home / skills / coowoolf / insighthunt-skills / demand-side-buying-timeline
This skill helps you align sales with customer psychology across the demand-side buying timeline, guiding content, demos, and conversations to each phase.
npx playbooks add skill coowoolf/insighthunt-skills --skill demand-side-buying-timelineReview the files below or copy the command above to add this skill to your agents.
---
name: Demand-Side Buying Timeline
description: A chronological model of the buying process from the customer's perspective—First Thought, Passive Looking, Active Looking, Deciding, First Use, Ongoing Use. Align sales to customer psychology, not your funnel.
---
# The Demand-Side Buying Timeline
> "Instead of trying to base the sales process on how we want to sell, we need to actually design the sales process on how they want to buy." — Bob Moesta
## What It Is
A chronological model of **the buying process from the customer's perspective**, dividing the journey into distinct psychological phases that require different support—fundamentally different from a company's sales funnel.
## When To Use
- Designing **sales funnels**
- Creating **content marketing** strategies
- Structuring **product demos**
- When sales cycle feels **too long** or conversion is low
## The Timeline
```
CUSTOMER BUYING JOURNEY:
1. FIRST THOUGHT
└── Struggling moment triggers awareness
└── "Something isn't working..."
2. PASSIVE LOOKING (Problem Aware)
└── Casually collecting information
└── NOT ready to buy or demo
└── Needs: Education, awareness content
3. ACTIVE LOOKING (Solution Aware)
└── Comparing alternatives
└── Researching specific features
└── Needs: Comparison content, case studies
4. DECIDING (Trade-offs)
└── Weighing options
└── Needs help with final choice
└── Needs: Decision frameworks, consultative selling
5. FIRST USE
└── Onboarding, setup
└── Needs: Activation support
6. ONGOING USE
└── Retention, expansion
└── Needs: Success content, upsell paths
```
## How To Apply
```
STEP 1: Diagnose Customer Phase
└── Where is this lead in their journey?
└── Are they passive looking or actively comparing?
STEP 2: Match Your Response
└── Passive Looking → Send educational content, NOT demo
└── Active Looking → Offer comparison materials
└── Deciding → Consultative conversation
STEP 3: Design Phase-Specific Demos
└── Demo 1: Story/Context (for early-phase)
└── Demo 2: Alternatives (for mid-phase)
└── Demo 3: Trade-offs (for late-phase)
STEP 4: Don't Skip Phases
└── Forcing close on passive looker = lost deal
└── Meet them where they are
```
## Common Mistakes
❌ Treating all leads the **same** regardless of phase
❌ Forcing a **closing demo** on someone who is only "passive looking"
❌ Assuming sales is about **convincing** rather than **enabling**
## Real-World Example
Autobooks split their single demo into three different types based on the buyer's phase (Story/Context, Alternatives, Choices/Trade-offs), which cut the sales cycle in half and increased conversion by 4x.
---
*Source: Bob Moesta, Co-creator of Jobs-to-be-Done, Lenny's Podcast*
This skill maps the customer buying process into six psychology-driven phases—First Thought, Passive Looking, Active Looking, Deciding, First Use, and Ongoing Use. It helps teams align messaging, demos, and sales motions to how customers actually think and act, not how the company wants to sell. Using the timeline reduces wasted outreach and shortens sales cycles by meeting buyers where they are.
The model diagnoses which phase a prospect is in, then prescribes phase-appropriate content, demo types, and sales actions. Early phases get education and context, mid phases get comparisons and proof, late phases get consultative decision support, and post-purchase focuses on activation and expansion. Teams design three demo types and a matching content map to avoid pushing buyers forward prematurely.
How do I identify which phase a lead is in?
Listen for language and behavior: vague problem statements suggest Passive Looking; explicit feature comparisons indicate Active Looking; questions about trade-offs, pricing, and implementation signal Deciding.
What if a lead skips phases?
Skipping is rare; more often sales teams mislabel leads. If a lead appears to skip, validate product understanding and readiness with diagnostic questions and provide missing context before pushing for a close.