Make your Product Onboarding Better by Trying It Yourself

Josh Elman
6 min readSep 21, 2020


What many products feel like without great onboarding — Photo by Patrick Hodskins on Unsplash

Apps are amazing. I use at least 15–20 apps every day to get information, connect with my friends, capture memories, make memories, order food, order everything, and more. I always enjoy learning about and trying out new products. So many times though, I get let down.

Here’s how it usually goes: I am excited. I set aside time to focus on this new app a friend eagerly invited me to or maybe one I found via an article or an ad. I open it. I go through a short little onboarding flow that asks me for my name, email, a TON of permission screens, and an attempt to find my friends by uploading my address book. I usually say no. I get dropped into the main screen of a new product I’ve never used before with some tabs, a settings menu, and a whole lotta information and words I don’t understand. There might be one tooltip or a few on the screen. But, I usually have no idea what to do next. Sometimes I call my friend who shared it with me and ask them what’s the deal? They explain it to me again and I try a little harder. I figure it out and try a few things. Sometimes it catches, but usually it doesn’t. All in all, I end up with hundreds of apps all over my phone that I don’t use again. Thankfully with iOS 14 they are starting to organize those for me and get them out of my way.

But there is a better way!

Onboarding can be the most welcoming part of your product. It can turn people who are curious about your app into your most committed users. It can turn doubters into superfans. Great onboarding is a superpower of your app. Great onboarding is what engages your users. It takes the users on a journey of entering your product and getting to know your product. It helps the users make decisions and set up the product so they can get the most out of it. And for users who decide it’s not for them, they can figure that out as they go along rather than just get confused later and bail.

The moment someone is trying your product is the MOST ATTENTION you ever get from that user. Take advantage of it.

I have learned that longer flows are better than shorter flows. This doesn’t sound right, but trust me, it’s true. Well, it’s true as long as the steps are simple, clear, and progressively build on each other to tell a story. Each step in a flow should be a very simple question to help the user set up the product. In each question and answer, the user should get one step further in their understanding of the product and its capabilities too.

How you measure onboarding can significantly change your approach. Too many people measure the success of onboarding of one flow (A) vs another flow (B) simply by how many people complete the flow and get to the “end.” The only true end of onboarding is when a user is habitually using your product. The best way to successfully measure onboarding is to understand how many engaged users each flow creates. You can do this by looking at the % of active users from those who started the flow one day, one week, or one month later. You may be surprised that an onboarding flow with a better “flow completion” rate may significantly underperform one that has fewer people complete the flow. Because in the latter case, the users who do successfully complete the flow are much more prepared to use the product and are more motivated and excited to use it as well.

My favorite Onboarding Exercise

The best way to make your onboarding better is to try it. Try it often. Every few weeks at minimum. Think of yourself as one of your user personas, or a dumb user rather than you, the expert who knows your product very well. Question every step. Act confused. Think about how nervous someone is about doing something wrong with your product. Think about how nervous someone is about giving all of their information to a product they have never used before. You can take all of these feelings and make it so much better.

Here is an exercise I like to run to improve an onboarding flow:


This exercise takes three people from your team. One person plays the “novice user” who is about to onboard to your product. One person plays the “coach.” One person is the “note taker.”


  1. Come up with a story for the novice user for how they discovered the app — eg from a friend, an ad, etc., and what they have heard about the app — usually just a little description or blurb. (You can run this with true novice users who aren’t familiar with your product. But I would run the exercise a few times internally before you do that.)
  2. Make sure the person playing novice user is willing to forget everything else they know about.
  3. Make sure the coach and note taker can see the novice user’s screen, and can hear the novice user. This can be done in person or over video.
  4. The note taker should be in a good, comfortable position to take notes.


The novice user talks out loud as they go through the onboarding. They call out anything that makes them nervous. They ask about anything confusing. They share anything that pops into their head through the process. If they get bored, or feel disinterested or turned off, they share that too. We all have stories in our head when we use software, and the novice user narrates this the best they can.

The coach can jump in at any time. If the novice user is nervous, the coach jumps in to calm their fears. If the novice user is confused, the coach explains. If the novice seems unmotivated to go on or stuck, the coach provides encouragement. The goal of the coach is to get the novice user through the flow and excited to keep using the product over and over.

The note taker captures what’s being said, where the novice user raises questions, and what the coach provides. They specifically capture, in exact words, what the coach says that effectively smooths things over. Words matter. It’s critical to use words that make sense to your customer not just to your product team.


Once you have run a number of these sessions, you should see a few patterns. You should know what parts a novice user is mostly likely to get stuck on. You should have a sense of what things a coach says that would be most likely to make the novice user more comfortable. You should know where extra motivation is required. You should know what words make sense and which sound like jargon.

Go back to your designs and change these sections. Add steps if it will create more clarity and better educate the user. Tweak the order if you found the coach always explaining something that would happen later in the process earlier. Or if the coach said “you don’t need to worry about this right now”, move that later in the flow or take it out. Add descriptive language that the coach often had to provide verbally. Add confirmations and success messages that the coach had to add like “yes, everything was done correctly!” People love to receive affirmations through a process.

Then run this again!

Pressure Test:

Once you have built an onboarding flow that you think will make customers comfortable, well set up, and motivated to use your product, now you should really go back out and test this.

Find a bunch of users who have never used your product and ask them to try it out. Don’t give them more than a sentence or two of what your product does. If your product is already known in the world, then don’t tell them anything.

The most important question to ask these users after completing your new onboarding is:

“What do you think the product does?”

If their description after going through your onboarding is pretty accurate, then it means you are onboarding them well. If they didn’t run into many obstacles or nervous moments, it means you’ve learned from running through it.



Josh Elman

I love building products that people use. I‘ve helped build Twitter, Facebook Connect, LinkedIn, Robinhood. Investor in Medium, Tiktok/, Discord