Growth & Retention 12 guests | 53 insights

User Onboarding and Activation

Bridge the gap between initial signup and realized value to maximize long-term retention.

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The Guide

5 key steps synthesized from 12 experts.

1

Define and validate your activation metric

Analyze historical behavior data to identify the specific actions and frequency that correlate most strongly with long-term retention. Aim for a milestone that has a high correlation with success but a low enough achievement rate (around 5 to 15 percent) to be a meaningful filter for high-value users.

Featured guest perspectives
"Two, you want to understand you usage behavior of those free users, which features do they use and which features kind of correlates with a higher conversion rate, retention rate, all of that. If you don't have a foundation of data and understanding of how to analyze those data, you are giving a way of free product for nothing."
— Hila Qu
"An activation rate that falls in a lower percentage range, maybe for most companies five to 15%, is better than one that falls in a higher percentage range because it means that there's likely much higher correlation with long-term retention and you're really working hard to get most of your users to reach a state that they're not reaching today."
— Lauryn Isford
"As a bonus, the Compass report in Amplitude also shows the impact of the frequency of activity on retention. For example, it helped us determine if logging food once in 7 days (versus, say, five times) is sufficient to detect improvement (it is)."
— Lenny Rachitsky
2

Audit the funnel for immediate time-to-value

Review the signup flow to remove any unnecessary steps, distracting calls to action, or human-mediated gates like required sales demos. Ensure the brand promise made on the marketing site is immediately fulfilled the moment the user enters the product.

Featured guest perspectives
"Onboarding is the only part of your product experience that a hundred percent of people are ever going to touch. Good luck getting a hundred percent feature adoption of anything else in your product, right? But onboarding is the thing that you have to go through in order to use the product. It's also the first opportunity that you have as a company to deliver on the promise that you made out in the marketplace."
— Adam Fishman
"A lot of the companies, if you go to their website, especially B2B companies, you'll see the biggest CTA is called book demo. They don't have anything else. The first step for you to do is submit a form and kind of basically explain yourself to this company, I'm from who and who company and I want to use the tool, can you come back to me and allow me to see a demo of your product? That means the entry point to PLG is cut off."
— Hila Qu
"Increasing activation rate is one of the highest-leverage growth levers across most products, and it’s often the single best way to increase your retention."
— Lenny Rachitsky
3

Implement diagnostic friction and personalization

Add benefit-oriented questions during onboarding to help the user feel the product is being customized for their specific use case. Use these inputs to provide sample content, templates, or personalized defaults that give the user a warm start instead of a blank screen.

Featured guest perspectives
"And the common thinking is, and most often correct, that if you reduce friction to the signup flow, your conversion will increase. This is kind of the law that we all live by. And yet, there is one example, one time, where this is just not true, that you can actually increase friction and increase conversion."
— Kristen Berman
"You also need to think about how to provide value to your users quickly. Give users a warm start and helping them get started with your product as soon as possible. This could mean offering sample content or tutorials to help users get started."
— Lenny Rachitsky
4

Teach the mental model through the first core action

Design the first-run experience to guide users toward performing one high-value action that demonstrates the product's utility. Front-load critical commitments and feature opt-ins when user motivation is highest to establish the correct mental model of the product on day one.

Featured guest perspectives
"We worked with one medical on how to increase setting doctor's appointments right away during the onboarding, and that worked and drove it up by 20%."
— Kristen Berman
"Part of it is how do you measure the success of your NUX, of the activation? To me, it is are you taking those new users and helping them understand the mental model of your product well enough that they start completing the core action."
— Sarah Tavel
"Day 1 is the day your users have the most momentum they will ever have. Catching them at this moment with the right features and mental model will drive higher opt-in rates and engagement than at any other time in the user’s lifecycle."
— Lenny Rachitsky
5

Apply behavioral nudges to bridge the intent gap

Use techniques like forced choice to make declining features feel definitive and leverage the goal gradient effect by showing progress toward completion. Introduce existing high-value features contextually at the moment they are needed rather than overwhelming users with a massive tour at the start.

