Customer Success

3 Mistakes To Avoid When Onboarding Customers (And What To Do About It)

August 22, 2019

Do you suffer from “revolving door” syndrome? You may feel like your product has a revolving door attached to it—free trial users leave as quickly as they came. Yet here you are investing time, manpower and resources into attracting more leads, only to have them move through an onboarding funnel wrought with more holes than a hockey net.

If you’re running a SaaS company, you’re probably among the thousands of companies who are only onboarding about 25% of their free trial users (if you’re lucky). It’s not uncommon for conversions to drop way below this.

Why are your conversions so low?

This topic is quite extensive and while there could be many reasons for your sub-par conversions, one commonality exists among SaaS companies who struggle with paltry conversions.

And, that is poor onboarding.

What does an ideal, high-converting onboarding process look like? A good onboarding experience exceeds your customers’ expectations, gets high marks for engagement, and streamlines the activation process, leading to increased retention.

A poor onboarding experience? Well, you don’t have to be a rocket scientist to know that it leads to early churn.

But the good news is that by avoiding some mistakes and implementing a few retention tactics, you can streamline your onboarding process and increase conversions.

If you want to create an epic onboarding process, here are three mistakes to avoid.

Mistake #1: Snoozing on the “Aha Moment” (wow em’ ASAP)

Your marketing is stellar and your lead generation skills are on point. You are attracting new users with your marketing copy, promising them incredible benefits when they sign on. Congrats, you’ve got users excited.

But, then this happens…

Users log into your app for the first time and within five minutes, the once dopamine-induced excitement downgrades to semi-hopeful with a twist of “What have I gotten myself into? I thought this was going to be easier.”

If you remember anything from this article, let it be this. When users sign on to try your app, they are focused on ONE thing — experiencing the result you promised them (as quickly as possible).

So what you have to figure out is, “What’s the easiest path to get users back to that dopamine-induced ‘aha’ moment they felt when they first joined? What will keep them excited (or make them excited) about using my software enough so they stay on?”

Before you can answer these questions, you have to first figure out what your users’ aha moments actually are. Ask yourself these questions:

  1. Why did users sign up to use my platform?
  2. What problems are they trying to solve?
  3. What is the ultimate goal users want to achieve when using my platform?

For example, an “aha moment” for a non-artistic, non-technical user of your graphic creation software may be when they create a professional-looking graphic. If you run landing page software, maybe it’s when they set up an actual landing page or upload one to the web. The moral of the story? Get users to their first WIN asap.

Canva enables users to experience a quick win by asking them a question right on the dashboard, “What would you like to design?”

Canva knows that if it can get users to create a professional graphic right away (their “aha moment”), the chances of them becoming a paid customer increases.

Too much, too fast (don’t overwhelm)

It’s not uncommon for companies to ask too much of new free trial users. They think that users will want to know about every feature immediately. But, what this is really doing is overwhelming users and deterring them from using the platform because they focus on the work first, instead of the benefits they will receive. Remember that we are trying to get users to get that aha moment and nail a win as quickly as possible. Don’t make them go through a 20-page instruction manual or complete 15 steps to get there.

Here’s a rule of thumb to test:

Productivity CRM Copper does this nicely by assigning users four quick tasks to complete immediately.

The app also sends emails reminding the user about the tasks:

Keep your instructions and task creation SUPER easy in the beginning (we talk more about this in mistake #3 below). Pretend your users don’t know a thing about your platform. Newsflash: they don’t.

How to discover your users’ “aha moments”

So you know you need to figure out your users’ aha moments. Besides answering some of the questions we already discussed, how do you know exactly what these moments are? Well, you can brainstorm and guess all you want but you will never really know what these moments are unless you ask your customers. Your assumptions are nothing more than guesses (or even worse, hunches).

Gather user feedback

To discover your users’ “aha moments,” have real conversations with your customers. One conversation can provide enough data to substantially improve your conversion rates. Drip had 10 conversations with their onboarded customers, which helped them double their trial-to-paid conversion rate.

When conducting conversations, talk to your newer customers, those who have been onboarded in the last 45-60 days. Older customers won’t remember the details of their initial experience so the data may not be reliable.

