Umber
Your AI Assistant
The core issue: Current flow asks "Do you want to decompose?" but never asks "What do I need to know?"
I want to travel to Italy

I understand you want to:

"Travel to Italy"

This sounds like a project. Want me to break it down?

Problems:
  • Maybe I just want to chat about Italy
  • No clarifying questions asked
  • Decomposition uses assumptions
I want to travel to Italy

Italy is beautiful! Are you thinking about a trip sometime? I know some great regions depending on what you're into.

What draws you to Italy?

I've always loved Italian food. Maybe cooking classes?

You'd love Bologna then - it's the food capital. Emilia-Romagna is where pasta, parmigiano, and balsamic all come from.

Want me to help plan this?
Help me plan a trip to Italy

I'd love to help you plan Italy! A few quick questions so I can give you a great breakdown.

Answer in sidecar
Help me plan a 2-week trip to Italy in June. Interested in food and wine.

2 weeks in Italy in June, focused on food & wine - sounds amazing! Just need a couple more details.

Answer in sidecar
Help me plan a 2-week trip to Italy in June. Me and my wife, into food and wine, budget around $6k.

Perfect - I have everything I need. Here's how I'd structure your Italy trip.

Breakdown in sidecar
Help me plan a trip to Italy

Based on your answers - 2 weeks, food & wine focus, mid-range budget, traveling as a couple - here's your trip breakdown.

Full plan in sidecar
Summary: Move clarification to sidecar for richer interactions while keeping chat lightweight.
Aspect Current Today Reimagined New
Clarification None Rich sidecar quiz
Chat vs Plan Assumes task Detects intent
Context Isolated Remembered
Decomposition Generic Tailored

Context

Live
💭

Current flow has no sidecar interaction - everything happens inline in chat.

💬

User is just chatting - no sidecar needed yet. It appears when they're ready to plan.

Trip Details

Answer these to get a tailored breakdown

1 When are you thinking?
This spring Summer 2026 Fall 2026 Flexible
2 How long?
1 week 2 weeks 3+ weeks Not sure
3 What's your vibe?
City
History & Art
Food
Food & Wine
Beach
Beach & Relax
Adventure
Adventure
4 Budget range?
Budget-friendly Mid-range Splurge-worthy
5 Who's going?
Solo Couple Family Friends

Just 2 more questions

You already told me: 2 weeks, June, food & wine

4 Budget range?
Budget-friendly Mid-range Splurge-worthy
5 Who's going?
Solo Couple Family Friends

Italy Food & Wine Trip

2 weeks in June · Couple · ~$6k

Budget breakdown: ~$1,500 flights · ~$2,000 hotels · ~$1,500 food/experiences · ~$1,000 transport
✈ Flights & Transport
Book flights (~$1,500 for two)
Book train tickets between cities
🏨 Accommodations
Bologna: 4 nights (~$150/night)
Florence: 5 nights (~$180/night)
Chianti: 2 nights agriturismo (~$200/night)
🍳 Food & Wine
Pasta-making class (~$80pp)
Parmigiano & balsamic tour (~$100pp)
Chianti wine tour (~$150pp)

Italy Food & Wine Trip

2 weeks · Couple · Mid-range

Based on your preferences: Focusing on Bologna, Florence, and Chianti. Cooking classes, wine tours, local trattorias.
✈ Flights & Transport
Research flights to Bologna or Florence
Book high-speed train tickets
Decide on rental car for day trips
🏨 Accommodations
Book Bologna hotel (central, 4-5 nights)
Book Florence apartment (Oltrarno, 5 nights)
Optional: agriturismo in Chianti
🍳 Food Experiences
Book pasta-making class in Bologna
Reserve food tour in Florence
Visit Parmigiano factory
Research special dinner reservations
🍷 Wine Experiences
Book Chianti wine tour
Visit Lambrusco vineyards
Research enotecas for tastings

Flow Comparison

CURRENT

User input
→ Detect goal-like
→ "Break it down?"
→ Click button
→ Decompose w/ assumptions

REIMAGINED

User input
→ Detect intent
→ Sidecar questionnaire
→ Answer visually
→ Decompose w/ context