believe how quick it was coming together and they loved the design even though they didn’t pick one. In our time together, we built out the entire architecture for their site, personalized it, set up multiple ways for people to contact them, and added some copy to get them going. The site wasn’t 100% complete but Mohamed was ecstatic that his business was no longer limited to his geographical location. He could now do business with people all over the world. I left them with some homework for next time we meet where we hope to wrap things up.

I walked away from this experience feeling really energized and excited about what I had learned. For one, it was great to see the impact our work has on people’s lives. I also learned a lot about our product and the people using it. My biggest take away was witnessing someone that hadn’t fully crossed the digital divide and how that affects his business. I noticed what a big role Mohamed’s mobile devices has on his work and ability to provide for his family. It’s so clear to me why a mobile-first, or even mobile-only, policy is so important when I see people like Mohamed turning to their phones over desktop computers to connect with the world around them. I highly recommend that people working on products seek out opportunities like these.

This post also appeared in Automattic’s product design blog.

Recruiting participants for remote user tests

I recently attended my first remote design sprint at Automattic. It ran over a two week period and  was attended by fellow designers, developers, data scientists, happiness engineers, and marketers. Together we created two prototypes and tested them out with real customers. I found the experience to be both rewarding and inspiring. We came up with a lot of great ideas and validated them too. It was also really nice collaborating with a number of people across the company that I don’t usually get to work with.

One of my major contributions to the sprint was recruiting real customers for the prototype test. The job was a whole lot easier thanks to an internal post written by my designer colleague Mike Shelton which also took part in the design sprint. He shared his experience recruiting customers from a previous test and also included the templates he created for people like myself to use. With that post, I had everything I needed once we determined exactly which type of customers we wanted to test.

Finding participants

Before the sprint even started, I had been running tests to see how many people I could recruit with a poll on our signup form at Fortunately my tests worked out well so I knew I could count on running another one to collect participants for our test. I created a new poll using HotJar and added a little prompt at the end of the poll that asked participants to sign up for other customer research initiatives. This is what it looked like:


Screening participants

Since we wanted to talk to a specific group of people, the link at the end of the poll lead to a Google form which asked visitors to complete a series of questions. We added questions that would help us qualify the people signing up for this test and other tests in the future. Since this was a remote prototype test, one of the key questions was if people were comfortable talking over a video conference.

View all the questions

Sending out invitations

I wanted the email to look like it was coming from a real person so I sent it with Inbox using my full name and company email address a week before we have our test date scheduled. It worked because some people replied back which was great — I was able to do some additional research for another project. I also made sure to add the qualified email addresses to the bcc field so that the recipients couldn’t see any other people being emailed.

These were the key points I included in the email:

  • Introduce myself and tell people where I got their email
  • Explain what we’re testing along with all the logistics
  • Identified what the recipient gets for participating — we decided to offer a $50 Amazon gift card because we felt like we were asking a lot for someone to take an hour out of their busy schedules
  • How to sign up for the test.


Coordinating schedules

Getting people across multiple time zones to agree on a date and time over email can be confusing and time consuming. There’s lots of back and forth involved and it’s easy to make mistakes.

That’s why we use Calendly to manage our calendar availability and bookings. It’s easy to setup, offers a number of customizable options, and displays times relative to the timezone of the viewer . You can also automate and personalize event reminders so that you have one less thing to worry about.


Sending a reminder

People’s lives are busy so it can be understandable if someone forgets something they committed to a week ago. Sending a reminder a couple hours before the test is a good way to avoid that and to add any last bits of logistical information required for the test. In my case, I made sure to include:

  • the time,
  • a link to download the software used for video conferencing — we use for it’s video quality, number of participants, screen sharing, and recording capabilities, and
  • a link to join your video conference.

Here’s what my email looked like:


Following up after the test

Lastly, we ended things off with one last email thanking our participants for their time. We included instructions for them to claim their $50 Amazon gift card and also took the opportunity to collect some final feedback about the test so we could make improvements for future participants.


I hope you enjoyed reading this post and remember it next time you’re planning on recruiting participants for your own user test or interview. If you do, let me know how it works out for you by reaching out on Twitter.

This post also appeared in Automattic’s product design blog.

Creating empathy for your customers

In my last post, I wrote how we use interviews to learn about our customers. They allow us to ask them questions and in their responses we find insights and get inspired. In this post, I’d like to share some other ways we build empathy for the people using our products.

Support Rotation 💬

It starts from our first day on the job. Everyone that joins Automattic spends three weeks doing what’s called a support rotation. We learn about our products by reading support documentation and running through exercises. Once we’ve completed our training, we get to business and start offering support to our customers with our Happiness team. We start by answering inquiries by email and then upgrade to doing live chat.

After we complete our rotation we are released into our new roles with a wealth of knowledge about our company and our customers. That’s not the end though, once a year we return back to the Happiness for a week to offer more customer support. It’s a great way for us to keep in touch with the challenges our customers are facing.

Business concierge 💼

When people sign up for the Business plan they get access to a one on one setup appointment from a member of our Happiness team. The sessions are conducted over live chat or screen share and usually last around 30 minutes. The goal for these sessions is for the user to walk away feeling comfortable and confident building their site on

In addition to helping our customers, we use these sessions to learn. Anyone can join in real time or listen to a recording at a time that suits them. There is no limit to how many sessions you can attend. After each session, the recording and notes are tagged and posted. Our support team uses these posts to generate monthly reports that give us great insights into who our customers are and the challenges they face. For someone like me that works on our signup and onboarding experiences the content in these reports is invaluable.

User research campfires 🔥

Every month members from across Automattic gather to share their stories about the research they’re conducting. We do presentations, have discussions, and talk about our processes. Through these sessions we hear about our customers and what we’re doing to overcome their challenges. It’s a great place to learn from each other and grow our skills a team. The meetups are recorded for people that can’t attend and serve as a reference to new people joining our team.

Web chefs 🍜

We are often encouraged to build sites for people we know or encounter. There is no better way to experience your product than using it in real world situations. With limited time, resources, and budgets you get a first hand encounter of the challenges people face using your product.

Out of all the activities I’ve written in this post, this is my favorite way of getting close to our customers and building empathy for them. The insights I’ve gained have helped me make better decisions in my design process and allow me to offer great feedback to my peers.

I’m always interested to learn how people conduct their research. What have you found to be an effective way of learning from your customers? Let me know in the comments below.

This post also appeared in Automattic’s product design blog.