9 minute read · Published April 20, 2024

Building a contextual help system for better UX and retention

Latest Update May 10, 2024

The idea behind contextual help is obvious:

When a customer faces a specific problem, provide them with specific guidance to help solve it.

This applies to every industry, not just SaaS.

Furniture brands have random folks test out a well-thought-out physical product requiring installation and identify pain points and difficult moments in installation. That’s why the instruction manual has extra detail and pictures included for that part of the set-up or a QR code to a video.

Even for simple things, some extra context goes a long way! Imagine you’re getting into your new electric vehicle for the first time. When you click into the “Charging” tab, you have small indicators and bolded text that appear and help explain the charging process.

Conceptually understanding and committing to providing great contextual help for your users.

But that’s not enough to actually execute on that vision.

Contextual help in B2B SaaS

Doing contextual help at scale AND in a personalized way is much harder, particularly for B2B SaaS products.

That's because executing a more complex task in your software is more difficult than plugging in an electric vehicle charger or assembling an Ikea table.

You also have users with a wider range of personas and knowledge levels of your software, all interacting simultaneously in your tool, meaning you can't necessarily send out one-size-fits-all instructions.

But it is possible and something you should strive for. Why?

Just-in-time learning (when a user needs it) is usually more effective than asking a user to learn something proactively (like in an onboarding checklist). It’s easier, less intrusive, and provides a smoother experience for the user.

Plus, contextual help can be embedded (like a tooltip) and still be specific to the user (e.g., the copy in the tooltip is personalized.) It's not an either-or these days.

Why is this need so dire in B2B SaaS?

Why do you need contextual help in your product?

B2B SaaS products tend to be more complex and thus have a larger learning curve than most B2C products. That's because their use cases are inherently more complicated. Using Salesforce is harder than using Duolingo. Using Trello or Notion is harder than using your iPhone's to-do list.

Plus, a B2B SaaS product can do one thing, while others can do 100 things. Many B2C products are single-purpose.

The power and versatility of these B2B products can also be a curse if you don't have the right in-application help. That's because there are a billion things your users can run into.

When onboarding, they can get confused, lost, or distracted.

When users navigate your product, they can fail to find what they're looking for because of the UI or because they lack the technical or terminological knowledge you've used to describe a part of it.

Or, they can get easily overwhelmed by all the features available. I remember the first time I interacted with Salesforce as an intern many moons ago. I thought their CRM would be a list of names with some details. While it had that, I was initially overwhelmed by all of the specific user flows, pathways, and knowledge I seemed to need to acquire to become a proficient user successfully. This made it harder to get going on the core task at hand.

All these obstacles and issues are natural and normal; I'm not saying they won't happen or shouldn't happen.

The issue is that without contextual help, they can go unaddressed and negatively impact your user's experience if this continues for a prolonged period. Over time, you'll see more churn and more user frustration. Even worse, if you’re a startup, you're unlikely to gain PMF and early product evangelists if you don't address these issues.

So, how does contextual help work?

Why does contextual help, help?

So why does contextual help perform so well?

What is just-in-time assistance?

Contextual help offers just-in-time assistance. This means that when users are frustrated, facing an issue, or otherwise blocked, you provide them with an immediate solution to their problem. This stands in huge contrast to both proactive and reactive user education.

Sure, you could have been too proactive and given your users a 50-item user onboarding checklist that covers everything your product does, but none of them would finish that, and it would be super clunky.

And yes, you obviously can have support agents and chatbots that assist you with reactive help and would eventually get your users the answers they need.

But those are slower, more time- and resource-intensive, and generally worse for you and your user.

Instead, you can assist your users on the spot with contextual help and cues to continue their actions.

To do this at the highest level, you also need to:

  1. Properly segment your contextual help assets to be personalized for each user.
  2. Aided and proved with more Visual and interactive elements, like a product tour or a nudge.

Why bother with all of this?

It not only improves your user experience and satisfaction but also saves you time and money, as you can help deflect tickets and reduce the workload of your support agents.

The three stages of deploying contextual help in B2B SaaS

Implementing contextual help in your product can be broken down into three stages

  1. Learn
  2. Build
  3. Optimize


You can't offer contextual help if you don't know what help you need to provide. That means you need to have a rigorous feedback collection program that surveys your users and the information you need to make informed decisions. You can combine that with the quantitative user data and product metrics to create a holistic view of your product experience.

You'll want to learn the pain points within your product where you see a lot of fall-offs or negative feedback. Look at the funnel within a specific user flow, such as onboarding or checkout, to understand how that specific set of steps performs.

With this analysis, you're trying to understand what areas of the product are most in need of additional help based on your qualitative and quantitative data


Now that you've identified the areas of your product that most need contextual help, you need to determine the right asset to build.

Now, this isn't a one-size-fits-all question. The right answer will vary depending on your product, user base, approach, and style. What works for a corporate finance tool will likely be very different from a small and Scrappy startup offering tools for creative businesses.

You have a variety of options at your disposal:


Pop-ups get a bad rep, as they should! They've been very intrusive, less helpful, and more harmful for many years. But when you take a user-focused, non-annoying approach, you can use what we call nudges to help users along the journey.

What is a nudge? It’s a subtle yet helpful call-out that helps a user.

That can take the form of a

  • Product feature
  • Modal
  • Tooltip

A product feature highlight and tooltip are best used for smaller and more minor items, like explaining the purpose of a feature in a sentence or offering additional context on a specific product terminology.

