Questions for the CEO
1. Scope and must-haves
Which of the listed capabilities are absolute must-haves for Month 1 versus nice-to-haves that can wait until Month 2 or 3? Any non-negotiable workflows or integrations that must be present before the team adopts the system?
2. Team roles and access
How many distinct roles do we need beyond Admin / Team Member / Client? Who should have the ability to create proposals, approve SOWs, or generate invoices? Any restrictions on client portal access by service line?
3. Commercial workflow details
What are the exact stages and required fields for Proposal → SOW → Invoice today? Are there standard templates or clauses that must be locked? How do retainers, milestones, and one-time projects differ in the current process?
4. AI layer expectations and constraints
What is the acceptable data-handling policy for the AI assist layer (client data, proposals, financials)? Preference for external API versus self-hosted? Any hard limits on cost or usage we should design around?
5. Hostinger VPS and operations
Confirm the target VPS plan and who will own ongoing administration, backups, and monitoring. Is there a preferred staging approach or maintenance window?
6. Proactive messaging
What are the top 5–10 daily and monthly messages or reminders each team member should receive? Who owns the rules for what triggers a Slack notification versus an email?
7. Client migration and pilot
Which existing clients or service lines should be the pilot for the first 30–60 days? What is the success criteria for declaring the CRM ready for broader use?
8. Budget and timeline
Is the three-month outline aligned with available internal capacity and any external help? Any hard external deadlines (e.g., end of year, specific client onboarding) that should drive priorities?
Action Item List
1. Schedule a 60–90 minute CEO discovery session to walk through the prioritization report and answer the questions above.
2. Document the current Proposal → SOW → Invoice steps, required fields, and templates (or gaps) for each major service line (Software Development, Consulting, AI Consulting, Marketing).
3. List the top 10 daily and monthly proactive messages / reminders the team needs, mapped to roles.
4. Confirm Hostinger VPS plan (recommended 8 GB RAM / 4 vCPU), access credentials, and backup strategy.
5. Decide AI provider and data-handling policy before any AI coding begins.
6. Identify the first 2–3 pilot clients or internal projects for Month 1 migration.
7. Assign an internal owner for the CRM project (product owner) and a technical lead.
8. Create a simple shared tracker (or first CRM records) for the action items and open questions so progress is visible.
9. Review security requirements (2FA, audit logs, encryption) and confirm minimum viable set for launch.
10. Set a go/no-go checkpoint at the end of Month 1 based on the expectations in the prioritization report.
These questions and actions are designed to turn the brainstorming into a clear, prioritized build. Update this list after the CEO session.
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