How to ask and use onboarding questions

1 The bottom line

Ask easy, one-at-a-time questions you will use, then feed the answers into the plan, the paywall, messaging and ad targeting. Answers that end at the survey waste the effort, while answers that shape the offer lifted paid conversion by 10% or more in two tests.

2 Key takeaways

• Make every question easy and ask one thing per screen. Users quit when questions make them stop and think.
  • Removing an open text question improved conversion by 40% Kristen Berman, Irrational Labs12:05.
  • Flo runs a very long onboarding but asks for one thing at a time Steve P. Young, Flo1:30.
• Ask what people want, who they are and what stops them. Each kind of answer feeds a different use later.
  • Headspace let users pick several goals instead of one, and free trial conversion rose 10% Headspace.
  • Four signup dropdowns at Twilio lifted signup conversion about 5%, with no personalization at all Laura Schaffer, Twilio23:00.
• Show users that their answers are being used. People pay for a product that feels built for them.
  • A "we are customizing your experience" screen alone gave a 10% conversion uplift Steve P. Young, App Masters3:36.
  • Apt's switch to a conversational AI quiz lifted onboarding conversion by more than 60% Tomas Hoyos, Apt36:24.
• Carry the answers into the plan, the price and the upsell. Onboarding data pays off when it shapes what the user sees before the paywall.
  • Grammarly's plan recommendations from a questionnaire raised upgrade rates 10 to 20% Grammarly.
  • Duolingo tied its upsell to onboarding questions, and it was one of their biggest wins last year Anmol Tiwari, Duolingo5:26.
• Track each answer against trials and purchases, then reuse the winners in marketing. The same data tells you what to say and whom to target.
  • If people who pick "boost memory" activate and pay more, the creative should change to that message Steve P. Young, RiseGuide2:50.

You can have more screens, you can have more questions, but it needs to be something that the person can keep the pace around

Leon Sasson, Rise

2.1 Write questions that are easy to answer

Pace matters more than length, so make each question quick, multiple choice and clearly worth answering.

• Keep every question light, even in a long flow. Source: Leon Sasson, Rise12:29
  • Avoid questions that make people think hard, and avoid open-ended text Leon Sasson, Rise12:29.
  • Use easy multiple-choice or dropdown questions. They can replace a benefits carousel Kristen Berman, Irrational Labs12:05.
  • Trunk Club reported a 133% conversion lift from a quiz step. On a device site, 53% of quiz completers bought versus 37% of non-completers Kristen Berman, Irrational Labs12:05.
  • Headway's long, interactive onboarding beat Calm's social-proof-only flow in an A/B test Steve P. Young, App Masters2:29.
• Ask one question per screen. Source: Steve P. Young, Flo1:30
  • Flo asks name, pregnancy status and last period on separate screens instead of overloading users Steve P. Young, Flo1:30.
  • Natal keeps onboarding at roughly 10 to 15 questions. Too many make people quit and too few leave them confused Nancy Anderson, Natal46:40.
• Explain the problem and the solution before the first question. Source: Daniel Heintzman, Sway AI23:35
  • Show short videos on the problem and how the app solves it, then ask Daniel Heintzman, Sway AI23:35.
  • Sway's users had emailed asking what they were even subscribing for, because the questions had no context.
• Ask easy questions before you ask for an account. Source: App Masters8:36
  • Start with easy yeses, such as whether the user is just starting or already selling. Each one builds momentum App Masters8:36.
  • Shopify asks everything before account creation, and it usually pays to collect more signup information than most teams think Archie Abrams, Shopify23:55.

2.2 Pick questions you will use

Choose each question for a job: goals, identity, objections, source or commitment.

