Alexa Innovators: Five Ways Drives User Engagement for the ‘Question of the Day’ skill

Staff Writer Mar 16, 2022
Alexa Skills

Since its launch in 2017,’s Question of the Day skill has inspired tens of millions of users to engage thought-provoking questions crafted from diverse categories ranging from arts and entertainment to literature and science.

According to its creators, Question of the Day has millions of users. The skill’s Facebook page has over 20,000 followers. The skill was awarded the 2020 Gaming Voice Experience of the Year by Project Voice, and has been featured in USA TODAY, CNBC, CNET, and other leading publications. 

Question of the Day was developed by Joel Wilson in December 2016. Wilson had worked in the technology industry for 25 years as a developer, solution architect, and entrepreneur. He was intrigued by the Amazon Echo when the device launched. Within a month of receiving his first Echo device, he had developed Question of the Day

The skill was an instant hit among Alexa users. The first two payments from the Alexa Developer Rewards Programwere substantial enough to convince Wilson that Question of the Day was more than a hobby – it had the potential to turn into a meaningful source of income. 

Wilson asked his wife if she would be willing to consider developing content for Question of the Day. At the time, Sarah Andrew Wilson, a classically trained flautist, was the director of music education for the Levine Music School in Washington D.C. 

Andrew Wilson joined her husband as’s chief content officer. Her musical background proved to be immensely useful in shaping engaging experiences for voice-forward skills. 

“I have trained my ear to hear even the slightest nuances when it came to sound,” she says. “That really helps me develop content that sounds natural and is compelling enough to keep users coming back for more.”

Since its earliest days, the team at has been laser focused on developing experiences that drive user engagement and retention. In a conversation with the Amazon Alexa editorial team, Andrew Wilson provided five tips for developers looking to drive engagement and retention for their skills. 

1.     Focus on high quality content

“It’s important to remember that users don’t really care about your clean code or clever design,” says Andrew Wilson. “What they care about is high-quality content.”’s content team (that has grown to six people) follows a carefully crafted set of guidelines for developing Question of the Day to ensure that users receive a consistently delightful experience. 

“For example, when we present users with multiple options to a question, we sometimes design the fourth option to be humorous or obviously silly.” says Andrew Wilson. “The goal here is to add a dollop of delight and positivity to a person’s day-to-day.” 

2.     Conduct extensive A/B testing

Teams at conduct extensive A/B testing to make design-related decisions to reduce customer friction, increase daily repeat visits, and greater revenue. 

Andrew Wilson gives the example of an A/B test the team conducted recently to increase the percentage of users that signed up for the paid version of Question of the Day. The skill’s ‘Trivia Club’ gives users access to three additional challenge questions every day, in addition to enabling placement on local, state, and national leaderboards. 

As with their content, wanted to ensure that the upsell messaging was consistent with the overall experience and delivered in a way that highlighted the benefits and utility of a paid membership to the end user.  

They turned to A/B experimentation after the first iteration of the upsell messaging failed to deliver a tangible lift in member uptake of the Trivia Club.

“We conducted an A/B test on the upsell messaging,” says Andrew Wilson. “We found that changing just one word resulted in a 14% increase in conversion rate.” 

3.     Be respectful of the user

When designing content for the skill, the team likes to think of themselves as being a welcomed guest in someone’s house.  

“Be it the content, our tone or the delivery, we don’t want to be too familiar with our users,” says Andrew Wilson. “At the same time, we don’t want to be like a stranger, and be overtly distant or formal.”

Not overstaying your welcome is one of the key attributes of a welcomed guest. To this end, Andrew Wilson says that team is always focused on delivering short and memorable experiences. She says that like a good guest, they are also deliberate and careful about the words they choose.  

“We don’t know anything about the people that are interacting with our skill – be it the cultures, the ages of the different people in the home or the family background. So, we take care to ensure that we are always very polite and very friendly.”


4.     Reduce the cognitive load for the user

Like with all Alexa skills, user interact with Alexa skills in several ways – by talking to their Amazon Echo device, or via a screen such as the Echo Show.  

“We always go for a voice-first design,” says Andrew Wilson. “This means that we don’t want to overwhelm the user with too much information. We don’t use long sentences or deliver labored explanations. When it comes to building content for the smart speaker, you usually want to keep things short and simple.” takes advantage of the multi-modal experiences available to Alexa users by utilizing visual screens to deliver supplemental information – such as the number of badges a user has earned, a listing of achievements by category, or a user’s position on the leaderboard. 

5.     Leverage social media

Andrew Wilson views social media as integral to driving user engagement and retention.  

“Social media allows us to connect with users in near real-time,” says Andrew Wilson. “It’s very painful for a developer to receive a one-star rating just because the user didn’t understand something, or because they were unable to offer feedback.” kicked off their social media efforts with customer service in mind. Over the years, their social presence has evolved to use social media to keep users engaged and coming back to their skill. 

"We realized that we could use social media to keep users engaged between sessions. As a result, we have conducted a series of tests in a very methodical manner to see what users are really responding to,” says Andrew Wilson.

The content team uses social media to post questions from the prior day and answer these questions in greater detail – the team provides a link to an article they have written about that subject. 

Social media has also served as a great discovery mechanism. The team polls users on a variety of topics that range from their favorite categories to the times of the day they interact with the skill, and other “must-have” features. 

User feedback from social media drove the development of a recent “send to phone” feature, where users could share stats sent to their phone on social media. These stats include the number of days in a row that a user has engaged with the skill, and their position on the leaderboard in their city or state.

“Being able to inspire wonder and curiosity in the lives of over twelve million people has been an incredibly fulfilling experience,” says Andrew Wilson. “Over the years, we’ve found that if you continue to exceed the expectations of your users consistently, they will keep coming back for more.” 


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