What is contextual onboarding?

When someone signs up for your software as a service (SaaS), you’re still a long way from converting them into a loyal customer.

Onboarding is key to ensuring that new users are comfortable with the software and believe it’s a good investment. With contextual onboarding, you can guide users at every stage and give them targeted customized help.

Signing up for SaaS always involves a learning curve. The onboarding process is similar to the kind of onboarding that happens when new employees are trained at a job. It’s in the interest of both software creators and customers to make onboarding as fast and painless as possible.

Remember that new users are not necessarily tech-savvy. They are mainly focused on finding a simple solution or automating a process.

SaaS onboarding is crucial for several reasons:

• It provides a strong first impression. This is essential for building strong customer relationships.

• It reduces customer churn. A customer who is satisfied with onboarding is more likely to stick with your company.

• It allows you to collect important customer data. This not only helps you provide a better experience, but it also helps you better design future products and features.

• It reduces customer interactions with customer support. A well-designed onboarding process means fewer support tickets or phone calls. This benefits your company as well as the customer.

Contextual onboarding is part of a wider trend that emphasizes the importance of providing guidance within the context of a user’s current activity.

Many apps and platforms now use this approach, offering timely tips or instructions exactly when and where they’re needed. This prevents the customer from feeling overwhelmed upfront.

A common example is a spelling or grammar checker that highlights mistakes as you type for immediate correction without the need to open external applications.

Generic vs. contextual onboarding

Generic onboarding is the alternative to contextual onboarding. From a product creator’s point of view, it’s a lot simpler to provide generic assistance—but it’s also less effective.

As the term implies, generic onboarding is providing the same content to everyone without regard to their individual needs.

Consider the kind of instruction manuals that accompany physical products such as appliances. When you need to look up a particular point, it can be difficult to find the right section. That’s because it’s a general manual that gives everyone the same information.

Providing contextual guidance for a physical product can be challenging, although technology is making it easier (for example, with voice assistants). However, this is much easier with digital applications.

The following are the main benefits of using contextual onboarding:

Improving customer retention

Onboarding users to new software might not always work out as you hope. People may drop out at any stage. They may be frustrated with how complicated the process is. They may decide the software doesn’t fulfill their needs. If they get confused and don’t know how to proceed, they may contact support—or they may procrastinate and never return.

Contextual onboarding can cut down on the number of dropouts. By helping users at every stage, they never have to feel lost. If they stop a session, they know that when they resume, they’ll be able to access the guidance they need. It’s the closest thing to having a live mentor in the room with them.

Allowing users to see immediate benefits

If a new user has to read through complex instructions or watch a lengthy video (or series of videos) before getting value from your product, your task becomes more challenging.

Consider the fact that attention spans are getting shorter. People may decide the learning curve is too long and seek a faster solution. Even the most advanced virtual product tour can prove too long and complicated for many users.

With contextual onboarding, people can start seeing benefits right away. They can start wherever they feel comfortable. A complete beginner will be guided on how to get started, while more advanced users won’t become bored because of the unnecessary instructions.

Providing a personalized experience

Personalization is everywhere, from email marketing to social media sites. People are used to platforms and bots calling them by name. However, personalization can go much further with contextual onboarding.

You can incorporate adaptive learning techniques into training. New users get started by providing information about their needs and experience, which the system can use to tailor the onboarding to their needs.

Now you know the advantages of contextual onboarding, you need to figure out how to implement it.

Triggers

A trigger is an action or condition that automatically creates a response. For example, if you are on a website, a popup ad may appear when you’ve been on the page for a certain amount of time or when you scroll to a certain point.

In onboarding, a user sets off a trigger to let the system know they need guidance. This can occur in several ways:

• When a page is loaded

• When the user hovers over a certain place on the page

• When the user exits a page

• When the user clicks on a certain element

• When the user has been on a page for a certain amount of time

Events

Events occur when a user sets off a trigger. Here are some examples:

• A message box with instructions

• A graphic, such as a chart or an infographic

• A short video

• Redirection to another page

So, how do you start experiencing the benefits of contextual onboarding?

You may need to reconsider some of your current assumptions and strategies. For example, it’s traditional to include a detailed tutorial for new users. However, this may actually be doing more harm than good. If people find your instructions too long and complicated, it may drive them away.