Featured guest perspectives
"To do this, it needs access to a user’s bank account—but this bank-linkage step creates friction. It’s a common drop-off moment for users: 92.9% give up during the process. We went through the behavioral design process with the goal of boosting the number of users who linked their bank account."
— Lenny Rachitsky

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Guest Perspectives

Deep dive into what 11 podcast guests shared about user onboarding and activation.

Adam Fishman 1 quote
Listen to episode →
"Onboarding is the only part of your product experience that a hundred percent of people are ever going to touch. Good luck getting a hundred percent feature adoption of anything else in your product, right? But onboarding is the thing that you have to go through in order to use the product. It's also the first opportunity that you have as a company to deliver on the promise that you made out in the marketplace."
Tactical:
  • Prioritize onboarding optimization since it is the only feature every user will interact with.
  • Ensure your brand promise and the actual product experience are perfectly aligned to prevent user disappointment.
  • Use the onboarding flow as the primary opportunity to deliver on the expectations set during the acquisition phase.
View all skills from Adam Fishman →
Anuj Rathi 1 quote
Listen to episode →
"So there's very interesting insight that I heard from Scott Belsky from Adobe, and then now, he's doing very interesting stuff, and that stayed with me which was you have to think about users on modern internet consumers having three attributes. So they are lazy, they are vain, and they're selfish."
Tactical:
  • Optimize for 'lazy' users by delivering a 'wow' moment immediately to capture their limited attention.
  • Address 'vanity' by proving your product is superior enough to justify the effort of breaking an existing habit.
  • Appeal to 'selfishness' by clearly showing the user exactly what is in it for them within seconds of landing.
View all skills from Anuj Rathi →
Gia Laudi 1 quote
Listen to episode →
"The conversion on the website went up with this new messaging by 89%. But the thing that I love the most about that particular story is that we didn't even touch anything after the signup experience. We hadn't even gotten there and the trial-to-paid conversion rate increased 40%, and we didn't touch it. It was just because a more qualified, better fit customer was coming through the door."
Tactical:
  • Shorten trial lengths to better match the customer's actual timeline for reaching a value milestone.
  • Audit your 'no man's land'—the messy middle of onboarding that neither marketing nor product clearly owns.
  • Proactively drive users toward the specific parts of the product they care about most via email and in-app messaging.
View all skills from Gia Laudi →
Hila Qu 2 quotes
Listen to episode →
"A lot of the companies, if you go to their website, especially B2B companies, you'll see the biggest CTA is called book demo. They don't have anything else. The first step for you to do is submit a form and kind of basically explain yourself to this company, I'm from who and who company and I want to use the tool, can you come back to me and allow me to see a demo of your product? That means the entry point to PLG is cut off."
Tactical:
  • Review your primary website CTAs to see if you are forcing users into a sales funnel before they can experience the product.
  • Build a dedicated 'free experience' or trial that functions independently of your sales-led pipeline.
  • Identify the specific steps a user must take to get to a 'demo' and replace them with direct product access.
"Two, you want to understand you usage behavior of those free users, which features do they use and which features kind of correlates with a higher conversion rate, retention rate, all of that. If you don't have a foundation of data and understanding of how to analyze those data, you are giving a way of free product for nothing."
Tactical:
  • Use behavior data to determine which specific features are most frequently used by your long-term, high-value customers.
  • Define activation as the point where a user has performed the specific actions that correlate with a high propensity to pay.
  • Establish a data baseline for free user behavior before attempting to optimize the activation flow.
View all skills from Hila Qu →
Kristen Berman 2 quotes
Listen to episode →
"And the common thinking is, and most often correct, that if you reduce friction to the signup flow, your conversion will increase. This is kind of the law that we all live by. And yet, there is one example, one time, where this is just not true, that you can actually increase friction and increase conversion."
Tactical:
  • Ask questions during the signup flow that get users thinking about the core benefits of the product.
  • Use questions to insert positive ideas or mental models into the user's mind at high-motivation moments.
  • Experiment with adding steps to the flow if they clarify the value proposition and increase the user's drive to finish.
"We worked with one medical on how to increase setting doctor's appointments right away during the onboarding, and that worked and drove it up by 20%."
