Opening Statement: "Your website platform choice directly impacts operational efficiency, crisis response capability, and stakeholder confidence—three areas where corporate executives cannot afford compromise."
The Assessment Purpose:
Executive Decision-Making Approach:
Technical Infrastructure: Security, performance, scalability assessment
Operational Efficiency: Content management, update processes, team dependencies
Strategic Capability: Crisis response, brand control, competitive positioning
Financial Analysis: Current costs, hidden expenses, migration ROI calculation
Risk Management: Security vulnerabilities, business continuity concerns
WordPress Security Vulnerabilities:☐ Plugin Security Audit: How many plugins are installed? (Score: >20 plugins = High Risk)☐ Update Management: When were core, theme, and plugins last updated? (Score: >30 days = Medium Risk)☐ Security Monitoring: Do you have active security monitoring in place? (Score: No = High Risk)☐ Backup Strategy: When was your last successful backup tested? (Score: >7 days = Medium Risk)☐ Access Control: How many people have admin access? (Score: >3 people = Medium Risk)☐ SSL Certificate: Is SSL properly configured and monitored? (Score: No = High Risk)☐ Vulnerability Scanning: Regular security scans performed? (Score: No = High Risk)
Risk Assessment Scoring:
Current Performance Metrics:☐ Page Load Speed: Mobile load time under 3 seconds? (Score: No = Performance Issue)☐ Core Web Vitals: Google PageSpeed score above 90? (Score: No = SEO Risk)☐ Traffic Handling: Site stable during traffic spikes? (Score: No = Scalability Issue)☐ CDN Implementation: Content delivery network properly configured? (Score: No = Performance Gap)☐ Database Optimization: Regular database maintenance performed? (Score: No = Performance Risk)☐ Image Optimization: Automated image compression active? (Score: No = Speed Issue)☐ Caching Strategy: Multi-layer caching implemented? (Score: No = Performance Gap)
Developer Relationship Assessment:☐ Response Time: How quickly can developer make critical updates? (Score: >24 hours = Business Risk)☐ Cost Predictability: Are development costs predictable and budgeted? (Score: No = Financial Risk)☐ Knowledge Transfer: Is technical knowledge documented and transferable? (Score: No = Dependency Risk)☐ Emergency Support: 24/7 technical support available? (Score: No = Business Continuity Risk)☐ Skill Availability: Multiple developers familiar with your setup? (Score: No = Single Point of Failure)
Executive Team Control:☐ Direct Editing: Can executive team update content without developer? (Score: No = Operational Dependency)☐ Brand Consistency: Content updates maintain brand standards automatically? (Score: No = Quality Risk)☐ Approval Workflow: Content approval process streamlined for speed? (Score: No = Response Delay)☐ Version Control: Can you easily revert problematic content changes? (Score: No = Risk Management Gap)☐ Multi-User Management: Team members have appropriate access levels? (Score: No = Security/Workflow Risk)
Crisis Communication Capability:☐ Rapid Response: Can critical messages be updated within 2 hours? (Score: No = Crisis Management Failure)☐ Message Testing: Can you A/B test critical communications? (Score: No = Strategy Limitation)☐ Stakeholder Targeting: Different messages for different stakeholder groups? (Score: No = Communication Gap)☐ Mobile Updates: Can critical updates be made from mobile devices? (Score: No = Accessibility Limitation)
Weekly Time Allocation Assessment:☐ Technical Management: Hours per week spent on WordPress technical issues? (Score: >2 hours = Operational Drain)☐ Content Updates: Time required for routine content changes? (Score: >4 hours = Efficiency Issue)☐ Security Monitoring: Weekly time spent on security concerns? (Score: >1 hour = Resource Misallocation)☐ Performance Optimization: Monthly time on speed/performance issues? (Score: >4 hours = Technical Burden)
Opportunity Cost Calculation:☐ Revenue Impact: Time spent on WordPress = time not spent on revenue generation☐ Strategic Focus: Technical concerns distracting from strategic business development?☐ Team Productivity: WordPress limitations impacting team efficiency?
Business Growth Alignment:☐ Traffic Scaling: Website can handle 10x traffic increase? (Score: No = Growth Limitation)☐ Feature Addition: Easy to add new business functionality? (Score: No = Innovation Barrier)☐ International Expansion: Multi-language/region support possible? (Score: No = Market Limitation)☐ Integration Capability: CRM, email, analytics integrations working smoothly? (Score: No = Business System Gap)
Digital Competitive Analysis:☐ Professional Presentation: Website matches executive credibility level? (Score: No = Brand Gap)☐ User Experience: Navigation intuitive for executive-level stakeholders? (Score: No = Professional Risk)☐ Mobile Experience: Mobile site reflects desktop professionalism? (Score: No = Stakeholder Experience Gap)☐ Loading Speed: Site speed competitive with industry leaders? (Score: No = Competitive Disadvantage)
Trust and Credibility Indicators:☐ Professional Design: Visual design supports executive positioning? (Score: No = Credibility Risk)☐ Security Indicators: Visible security badges and SSL indicators? (Score: No = Trust Issue)☐ Contact Information: Professional contact options prominently displayed? (Score: No = Accessibility Gap)☐ About Information: Executive team credentials clearly presented? (Score: No = Authority Gap)
Strategic Capability Requirements:☐ Technology Evolution: Platform supports emerging web technologies? (Score: No = Obsolescence Risk)☐ Team Training: New team members can quickly learn content management? (Score: No = Onboarding Barrier)☐ Vendor Independence: Reduced dependency on single developer/agency? (Score: No = Business Risk)☐ Cost Predictability: Platform costs scale predictably with business growth? (Score: No = Financial Planning Risk)
Current WordPress Costs (Annual):☐ Hosting Costs: $/year☐ Premium Plugins/Themes: $/year
☐ Developer Retainer/Support: $/year☐ Security Services: $/year☐ Performance Optimization: $/year☐ Emergency Fixes: $/year☐ Content Management Time: $______ (hours × executive hourly rate)
Hidden Opportunity Costs:☐ Delayed Responses: Business impact of slow content updates☐ Technical Learning: Time spent learning WordPress instead of business development☐ Crisis Response: Cost of slow response during reputation-critical moments☐ Team Productivity: Efficiency lost to WordPress limitations
Webflow Annual Costs:☐ Platform Subscription: $504/year (Business plan)☐ Migration Investment: $_______ (one-time)☐ Training Time: $_______ (executive team learning curve)
Projected Savings:☐ Eliminated Developer Dependency: $/year☐ Reduced Technical Management Time: $/year
☐ Improved Crisis Response Capability: $/year (risk mitigation value)☐ Enhanced Stakeholder Confidence: $/year (business development value)
ROI Calculation Formula:(Annual Savings - Annual Webflow Costs) / Migration Investment × 100 = ROI%
Risk Categories: