Tuesday, January 13, 2026
18 Questions to Ask When Redesigning a Website
Most website redesigns fail before a single wireframe is drawn. The problem isn't bad design or the wrong CMS. It's teams that skip the strategic questions that determine whether a site becomes growth infrastructure or another project requiring replacement in 18 months.
You've seen this pattern before. A company invests six figures and six months into a redesign, launches to internal applause, then watches the site calcify as marketing requests pile up, developer bottlenecks return, and the CEO asks why conversions haven't improved. Soon, conversations about "the next redesign" begin.
The difference between websites that scale and websites that stall comes down to what happens before the project kicks off. Teams that treat a redesign as a visual refresh get a visual refresh. Teams that interrogate their business goals, governance model, stakeholder needs, and technical architecture build something that evolves with the company.
These 19 questions force the conversations most teams avoid: who actually owns the site post-launch, how you'll measure success beyond traffic, what content workflows need to exist, and whether your technical choices will create flexibility or lock-in. They won't make the redesign easier, but they'll make it worth the investment.
Strategic Alignment Questions
Before discussing designs or platforms, establish why the redesign matters to the business and how success will be measured. This foundational step prevents organizations from selecting technology before defining business objectives—a critical mistake that undermines many website design initiatives.
Strategic alignment requires cross-functional stakeholder engagement spanning C-suite leadership, marketing operations, sales enablement, and technical teams. Each stakeholder group brings distinct perspectives:
- Executives focus on revenue impact and competitive positioning
- Marketing teams prioritize lead generation and brand perception
- Sales organizations need tools that accelerate deal velocity
- Technical teams assess feasibility and integration requirements
Without this alignment, redesign projects devolve into subjective design debates rather than data-driven decisions anchored in measurable business outcomes. Companies that establish
1. What business outcomes must this website drive in the next 12-24 months?
This question forces you to distinguish between cosmetic improvements and strategic business objectives. Without clear outcomes, redesign decisions lack an anchor—teams debate subjective preferences rather than evaluating choices against concrete goals.
Interview stakeholders across departments to identify where the website currently limits business performance:
- Is sales velocity constrained by poor lead quality?
- Are prospects abandoning the site before requesting demos?
2. What can't our current website do that's costing us opportunities?
This question shifts focus from what you want to what you genuinely need by identifying specific functional gaps rather than aesthetic preferences. Audit your current workflow bottlenecks:
- Where do content updates require developer intervention, delaying campaign launches?
- Which integration gaps prevent marketing and sales data from flowing seamlessly?
3. How will we measure success six months post-launch?
Without pre-defined metrics, you can't distinguish between genuine improvement and change for its own sake. B2B organizations should establish meaningful KPIs, using measurement frameworks aligned with their business model, such as:
- Marketing Qualified Accounts (MQAs) rather than raw lead volume
- Multi-touch attribution models that reflect long sales cycles
- Website engagement that influences pipeline and connects to revenue outcomes
Explicitly connect website redesign metrics to business value drivers rather than vanity metrics like page views or session duration.
Governance & Ownership Questions
Redesigns fail when ownership is unclear. Without designated owners, critical decisions stall in endless committee discussions, content updates require chasing down multiple stakeholders, and post-launch optimization becomes everyone's responsibility (meaning no one's responsibility). Poor planning and unclear objectives are some of the most frequent causes of enterprise project failures.
4. Who owns the website as a product, not just a project?
This question distinguishes between temporary project leadership and ongoing product ownership. Many organizations assign project managers who exit once the site launches, leaving no one accountable for performance, optimization, or strategic evolution.
Map ownership across three levels:
- Who makes strategic decisions about the website's role in your business (typically C-suite)?
- Who manages day-to-day operations, content strategy, and performance optimization (Director/Manager level)?
- Who handles technical maintenance, updates, and troubleshooting (IT/Engineering)?