Ask these newer customers what their first “aha moment” was. What made them want to sign on and become a regular user?

Have real conversations. Get on the phone and do a LOT of listening. This isn’t a quick question-and-answer exchange. Your goal is to figure out what those “aha” moments are and that requires a little digging and a lot of listening.

Turn those “aha moments” into high-converting behaviors

So your users get an “aha moment” and they feel that you can help them solve their problems—now what? Unless this is attached to an action that becomes a behavior, you still may lose them.

You need to show new users that this new way of doing things is much better than the more difficult way they were doing things before—and it’s worth paying you for it.

One way to help users adopt these new behaviors (and leave their old, more difficult way of doing things behind) is by looking at the BJ Fogg Behavior Model.

Founder of the Behavior Design Lab at Stanford University, Fogg espouses that motivation, ability and prompts (previously known as triggers) must all converge in order for a behavior to materialize.


To get users to experience your target behavior (sign on as a paid customer), they must have:

      • Motivation. Experiencing an “aha moment” gives users the motivation to continue. At this stage, they are simply assessing if your app will be a good fit
      • Ability. Is it easy or difficult to use your product? See mistake #3 below
      • Prompts. What can you provide to users to trigger this behavior?

One way to facilitate new behaviors is to connect a new user action with a current behavior, something they are already used to doing regularly.

GrooveHQ does this by auto-populating its dashboard with “fake” emails. This helps users connect this new action (using GrooveHQ) with current behaviors or something they already do regularly (opening and replying to emails).

If the dashboard were empty, would users get an “aha moment” and be able to envision themselves adapting to this interface? I think not.

Mistake #2: Dehumanizing the onboarding experience

Your users are humans. Not credit cards, not tech robots, not computer screens.

The second you forget that your users are humans who have psychological needs and desires, is when you lose the ability to deeply connect with their needs.

Onboarding really has little to do with product usage.

As mentioned in the last section, one main focus of a positive onboarding experience is to get users to perceive your product’s value as quickly as possible. That moment when they realize your product will meet their deep need. And this can only happen when you see your users as humans and you desire to make real connections with them.

One of the ways to humanize the onboarding experience is to create videos. Videos make the whole onboarding experience more “real” and allow you to strike a deeper chord with your users. They make the “invisible,” behind-a-glass-screen world of the internet more tangible and easier to connect to.

Here are some ways to incorporate videos into the onboarding process:

Create a welcome video

Welcome videos can forge deeper bonds with new users and solidify your relationship with them and also introduce them to your platform and its features. Wistia’s welcome video gives users a quick rundown of the platform. But, what’s notable is that the brand also evokes an emotional connection from users by showing the Wistia team’s positive reaction to new viewers joining the platform:

The video then engages viewers with a quick and thorough (but fun) overview of how to get the most out of the platform:

Don’t be afraid to get creative and add some engaging factors to your videos. If you can make users smile or feel something, you create invisible bonds that don’t break too easily when it comes time for them to sign on more permanently.

Instructional videos

Instructional videos help users easily engage with your platform and realize how it can benefit them.

The project management platform Asana provides quick and engaging instructional videos for its new users to show them how to get up and running quickly. Asana scrolls the video up from the bottom of the screen when you open each new feature.

Quick tip: Notice how Asana mentions that you can learn how to use Asana in only “60 seconds.” This handles any objections that it will take too long and be too hard to learn the feature. Small copy details like this can make a big difference
Asana’s instructional videos are quick, concise and also include captions.

Personalized recommendations

Another way to humanize the onboarding experience for users is to personalize their experience. Personalization makes users feel “special” instead of another number on your conversions spreadsheet.

The language learning app Duolingo personalizes the user experience by asking about users’ time commitment to learning their desired language and what level of experience they have.

The app then directs users to a custom experience based on their answer (beginners start with actual lessons and experienced users take a test to determine their skill level).

Personalized landing pages

One other way to humanize the onboarding experience is to personalize your landing page based on the user’s role:

The landing page the user would see depends on what role they select (sales, marketing or engineering).

