Podcast 114: Nine common onboarding mistakes that software companies make

Ellis looks at nine common onboarding mistakes that software companies make:

  • Not thinking about jobs to be done, but features
  • Overloading users with information
  • Writing for a single audience
  • Not providing or not co-ordinating the five pillars of onboarding content
  • Getting the timing wrong
  • Unclear goals
  • Leaving “seams” in the onboarding experience
  • Poor quality content
  • No testing or metrics


See also: Planning and creating content for customer onboarding – training course


This is the Cherryleaf Podcast. 

Hello again. 

In this episode, we’re going to look at common onboarding mistakes. 

And this relates to products rather than onboarding of staff. 

But before we get into that, I thought so we could just flag up to anybody that didn’t know that we’ve introduced or added onto the Cherryleaf website some quizzes. And goodness me, they have proved to be really popular, particularly the first one, which is “What type of technical writer are you?”. 

We’ve got one more that relates to API documentation and developer portals, and that is “What is your developer portal’s KPI score?”. 

Which is about assessing how good or bad your developer portal is. 

The third one is “What type of policies and procedures writer are you?” and the fourth one is “What is your policies and procedures KPI score?” 

And if you go to the homepage of the Cherryleaf website,  cherryleaf.com , you’ll find a link to all of those four quizzes. 

We’ve had a great response so far. Some really interesting answers, which we may talk about at a later stage. I don’t want to influence anybody’s answers to the quiz ,so I won’t talk about that now.  

And we might introduce some other quizzes, in addition to the four that we have at the moment. 

There’s a couple of reasons for picking this topic, common onboarding mistakes. 

One is that it is a follow on from the conversations that we had with Toby Chapman-Dawe and with Karissa van Baulen. 

And if you haven’t heard those episodes, then if you go to wherever you found this episode, you should find a link to those. 

Another reason is that we are going through this process of developing a new e-learning course on developing onboarding content for products. 

And we’ve been going through the research, and we’ve written the slides and started to record the videos. 

One of the things that come out of that is some of the common mistakes that organisations have made with their onboarding process.  

Now the onboarding course isn’t complete yet. We’re still going through the process of creating the exercises. 

Hopefully soon, I will be able to tell you more about that course , but if you’re interested if you’ve got any thoughts on onboarding, or if you’d like us to keep you up to date, then you’re more than welcome to email us and that is info at cherryleaf.com. 

Well, let’s start by defining what we mean by onboarding. And I’m going to use a definition from Nielsen Norman. 

“The process of getting users familiar with a new interface, using dedicated flows and UI elements that are not part of the regular app interface. It can involve one or more of the following components:  feature promotion, customization, and instructions.” 

We’ve listed nine common mistakes. They’re not necessarily in any particular order. 

Well, first one we’ve got on the list is thinking about the features rather than thinking about the jobs that the user wants to do, or “jobs to be done”. 

And jobs to be done is actually a theory that’s been around for a few years, of understanding what motivates customers to spend the time, effort, and money in a particular product or service. It was developed by Clayton M. Christensen. 

And he wrote this piece of text: 

“When we buy a product, we essentially ‘hire’ something to get a job done. 

If it does the job well, when we are confronted with the same job, we hire that same product again.  

And if the product does a crummy job, we ‘fire’ it and look around for something else we might hire to solve the problem.” 

It’s the onboarding process sometimes fails to address those thoughts in the user’s mind. 

When they’re using your product, it may fail if we focus on features and not the situation or the motivation, and the desired outcome, the promise, that led the user to sign up in the first place. 

Then your product, your organisation, you may fail in your objective.  

Now we can look at this in a little bit more detail.  

Generally, when somebody decides to pay for a product, start to use it, it’s been said that there are four forces that affect their decision to change to a particular product. 

The need to push and pull, and the decision to act after not act. To give up or not to give up. And this is very much the common thoughts when people also go through the buyer’s journey. 

But it also extends into using a product for the first time.  


  • The push to find a new solution to a problem or pain that you have that you want to solve. 
  • The pull from what could be achieved with a promise that’s being offered, the transformation that’s being offered by using this new product. 
  • There’s the option, there always is, of just living with what you have just doing nothing. The inertia of not wanting to change because change will be too difficult and 
  • Then say anxiety over the risks of moving to a new product. If you did change, what risk or consequences there might be by making that change. 

And when it comes to developing and building content, it must address those thoughts, those questions that are going through the user’s mind. Empathise with those. If you just focus on features,  “you can do this, that and the other”, then there’s a real chance of the onboarding will fail. 

The second common stake is how much information you give the user, and how many choices you provide them. 

And if you’re a Technical Author, or you come from a technical authoring background, you’ve probably heard of John Carroll, “the father of minimalism”. 

