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How to design AI agents people can trust

Shared by Caddie Library · Updated
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Chapter 10 of 15 · Building AI Products
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1. Finding Product-Market Fit
How to test for real customer pull earlyHow to pick a narrow niche to start inHow to launch a simple first version fastHow to learn from users and customersHow to read early signs of product-market fit
2. Onboarding and Activation
How to structure onboarding as a storyHow to ask and use onboarding questionsHow to get users to the aha moment fastHow to decide how long onboarding should beHow to build quiz funnels for paid traffic
3. Paywalls and Pricing
When to choose a hard paywall over freemiumHow to design a paywall that convertsHow to price annual and monthly plansHow to set, raise and localize pricesHow to run free trials and free tastes
4. Business Models and Revenue
How to structure subscription tiersHow to keep a free tier that pays offHow to charge for usage and AI creditsHow to pair hardware with a subscriptionHow to add ads, affiliates and partners
5. Retention and Engagement
How to measure retention honestlyHow to build habit loops that bring users backHow to use notifications and lifecycle messagesHow to reduce churn and handle cancellationsHow to build social loops and community
6. Brand and Positioning
How to position against bigger incumbentsHow to name and describe your productHow to earn trust in high-stakes categoriesHow to borrow credibility from celebrities and experts
7. Organic Content and Creators
How to find, vet and recruit creatorsHow to pay creators fairly and safelyHow to brief and manage creatorsHow to find and copy viral formatsHow to scale one format across many accountsHow to rank in AI search and SEO
8. Paid, App Store and Viral Growth
How to make ads that convertHow to turn organic winners into paid adsHow to structure and scale Meta campaignsHow to tell if paid acquisition is profitableHow to win in the App StoreHow to build viral and referral loops
9. Experimentation and Analytics
How to run trustworthy experimentsHow to judge test results correctlyHow to run more experiments fasterWhat metrics to track and how to define them
10. Building AI Products
How to build for the models of tomorrowHow to design AI interfaces beyond chatHow to design AI agents people can trustHow to measure AI quality with evalsHow to control AI costs and pricingHow to build products with AI coding tools
11. Teams, Hiring and Funding
How to hire people who thrive on ambiguityHow to organize small product teamsHow to run exploratory bets and kill themHow to work as a team with AI agentsWhen to raise money or sell your company
12. Founder Principles
How to pick a mission worth building a company aroundWhy to trust your own judgment over the consensusHow to turn failure and setbacks into the next stepHow to learn from rivals and copy what works
13. Choosing Where to Compete
How to make low cost your competitive advantageHow to create a market instead of fighting for shareWhy scarcity and brand can beat volumeHow to build an advantage that feeds itselfHow to attack a bigger rival where it cannot followWhen to stay focused on the core business
14. Building and Leading the Company
How to hire great people and give them roomHow to align pay and ownership with the missionHow to keep your culture and standards as you growHow to build candor and fast decision-makingWhy leaders must stay close to the work and customersHow to choose and prepare a successor
15. Capital and Deals
How to fund growth without losing controlHow to acquire companies and keep what makes them workWhat to do with cash: reinvest, buy back or holdWhy to keep a cash cushion and avoid heavy debtHow to structure ownership to protect your missionHow to negotiate deals that keep your leverage

1 The bottom line

Start agents with narrow tasks, tight access and a human in charge, then widen both as reliability is proven. Predictable behavior is what lets people hand over real work.

2 Key takeaways

we want the agent to start from being very safe and then we iterate towards you know being productive

Patrick and Pablo, Social (Superwall)

2.1 Start narrow with a human in charge

Hand agents autonomy one undoable step at a time
Every domain follows the same ladder, and the first rung is a task a person can easily reverse.

Begin with one agent and one small task where a person can undo mistakes.