Effective website governance requires documenting these roles in RACI matrices with clear escalation paths for decisions that span multiple owners.
5. How will different teams (marketing, product, sales) contribute to and control site content?
This question surfaces potential conflicts before they derail your redesign by clarifying which teams control which content areas and who has final approval authority.
Map your content inventory to team responsibilities:
- Which team creates each content type?
- Who reviews and approves it?
- What's the SLA for updates?
Consider how your CMS will enforce these boundaries through role-based access controls and approval workflows.
6. What's the decision-making process for changes, updates, and new features?
Establish appropriate decision-making tiers based on change impact and risk. Categorize your typical changes:
- Which updates are routine (content edits, image swaps) requiring minimal approval?
- Which are significant (new page templates, navigation changes) requiring cross-functional review?
- Which are strategic (new functionality, major redesigns) requiring executive-level sign-off?
Document approval workflows for each tier, including who reviews, approval timeframes, and escalation procedures. Your CMS should automate these workflows through routing rules rather than relying on manual coordination.
Architecture & Scalability Questions
Your website's technical foundation determines whether it evolves with your business or becomes an obstacle to growth. Architecture decisions made during redesign have compounding effects: the right choices enable rapid iteration and marketing autonomy, while poor decisions create technical debt requiring expensive refactoring or premature rebuilds.
Modern website architecture spans two primary approaches:
- Monolithic platforms: Traditional CMSs like WordPress or Sitecore with tightly coupled content, presentation, and business logic
- Composable architectures: Headless CMS, separate frontend frameworks, and API-driven integrations
Today's architectural decisions determine your website's capabilities for the next 3-5 years.
7. Do we need a monolithic platform or a composable architecture?
This question helps you evaluate the fundamental tradeoff between simplicity and flexibility. Monolithic platforms offer faster initial implementation and require less technical sophistication, while composable architectures provide greater flexibility but demand more mature development practices.
Assess your team's technical capacity:
- Do you have experienced developers comfortable with APIs and microservices?
- How frequently do you need to integrate new tools or adapt to changing requirements?
Composable architectures require organizational maturity—advanced content operations, mature DevOps capabilities, and microservices experience.
8. How will this architecture support changes without developer involvement?
The goal is marketing autonomy for appropriate tasks—launching campaigns, updating content, creating landing pages—without sacrificing technical quality or brand consistency.
Map your team's current workflow friction points:
- Which marketing activities currently require developer intervention?
- How long do these requests typically take?
Then evaluate whether your proposed architecture addresses these constraints through component-based design, role-based CMS access, and pre-built templates that enable self-service within guardrails.
9. What integrations must the website support now and in the next two years?
This question prevents the costly mistake of selecting a platform before understanding integration requirements—a common error that forces expensive workarounds or platform migrations later.
To answer this comprehensively, inventory your current technology stack and planned additions:
- Which CRM system (Salesforce, HubSpot) must receive lead data in real-time? What marketing automation platform drives nurture campaigns?
- Which analytics systems need event tracking?
- What digital asset management system controls brand assets?
- Are you planning new tools for personalization, account-based marketing, or customer data platforms in the future?
Your architecture must support both synchronous integrations (real-time data flow) and asynchronous workflows (event-driven processes) while maintaining security and compliance standards.
10. How will we add new page types, campaigns, or products without rebuilding?
To ensure your architecture supports this flexibility, start by defining your expected evolution:
- How frequently do you launch new products or campaigns?
- What content types do you need beyond your current inventory?
- How do these content types relate to each other?
Scalable architectures require component-based content modeling that treats content as structured, reusable blocks rather than one-off page designs. This enables rapid assembly while maintaining brand consistency and technical quality.