If you want to keep a tutorial, consider including reminders telling the user they can start using the software at any point and receive contextual guidance instead. Instead of a traditional comprehensive tutorial, you can offer more concise checklists that cover the essential points of every section or function of your product. This way, users can skip sections that don’t currently interest them and get right into what they care about.

Let’s explore some examples of how contextual onboarding is used in various apps.

Grammarly

One of the most widely used spelling and grammar checkers, Grammarly, uses contextual onboarding to teach new users how to navigate the app.

Grammarly users include business people who are writing emails, students who want to turn in quality papers, and people whose first language isn’t English. This diversity of needs and levels makes contextual onboarding essential.

You can start using Grammarly on a document you’re writing and get contextual guidance. However, the solution also offers a demo document for users who want to learn the system before using it. The demo clearly illustrates how mistakes are highlighted and corrections suggested.

Grammarly sign up screen, via Mobbin

Canva

People use Canva for many different purposes, including creating logos, videos, memes, business cards, posters, and much more. Because there’s so much on offer, it would be cumbersome for new users to try to learn how everything works.

The contextual onboarding begins by asking users what they’re using the app for. They are offered a wide range of templates for different purposes, along with user flows that start with the question, “What will you be designing today?” The user then gets to specify the thing they want to create—for example, under “Websites,” you can choose from business, event, educational, and other kinds of websites.

Canva has a Quick Action button that provides further guidance, such as Magic Write, which offers AI-generated suggestions.

Creating an account on Canva, via Mobbin

Duolingo

Duolingo is a popular app for people who want to learn a second language. Signing up and getting started is quick and easy.

Kick things off by choosing the language you want to study (there are 40 options). You’ll be prompted to answer a few questions about where you heard of Duolingo, your reasons for learning the language, your current level of proficiency, and how many minutes or hours per day you want to study.

You’ll be assigned a level and given exercises straight away. Gamification makes the lessons fun and engaging, and there are also leaderboards where you compete with other users.

Kicking things off on Duolingo, via Mobbin

Dovetail

Dovetail provides targeted solutions for businesses in areas such as analytics, customer insights, testing, and more. Our solutions can be applied to many areas, such as customer interviews, usability testing, creating user personas, and empathy mapping.

Our onboarding process ensures that customers are directed to the tools and resources appropriate for their needs. After a streamlined signup process, users are guided to create their first project. As you proceed, you’ll receive helpful guidance at every stage.

Handy tips guide you on classifying data with tags, using the editor to format content, using insight templates, adjusting permissions, and sharing insights with your team.

Getting started on Dovetail, via Mobbin

ClickUp

ClickUp offers many project management, resource management, and collaboration solutions for businesses.

Users can choose from several paid plans, but the “free forever” plan, which includes unlimited tasks, lets new users sign up without a credit card.

As a new user, you’ll immediately be asked which apps you currently use. This enables ClickUp to show you how much time and money you can save. The New User Template guides you in creating your first task. This includes customizing the task, setting deadlines and priorities, collaborating with team members, and managing the project.

Editing task statuses on ClickUp, via Mobbin

Notion

Notion is a comprehensive workspace solution designed to let users organize their tasks, schedules, and notes in one place. The platform’s minimalist design makes it straightforward to create an account and get going.

Users can import work from other platforms, such as Google Docs, Dropbox, and Evernote.

Notion has a helpful interactive guide that helps users create their first projects. There are over 1,000 templates to choose from, covering areas such as school, work, freelancing, food and nutrition, and more.

You’ll be given a few targeted suggestions based on your needs. When you click on a template, you’re given a preview with suggestions on how to move forward. The Wizard guides you through your first task.

Notion also sends out customized emails based on the user data you provide.The “Plus Plan” workspace on Notion, via Mobbin

WordPress.com

As WordPress.com is a website-building tool popular among people who don’t have advanced coding knowledge, it’s crucial to provide step-by-step guidance.

WordPress.com provides managed hosting and more guidance than its WordPress.org counterpart, which requires users to download the software from a web host and set up the site on their own. This makes it more suitable for beginners and non-coders.

