The Right Context at the Moment of Choice — AI Readiness, Part 3
- Trisha MerriamHost
- Chris CarolanHost
- Erin WiggersHost
October 21, 2026
Part 3 of AI Readiness asks what makes information truly accessible: can I find it, can I consume it, can I understand it? Chris Carolan, Trisha Merriam and Erin Wiggers on putting the right context where the work happens, and on why missing context is the worst outcome.
Key takeaways
Information is accessible when three questions get a yes: can I find it, can I consume it, can I understand it?
Can I find it is exposure and discovery. If the message is on LinkedIn or email and the person lives on Reddit, they will never see it.
Can I consume it is format, device and situation. A detailed diagram squeezed into a banner ad shows a logo and nothing more.
Can I understand it is language. A client who doesn't know what a "deal" or an "opportunity" is will decide the system isn't for them.
The right context changes with timing, relevance and form, and it has never been easier to ask AI to help make each version.
The moment of choice is wherever someone's process is at that moment. Put the information there and people are likely to find it, and usually work harder to consume and understand it.
Before you blame adoption on the person, check what they can see. A different view or missing permissions can hide everything you built.
Teams turn over, every 18 months or so in Trisha's B2B SaaS experience, so whatever you set up has to be explained and discovered again and again.
Once you don't trust the CRM, you might as well not have one. In Trisha's experience a portal often has 50 or more source fields, and people interpret them differently and pull different numbers.
Missing context is the worst outcome. Three bullets read ten hours later have lost the context between them.
You don't have to send all the context all the time. Slice it by persona and timing, and send what is actionable, not the nice to know.
Readers who have shown interest in a topic read more. In Trisha's publisher example, the ones who got the long version consumed 11 times as much content as the rest.
If people will read email with AI, give their AI the whole context. Real human communication still happens on a call.
A persona dropdown on a form gets you weak data. A short call gets you real context, and a transcript lets AI carry it.
Take stated preferences with a grain of salt. In Chris's rough figure, we don't know 80% of what's possible, and preferences change once people can just ask an AI assistant.
Chapters
- 00:00Part 3: the right context at the moment of choiceTopic
- 01:18Why complexity is hard to communicateTopic
- 02:58Three forms of accessibilityTopic
- 04:38Can I find it? Can I consume it?Question
- 05:58Can I understand it? What is a deal?Question
- 07:42Documentation people actually readTopic
- 10:28The right context changes with timing, relevance and formTopic
- 14:24Why isn't anyone filling out the property?Question
- 16:03Not tech savvy, or never set up?Topic
- 18:09Put it where their process isTopic
- 20:05People be people, and every new team starts overTopic
- 23:18Fifty or more source fieldsTopic
- 24:44The email is too long. Now what?Question
- 29:13The worst thing we can do is miss contextTopic
- 33:44Slice the context by persona and timingTopic
- 36:58Can your AI assistant see the context?Question
- 40:43The 15-minute call beats the persona dropdownTopic
- 42:28Will email get its own schema markup?Question
- 46:00Who writes the schema, and a grain of salt on preferencesTopic
- 48:28Next: why a bad process becomes bad automationTopic
Transcript
This transcript was generated by AI and may contain errors. It is provided to help you skim and search the conversation.
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