Content Strategy Questions
Content architecture decisions should drive technology selection, not vice versa—yet redesign projects frequently invert this principle with costly consequences. Organizations that select a CMS before defining their content model discover critical limitations months into implementation:
- Unsupported taxonomies
- Incompatible content relationships
- Workflows requiring constant workarounds
Consider what happens when an enterprise selects a headless CMS for flexibility without first defining how product information, case studies, and technical documentation should be structured as reusable content blocks. Six months into implementation, they discover their content model can't support the planned personalization strategy, forcing platform migration or abandoning objectives. This repeats because technology decisions feel concrete and decisive, while content architecture appears abstract and deferrable—until constraints emerge.
Starting with content modeling workshops that map business requirements to content types, define relationships, and establish governance rules before evaluating platforms ensures technology supports content strategy rather than constraining it.
11. What content migrates, what gets rewritten, and what gets retired?
This question forces a strategic content audit rather than the default assumption that everything migrates unchanged—an approach that perpetuates existing problems and bloats your new site with outdated material. Many organizations discover too late that migrating content "as-is" transfers technical debt, SEO penalties from thin content, and messaging that no longer aligns with current positioning.
To answer this systematically, evaluate each content asset across multiple dimensions:
- What business value does it provide today?
- What SEO value does it hold based on current traffic and rankings?
- Does the content quality meet your current standards?
- Is it technically compatible with your new platform?
Based on this evaluation, categorize content into four decision paths:
- Migrate unchanged
- Migrate with updates
- Consolidate with similar content
- Archive
Phase rollouts that prioritize high-value content first, enabling early wins while managing migration risk.
12. How should our information architecture reflect how buyers actually navigate?
This question challenges the common mistake of structuring websites around internal organizational hierarchies rather than external buyer needs—a pattern that creates friction for prospects trying to find relevant information.
B2B information architecture must often serve multiple stakeholder roles simultaneously:
- Technical evaluators seeking specifications,
- Business decision-makers requiring ROI calculators,
- End users wanting implementation guidance
This necessitates parallel navigation paths, cross-referenced content architectures, and a site structure that balances these competing needs.
To answer this effectively, you must understand your buyers' mental models:
- How do they categorize your offerings?
- What questions drive their research?
- Which information do they need at different buying stages?
This requires user research beyond stakeholder opinions:
- Analyze search queries to understand buyer language,
- Conduct card sorting exercises to reveal natural categorization patterns
- Review session recordings to identify navigation friction points
- Interview recent customers about their research journey
Team Enablement Questions
A website's value extends far beyond its launch when the right team dynamics are in place. Yet many organizations struggle with a fundamental tension: marketing teams need velocity to respond to market opportunities, while technical dependencies create bottlenecks that slow execution.
Consider a common scenario. A product launch requires a new landing page. Marketing drafts content and provides specifications, but implementation depends on developer availability, QA cycles, and deployment windows. What should take hours stretches into weeks, missing launch windows and reducing campaign effectiveness. Meanwhile, competitors move faster.
This pattern repeats across organizations, raising critical questions about how teams should work together, what authority different groups need, and how technical architecture either enables or constrains marketing execution. The balance between autonomy and control, speed and quality, marketing independence and technical governance determines whether your website becomes a strategic asset or an operational bottleneck.
The following questions help clarify what your organization needs: how to structure team responsibilities, what capabilities different groups require, and how to build systems that support both marketing velocity and technical excellence.
13. What can marketing do independently, and what requires engineering?
Establish clear boundaries between marketing self-service and engineering ownership. The right boundary varies by organization:
- What technical skills do your marketing teams possess?
- How frequently do you need to launch campaigns or update content?
Some organizations empower marketing to control all content and page creation within pre-built templates, while others restrict marketing updates to specific content types with engineering oversight on structural changes. Map your current friction points, assess your team capabilities honestly, and design boundaries that balance velocity with appropriate governance.
