Apps often have to ask for a lot—fill out this form, enable this integration, keep up with these updates—before users can benefit from the product’s full value.

After a while, necessary actions can start to feel like chores.

The key to motivating users to take meaningful actions over and over again? Well-crafted in-app messages that inform, guide, and delight users from their first onboarding experience to their 100th login.

A good in-app message can help turn simple actions into pivotal aha moments. 

In this article, we'll explore how 10 popular apps have designed, positioned, and personalized their messages in ways that build deep, lasting engagement throughout the user journey (and high user retention rates). 

Let’s get started.

1. Mailchimp nudges users to take action with personalized messages

Amid crowds of confused travelers at the airport, a woman bee-lines for a sign displaying her name. Even the simplest personalization can mean the difference between chaos and calm. It's a great user onboarding tactic, but can also be used at any stage of the user lifecycle to help users engage more deeply with your product.

Mailchimp's welcome page following sign-up is a masterful example. Large text welcomes the user, calling her by name. The greeting is based on the time of day in the user’s time zone.

From here, Mailchimp wants to customize this first customer experience with personalized marketing recommendations. To do that, they use a banner to invite users to answer a few questions.

And Mailchimp continues to personalize the dashboard long after onboarding. Returning users see that same friendly greeting, along with tips that will help them take the right actions for growing their audience.

Utilize personalization for user segments to build familiarity and encourage a sense of ownership that will lead to greater exploration and user engagement across the entire customer journey.

2. GoToWebinar walks users through a new feature step by step 

A user’s first aha moment kicks off a journey toward becoming a loyal customer and brand advocate down the road. But getting users to achieve activation is only the beginning.  To become a regular user and eventual champion, you need to help app users discover deeper and ongoing value with your product. A big part of this involves continuously iterating on your product and app features—but it’s equally important to show your users how to use the features you’ve already got.

GoToWebinar, a webinar and online conference software, offers a wide range of features. This means that new features or functionalities have the potential to go unnoticed if they aren’t easy to see and discover within the main dashboard (even—perhaps especially—for the most experienced users who have already built habits around the product).

To announce their new Transcripts feature, GoToWebinar used Appcues to create an animated slideout that briefly describes the feature and invites users to see how it works.

From here, they show the user exactly where to click to navigate to the new feature.

Each hotspot is accompanied by a tooltip that describes each step.

This feature announcement was targeted to returning GoToWebinar users who already know their way around the app and probably don’t need too much hand-holding. This walkthrough feels thorough, but not dragged out.

New and returning users need different levels of guidance at different moments in their experience, and features that experienced users find exciting might be too much for new users to take in. When designing your in-app messaging and announcements, it’s important to consider the relationship your users may already have with your product.

3. Dropbox makes it easy to focus on the most impactful product improvements

If you redecorated your entire house, you’d probably be pretty excited to show off the result to your friends. At the same time, you’d (hopefully) realize that  your choice of wallpaper is probably more interesting to you than it is to them. When you’re dealing with a product redesign or sweeping product updates, the same logic should apply. You want to show users how to take advantage of new features, but you don't want to force them into every nook and cranny.

When Dropbox launched their desktop app, they introduced some pretty big changes to users' workflow.

Instead of showing users everything they can do with the desktop app (and there’s so much they can do), Dropbox hones in on the most significant shift of all: powerful, seamless integrations in one place.

After greeting returning users with a simple, high-contrast welcome modal, Dropbox uses a tooltip to call out 2 specific tools—Dropbox Paper and Google Docs—and show users where to click to get started.

Rather than taking users through each and every feature and basic new functionality, which remains the same across platforms, Dropbox smartly focused their desktop app introduction around a couple key features. The result gives existing Dropbox users a sense of both familiarity and novelty—and perhaps even a second aha moment to drive deeper product adoption.  

4. Harvest continues to train users with bite-sized tips

A high-level overview of a few features can be great for a user onboarding process or for introducing a product redesign. But when users have gotten into a routine with your app, you want to ration out those tips so they don't feel like a to-do list.

Harvest, a time-tracking app for teams, displays a simple modal when users log into the mobile app. The tip positions the value first, so it's quick to skim, and then follows up with a “get started” CTA that takes the user right where they need to go.

This is a great example of mobile permission priming. Users are increasingly wary of granting device permissions to mobile apps—use your permissions requests as an opportunity to educate them and make the benefits of granting those permissions obvious—like Harvest did.

