Sales & Marketing | 5 min read

Turning amateur users into experts

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The question of what it takes to become an expert has occupied psychologists for decades.

As user onboarding and customer success have become more important, it’s pre-occupied businesses too.

So how do you get users to master your product? Most businesses try in one of the following ways.

  1. You can drag them kicking and screaming towards the finish line. Sure, you can successfully push people to do something in the short term, but the minute you stop, they stop.
  2. You can patiently hold their hand, and spoonfeed them the answers. Again, this works well in the short term, but because users are relying so much on autopilot, it’s hard to get anyone past the “OK plateau”.
  3. Or you can give people the tools they need to teach themselves, coupled with gentle prompts towards success.

While options 1 and 2 might work for you in the short term, they still rely heavily on one-to-one interaction. Unless you plan on building a business around white-glove onboarding, you’re going to need to help customers become experts by themselves. (Self-service customer support tools like Intercom Educate will help with that) That means giving them the tools to succeed, with graduated hints and gentle prompts along the way. Here’s a few ways you can do that.

For every hunter, there will be a grazer

For every passionate user who will do everything they can to upskill on your product, you’re going to have to try teach those who are little more reluctant. In educational theory they’re referred to as “grazers”. Unlike the hunter, they rely on being “fed” information to upskill them on a specific topic. Your product, for instance.

That’s where lifecycle emails come in. The trick is to craft your messages around key moments in the user’s lifecycle (when somebody first signs up, when they use a feature for the first time, etc) and tailor each email accordingly. It’s all about proactively teaching people how to be successful with your product, rather than hoping they stumble upon success themselves.

Just look at this email Buffer sends to new users. Their browser extension makes it easier to share items you’ve found while browsing. New users who fail to install the Buffer browser won’t share as much, and therefore won’t experience the full value of the product. All these little mini-aha moments (learning a shortcut, uncovering a new feature, etc) are what motivates people to stick with something, or helps them retain more deeply what they’ve learned already.

Buffer onboarding email

Experts are created through the quality of the time, not the quantity

The secret to continued improvement isn’t the amount of time invested but the quality of that time. It sounds simple, yet so much of what we know about “expertise” is built around the premise of sheer time investment.

Slack are the masters of improving particular aspects of how you’re using their product, and making sure the time inside the product is well spent. Slack’s mantra is all about reclaiming your work day – less unnecessary messaging, more productivity. In order to manufacture this “quality time”, they built some triggered messages that respond to actions in the product. If I’m not engaging with some channels, they suggest I leave and reduce the noise. When I’m stuck on a problem, they’ll suggest some useful articles from their help center. Rather than wait for people to spend hundreds of hours in the product to know what works and what doesn’t, they subtly teach users the right way to use Slack through the interface.

Slackbot onboarding

Feedback is what turns practice into expertise

There’s a good reason every world-class sports champion has a coach. It’s because they’re able to give meaningful feedback that turns practice into expertise. If you practice but don’t get that feedback, you’ll never get to the top ranks.

If you work in software, you might not think of yourself as a coach. But you do have the expertise to give users feedback when things aren’t going right. You can spot errors as people are getting up to speed with your product, and remove any stumbling blocks in their way.

creating experts through feedback

If you’re not giving users feedback over time, they’ll get stuck at the amateur threshold or, even worse, drop out entirely.

Let’s take a real example. When I start and abandon a new project in Kickstarter, they check in frequently and coach me towards completing my project – with blog posts, help center links, etc.

kickstarter onboarding email

There are two key benefits:

  1. You show your user how to use your application, most especially the key activation features (in this case, creating a project)
  2. You get to familiarise the user with self-service tools and how-to guides, that will help them upskill over time.

Following a few feedback messages like these, the user will not only know how to use your product, but will feel like a power user.


The goal of any product owner shouldn’t just be to get people to sign up. It should be to take users up the expertise curve as much as possible, as fast as possible. As a user becomes more familiar with a product, they find out new things – and find more value. As they find more value, they become more embedded. As they become more embedded, they’re likely to advocate for your product. By proactively reaching out to customers with helpful self-service resources, you’ll get them unstuck from the immediate problems, and put them on the path towards expertise at the same time.

customer engagement