  • Start with low agency and high human control Aishwarya Naresh Reganti and Kiriti Badam, OpenAI15:22.
    • Hand over more decisions only as the system earns trust.
    • Starting with a full agent makes it impossible to control the complexity or tabulate the many ways it fails.
    • A coding assistant goes from inline completions to larger blocks for review to autonomous PRs.
    • Marketing goes from drafted copy to multi-step campaigns to auto-optimized campaigns.
  • Pick a first task that humans can undo Aishwarya Naresh Reganti and Kiriti Badam, OpenAI51:10.
    • In a support build, version one only classified and routed tickets, because humans can undo wrong routing.
    • Even routing is hard at enterprises. Shoes, women's shoes and men's shoes can sit at the same level, and a dead node may have been last updated in 2019.
    • Early stages surface these data problems and the context engineering needed before you add drafting and end-to-end resolution.
  • Launch a single agent first and learn from real use Tibo Sottiaux, OpenAI10:55.
    • Dots launched with one primary dot that learns preferences most deeply.
    • Launch to Pro users first, see what they do, and tune with the community before adding a second, third or fourth dot.
    • Tibo uses one dot only to monitor Twitter, and that is enough work for an entire dot.
  • Choose the right tool for each workflow step Aishwarya Naresh Reganti and Kiriti Badam, OpenAI29:35.
    • Understand the workflow, then decide which parts suit AI and which need a human in the loop.
    • Often an ML model does one part and deterministic code does another.

2.2 Give safe access first

Limit what the agent can touch at launch, watch it closely, and widen access in steps.

  • Start from very safe and iterate toward productive Patrick and Pablo, Social (Superwall)38:50.
    • WiseSam runs on a pre-configured virtual machine with its own email address and an allow list of senders.
    • The team admits this was a bit too conservative and plans to add read access to the inbox over the next weeks.
  • Give the agent its own computer and keep the harness off your machine Roman Ugarte, Grok Bot (SpaceXAI)32:05 and Tibo Sottiaux, OpenAI22:02.
    • A bot with its own computer avoids sharing credentials and tripping over the user.
    • Run the harness separate from the machine, so one agent can connect to many devices.
    • Give specialist agents that touch production extra guardrails and monitoring, on their own hardware.
    • Some of OpenAI's specialist dots run on Mac minis, and Tibo's dot flagged a ChatGPT outage 5 minutes before a live demo.
  • Run a second system that watches the first Tibo Sottiaux, OpenAI34:33.
    • The monitor stops high-risk actions or interrupts the agent if it may be getting prompt injected.
    • The majority of OpenAI's API stack investment goes into the safety stack, and the model 6.1 Astra was not released.
  • Guide new users with preset first tasks Patrick and Pablo, Social (Superwall)34:25.
    • Open the chat with buttons like helpful tasks, calendar and mailbox that send a prepared prompt.
    • Nail the first three to five steps and build trust before sensitive tasks like reading mail.
    • The team is identifying about 10 use cases that anyone feels value from quickly, such as birthdays or price checks.

2.3 Make behavior predictable and visible

Users should foresee what the agent will do, check how it got there, and control their data.

  • Let users predict what the agent will probably do Tara Seshan and Nan Yu, OpenAI22:40.
    • At any point, a user should be able to predict what a feature or primitive will likely do.
    • Users also need to understand privacy, how their data is used, and the norms of the product.
    • With semi-autonomous agents, you can no longer excuse surprising behavior with a settings menu or popup.
  • Show process, inputs and citations, not just output Tara Seshan, OpenAI1:05:38.
    • Expose in-progress work, citations and reasoning so users can verify the result.
    • Make the model a collaborator the user goes on a journey with.
    • Coding can be verified by tests on the output. Knowledge work cannot be trusted from a final deck number alone.
  • Give users per-item control over what the AI learns Casey Winters, SuperMe22:12.
    • Do not let the AI alone decide what is public.
    • For each synced item, the owner picks private, company only, network only, or public.
    • This makes people willing to connect sensitive sources like meeting notes and Slack.
  • Watch for over-moderating Connor Zwick, Speak19:50.
    • Speak added heavy moderation to avoid a viral inappropriate screenshot, then dialed it back.
    • Speak tested GPT-4 with 30 power users, and one used it about 8 hours a day to simulate a boyfriend.
    • Over time the bigger risk was users being offended by censorship in their specific scenarios.

2.4 Make sure the task always finishes

Layer capabilities and add human help so a stuck agent never leaves the user with a broken promise.