Data Infrastructure company Segment runs user emails through the tool Clearbit to determine what tools they are using on their website.

Based on this data, Segment sends users personalized landing pages that include apps Segment integrates with (based on the apps users already integrate with).

For example, if a company uses Optimizely, Segment’s landing page may look like this:

If you aren’t using a tool like Clearbit, you can still get information from customers (pre-qualify them) to help you customize the onboarding experience, whether emails, landing pages or in-app messaging and design.

Groove’s onboarding experience includes several questions. The data from these answers will help them to provide a personalized experience for users.

Mistake #3: Confusing and overwhelming the user (not recognizing your blind spots)

If there is one thing to remember while onboarding, it’s this. Your users are not inside your head. I repeat, your users are not inside your head.

Your users are not developers. They are not on your team. They have NEVER seen your product before. But, it’s not uncommon for companies to suffer from massive blind spots because they are so used to using their own product. They lose their ability to think and act like a new user.

Confusing instructions and a poor user experience are inevitable byproducts of failing to recognize your blind spots. This also introduces friction into the onboarding process, which hinders users’ desire to continue using your platform.

How do you improve this?

Imagine you are an expert painter and your job is to teach your beginner students how to paint. But wait, they not only don’t know how to paint, they have never even held a paintbrush. How would you proceed? You wouldn’t bombard them with instruction on how to display depth perception and create shadows on a canvas. You show them what types of paintbrushes to buy first and how to hold the brush. The key here is to never assume they know what you know.

Here’s how to teach your software users how to “hold a paintbrush.”

Provide Clear Onboarding Instructions

Onboarding should be simple and straightforward. In fact, the simpler, the better.

Provide tutorials and interactive guides on how to use each feature of your platform, but avoid bombarding users with too much information at once. Offer your instructions in doses and make them visible exactly when users need to see them.

For example, Drip doesn’t overwhelm users with an entire user manual the second they sign on to the platform. The instructions are drip-fed (no pun intended) to users as they access each feature. When users click to use any feature for the first time, they see an interface like this:

Users are greeted with a welcoming message and:

      • A short intro into what the features does
      • A bright, on-brand visual to help them visualize the feature
      • A link to start using the feature right away
      • A link to watch a help video to learn how to use the feature
      • A link to a library of pre-built workflows so users can visualize what a completed one looks like (this is also a nod to getting to the “aha moment” as quickly as possible – see Mistake #1)

Users see instructions on only this ONE feature. They can choose what they want to do first and they have all of the info at their fingertips, without being overwhelmed.

Create a Knowledge Base

Another way to make it easy for users to access information on how to use their products is to create a knowledge base. For best results, create a text manual and video instructions to satisfy all learning styles.

Squarespace offers a detailed user manual, organized by categories for easy navigation. It also offers “First Steps” and FAQs” to satisfy new users and help answer their questions.

Squarespace also provides an extensive video knowledge base of 133 videos that walk users through every platform feature and how to use it. The videos are quick and concise and they give users a visual walkthrough of each feature so they can jump right in and use the software easily.

Accessing support should be very easy

Make it easy to get support inside the platform. Remove the friction.

Below is an interface from Drip’s new user onboarding sequence. Notice the support button on the lower right-hand side. Drip adds this button to every page of the onboarding experience, including the platform dashboard.

Another way to make support easily accessible is to mention it in your emails. Let your new users know how to get answers to their questions. In its welcome email, Groove gives users an easy way to get help. All they have to do if they have a question is reply to the email. No links, no forms, no hassle.

Improved onboarding leads to higher conversions

How would a 5-10% conversion rate improvement impact your monthly and annual recurring revenue? If you are making any of these mistakes above, some simple tweaks could tip the revenue scales in your favor. Here’s a quick rundown again of how to fix your mistakes so you can improve your customer onboarding experience and increase conversions:

      • Provide users with an “aha” moment as quickly as possible
      • Humanize the onboarding experience and facilitate emotional connection
      • Keep the experience simple and straightforward and don’t overwhelm the user

While these aren’t the only fixes you can implement to increase conversions, it’s a good place to start.