When to “Ask”

The UX field is naturally focused on the user’s experience and that means that we sometimes identify conflicts between user needs and business needs. There was an anecdote floating around not too long ago that one of the Facebook redesigns improved the experience so much that people were able to get what they needed faster and spent less time on the site. Facebook is providing their product for free to its users, thus it makes all of it’s money off of advertising revenue. Therefore, people spending less time on the site translates directly into Facebook making less money. They quickly released another update that was “even better”, but looked a whole lot like the original newsfeed. I’m not a heavy Facebook user, so I couldn’t tell you if this was true from my personal experience and I have not seen any data–though I doubt they’re keen on releasing that.

As someone who cares passionately about the user’s experience, I really dislike when the business gets in the way of good product design. Most often, this happens when there is a specific behavior that the business must see (e.g. session duration or ad exposure for Facebook). The trick is to find the right way to present your value, so that when you do ask for the behavior, users are more than willing to comply.

How do we ask for the behavior without sacrificing the user experience?

The answer to that question is driven by these:

  1. What problem is this user trying to solve with the product?
  2. What behavior does the business need to see in order to make money?
  3. When have we sufficiently proven the product’s value through the experience to justify the ask ?

Unfortunately, I can’t give you a template for how to ask. That is utterly dependent on the product and the user, the problem the user is attempting to solve, and the behavior you need to see as a business.

When to Ask

But there are best practices on when to ask…
Regardless of the product or service, users are going to enter into that experience with expectations. To be effective we need to understand what those expectations are. This goes back to scenario-driven design. If we are unclear on the circumstances that lead to this interaction occurring, then how could we possibly address the user needs in any satisfactory way? These are only a few examples of the user’s problem:

  • The user is seeking entertainment or a distraction (game)
  • The user is looking for information about a future decision they will have to make (research)
  • The user is interested in interacting with other people (social media)

Each of these examples is unique and they carry with them vastly different sets of expectations. However, they all have a common thread: the user often cares much more about solving their problem than they do about your product. So if another product meets the need better, you could lose them forever. You need to keep your users interacting with your product long enough to justify the ask, and that means you have to prove your value and quickly.

Product Models

There are three basic product-revenue models:

  • Pay-to-Play (e.g. a car)
  • Freemium (e.g. Farmville)
  • Subscription (e.g. Netflix)


We pay for most things before we get to use them: groceries, movie tickets, gas, etc. We have a certain level of expectation for these items and if they don’t meet that expectation, we tend to regret the purchase and look for a way to reverse the decision. This disparity between expectation and reality is called cognitive dissonance. Businesses can get into a lot of trouble when their advertisements create an expectation that is vastly different than the experience. Nevertheless, advertising serves to create a desire that can only be satisfied by purchasing that product. After all, it’s the anticipation of the enjoyment that drives us more than the actual enjoyment we will get from the product or service (based on a study conducted by Brian Knutson at Stanford1). Think of it like an itch. You might not normally enjoy being scratched really hard, but when you have a serious itch, the anticipation of relief creates an expectation that a hard scratch will be pleasurable.

When to “ask” for Pay-to-Play products:

Successful “asks” will be placed in advance of the purchase to create an “itch” that can only be scratched by purchasing the product. Some businesses will also let you sample products (food samples at Costco, test drive at the car dealership, etc). The enjoyment you get from that limited experience can create enormous anticipation for the next experience and will potentially be very effective at inducing a more positive response to the ask.

Once the purchase is in progress or complete (e.g. you’ve just swiped your card and are about to hit “Accept”), it’s often too late for any additional “asks”. You’re so close to relieving your itch, the anticipation of relief is driving you to get out of the store as quickly as possible. This is why extended warranty plans often fail. You’ve been looking forward to the release of the PS4, you’re eagerly anticipating playing the PS4, you’re at the register about to pay for your PS4, you’re so close you can taste it… then the cashier wants to know if you’re like to add an additional $24.99 for something that may become useful at some unknown point in the future.

The overall shopping experience has done a poor job of creating any anticipation or itch related to an extended warranty; everything up until this point has been about the core product. A sudden ask before you’ve been given a reason to expect or time to realize value is not likely to make you want to delay your gratification, even for only a few minutes. For most people, it’s less about the money and more about the delay of gratification and the disruption of their experience without any expectation of value. The shopping experience would have needed to create a separate anticipation for the warranty plan long before you’re standing in front of the cashier, card in hand.

Pay-to-Play purchases are generally one-time behaviors. Once the purchase is complete, there’s going to need to be a new cycle of anticipation created before another ask would be acceptable.

Imagine you just completed the transaction and signed the receipt for the PS4. Now, the cashier recommends that you buy rechargeable battery packs for the controllers and begins to tout the benefits. It’s simply too late. Even if you want them, you are not likely to go back into the store to pick them up and then wait in line again to pay for them separately. That purchase will occur in the future, after you’ve had a chance to realize the value (when your batteries die during a Call of Duty Deathmatch).


Freemium & Subscription
For the purposes of creating anticipation and justifying your ask, Freemium and Subscription models are almost identical.
During the peak of Farmville and similarly-modeled products, “freemium” was a buzzword, but the basic concept is that the core product is free to use and there are many “advanced features” or exclusive benefits that can only be bought. The initial “ask” is often very small, since the product is free. These products are designed to hook you with the bare minimum needed to create the anticipation that will make you want pay for the “advanced experience”.

When to “ask” for Freemium & Subscription products:

It almost never makes sense to ask for anything big prior to “purchase”, which in this case, the purchase is likely a download or trial of some sort. The best thing to do is to make it as easy as possible for users to enter the experience and then make your ask after they are hooked.

This is the best time to ask for the behavior you really want to see. Give them a taste of the real experience. Take the time to show your users how much value the product could add to their lives, but hold back just enough to create the desire for the “advanced experience”.

LinkedIn does this really poorly. The base product is already unfriendly. We use it because it’s the lesser of evils and the only thing that really solves the business networking problem we have right now, but there is little to enjoy about the experience. There is no flow, the website and mobile app are glitchy, and there are a multitude of constraints. However, there is a Premium function that you can pay for and it is supposed to greatly improve your experience as a user. The last time I was looking for a job, I thought I would try LinkedIn Premium because it said it would help and I had nothing to lose. Eight days into my free trial, I canceled the subscription. They had not done a good enough job of creating anticipation and the additional benefits had no material affect on my experience.

It is imperative that you clearly articulate what the user is missing by not paying for the additional functionality, but it is more important that the functionality materially improves the user’s experience. If you do this in the right way, users will have little objection to your ask, but if the reality does not match the expectations you set, you could lose the opportunity to ever ask them again.

There isn’t really an “after” for these product models, since this isn’t a one-time purchase and the interaction is ongoing.

The Bottom Line

Regardless of the problem or the product model, a successful ask depends on pre-existing anticipation of future value. The burden is on you to clearly articulate that future value in terms that resonate with your users prior to asking for anything from them. And you have to ask at the right time in order to get a positive response.

1Brian Knutson, G. Elliott Wimmer, Camelia M. Kuhnen, and Piotr Winkielman, “Nucleus Accumbens Activation Mediates the Influence of Reward Cues on Financial Risk Taking,” Neuroreport 19, no. 5 (March 2008): 509-13, doi:10.1097/WNR.0b013e3282f85c1