This checklist helps mission-driven organizations assess where their website actually stands before committing to any investment.
Most website frustration starts with the wrong diagnosis. An organization decides it needs a redesign when what it actually needs is a content update. Another commits to a full rebuild when targeted improvements would solve the real problem at a fraction of the cost. A third defers the decision entirely while the site continues to quietly underserve donors, funders, and community members.
This checklist is designed to help your organization arrive at the right diagnosis before committing resources. It is organized into five areas, each revealing a different dimension of your website’s current health. Work through it with your internal team before speaking with any web partner. The patterns that emerge will tell you more than a portfolio review or a sales conversation will.
A note on terms before you begin. A redesign updates the visual presentation and content of an existing site without replacing the underlying architecture. A rebuild replaces the entire structure from the foundation. Both are addressed in this checklist because the right answer depends on what you find, not on what you have already decided.
This section reveals whether your website still reflects the organization as it exists today, not as it was when the site was last built.
When someone visits your website for the first time, can they immediately understand what your organization does, who it serves, and what makes it distinct, without scrolling or clicking? Does your website reflect your current programs, leadership, and priorities, or does it describe the organization as it was two or three years ago?
If a major donor, a grant-maker, or a board candidate visited your site today without any prior knowledge of your organization, would they come away with an accurate and compelling picture of your work? Has your organization’s mission, audience, or strategic direction shifted significantly since the last time the website was built? Do your staff, leadership, and board members feel comfortable sending the website link to high-stakes audiences without qualification or apology?
If most answers are no, your website has an organizational fit problem. The structure and content no longer reflect who you are. A rebuild is likely warranted, one that begins with the Brand phase to resolve clarity before building begins.
If some answers are no, your website may need targeted content updates and structural adjustments rather than a full rebuild. A redesign focused on specific pages or sections may be sufficient.
If all answers are yes, the problem lies elsewhere in this checklist.
This section reveals whether your website is structured to serve the audiences that matter most, and whether each of them can find what they need.
Can a first-time visitor identify within five seconds whether your organization is relevant to them, without reading body copy? Does your website provide distinct, clear paths for your different audiences: donors, funders, program participants, community members, board members – or does everyone arrive at the same undifferentiated homepage? Is it immediately obvious how to give, partner, apply, register, or get involved for each audience that needs to take those actions?
Does your website use language your audiences actually recognize and search for, or internal organizational language that requires prior familiarity to understand? When you look at your website’s analytics, are the pages that matter most: donation pages, program pages, contact pages, receiving meaningful traffic and converting at reasonable rates?
If most answers are no, your website has an audience clarity problem. Visitors are arriving but not finding what they need. This can sometimes be addressed through a redesign of navigation and key pages without a full rebuild, depending on the underlying platform health.
If some answers are no, specific audience paths need attention. Targeted page rebuilds or navigation restructuring may resolve the issue without a full rebuild.
If all answers are yes, audience clarity is not the primary problem. Continue through the checklist.
This section reveals whether your website’s technical infrastructure is stable, secure, and capable of supporting what comes next.
Is your website running on a current, supported version of its platform – with plugins, themes, and core systems that are actively maintained and regularly updated? Does your website load in under three seconds on a mobile device on a standard connection? Has your website had a security incident, a plugin conflict, or a significant technical error in the past twelve months?
Do your staff feel confident making content updates, or do they hesitate because the backend feels fragile, confusing, or unreliable? Does your website meet current WCAG 2.1 AA accessibility standards, including keyboard navigation, color contrast, alt text, and screen reader compatibility? Is your website built on a multisite installation, a proprietary platform, or a heavily customized legacy system that creates ongoing maintenance complexity?
If most answers indicate problems, your website has a technical health problem. Surface updates and content changes will not solve it. A rebuild on a stable, maintainable platform is warranted, one where the Foundation phase addresses platform selection, security, accessibility, and technical infrastructure before any content work begins.
If one or two answers indicate problems, targeted technical remediation may be sufficient without a full rebuild. The SEO and AI Search Visibility Audit can identify specific technical issues and their impact.
If technical health is sound, the problem lies in content, structure, or visibility rather than the underlying platform.
This section reveals whether your website is visible to the right audiences through search and AI tools – before they ever visit the site directly.
If you search for your organization’s primary programs or services in Google – not by name but by what you do – does your website appear on the first page of results? If you ask ChatGPT, Perplexity, or Google AI Overview to recommend organizations doing your kind of work in your area, does your organization appear in the answer?
Do your key pages, homepage, program pages, about page – have sufficient depth and specificity for AI tools to accurately describe your organization’s work when asked? Does your website include FAQ sections on key pages that directly answer the questions your audiences are searching for? Has your website’s search traffic increased, stayed flat, or declined over the past twelve months?
If most answers indicate visibility problems, your website has a search and AI visibility gap. This can sometimes be addressed through content additions and structural improvements to existing pages without a full rebuild. The SEO and AI Search Visibility Audit is designed specifically for this situation – it identifies what is suppressing visibility and what changes would have the most impact.