A modal or larger nudge might be better for a larger problem that users consistently run into, as it will take up a little bit more space and be more direct in its language

Checklists and product tours

Sometimes, it's better to be more interactive to get users to follow a specific sequence of steps. This is highly suitable for onboarding, checkout, or activating a new feature in which a specific order or hierarchy needs to be followed.

You can easily build these within CommandBar and launch them based on a specific triggering event.

Assess and optimize

Step three in this flow is to optimize your contextual help program. It's not enough to set up some tooltips and nudges and let them run forever. You need to constantly monitor the data you're getting, A/B test different nudges, and ensure that you stay abreast of your users’ product engagement.

You want to measure and monitor the effectiveness of your contextual help cues. Do you see definitive increases in user engagement, fewer users who fall off in a specific flow, fewer support tickets, and higher overall user retention and satisfaction?

Hopefully, the answer is yes!

But you won't always see that on your first try.

One of the most common mistakes we see folks making is thinking that user assistance is a set-and-forget flow. It's not always the case. Yes, it's easy to set up, and if your product is fairly static, there might not be many changes needed.

Imagine that you set up an onboarding checklist, but since you initially set that up, you've got a new type of user persona joining your product. They have different needs and wants, and the items they must address during their onboarding walk-through might differ greatly from your core persona.

That's why you must ensure that you update your product and contextual help as your business evolves.

Pro-tip for better in-app help

To improve your contextual help, you can incorporate smart triggers into your nudges and assistance elements.

For example, a rage-click trigger activates the help when users click frustratedly across the page.

Or, you can use a smart delay. Imagine your user hits a step in an onboarding flow and pauses longer than usual. You can set a smart delay for that time and then have the nudge trigger after that specific number of seconds.

Finally, you might try a walkthrough that activates after a positive response to a nudge! “Hey, need help?” If they answer Yes, you can run the walkthrough automatically!

These help level your contextual help and provide a better UX with little extra effort.


Just-in-time help arrives exactly when a user needs it, and is usually more effective than asking a user to learn something proactively (like in an onboarding checklist).

Contextual help can be embedded (like a tooltip) and still be specific to the user (e.g. the copy in the tooltip is personalized)

When you have timely and personalized contextual help, everyone, from your user to your support team to your growth team, wins.

Frequently Asked Questions about contextual help

1. What is contextual help in B2B SaaS?

  • Contextual help in B2B SaaS refers to providing relevant assistance and support directly within the software environment, tailored to the specific needs and actions of the user at that moment. It enables immediate help based on the context of what the user is doing, aiming to reduce confusion and enhance productivity without pulling them out of their workflow.

2. Why is contextual help important for B2B SaaS platforms?

  • Contextual help is crucial for B2B SaaS platforms because it significantly improves user experience by providing instant guidance. This is especially important in complex software environments where users may struggle with navigation and utilization. Effective contextual help reduces frustration, increases adoption rates, and improves user satisfaction and retention.

3. How can contextual help improve user engagement in SaaS applications?

  • Contextual help improves user engagement by providing immediate assistance right when users need it, which helps maintain their flow and focus. It also offers customized experiences that adapt to user behaviors and preferences, and interactive elements like guided tours or dynamic FAQs keep users actively learning and engaged with the application.

4. What are the cost benefits of implementing contextual help in SaaS?

  • Implementing contextual help can significantly reduce the volume of routine support queries and allow support staff to focus on more complex issues. This optimizes the use of human resources, lowers operational costs, and enhances the efficiency of support services by automating many aspects of user help.

5. What types of content are most effective in contextual help systems for SaaS?

  • Effective contextual help content includes tooltips and pop-overs for quick tips, inline help and modals for detailed guidance within the workflow, and video tutorials and screenshots for visual, step-by-step instructions on complex tasks. Each type serves different needs and helps cater to various user preferences for learning and problem-solving.

6. How to identify user pain points for effective contextual help in B2B SaaS?

  • Identifying user pain points for effective contextual help involves collecting user feedback through surveys and interviews, analyzing data on user behavior and application usage patterns, and conducting beta testing to observe how users interact with new features and identify where they encounter difficulties.

7. What tools and technologies enhance contextual help systems in SaaS?

  • Enhancing contextual help systems in SaaS can involve integrating helpdesk software like Zendesk or Freshdesk for seamless support ticketing, utilizing AI and machine learning for predictive assistance, and incorporating third-party plugins and APIs that broaden the functionality and reach of help systems within the software.

8. Can contextual help reduce overall support costs for B2B SaaS companies?

  • Yes, contextual help can significantly reduce support costs by decreasing the number of routine inquiries that require human intervention and by providing users with tools to resolve issues independently, frees up resources, and allows companies to scale more efficiently.

9. How does contextual help facilitate better onboarding of new users?

  • Contextual help facilitates better onboarding by guiding new users through the initial setup and basic operations of the software through step-by-step instructions, which helps them quickly understand and appreciate the value of the application, encouraging long-term usage and loyalty.

10. What are the best practices for implementing contextual help in B2B SaaS?

  • Best practices for implementing contextual help in B2B SaaS include thoroughly understanding user needs through feedback and analytics, choosing the right types of help content for different scenarios, integrating advanced technologies to enhance delivery and effectiveness, and continuously iterating the help content based on user interactions and feedback to ensure it remains relevant and helpful.
Copy icon
X logo
LinkedIn logo

Zero fluff.

Our stories 🤝 your inbox

Email Icon

Up Next

3 tried and true ways to improve product adoption rate

Never miss another
fabulous article.

Weekly digest in your inbox.

Email Icon
Continue Reading

Up Next

The future of user interfaces: Allison Pickens and James Evans

Read Now

What's hot