• Ask why users are here, and let them pick more than one answer. Source: Headspace
  • Headspace replaced a single reason with a multi-select, so users could pick anxiety relief and mindfulness together Headspace.
  • Calm asks what brings you to Calm, with options like better sleep, improve performance or develop gratitude Steve P. Young, Calm2:46.
  • Even if you do nothing with the goal answers yet, users feel the experience is personalized, so store them Steve P. Young, Gamezop3:21.
  • Offer both stress and low-energy wording. Over half of women, perhaps 70%, say they are low on energy, tired and drained Asia Paloni, Welltory29:16.
• Ask what is hardest or what is stopping them. Source: Steve P. Young, Cal AI5:16
  • The answers are the objections your marketing has to overcome Steve P. Young, Cal AI5:16.
  • Routinery asks "What's most difficult?", plus a nickname instead of a real name, an age range and the time of the user's morning TP Young, Routinery2:18.
  • Quiz questions like "Do you think it's too hard to learn AI?" separate likely buyers from likely non-buyers CP Young, Coursiv6:03.
• Ask how much time they will commit each day. Source: CP Young, Coursiv7:47
  • People who commit to a goal are more likely to stay, and a higher commitment predicts retention CP Young, Coursiv7:47.
  • RiseGuide sets the first lesson to the 15 minutes the user chose, and cites Duolingo for the retention effect Steve P. Young, RiseGuide5:56.
• Ask where they heard about you, and read it as direction, not exact attribution. Source: Steve P. Young, RiseGuide1:49
  • A self-reported source works without the Meta SDK or an MMP, and catches App Store installs that paid social lifted Steve P. Young, RiseGuide1:49.
  • List App Store as an option if you rely on ASO, or you cannot see what it contributes Steve P. Young, Cal AI4:20.
  • After viral posts, a channel can climb from about 4% to 10% of responses in a week Albert Cheng, Chess.com27:30.
  • Adding "on TV" and "from a lawyer" options raised ARPU 30% for one client with an older audience Steve P. Young, App Masters4:07.
• Collect only data you will use for segmentation or personalization. Source: Elena Verna1:10:40
  • For a work product, four questions cover it: company size, department, seniority and use case Elena Verna1:10:40.
  • People who drop off at a profiling question were low intent anyway and were never going to activate.

2.3 Show users their answers at work

Reflect the answers back, so users believe the product understands them.

• Add a "customizing your plan" moment before the paywall. Source: Steve P. Young, App Masters3:36
  • The screen alone gave a 10% conversion uplift, even if it does nothing else Steve P. Young, App Masters3:36.
  • Breathwrk asks goals and preferred time of day, then shows a "customizing your plan" screen before the paywall Steve P. Young, Breathwrk3:25.
• React to each answer with reassurance or social proof. Source: Steve P. Young, Flo2:35
  • Flo shows a short prompt after every option, saying how the app helps or that the user is not alone Steve P. Young, Flo2:35.
  • Twilio's questions told new users they were in the right place and that their language was supported Laura Schaffer, Twilio23:00.
• Give identity answers a label. Source: Brent Zajaczkowski, Noom12:36
  • Noom's questions surface thoughts like clean plate club guilt. A label lets people start to challenge the pattern Brent Zajaczkowski, Noom12:36.
  • Headway asks about work life balance and self doubt. These do not personalize the product, but they show support Igor Lyubimov, Headway15:31.
• Use the answers to cut choices and point to a first step. Source: Nancy Anderson, Natal46:40
  • Natal asks if the user is trying to conceive, pregnant or postpartum, and shows only that phase's content Nancy Anderson, Natal46:40.
  • That cuts about 50 programs to about 15 per user.
  • Natal built five to seven rehab programs but did not route users to one. Decision fatigue followed and users did not activate. Nancy called it the biggest fail of the year Nancy Anderson, Natal1:00:59.
• Explain why the result fits this user. Source: Simon Mizzi, Preply18:38
  • Preply plays back what it knows about the learner and says why a tutor fits Simon Mizzi, Preply18:38.
  • Simon names this among the best wins in the matching funnel.

2.4 Feed answers into the plan, paywall and price

Let the answers decide what the user is offered, not only what they see first.

