home / skills / coowoolf / insighthunt-skills / demand-side-buying-timeline

demand-side-buying-timeline skill

/product-growth/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-timeline

Review the files below or copy the command above to add this skill to your agents.

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SKILL.md
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---
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*

Overview

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.

How this skill works

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.

When to use it

  • Designing or reworking sales funnels and outreach sequences
  • Building content marketing aligned to buyer intent
  • Structuring product demos for different maturity levels
  • Diagnosing long sales cycles or low conversion rates
  • Planning onboarding and retention journeys

Best practices

  • Start by segmenting leads by behavior and questions, not by company size
  • Map existing content to the six phases and fill the gaps with targeted assets
  • Create three demo scripts: context/story, alternatives/comparison, and trade-offs/decision
  • Train sales to ask phase-diagnostic questions before proposing demos
  • Respect the buyer’s readiness—offer education to passive lookers and consultative help to deciders

Example use cases

  • Audit your funnel and reassign leads to phases to reduce inappropriate demo invites
  • Create a content calendar: awareness articles for Passive Looking, case studies for Active Looking
  • Split one generic demo into three phase-specific demos to shorten cycle time
  • Design onboarding flows triggered by First Use signals to boost activation and reduce churn
  • Build upsell paths tied to Ongoing Use milestones and success metrics

FAQ

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.