5. ExaVault helps users reach their goals

Unless you have a user base of one, chances are high that your product isn’t solving just one problem for a single type of user. User’s needs and the context in which they occur can vary. If you’re selling to companies, it gets even more complex. Different company and team sizes, communication habits, and workflows mean you’re dealing with a wide range of user goals.

ExaVault, a branded file-sharing service, enables their users to manage and share their documents in a way that suits their needs. Small teams work differently than huge enterprises, and ExaVault makes sure to onboard their users in a way that fits their context.

Following registration, ExaVault prompts users to select what they hope to achieve with their new account. Options are divided into basic and advanced.

From here, a slideout appears in the corner. This slideout lists the tutorials a user is most likely to find useful, based on the goals they selected in the previous step. It also gives users the option to change topics or to contact support if extra assistance is needed.

Instead of guessing what your users are trying to do, ask them upfront and use their responses to personalize their individual user experiences with topical in-app messages and guidance.

6. Spotify primes freemium users for the upsell without the shock factor

Unlike a free trial, which typically involves a firm expiration date, freemium products often let users access a product for free indefinitely—with important restrictions. While many users are savvy to the fact that certain features will be off-limits until they pay, getting hit with a paywall can still be jarring.

Spotify makes their freemium restrictions more palatable by gently warning users when they’re getting close to their usage limit. Freemium users can listen to music for as long as they want, but they can only skip 6 tracks per hour.

Instead of simply hitting them with an upgrade prompt when they reach the limit, Spotify  gives user a heads up when they’re moving through their hourly skips too quickly.

When users do exceed the limit, Spotify gets clever with its messaging. They position the paywall as an opportunity (“you discovered a Premium feature”) rather than a restriction.

Rather than making users feel bad for not paying up, use your in-app upsell prompts to convey the extra value a user can access if they upgrade. 

7. Slack helps users stay up to date with tempting in-app notifications

When users log in, they don't want to spend time sorting through product updates to get on with their work. Keep a separate but visible place for new features and updates in your app's interface, where users can be tempted (but not interrupted) by product updates.

See how Slack hides their updates behind a little red gift box in the corner of the screen.

When users are ready to explore, the icon expands without obstructing the user’s primary workspace. The content is super clear and user-driven: The title of the update and the short excerpt are focused on the user's pain point, allowing them to see the update's value immediately.

Give users the power to get straight to their work by keeping updates out of the way and letting users access them at the moments when they're actually ready to take action.

8. HubSpot minimizes the fear of making a mistake

Some products have an outsized impact (like helping companies reach a big audience all at once). Powerful tools are great, but they also involve an equally huge risk (like sending the wrong message to that same big audience). The ability to make an important mistake in just a few clicks can translate to anxiety,—and the last thing you want is for your product to make your users anxious.

HubSpot combats the anxiety of scheduling an email to a large list by doing the unthinkable: They actually add friction to the user's workflow. What does good product friction look like? In this case, it’s a simple modal window that confirms the date, time, and time zone, along with reassurances that, yes, the email can still be edited or canceled after scheduling.

HubSpot does two things well here: First, they’re confirming that the user will indeed accomplish their goal once they hit the orange button. And second, they’re telling users that the action isn’t irreversible. This reassuring copy gives HubSpot’s user a sense of control over an important action.

Think about how your own users feel after completing certain high-impact tasks within your product and look for ways to add relief to their app experience—whether that means removing unnecessary friction, or adding it back in.

9. Webflow delights users with useful product update announcements

Not all product updates are made equal. Most of them are minor, often not even evident to the majority of users. Some will have an immediate impact on your entire user base, while others will be relevant only to power users.

Webflow, a WYSIWYG website builder, publishes product updates several times a month. Webflow uses a simple, uncluttered modal window to provide regular product updates.

This approach keeps all users aware of new features and bug fixes that they may have been waiting for. From here, they can choose to read more about an update or easily dismiss it in case it doesn’t apply to them.

Make it easy for your users to keep an eye on product updates that impact their workflow in your product—but make it equally easy for users to get on with their work.

10. Turbotax celebrates milestones to create a sense of progress

The ultimate challenge for making app chores fun? Tax prep software. If an app can make you feel good while doing your taxes, you know it's doing something right.