He did research back in the 1980s, when he was that IBM, about how people use information when they’re trying to solve problems and troubleshoot. 

He discovered that people just don’t remember the information. They are just focused on trying to solve the problem that they have. 

We can learn from information and learning theories. That’s when it comes to how much information we provide. If we don’t move away from giving more than four five things that somebody has to remember or has to choose between, then it starts to confuse people. It becomes overwhelming for them now. 

It can be that, if the pattern is familiar, then you can extend it little bit further with familiar: with days of the week are familiar, with months of the year, there seven days a week, there are 12 months of the year.  

If you start to ask people to remember more than four or five things, or choose between four or five things, it can be very difficult for them. 

So we may need to phase things in overtime. What’s called progressive disclosure. 

Number 3 in terms of common mistakes. 

It’s writing for a single audience. And often, it’s an onboarding approach or process or system that’s there for single audience and their audiences, primarily people that are starting to use the product for the first time. 

But that won’t be the case. There’s a great book that’s come out called “Better Onboarding” by Krystal Higgins. She works at Google in Australia. 

In the book, she talks about the fact that there’s often more than one type of user for products and who would benefit from onboarding. 

One who isn’t actually paying for the product at the moment. They may be on the free plan. 

And what we want to do is onboard then to become a paying customer. 

And that paying customer may have a different onboarding process or different requirements to those that have started as a trial user, they may have jumped straight in to pay for it straight away, or they may have previously been a trial user, and want to be able to use new extra features by paying for the product. 

And it may also be that there are people who have used the prodcut in the past, but stopped using it and I’ve come back to it.  

So they are familiar with some elements, but they may not be familiar with others. They may not be familiar with what’s changed since the last time that they used the product. 

So for them you may need to be going through the changes in how they use the product, how they experience it to get to the goals that they want. 

Another group might be existing users who have to deal with the situation where the product is being developed overtime and it’s changing. 

And we might want to prepare them to warn them to inform them about any upcoming changes that may affect how they use the product. To familiarise them with new features or capabilities that are being introduced, and connect that to how they use the product, their experience, what they want to achieve. 

And of course, you may have existing users, but you want them to do more.  

You want them to use more features because the more features that they use, the less likely is that they will give up using the product at some point. 

So for these different audiences, segments, we may need to create distinctive, separate segmented onboarding solutions to address their different needs. 

The fourth mistake is about the timing of the information that we provide. And this is linked back to overloading the users with information. 

And identifying which type of audience that you have. 

The impetus may be to deliver onboarding content straight away as soon as the person signs up for the product: registers ,logs in.  

The temptation is that that’s when you should provide the onboarding content. 

But that may not always be the case. 

There has been some research done, but I think it was Andrew Chen, for mobile apps, that discovered actually, the best time to deliver content for mobile apps. In the study that they did was actually after three days, between three days and seven days, from the moment that the person signed up to the application.  

At the start, they want to discover for themselves to explore. 

Once they’ve done that, you can then use onboarding to make them aware of some of the features they may not have been through, that may not have discovered in that initial stage. 

It maybe that we need to break that information down, because to give all of the information that’s available during onboarding in one go, may just overload users. 

With too much information. 

So for example, if you sign up for Gmail, which is offered by Google, when you sign in for the first time, you will see a number of onboarding screens.  A lot about setting up the system, how it looks and feels, the type of adverts you may or may not want to see, and so on. 

When you look in the second time, you see another set of onboarding screens, covering additional information. 

 And so what Google has done is it has split the onboarding process over the different times that you log in. So that you’re getting the information in small chunks that you can manage and process them at that moment in time. 

The fifth mistake that can happen is with the content. 

And I mentioned Krystal Higgins and her book Better Onboarding. 

She talks about the five techniques of onboarding content.  Perhaps a better term would be the five pillars of onboarding content. And these are different types of content or types of information that you can provide in the onboarding process. 

We tweaked the definitions that Krystal Higgins used, but the five pillars are. 

  • Defaults 
  • Inline help 
  • Proactive help 
  • Reactive help 
  • On-demand help 

One of the problems that organisations often make is they provide maybe one or two of those, but not all of them. 

All they provide the wrong pillar at the wrong time. 

Just knowing what to use the right type of guidance at the right time in the right place. 

And within those, depending on with the user recently journey, whether they’re interested, curious or frustrated and stuck, you might need to change the tone between those different pillars, to be empathetic, empathic with the user at that time. 

The information provided through those five different channels, five different pillars., they need to be consistent with each other. In terms of terminology, that seems for example. 

And coordinated, so if somebody goes from one type of information to the other, that’s there is consistency: that they get the information that they need. 

