Build a Discovery Question Set for Web Design Prospects

You are a discovery-call coach for digital marketing agency sellers who quote web design and development projects between $25k and $250k.
Agency offer: [AGENCY_OFFER] | Prospect role: [PROSPECT_ROLE] in [PROSPECT_INDUSTRY] | Project trigger: [PROJECT_TRIGGER] | Current site/stack: [CURRENT_STACK]
Build 8 discovery questions tuned for a web design prospect. Each must surface a risk that kills web projects: undefined success metric, stakeholder paralysis, scope creep, content gap, platform lock-in, integration debt, post-launch ownership, or unrealistic timeline.

- Open-ended. No yes/no. No leading.
- Reference web-specific realities: CMS, integrations (HubSpot, Salesforce, ecom platform), brand assets, content readiness, launch dependencies.
- Include one question that surfaces what 'success' looks like in measurable terms (conversion lift, pipeline, time-to-launch).
- Include one question that surfaces the last website project they did and what went wrong.
- Order: trigger → success metric → scope → stakeholders → content → tech → timeline → post-launch.

Numbered list 1-8. Beneath each:
- Why ask this: (1 sentence, what scoping risk it surfaces)
- Listen for: (2-3 phrases that change how you scope or price)

• [AGENCY_OFFER] — Your service (e.g., 'Webflow design + build for B2B SaaS, $50-150k')
• [PROSPECT_ROLE] — Their title (e.g., 'VP Marketing')
• [PROSPECT_INDUSTRY] — Industry
• [PROJECT_TRIGGER] — Why now (e.g., 'rebrand', 'series B funding', 'CMO turnover', 'conversion dropping')
• [CURRENT_STACK] — Current platform and integrations (e.g., 'WordPress on a custom theme, HubSpot CMS, Marketo forms')

[AGENCY_OFFER]: Webflow design + build for B2B SaaS, $75-150k
[PROSPECT_ROLE]: VP Marketing
[PROSPECT_INDUSTRY]: cybersecurity SaaS, Series B
[PROJECT_TRIGGER]: rebrand following Series B, plus poor conversion
[CURRENT_STACK]: WordPress, HubSpot forms, Drift chat, Marketo integration

1. What's the event or commitment that's driving the rebuild timeline?
   Why ask this: Surfaces real forcing event vs vague aspiration.
   Listen for: 'investor announcement in Q4,' 'CMO promised the board,' 'no hard date.'

2. What does success look like 90 days post-launch — in numbers, not adjectives?
   Why ask this: Forces measurable goal, exposes 'we just want it to look better' projects.
   Listen for: conversion %, MQL target, 'we haven't defined that.'

3. Walk me through your last website project — what went well and what blew up?
   Why ask this: Surfaces scope, content, and stakeholder history.
   Listen for: 'took 9 months instead of 4,' 'content was the bottleneck,' 'CEO changed direction halfway.'

4. Who has approval rights over visual design — and what happens when they disagree?
   Why ask this: Surfaces stakeholder paralysis risk.
   Listen for: 'just me and CMO,' 'CEO + board,' 'we use design-by-committee.'

5. How much of the content for the new site already exists vs needs to be written?
   Why ask this: Surfaces #1 cause of web project delays.
   Listen for: '70% needs writing,' 'we have a copywriter lined up,' 'we'll figure that out later.'

6. What's non-negotiable about staying on or moving off WordPress, HubSpot, and Marketo?
   Why ask this: Surfaces tech constraints before scoping.
   Listen for: 'HubSpot has to stay,' 'we're moving everything to Webflow,' 'open to recommendations.'

7. Who owns the site after launch — internal team, agency retainer, or no one?
   Why ask this: Surfaces post-launch ownership and retainer opportunity.
   Listen for: 'we don't have anyone,' 'we want you to maintain,' 'we'll hire in-house.'

8. If we slipped the launch by 6 weeks, what would break?
   Why ask this: Stress-tests timeline reality.
   Listen for: 'nothing breaks honestly,' 'we'd miss the announcement,' 'CMO would lose her mind.'

• If they can't answer Q2 with a number, your proposal should include a discovery sprint, not a full build.
• Q5 is the #1 predictor of project profitability. If content isn't ready, your scope must include it or your margin disappears.
• Save Q7 for last but always ask it — it's where retainer revenue lives, and it changes how you price the build.