Creating a new account with WordPress.com using Google, Apple, or your email address is simple. As you’re setting up your site, WordPress provides an interactive slideshow that explains the feature you’re using. It also has a progress meter, letting you know how many steps you’ve completed.

Navigating the Site Editor on WordPress

There are reasons why many products have generic user guides or tutorials rather than contextual onboarding. Implementing a more customized approach takes creativity and effort.

Here are the main challenges you’re likely to face when setting up contextual onboarding.

Keeping users motivated

As noted in examples such as WordPress.com and Duolingo, a key benefit of contextual onboarding is providing users with encouragement. Beginners want to feel they are making progress. Celebrating milestones, which can include gamification, helps keep users engaged.

Integrating in-app and off-app messages

In-app guidance using chatbots, slideshows, or other automated help tools is an essential aspect of contextual onboarding. However, you’ll also have off-app communications such as email. Seamlessly connecting the two is important for providing targeted support.

For example, new customers may get an email series explaining how the software works—but it’s more powerful if they receive emails that are relevant to where they are on the customer journey.

If a customer is using a website-building tool, you wouldn’t want to send them an automated email congratulating them on their new site if they haven’t built it yet.

Collecting the right data

Contextual onboarding depends on knowing as much about your customer as possible. If you don’t start by asking the right questions, you won’t be able to provide relevant guidance.

Here are some examples of the kind of crucial information you might ask for:

• Is the user an individual or part of a team?

• What industry are they in?

• What are their main goals for using the software?

• What is their level of experience?

Here are some guidelines for ensuring customers get the most out of your onboarding process.

Provide ongoing support

While “onboarding” may imply a process that only lasts until the user is comfortable with the software, in reality, that process needs to be ongoing. SaaS tends to be dynamic, with new and evolving features. What’s more, users’ needs are always changing.

Make signup frictionless

Before anything else, you need users to sign up.

Every extra step means losing potential customers. In a time when people expect quick signups via Google, Apple, or Facebook, even filling out a form can be too arduous. Asking for credit card information will reduce your signups even more. You can focus on collecting more information from them after they have signed up.

Let users start right away

The advantage of contextual onboarding is that it removes the traditional line between learning and doing. You want people to learn while they’re doing. The most successful software products let users begin their projects, tasks, or documents immediately.

Not everyone will have a project of their own to start with, or they won’t be comfortable jumping into a real project right away. Providing demos or templates lets them start working and learning using sample data.

Use checklists

Everyone likes to chart their progress, whether they’re completing an exercise program, a school assignment, or their first project using your software. Provide checklists to let them know what they have accomplished and what they still need to do.

Identify pain points

Using email and in-app surveys, find out what challenges new users are experiencing. When people cancel their membership, ask why. This helps you identify objections and make improvements.

Engage with inactive users

No matter how effective your onboarding process is, you’ll always lose some users along the way. However, some reluctant customers will re-engage if you give them a nudge. You can send an encouraging email that reminds them where they left off.

Contextual help in user experience is designed to help users with common issues and challenges. Ideally, you’ll anticipate questions before the user is even aware of them.

These vary according to the product, but the typical stages are:

1. Introduction: this is the user’s first impression, often involving a welcome message, account setup, or product overview. The goal is to create a positive first experience.

2. Orientation: ensure the user is familiar with key features through guided tours, tutorials, or introductory tooltips. This helps them understand the product’s core functions.

3. Activation: at this stage, users start interacting with the product by completing essential tasks, such as setting preferences or using a key feature for the first time. This is often tied to a product’s “aha moment” when users see the value.

4. Engagement: once users are more comfortable, shift your focus to enabling deeper engagement. Contextual tips, reminders, and suggestions guide the user to explore more advanced features and make the product part of their regular routine.

5. Retention: this involves providing ongoing support through notifications, personalized recommendations, or resources to ensure users continue to find value and stick with the product over time.

“User onboarding theory” focuses on the idea that guiding new users through the key functions of a product in a clear, engaging way helps them reach an “aha moment”—the point where they understand the product’s value.

It’s grounded in behavioral psychology, aiming to reduce friction, provide timely support, and gradually introduce users to more complex features. This increases the likelihood of long-term engagement and satisfaction.