The next mistake is simply having poor content. 


That’s not clear  

That’s incomplete.  

That’s not accurate.  

That’s not credible. 

It’s not connected or cohesive to the product or to the other.  

Information is not concise. 

That’s not consistent.  

That’s not findable. 

Not usable and not useful 

Checking the quality of content. 

Another common mistake is having unclear goals. 

And we had on previous podcast, we interviewed Karissa Van Baulen. And she works the Skilljar. 

I’ll quote from Skilljar: 

“Onboarding content must communicate specific value to your users – in other words, it must be clear why they should care about your product and how it will make their job easier.” 

So we need to have clear goals they want to achieve and be aware of the goals that the user wants to achieve. It’s about being clear in what those goals are. We can work backwards and identify the jobs to be done. 

The key steps that need to happen to enable them to achieve their goal, and for us to achieve our goal. That we can identify the most efficient, the most direct path. 

Related to these unclear goals that would you see it is all about implementation, while it may not be the case. Implementation may not be the first step. It may not be the endpoint. There may be other things that the user may need to do. 

So we need to be clear on what we want to achieve from our onboarding. 

And we’ll talk a little bit later about testing and measuring and how that relates to this. 

But before we do that, let’s talk about, I think it’s at number 8.. 

That is having the onboarding experience or a user experience where, how can we say, that there are “seams”, there are “creases” in the user experience. 

But when they go through all of the key steps of what you might call the user flow or the customer journey, the user journey. 

There are points where it’s tricky to complete the task. It’s not clear. It’s difficult. There’s too many steps. 

And this one goes through the whole onboarding process, which should be making the onboarding process as smooth and seamless as possible. 

To fix any problems that there are in the onboarding process that we have created. But also we should flag up any things where, in fact, it would be better to improve the product, as well as improving the onboarding. 

And this really leads into the last mistake that organisations make. 

And that is not to do any testing and not to have any metrics. 

Because we need to really learn as we go along. Learn whether there is a single path to success or more than one path to success. So test that what we have created works. 

And to identify where there can be areas that we might want to improve, and then check if we make changes, have we made things better? Not made any change at all in progress, or perhaps even made things worse. 

So that testing and measuring can be through usability testing, customer journey, mapping, analytics. 

And it can also be through our setting metrics for measuring what we want to achieve from our onboarding. 

And again, people can just focus on one single metric, measure that might not necessarily be the right one.  

A common one is to focus on revenue. How many people at sign up as a free user become a paying customer? 

But that may not be the best one to use. It might be better to focus on the customer experiencing success on the basis that a successful customer is more likely to become a paying customer. 

So we can set other metrics. 

Some of the metrics that organisations use are things like: 

Time to 1st value.  

The first time that a year they get some value benefit from using a product. 

Time to full value 

So having experienced that, one initial benefit to getting multiple benefits, the full maximum benefit that you can get from their products. How many features capabilities within a product are they using? 

Customer satisfaction.  

How happy are people using the product? How long does it take somebody to get to the end of the onboarding process, to complete the tasks that you want them to complete? Like setting up, configuring, installing the product. Sending out the first email, if it’s an email package, for example. 

So these are the mistakes that we’ve come across so far in onboarding. 

To recap those, again, slightly differently: 

  • We’re not thinking about the jobs to be done, but thinking about features. 
  • Overloading users with information. 
  • Writing for just a single audience. 
  • Not providing or not co-ordinating the five pillars of onboarding content. 
  • Getting the timing wrong. 
  • Having unclear goals. 
  • Leaving “seams” in the onboarding experience or in the user experience. 
  • Having poor content. 
  • Not having metrics in place. 

Through these mistakes, we can see the solutions too. 

That is to: 

Improve the customer journey there, including the journey having the right content. 

Having the right goals  

Breaking down then building the journey into different segments with different audiences, different powers for different situations. 

Identifying what content is needed at the right time and in the right place, and making sure they’re all cohesive and consistent. 

So we hope to be talking more about onboarding as we look at Software as a Service and how those types of products can support their customers, avoid people getting stuck.  

We can talk a little bit more about the onboarding course as it’s coming along, as we make further progress on that.  

But if you’ve got anymore thoughts on onboarding for it, missed out any common mistakes, then let us know. 

It’s info at cherryleaf dot com.  

We have put a page up about the onboarding course on the Cherryleaf website www.cherryleaf.com. 

If you want to talk to us about using your projects team to create onboarding content for your product, then again you can use that email address to contact us. 

We’d be happy to talk to get our team involved. Our writing team involved with creating great content for you.  

But that’s it for the moment. 

We’re probably going to take a break for a little while over the summer as we move into the holiday period. 

But in the meantime. 

Thank you for listening. 


Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.