If you are uncertain about any of these answers, Google Search Console provides free data on which queries are bringing visitors to your site and where your pages are ranking. Setting it up is a useful first step before making any investment decision.
This section reveals whether your website has the ongoing care infrastructure to remain healthy, or whether it is already decaying between projects.
Does your organization have a designated person responsible for content updates, and do they have the access and confidence to make those updates without external help? Is there an active maintenance plan in place covering plugin updates, security monitoring, backups, and performance checks – or is the site largely unmanaged between projects?
When was the last time your website’s plugins, theme, and core platform were updated? Does your organization know who to contact if something breaks – and is that contact relationship active and accessible? Is there a clear plan for how the website will evolve as your organization grows, adds programs, or changes direction?
If most answers indicate gaps, your website is at risk of accelerating decay regardless of how recently it was built. The Sunlight Monthly Retainer addresses ongoing care. If the maintenance gaps are combined with technical health problems identified in the previous section, a rebuild with an integrated care plan is the right path forward.
If care is largely in place, your website has the infrastructure to remain healthy. The problem, if one exists, is more likely in content, audience clarity, or visibility.
The five sections of this checklist tend to point toward one of five paths.
If your answers reveal mostly organizational fit and audience clarity problems, your website’s structure and content no longer serve the organization as it exists today. A full rebuild through the Website Masterpiece Journey is likely the right investment, one that begins with the Brand phase to resolve clarity before building begins.
If your answers reveal mostly technical health problems, surface updates will not solve what is wrong. A rebuild on a stable, maintainable platform is warranted. The Foundation phase of the Website Masterpiece Journey addresses platform selection, security, accessibility, and technical infrastructure before any content work begins.
If your answers reveal mostly search and AI visibility problems, your website exists and may be structurally sound, but the right audiences are not finding it. The SEO and AI Search Visibility Audit is the right first step, it identifies specifically what is suppressing visibility and what changes would have the most impact.
If your answers reveal mostly maintenance and longevity gaps, your website needs a care plan more than a rebuild. The Sunlight Monthly Retainer provides consistent, documented maintenance that prevents a sound website from decaying back into the problems this checklist identified.
If your answers reveal mixed results across multiple areas, which is the most common pattern for established organizations whose websites have been in place for two or more years without structured care, the Executive Website Clarity Assessment is designed for exactly this situation. It provides a structured, objective evaluation of your current site across all five dimensions of this checklist, with a clear recommendation before you commit budget or board approval.
Take this checklist into your next internal conversation before reaching out to any web partner. The patterns it reveals will help you ask better questions, evaluate proposals more accurately, and make a more confident investment decision.
If you want an objective, expert evaluation of where your website stands across all five areas, with specific recommendations and a written report you can use internally, the Executive Website Clarity Assessment provides exactly that before any build begins.
A redesign updates the visual presentation and content of an existing website without replacing the underlying architecture. A rebuild replaces the entire structure from the foundation: platform, architecture, navigation, and content systems – and builds a new site that serves the organization’s current needs.
A redesign is appropriate when the underlying structure is sound and the system is maintainable. A rebuild is warranted when the structure itself is the problem, when staff hesitate to make updates, when the platform is outdated, or when the site no longer reflects the organization as it exists today.
Work through the five areas of this checklist with your internal team. If the problems you identify are primarily in the first two areas: organizational fit and audience clarity – a rebuild is likely warranted because these problems are structural. If the problems are primarily visual or content-based and the underlying platform is sound, a redesign may be sufficient. If you are uncertain after completing the checklist, the Executive Website Clarity Assessment provides an objective, expert evaluation before you commit.
Yes. The five areas of this checklist align with the kind of technology needs assessment that capacity-building grant applications typically require. Documenting your answers, particularly the technical health, visibility, and maintenance sections, provides a structured picture of current gaps and the case for investment. The Executive Website Clarity Assessment report provides a more formal, third-party version of this documentation that can be attached directly to a grant application.
Once per year at minimum, ideally as part of an annual planning or budget process. Organizations that review their website health annually catch problems earlier, make smaller and less expensive corrections, and avoid the compounding technical debt that eventually requires a full rebuild. Organizations with active maintenance through the Sunlight Monthly Retainer receive ongoing monitoring that surfaces most technical health issues before they become visible to visitors.
Disagreement among internal stakeholders about website health is itself useful information. It usually signals that the website is serving some audiences or priorities better than others, and that the organization has not yet reached internal alignment about what the website’s primary purpose should be.
The Executive Website Clarity Assessment is particularly useful in this situation because it provides an objective, third-party picture that gives leadership a common starting point rather than competing internal opinions.
The checklist is written specifically for museums, nonprofits, cultural institutions, healthcare organizations, and mission-driven organizations – audiences that serve multiple stakeholders simultaneously, operate in high-trust environments, and have governance structures that affect how website decisions are made.
The principles apply broadly to any organization, but the framing and the implications of each area are calibrated for mission-driven environments where credibility, accessibility, and long-term institutional trust carry more weight than conversion optimization.
A formatted, printable version of this checklist – designed to be shared internally with your leadership team, board, or communications committee before a website decision begins.
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