Here, TurboTax makes filing easier and more fun by breaking up the filing process with milestones, marked by friendly in-app messages and notifications. Celebratory messages serve as mile markers and give users a sense of progress.

With these notifications, TurboTax makes something objectively dreadful kind of pleasant. Take a page out of their book and spend some extra time on the unpleasant parts of your product. Break up complex tasks, celebrate progress, and give users a clear indicator of where they are in a lengthy process. That way, users will be more likely to stick around for the fun stuff.

11. Evernote turns organization into a personal art form

Stepping into Evernote is like walking into your favorite coffee shop, where the barista knows your order by heart. This personalized touch is the core of Evernote's in-app messaging. And it starts from the moment you begin your onboarding journey.

The platform prompts you to customize your view, ensuring you get the most out of your product experience. Even better, it allows you to try it for free. 

From there, you’re guided into making your home layout work best for you. The platform lets you click, drag, and drop your way to a personalized home page that really gets your note-taking fuels pumping. 

The kicker? The only way to save the view is by upgrading—turning this simple usability into a call-to-action toward increased conversion rates. 

The beauty of Evernote's approach? It grows with you. As you continue to interact, the in-app messages evolve, suggesting tools and layouts that click with your habits.

12. Miro eases app exploration with visual charm

Ever felt like you're wandering in an app jungle, where every click feels like a step into the unknown? Miro gets it, and they've turned their in-app messaging into a friendly, visual sherpa to guide you through. In the world of apps, where about one in five users bail after just one use, Miro's approach is like finding a clear, well-marked trail in a dark and wooded jungle.

When starting your first board, Miro’s product tour messages guide you through click-by-click to be sure you’re aware of everything you need to know without throwing it at you all at once.

Each in-app prompt is like those handy trail markers in a hike, showing you just enough to keep you moving forward without spoiling the surprise of discovery. As you continue to click ‘next,’ Miro shows you more ways to make Miro work for you.

Miro makes sure that by the time you’re done exploring, you’re not just familiar with the app, but you’ve also had a good time figuring it out.

13. ConvertKit turns updates into a daily dose of insights

Ever walked past a bulletin board that caught your eye with its colorful, interesting snippets of information? That's the kind of appeal ConvertKit brings to its in-app messaging. They've turned the routine task of checking updates into a fun and easy way to catch up on the latest news.

Every time you log into ConvertKit, you’re greeted with a simple notification that expands into bite-sized updates. New features are unveiled, exclusive insights for premium users are shared, and actionable tips are offered up. These messages are less like announcements and more like casual yet informative conversations with a nosey neighbor who's always got the inside scoop.

New integrations? These messages make understanding them a breeze. They provide the information you need to make a decision about the next best steps for your business. If it’s a win, simply click on the support article link to learn how to implement the newest change. 

What ConvertKit does brilliantly is make staying informed feel less like a chore and more like an enjoyable part of your day.

14. ConvertKit turns updates into a daily dose of insights

Descript's in-app messages are like those cleverly placed Post-It notes in your digital workspace—unobtrusive yet effective at capturing your attention for specific actions. It's there to give you a heads-up without getting in your face. 

Picture this: you're deep in your workflow, and Descript subtly drops a hint at the top of the page. It's in the same comforting color scheme you're used to, blending in but still catching your eye—kind of like a chameleon in a party hat.

Ready for a deeper dive? A simple click on 'Learn More' unfolds a new aspect of your Descript journey, without derailing your current task. It's the digital equivalent of a teaser for a much-anticipated sequel—intriguing but not intrusive. You get to stay on your path with the freedom to explore more without any fuss.

And the next time you swing by Descript's digital neighborhood, there's something new waiting for you, so you never miss a beat. Descript's messages keep evolving, giving you more ways to make the platform dance to your tune.

If you haven't got anything engaging to say...

Don't say anything at all. Chores have no place in your app. Just because you can publish a tooltip tour in minutes doesn’t mean you always should. Make sure to step back from your product and put yourself in your users’ shoes Take the time to understand your users (who needs what and when), and target your messaging only to the people who will find it useful. That’s the key to grabbing user attention without overwhelming them.

Targeted, thoughtful in-app messaging can deepen customer engagement and drive product adoption. A clumsy barrage of popups, on the other hand, only drives people away.  

Check out the do’s and don’ts of in-app notifications for more tips on how to strike the right balance in your own product.