Editor's note: This series is based on our new Alexa Skills course, How to Design for In-Skill Purchasing. This free course outlines the best practices for designing a great monetized Alexa skill experience.

Welcome to Part 3 of our series on designing skills with in-skill purchasing! In Part 2, we discussed design best practices for deciding where you might consider (or not consider) asking customers to purchase content, whether via subscription, one-time purchase, or consumable. You can learn more about those ISP types in Part 1.

Now that we’ve considered the most (and least) ideal locations and intervals for surfacing upsells to our customers, how should we ask them to purchase? What will we say? As I’ve stated before, there are no popup windows, buy buttons, or any other way for a customer to passively consume information about purchases. Your skill will have a short amount of time to tell the customer clearly what an ISP offers – the value proposition – and ask if they’re interested before routing them to the Amazon purchase flow.

Our value proposition should be relevant to the customer with specific and transparent language spoken in a friendly, conversational tone … and be quick about it! We may be interrupting the customer’s experience briefly, but we shouldn’t disrupt them.

Be Relevant to Be Trusted.

Customers abandon skills that surface too many irrelevant or uninteresting offers for in-skill purchases. Conversely, skills may build rapport with customers by offering exactly what they need, when they need it, and avoiding offers they don’t need or aren't likely to find interesting. We want to begin by offering the customer something they're likely to want or need appropriate to their context.

In our hypothetical trivia skill –Seattle Super Trivia – we wouldn't want to try to sell the player hints (as a consumable) when they haven't yet used their free hint we're giving each player daily. We should never offer an in-skill purchase a customer doesn’t need, has already purchased, or is out-sized to their needs. On the other hand, we're more likely to interest the customer in a 50-question Seattle Sports Superstars trivia pack (a one-time purchase) if they've just aced our free daily 5-question trivia that was all about Seattle sports.

Some instances in which we may want to be careful of offering our customers something they don’t need include:

• Offering a one-time-purchase content pack the customer already owns. For this reason, randomized product upsells are not very effective and quickly become annoying.
• Offering a purchase when the customer already has one (or many) they haven't used yet.
• Offering the most expensive type of consumable content to customers who haven't been using the skill very long or successfully.
• Offering an ISP out-sized to what the customer may need to finish their experience successfully, such as offering a large “bundle” of hints to a trivia game with only one question left in the round.

Include a Clear Value Proposition.

In other words, tell the customer exactly what kind of new or enhanced experience their purchase will buy. Why would they be interested? How much content is there? How will their expected experience change? Be specific, but concise. You should consider these questions as your litmus test to writing a good upsell.

Now that we know what questions we should answer while crafting our upsell, let’s take a look at one that we created for Seattle Super Trivia, mentioned above:

Congrats! You finished today’s Seattle Super Trivia challenge featuring your favorite Seattle sports stars with a score of 4 out of 5. Since you’re such a rabid fan of the greens and blues, you might want to try the Seattle Sports Superstars pack with 50 more questions to test your mettle as 12th man. Want to learn how to get it?

Let’s take a moment to dissect this. From the very first sentence, you can immediately tell that we’re offering this upsell after our customer has completed a game and did quite well. This is a great place to offer a pack of new questions since they’ve just finished a game, scored well, and are probably wanting more. We’ve chosen a pack to offer that matches the theme of the day since the player seems knowledgeable about it. We’ve also included the number of questions in the pack.

Writing a great upsell becomes even more critical for subscription skills that will offer a free trial to fulfill the free content requirement (you can learn more about the free trial requirement in Part I: Scoping a Skill). A customer won’t get the chance to access the experience for free without saying “yes” to that upsell message, so we’ll have to tell them more about it. We’ve decided to give our Seattle Super Trivia player a few free questions daily so this won’t be a concern, but what if we offered a free trial model instead? We’ll need to write an upsell that answers our litmus test. Let’s start by looking at a weak upsell for our free trial.

Customer: “Alexa, play Seattle Super Trivia”
Alexa: “Sorry, you need a subscription to Seattle Super Trivia to start playing. New members get it free for 30 days. Want to learn how to subscribe?”

Right from the beginning we committed a cardinal design sin. We start off with an apology and then ask our customer to subscribe. Now let’s take a look at a better upsell that answers our litmus test questions.

Customer: “Alexa, play Seattle Super Trivia”
Alexa: “You can start playing with a subscription to Seattle Super Trivia. Unlock ten daily challenge questions and half-price mega-trivia question packs and extra free hints every month. New members get it free for 30 days. Want to learn how to subscribe?

This upsell is much better. Our customers now understand that purchasing a subscription grants access to ten daily questions, discounts, extra free hints and a 1-month free trial, and that they can try the skill for a trial period for free.

Let’s take a look at a few different upsells in a real conversation. Some have stronger value propositions than others. Which one would you be most likely to respond to?

