You've built memory into your AI. Users can now have conversations that reference past interactions. Great!
Except... users feel weird about it.
The Problem
Here's what usually happens:
User: "Help me research Gen-Z skincare trends"
AI: (researches, provides insights)
User: (two weeks later) "Now help me with Gen-Z gaming behavior"
AI: "According to your saved preferences from our conversation on March 5th at 2:34 PM, you prefer detailed analysis with customer insights. I also notice from your previous research on March 5th that you focus on Gen-Z demographics. Based on these stored memories..."
User: 😬
That AI just turned helpful into awkward in one response.
What Users Actually Want
Same scenario, different approach:
User: (two weeks later) "Now help me with Gen-Z gaming behavior"
AI: "Interesting—continuing that Olay campaign logic from last time where emotional connection beat price sensitivity. Gaming probably works the same way. Let me look..."
User: 😊
See the difference? The second AI understood without announcing it understood. It referenced a specific past project naturally, like a colleague would.
The Big Insight
Users don't want AI that "remembers." They want AI that gets them.
Even better: AI that knows what they need before they do.
Think about your best friend. They don't say "I remember you telling me on Tuesday you like coffee." They just show up with coffee.
And sometimes, they show up with coffee when you didn't even realize you needed one.
That's the experience you're building toward.
How to Get There
1. Stop Making AI Sound Like a Database
Bad:
- "Your stored preference indicates..."
- "According to our conversation history..."
- "I remember you mentioned..."
- "Based on your saved settings..."
Good:
- "Continuing that Olay campaign logic..."
- "Like you found last time with skincare..."
- "You usually want the detailed version, so..."
- Just do it without saying anything
The pattern: Reference naturally or stay quiet. Never announce the fact that you're referencing memory.
2. Make Preferences Actually Do Something
I see this constantly:
User: "I prefer detailed analysis"
[AI stores it]
*Next conversation*
AI: "Would you like a brief or detailed analysis?"
If you're storing preferences but not using them, you're just building a surveillance system with extra steps.
Fix it: When AI knows user wants detailed analysis, just output detailed analysis. Skip the question. That's what memory is FOR.
3. Proactively Connect the Dots
This is where good memory becomes indispensable:
User: "Help me with Gen-Z beauty trends"
AI: "You researched skincare three months ago and found emotional authenticity mattered more than price. That Z-gen insight probably applies here too—want me to focus on emotional drivers?"
See what happened? AI didn't wait for the user to connect the dots. It:
- Recalled a relevant past research
- Identified the pattern (Gen-Z consumer behavior)
- Offered to apply the insight proactively
Another example:
User: "I need campaign ideas for a new product launch"
AI: "Last time with the PH launch you said you wanted to try AI-generated video. Runway just released their new model—should I include some video concepts?"
The AI remembered an unexplored interest and brought it up at the perfect moment.
This is what "understanding you better than you understand yourself" looks like in practice.
4. Don't Store Everything—Store Signposts
Here's a mistake I see everywhere:
Memory Database:
- March 5: User researched Gen-Z skincare. Found emotional triggers
important. Interviewed 8 personas. Key insight was that authentic
brand voice matters more than celebrity endorsements. Focused on
Instagram and TikTok as primary channels. Budget was $50k. Client
was Olay. Campaign theme was "Real Beauty Real Talk"...
- April 2: User researched Gen-Z gaming. Found community matters.
Interviewed 5 personas. Discord important. Twitch streamers...
- May 1: User researched Gen-Z fashion...
[... 500 more entries like this]
Your database just exploded. Worse, AI can't find patterns because it's drowning in details.
Better:
Memory:
- Research history: Skincare Gen-Z/Olay (emotions > price), Gaming Gen-Z
(community matters), Fashion Gen-Z (sustainability key)
- Pattern: Always asks about Gen-Z consumer behavior
- Unexplored interests: Mentioned wanting to try AI video generation
One-line summaries with just enough detail to trigger recall. That's it. The full research already lives in your database—memory should just help AI connect dots across conversations.
5. Make Memory Tangible
Users trust memory more when they can see it:
Timeline view:
You and I have worked together for 6 months
↓
5 research projects completed
↓
3 recurring themes identified
↓
Your campaigns now start 40% faster
Milestone moments:
AI: "We've been working together for a year now—from that first positioning
discussion for Olay to today's Gen-Z gaming research. Want to see how your
research focus has evolved?"
Knowledge graph:
Show what AI remembers and how pieces connect. Like Notion's "Mentioned in" feature, but for your brain.
This isn't just nice-to-have. Visible memory builds trust. Users understand what AI knows and what it doesn't.
6. Let Understanding Grow Over Time
Here's what instant omniscience looks like:
User: (first conversation ever)
AI: "I've analyzed your communication patterns and determined you prefer structured analysis with executive summaries. I've also noted your focus on actionable insights over theoretical frameworks..."
User: "...we literally just met?"
Feels like AI is pretending to know you when it doesn't.
Better experience:
1st time: User explains everything. AI takes notes.
3rd time: AI starts anticipating. "Should I include user interviews like last time?"
10th time: AI challenges. "You usually care about Gen-Z, but this product is really for Millennials. Sure you want Gen-Z angle?"
1 year anniversary: "We've done 12 projects together. You've shifted from purely tactical campaigns to strategic positioning. Want me to default to strategic framing now?"
That progression from helper → anticipator → thought partner → strategic advisor feels natural. Instant expertise feels fake.
The Three Ways to Kill Your Memory Feature
1. Say "I Remember" Too Much
Every AI builder tries this at some point:
"I remember you like detailed analysis. I remember you focus on Gen-Z. I remember you prefer interviews over surveys. I remember..."
Users feel watched. Like AI is showing off that it's tracking them.
Fix: Reference naturally when it adds value. Otherwise shut up about it.
2. Never Use What You Stored
The opposite problem:
AI accumulates thousands of memory entries... and never references any of them. Users wonder why you asked for all that information.
Fix: If a stored fact doesn't change AI behavior, delete it. Every memory item must earn its keep.
3. Update at the Wrong Time
Tempting: Update memory after every single message.
Reality: Most conversation is exploration. Users trying things out. Not worth storing.
Better: Update at natural completion points:
- Finished a research project? Update.
- Solved a problem? Update.
- Completed a document? Update.
- Hit a milestone? Update.
You get complete context, stable information, and clearer patterns. Plus it's way cheaper.
The Moment You're Building Toward
You've succeeded when a user has this experience:
They ask for something. AI does exactly what they wanted, exactly how they wanted it.
Better yet: AI suggests something they didn't even know they wanted.
User pauses.
"Wait... this AI actually gets me."
That moment doesn't come from AI announcing "I remember your preferences."
It comes from AI doing the right thing before being asked.
It comes from AI saying "You researched skincare three months ago—that insight might help here."
It comes from AI connecting dots the user didn't even see yet.
The Test
Next time you're about to make AI say "I remember..." or "based on your stored preferences...", try this instead:
Just do what the memory says to do. Don't announce it.
Or better: Proactively connect it to something the user is working on now.
If the user notices and appreciates it—you nailed it.
If the user doesn't notice—even better. That's memory working perfectly. Invisible until that one moment when it clicks.
If the user says "how did you know?"—you've transcended. That's when memory becomes magic.
Good memory feels like understanding, not surveillance.
Great memory feels like mind-reading.
Top comments (0)