  • Finish the last mile Tara Seshan and Nan Yu, OpenAI15:59.
    • A product that gets 99% there and then fails is an unfulfilled promise, and feels worse than one that never started.
    • Use computer use as the fallback when plugins or MCPs are missing. It may be slower and cost more tokens.
    • Nan notes computer use will 100% do the job while the ecosystem catches up with hooks and MCPs.
  • Structure capabilities as layers Tara Seshan and Nan Yu, OpenAI14:35.
    • Order them as native features, first and third party plugins, then computer use as a fallback.
    • Expose hooks so developers can build cohesive, composable experiences.
    • A meetings plugin pulls meeting data, and computer use covers the case where the plugin interface is missing.
  • Build a fallback experience for when safeguards block a model Dianne Penn, Anthropic37:00.
    • Improve safety systems and user experience together.
    • Before the Fable models Anthropic had no strong fallback UX, so it built systems that route users to a great Opus 4 response.
  • When the agent is stuck, have it call a human and learn Anish Acharya, a16z19:30.
    • Treat every failure as a knowledge gap or data gap to fill, so the agent does not need to call next time.
    • Kavak runs an agent per customer for online used car sales. A human coaches it through and the agent captures the traces.

2.5 Group agents and give them work

Manage one lead agent, not a mesh of peers
People can't handle 40 direct reports, and a supervisor over sub-agents keeps both the user and the guardrails manageable.

Keep the number of things a person manages small, with one lead agent over the rest.

  • Bundle agents so people can hold them in their heads Tara Seshan and Nan Yu, OpenAI9:05.
    • People struggle to manage 40 direct reports, and they do the same with agents.
    • Map agent design to human nature and group activity into bundles.
    • Users often create a chief of staff agent, so "you're not managing seven you're managing one."
  • Use a supervisor with sub-agents, not peer-to-peer agents Aishwarya Naresh Reganti and Kiriti Badam, OpenAI1:02:00.
    • Agents talking to each other in a gossip-style protocol do not work with current capabilities.
    • In customer support, peer-to-peer agents make it hard to control which agent replies and force guardrails everywhere.
  • Let users promote a bot to chief of staff, but keep it a two-way door Roman Ugarte, Grok Bot (SpaceXAI)13:20.
    • The team did not lead early users there, saw many reach it themselves, then encouraged it slightly without making it mandatory.
    • The pattern emerged around the end of week two of internal rollout.
  • Settle single versus multiple agents by working through edge cases Tara Seshan and Nan Yu, OpenAI9:33.
    • Decide how memory is segmented, for example per private Slack channel.
    • Decide how the agent talks to each person, and whether it uses the user's credentials or a universal service account.
    • Make that behavior easy for the user to understand.

2.6 Widen autonomy as surprise falls

Hand over more only when the system has stopped teaching you anything new.

  • Make the agent earn autonomy Aishwarya Naresh Reganti and Kiriti Badam, OpenAI10:00.
    • Constrain autonomy by number of actions, or by topic and risk.
    • In insurance pre-authorization, AI can auto-approve MRIs and blood tests while invasive surgery stays with humans.
  • Move up when you get little new information Aishwarya Naresh Reganti and Kiriti Badam, OpenAI58:20.
    • If you calibrate every day or two and see no new data distribution patterns and consistent user behavior, you can move up.
    • Recalibrate when events change the system, or when user behavior evolves.
    • Swapping a deprecated model like GPT-4o for GPT-5 is one such event.
    • A bank underwriting assistant worked well for about three months. Then users asked deep questions about what previous underwriters did, which required rebuilding parts of the system.
  • Budget months and distrust one-click agents Aishwarya Naresh Reganti and Kiriti Badam, OpenAI31:00.
    • Enterprise data is messy, so an agent needs time to learn the system.
    • Prefer a team that builds a pipeline that learns over one promising instant gains.
    • Meaningful ROI easily takes four to six months, even with the best data and infrastructure layers.

2.7 Where they disagree

Some tips pull against each other, and the right call depends on your product and its risks.


Sources

Part of Building AI Products in the growth library.