Strong Value Proposition:

Weak Value Proposition:

No Value Proposition:

Build Trust

To increase your chances of converting your upsells into a sale, it’s important to build trust. We’ve demonstrated some ways to build trust by offering a quality free experience and surfacing upsells for relevant products at carefully chosen moments. Building trust also means avoiding skill development and marketing jargon, and formal and non-conversational language. Terms and phrases such as those below are a red flag that the skill’s upsell messages may be un-relatable, confusing, or sound untrustworthy to the customer:

• Purchase, in-skill purchase, monetization
• Bundle, pack, expansion (without any accompanying descriptors)
• Menu, options
• Content, premium content
• Access

You’ll notice we haven’t included pricing in any of our upsell examples. That’s because this information will be delivered by the Amazon purchase flow after the skill routes the customer there to handle the final purchase during final purchase confirmation (which we will discuss in Part IV: Handle Transactions & Transitions). Skills that include prices in their ISP upsells will fail certification.

Be Transparent. No “Landmines”.

Since a customer is purchasing a product they cannot see or touch, upsells and product descriptions must help the customer imagine the product and ensure they have all the details they’ll need to confidently agree to the purchase. That begins with introducing our premium content clearly. We shouldn’t offer paid options in the same list as other free content, hoping the customer will select the premium option so we can deliver our upsell. That sets our customers up for a “landmine” type of experience. They’ll lose trust in our skill if they never know when they’ll get an upsell message instead of the content they thought they had selected.

How long would you continue to use Seattle Super Trivia if this happened:
Customer: Alexa, Play Seattle Super Trivia
Alexa: Welcome back to Seattle Super Trivia. You can play the daily challenge, or start the Seattle Sports Heroes pack. Which would you like?“
Customer: Sport heroes!
Alexa: The Seattle Sports Heroes pack is available for purchase. It has 50 sports questions to stump fans of the Sonics, Seahawks, Storm, and more. Want to learn how to get it?"

Our messaging should be proactive, not reactive. A more effective approach for offering this pack to our customer would be:
Customer: Alexa, Play Seattle Super Trivia
Alexa: Welcome back to Seattle Super Trivia. You already knocked it out of the park on today’s trivia challenge. I can’t wait to see how you do tomorrow. In the meantime, would you like to learn how to go into extra innings with the Seattle Sports Heroes pack?“

You may have also noticed by now that none of our examples ask the customer if they’d like to buy something or subscribe explicitly. That’s because we don’t want to mislead them into thinking a purchase will be made immediately if they say “yes” because it will not. Since the Amazon purchase flow will ask for final confirmation after giving the price, it will ask “Do you want to buy it?” or “Should I start your subscription?” If we use “buy” or “subscribe language in the skill, a customer is likely to say ”no,“ since they haven’t heard the price yet!

Ask for the Sale. One Sale.

Upsells are most effective when they present one option as a simple question with a yes or no answer. We don’t have much time to explain one product to a customer, much less two. Either-or prompts can be confusing. If the skill offers multiple ISP options, surface only the one most relevant to the customer.

Let’s take a look at the difference between an upsell that offers one ISP versus several.

Do Sell One Relevant Product:

Do NOT Sell Everything at Once:

Passively telling customers about purchases and not asking for the sale is even less effective at converting customers to a sale. Doing so requires the customer to remember an utterance for later without being prompted. This kind of unsolicited messages often feels disruptive to customers, too.

Don’t: “Before we start the daily challenge, did you know that you can buy extra Seattle Super Trivia hints to help you through those tough rounds? Just ask me to buy hints at any time during your game. Let’s get started …”

Strike the Right Tone.

Customers have expectations of Alexa’s personality characteristics and tone they've learned over time. Customers may respond more positively to messages that are consistent with their expectations of Alexa and the experiences they've previously had in your skill. Customers lose trust in skills that badger, threaten, or nag them about purchases.

Messages should be positive and delightful and remind customers of its value before and after a purchase is made.

Do: “Want to bring on the rain? Er, I mean more trivia? Seattle needs a hero like you. A Seattle Sports Heroes pack with 50 more questions, that is! Want to learn how to get it?”

Celebrate the benefit after the purchase, offering an immediate opportunity to use it where possible.

Don’t: Your purchase is complete. <ends skill session>

Do: “Bring on the rain–er … trivia! Thanks for buying the Seattle Sports Heroes trivia pack! Want to start playing it?”

Avoid taking on a nagging tone, and avoid implicit or explicit threats. Friendly hints over nagging are a more trustworthy means of communication.

Don’t: “If you stock up on hints before you start the round, you could avoid a mistake that could hurt your rankings. You are currently in danger of dropping in rank. Want to buy more hints?”

Do: “Recovering from a small mistake during this round could help you reach the next level. You might consider an insurance policy. Want to stock up on hints?”

Positive vs. Negative Tone Examples:

Now that we’ve learned how to write dialog that gets customers interested in your in-skill offerings, it’s time to think about what happens next. A customer will interact with an Amazon purchase flow to complete the purchase, and our skill dialog will need to transition to and from that flow gracefully. Stay tuned for Part 4 of this series, where we’ll discuss how to handle transactions and transitions.