Tactical:
  • Identify the core action most closely linked to long-term user retention.
  • Structure the onboarding flow to prompt that specific action as soon as the user signs up.
  • Remove competing choices and distractions that delay the user's first successful interaction with the product.
View all skills from Kristen Berman →
Lauryn Isford 2 quotes
Listen to episode →
"So, what you've probably experienced if you signed up for Airtable recently or what you might experience if you create a new account soon is we've built an immersive wizard that we called Guided Onboarding that helped guide you through setting up your first workflow on Airtable, and in doing that reduced the cognitive load of getting started, helped you make more progress faster, and created scaffolding that more than 90% of customers would benefit from to be able to get up and running on a product that's pretty complicated."
Tactical:
  • Build an immersive wizard to guide users through their first workflow.
  • Personalize the onboarding experience to align with the user's specific use case.
  • Implement ongoing education patterns like 'Mole' tips to transition users from beginners to power users.
"An activation rate that falls in a lower percentage range, maybe for most companies five to 15%, is better than one that falls in a higher percentage range because it means that there's likely much higher correlation with long-term retention and you're really working hard to get most of your users to reach a state that they're not reaching today."
Tactical:
  • Identify an activation metric that has a high correlation with long-term retention.
  • Set the bar for activation high enough that only 5-15% of users currently achieve it.
  • Operationalize the metric to focus the team on moving users to meaningful high-value states.
View all skills from Lauryn Isford →
Nikita Bier 1 quote
Listen to episode →
"Mobile apps have such a low margin for error when it comes to designing them. Because I have this dogmatic view that every tap on a mobile app is a miracle for you as a product developer because users will turn and bounce to their next app very quickly."
Tactical:
  • Minimize the number of taps required to reach the product's 'aha' moment.
  • Observe users physically using their phones to see how quickly they bounce between apps.
  • Optimize every pixel and flow to respect the high frequency of user context-switching.
View all skills from Nikita Bier →
Sarah Tavel 1 quote
Listen to episode →
"Part of it is how do you measure the success of your NUX, of the activation? To me, it is are you taking those new users and helping them understand the mental model of your product well enough that they start completing the core action."
Tactical:
  • Design your onboarding to teach the mental model and utility of the product immediately.
  • Measure the success of activation by whether users begin completing the core action.
  • Ensure every element of the new user experience leads directly to the product's primary action.
View all skills from Sarah Tavel →
Scott Belsky 1 quote
Listen to episode →
"In the first 30 seconds of using a new product, you are lazy, vain, and selfish. You want to get it done super quickly. You want to look good to your colleagues or to your friends. You don't want to have to watch a tour or read anything, really endure any learning curve whatsoever."
Tactical:
  • Help users feel successful within the first 30 seconds of engagement by appealing to their laziness and vanity.
  • Optimize onboarding flows, orientation, and default settings to minimize any learning curve.
  • Reimagine the onboarding experience for later-stage pragmatic customers who are less forgiving of friction than early adopters.
View all skills from Scott Belsky →
Upasna Gautam 1 quote
Listen to episode →
"So when we're thinking about onboarding especially the teams, our onboarding cycle's very long. It involves training, testing, lots of dialogue and feedback. And then only do we actually test, and then we onboard. And so it is a long cycle, and it's longer than it maybe seems like it needs to be because we have to build in those buffers."
Tactical:
  • Build in significant time buffers for training to account for stakeholders' primary work responsibilities.
  • Run multiple deep-dive sessions to recreate specific user workflows in the new platform.
  • Use smart repetition across different forums to help users transition away from legacy tools.
View all skills from Upasna Gautam →
Yuriy Timen 1 quote
"Well, based on our data, about a third of people will consider switching to another company after just one bad experience during onboarding. So if your CSV importer doesn't work right, which is super common, considering customer files are chalk full of unexpected data and formatting they'll leave."
Tactical:
  • Fix high-friction technical steps in onboarding, like broken data importers, to prevent early drop-off.
  • Guide users based on their specific intent rather than exposing them to the product's full complexity immediately.
  • Prioritize onboarding improvements as they simultaneously drive higher activation, conversion, and long-term retention.
View all skills from Yuriy Timen →