14. How will we train teams and ensure ongoing competency?
One-time launch training rarely suffices; teams need ongoing support as they encounter new scenarios and as platforms evolve. Design a multi-phase approach:
- Start with stakeholder alignment on autonomy goals and success criteria
- Provide platform-specific training organized by marketing role and common tasks rather than technical system architecture
- Establish ongoing support mechanisms like monthly office hours, a searchable knowledge base with role-based documentation, and a Slack channel for quick questions
15. How will we maintain brand consistency as multiple people edit the site?
The solution isn't restricting access, which recreates bottlenecks, but rather building systems that enforce standards automatically. Implement a component-based design system where pre-built, brand-compliant components are the building blocks for all pages—similar to how LEGO pieces enable creative assembly while maintaining consistent quality. Use centralized design repositories, marketing-accessible component catalogs, and design tokens (systemized colors, typography, spacing) that prevent brand drift through code rather than policy.
Measurement & Optimization Questions
Companies that build testing and improvement into their process from day one see much better results than those who launch and walk away.
Your website isn't finished when it launches—that's when the real work begins. You start with a baseline, then make small improvements: better headlines, clearer buttons, shorter forms. Each tweak gets a few more people to convert, and over a year, those small wins add up to big gains.
16. What tracking and analytics infrastructure do we need from day one?
Build measurement capabilities into your architecture from the start rather than retrofitting them later. Define your measurement requirements before selecting analytics tools by asking these questions:
- What account-based tracking capabilities do you need to identify and score target companies?
- Which multi-touch attribution model reflects your actual sales cycle spanning multiple touchpoints over months?
- How will you connect website engagement with CRM pipeline data to calculate true ROI?
17. How will we run experiments and A/B tests post-launch?
Without experimentation capabilities, you're limited to opinion-based changes and can't systematically improve performance over time. For B2B contexts, recognize that your testing approach must differ from B2C given lower traffic volumes and longer conversion cycles:
- Focus on A/B tests rather than complex multivariate experiments that require massive sample sizes
- Prioritize high-impact elements like value propositions, calls-to-action, and form friction over minor design tweaks
- Plan for longer test durations to achieve statistical significance
Your platform selection should support custom conversion goal setup beyond standard analytics events, segment-specific testing that targets enterprise visitors differently than SMB prospects, and multi-page funnel tracking that captures B2B buyer journeys spanning multiple sessions.
18. What's our process for identifying and acting on optimization opportunities?
Once your tracking infrastructure is in place, you need a process for testing improvements. Without testing capabilities, you're stuck making changes based on gut feelings instead of data. You can't know what actually works.
B2B testing looks different from B2C because you have fewer visitors and longer buying cycles. Adjust your approach accordingly:
- Keep tests simple: Stick to A/B tests comparing two versions. Complex tests with multiple variables need huge traffic volumes you probably don't have.
- Test what matters most: Focus on headlines, button copy, and form length—not minor design tweaks like icon styles or font weights.
- Be patient: B2B tests take longer to reach meaningful results. Plan for weeks, not days.
When choosing a testing platform, make sure it can:
- Track conversions beyond basic page views (like demo requests or content downloads)
- Test different experiences for different audience segments (enterprise vs. small business visitors)
- Follow visitors across multiple pages, since B2B buyers rarely convert in a single session
From Questions to Strategic Outcomes: Building Your High-Performance Website
The difference between a redesign that drives growth and one that requires replacement comes down to the questions asked upfront.
- Strategic alignment questions connect the redesign to business outcomes.
- Governance questions prevent post-launch chaos.
- Architecture questions determine whether the site scales with the business.
- Content strategy questions ensure information serves buyer needs.
- Team enablement questions ensure autonomous marketing execution.
- Measurement questions establish the foundation for continuous improvement.
A website redesign is an opportunity to build strategic website infrastructure, not just refresh visuals. The right questions transform the process from a time-bound project into the foundation of a continuously optimized system that compounds value over time. Understanding website ROI helps quantify these outcomes and justify strategic investments.
Ready to ask the right questions? Talk to Webstacks about designing your strategic website approach.