• Recommend a plan from the answers, and carry the answers onto the pricing page. Source: Grammarly
  • Grammarly asked a short set of questions and suggested the plan that fits Grammarly.
  • The pricing page was updated to reflect the stated needs, so the survey connects to the upgrade decision Grammarly.
  • The test raised upgrade rates 10 to 20%. Use that as your benchmark.
  • Fastic's paywall displayed the weight the user had entered Steve P. Young, Fastic5:38.
• Change the paywall type or price by answer. Source: Steve Young, App Masters40:10
  • Use questions like professional versus personal use to pick a soft or hard paywall and a higher or lower price Steve Young, App Masters40:10.
  • In Flo's sick-days example, users with a headache right now are more likely to pay, so they get a hard paywall Steve P. Young, Sick Days24:40.
  • Showing Canva professionals a higher price than personal users is the example given. Few apps do this yet.
• Tie the upsell to the onboarding questions. Source: Anmol Tiwari, Duolingo5:26
  • Duolingo asked whether users want to learn with or without ads, or faster versus at their own pace, and framed the offer as part of that choice Anmol Tiwari, Duolingo5:26.
  • A generic Super upsell dropped into onboarding worked worse than the contextual one.
• Use an LLM to turn answers into a personal first session. Source: Rik Haandrikman, RevenueCat42:59
  • Health and fitness apps pass goal answers to an LLM that configures the first workouts or matches a trainer. That cuts time to value from hours to seconds Rik Haandrikman, RevenueCat42:59.
  • Runna and Ladder keep adapting plans from ongoing behavior Phil Carter, Elemental Growth13:53.

2.5 Feed answers into messaging and ad targeting

Track which answers lead to purchases, then say that back in your ads, copy and targeting.

• Record every answer and compare it with trial starts and conversion. Source: CP Young, Coursiv6:03
  • Find the answers with the highest trial activation and conversion, then tailor your audience and targeting to them CP Young, Coursiv6:03.
  • Track combinations too, such as people who sometimes procrastinate and sometimes lose focus Steve P. Young, Productive3:40.
  • One example: 35 to 44 year old males who like non-fiction convert best, so target that segment on Meta Steve P. Young, App Masters2:29.
• Write ads and screenshots in the words users gave you. Source: Steve P. Young, Cal AI5:16
  • Turn objections into ad copy, such as "Does lack of consistency make you stop tracking calories?" Steve P. Young, Cal AI5:16.
  • Reuse the most common goals in screenshots and copy Steve P. Young, Calm2:46.
  • If "boost memory" pickers pay more, shift the creative to that message. Knowing if most users are beginners or advanced also shapes who you target Steve P. Young, RiseGuide2:50.
• Use the same answers for lifecycle messaging and lookalike audiences. Source: Amol Avasare, Anthropic23:38
  • Knowing who the user is improves activation and lifecycle messaging Amol Avasare, Anthropic23:38.
  • Sophisticated teams also use it for lookalike targeting, to re-reach people who dropped off at the ad layer.
• Use quiz data to decide what to build next. Source: Greg Stewart, Ladder27:04
  • Millions of quiz responses show training styles, goals and equipment, and where the coach roster has holes Greg Stewart, Ladder27:04.
  • Ladder launched only three coaches last year and still grew the business more than 2.5x.

2.6 Where they disagree

Some tactics only fit certain products, and some advice conflicts.

• Real personalization versus the feeling of it. Sources differ on whether answers must change anything.
  • Gamezop says users feel personalized even if you do nothing with the answers Steve P. Young, Gamezop3:21.
  • Phil Carter argues for a one-of-one experience built from the answers Phil Carter, Elemental Growth13:53.
  • Noom avoids hardcoding users into three types, because users want to feel it is built for their own struggles Brent Zajaczkowski, Noom16:27.
  • Airtable suggests shipping one generic flow first, since it served more than 90% of needs, then personalizing Lauryn Isford, Airtable21:43.
• Chat quiz versus multiple choice. The strongest number comes from one product, and the rest is hearsay.
  • Apt saw a 60% lift from a conversational quiz, but free-form text loses clean segments, so it needs LLM analysis afterward Tomas Hoyos, Apt37:58.
  • Other founders and clients say chat flows perform better, with no figures. It is hard to build, though AI may make it easier Steve P. Young, Flow9:48.
• How much friction is too much. Length suits some products more than others.
  • Long flows suit health and fitness, as seen with Noom Steve P. Young, Flo1:30.
  • "Good friction is good" and can even raise conversion, but test it on your own flows Amol Avasare, Anthropic20:39.
  • Natal keeps tuning, since too many questions make people quit and too few confuse them Nancy Anderson, Natal46:40.
• When to ask where users heard about you. Timing and precision vary.
  • RiseGuide asks early in onboarding Steve P. Young, RiseGuide1:49.
  • Calm asks after the paywall, for simple manual attribution on channels like TV and podcasts Steve P. Young, Calm5:19.
  • Treat the result as directional rather than precise Albert Cheng, Chess.com27:30.