Questions The CEO Should Be Asking About Their Website (But Rarely Does) via @sejournal, @billhunt

Few CEOs ever ask hard questions about their company website. They’ll sign off on multimillion-dollar redesigns, approve ad budgets, and endorse “digital transformation” plans, but rarely ask how much enterprise value their digital infrastructure is actually creating.

That’s a problem, because the website is no longer a marketing artifact. It’s the factory floor of digital value creation. Every lead, sale, customer interaction, and data signal runs through it. When the site performs well, it compounds growth. When it underperforms, it silently leaks shareholder value.

Executives don’t need to understand HTML or crawl budgets. But they do need to ask sharper questions.  They need to ask the kind that expose hidden risk, surface inefficiencies, and align digital investments with measurable business outcomes. In the age of AI-driven search, where visibility and trust are determined algorithmically, these questions aren’t optional. They’re fiduciary.

Why CEOs Must Ask – Even If SEO’s Believe It Is “Beneath” Them

There’s a persistent misconception in digital circles: that CEOs shouldn’t concern themselves with SEO, site performance, or technical issues. “That’s marketing’s job,” people say. But the truth is, these issues directly affect the metrics that boards and investors care about most – operating margin, revenue growth, capital efficiency, and risk mitigation.

When a website is treated as an expense line rather than a capital asset, accountability disappears. Teams chase traffic over value, marketing spend rises to offset organic losses, and executives are left with fragmented data that hides the real cost of inefficiency.

A CEO’s job isn’t to approve color palettes or keyword lists. It’s to ensure the digital infrastructure is producing measurable returns on invested capital just as they would for a factory, logistics system, or data center.

The Cost Of Not Asking

Every company has a “digital balance sheet,” even if it’s never been documented. Behind every campaign and click lies a network of dependencies, from page speed and content accuracy to structured data, discoverability, and cross-market alignment. When those systems falter, the losses are invisible but compounding:

In one multinational I audited, over $5 million per month in paid search spend was compensating for lost organic traffic caused by broken hreflang tags and indexation gaps.

A similar disconnect played out publicly when the CMO of a major retail brand was asked during an earnings call about their online holiday strategy. He confidently declared, “As the largest reseller in our category, we’ll dominate the season online.” Within seconds, a reporter searched the category term, and the brand didn’t appear on page one. The CMO was stunned. He had assumed offline dominance guaranteed online visibility. It didn’t.

That thirty-second fact-check illustrated a billion-dollar truth: market leadership offline doesn’t ensure findability online. Without the right questions and governance, digital equity erodes silently until someone outside the company exposes it.

No CEO would tolerate that level of inefficiency in their supply chain. Yet it happens online every day, unnoticed, because few know which questions to ask.

The 10 Questions Every CEO Should Be Asking

These questions aren’t tactical; they’re financial. They surface whether the digital system that represents your brand to the world is operating efficiently, effectively, and in alignment with corporate goals.

Each question reframes a “marketing” issue as a governance issue. When CEOs ask these questions, they encourage teams to think systemically, connecting content, code, and conversion as interdependent components of a single digital value chain.

From Questions To Action: Building A Culture Of Digital Accountability

Asking the right questions isn’t micromanagement – it’s leadership through intent.

When a CEO defines the Commander’s Intent for digital, it brings clarity of purpose, alignment of teams, and shared metrics, and it changes how the organization approaches the web. Instead of chasing redesigns or vanity KPIs, teams operate with a shared understanding:

“Our website’s job is to create enterprise value – measurable, sustainable, and scalable.”

That intent cascades into structure:

This is where the Web Effectiveness Score or Digital Value Creation Framework bridges web metrics (load time, index coverage) to enterprise KPIs (ROIC, margin, growth). Once that link is visible, executives start managing digital performance as a financial asset because it is.

The CEO’s Digital Playbook

CEOs who ask these questions consistently outperform those who don’t – not because they know more about SEO, but because they lead with system awareness. When they do:

Wasted Spend Decreases.
Duplicative content, overlapping agencies, and redundant tools are identified and rationalized.

Visibility and Trust Increase.
Content becomes findable, structured, and cited by both search engines and generative AI.

Risk Declines.
Technical debt, migration shocks, and compliance failures are detected early.

Innovation Accelerates.
Modular systems and shared data layers enable faster experimentation.

Enterprise Value Compounds.
Web performance improvements flow into revenue growth and cost efficiency.

This is the same logic CFOs apply to physical assets. The only difference is that digital assets rarely appear on the balance sheet, so their underperformance remains invisible until a crisis.

Why Now: The AI Search Inflection Point

The rise of generative search makes these questions urgent. Search is no longer a static list of links; it’s a recommendation system. AI engines evaluate authority, trust, and structured data across the web to synthesize answers.

If your website isn’t structured, trusted, and machine-readable, your company risks digital disintermediation and being invisible in the ecosystems that shape decisions. For CEOs, that’s not a marketing problem; it’s an enterprise risk.

As AI systems determine which brands get cited and recommended, your digital infrastructure becomes the new supply chain for relevance and reputation.

Final Thought

The CEOs who win the next decade won’t outspend their competitors – they’ll out-align them. They’ll treat digital infrastructure with the same financial discipline as physical assets, measure contribution instead of activity, and lead teams to think in systems rather than silos.

Every boardroom already measures financial capital. It’s time to start measuring digital capital, and your website is where it compounds.

In the AI era, your website isn’t just how people find you.
It’s how machines define you.

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Featured Image: Master1305/Shutterstock