The demand letter/lawsuit lands first. The questions come next.

“Why didn’t anyone tell me?” one or more of the CEO / COO / CFO / Corporate Counsel asks, genuinely surprised.

If you work in accessibility leadership, you already know the answer. You told them about the website’s/product’s accessibility problems, likely multiple times. You documented the risks, flagged the exposures, and asked for time, budget, or prioritization to address them. What you did not get was their agreement to solve the problem.

This moment is not rare. It is a pattern.

Most executives are not openly hostile to accessibility. Very few people are antisocial enough that they wake up in the morning and say, “I want to bleep over a disabled customer today.” What leaders are, instead, are optimistic, growth-focused, with an eagle eye on new product features. They are also deeply averse to conversations that signal product risk, delay, or increased costs. Anything that prevents them from getting to market with the “next great feature” ahead of their competitors is to be avoided like the bubonic plague. Thus, this is the predictable outcome: Executives treat accessibility issues as abstract and “things that happen to other companies” until they arrive as legal filings, regulator inquiries, lost sales, or public complaints, bringing bad PR to their front door.

When that happens, the organizational script kicks in, where people start screaming about how this could have happened and the need for better processes rather than accountability at the executive level for solving the problem when it was first raised. Accessibility managers live in this gap between what was known and what was acknowledged. Over time, most of us have firsthand experience that success in our roles has less to do with being correct and more with being heard. Here are a few ideas for how to do that.

Stop relying on a single communication channel

Accessibility risks rarely happen because they are undocumented. They happen because decision-makers found them easy to ignore.

• If long emails disappear into inboxes, shift the message into a short leadership standup with a clear ask.

• If meetings keep getting postponed, send a one-page brief that tracks who has opened the file.

• If that doesn’t work, send a narrowly-tailored email that explicitly states what decision is needed and by when.

Accessibility issues need to be framed as decisions, with a minimum of background information to avoid bogging things down.

Sometimes silence means they are avoiding the issue, not disagreeing with you.

Persistence is critical.

Make the problem concrete and bounded

High-level, abstract warnings like “we are exposed under the ADA” or “this does not meet WCAG” are begging to be ignored. They feel large, vague, and expensive.

Specifics change the conversation. Use details based on “object - verb - impact” sentence structure, such as:

• This checkout flow blocks keyboard users from completing a purchase.

• The PDF prevents screen reader users from accessing required disclosures, meaning they aren’t really consenting.

• When the French Government contract comes up for renewal, it may be canceled because we aren't following the European Accessibility Act.

Then, if you can, follow up that statement by drawing a parallel between your situation and a very expensive and highly similar litigation that did not go well for the defending party.

Small, concrete problems create the possibility of action.

Broad alarms create room for delay.

Pair the risk with a path forward (aka don’t raise issues without solutions)

Raising accessibility risk without a proposed next step often stalls. Sometimes executives engage only when they can see a route that does not end in paralysis.

Frame your message as a sequence.
1) Here is the risk.
2) Here is who is affected.
3) Here is the business impact for the worst-case scenario.
4) Here is the specific action I am asking you to approve.

(Note: this format is identical to the IRAC format every law student is taught, Issue, Risk, Application, Conclusion)

Accessibility progress is more likely happen when it is presented as solvable work with a fixed investment, not an open-ended obligation.

Document to learn, not to win

Documentation matters, but not for the reason people assume. This is not about saying “I warned you” after the fact. You only get to say “I told you so” in your head. It is about identifying patterns in what gets traction and what does not.

Which formats get responses?
Which leaders engage when risk is framed in customer terms?
Which issues move only under external pressure?

That information lets you adjust your strategy before the next missed opportunity turns into a crisis.

The hard truth about accessibility leadership

You cannot force an organization to face accessibility reality before it is ready. You can, however, make that reality harder to dismiss by grounding it in user impact, business consequence, and clear decision points.

It is not accessibility leadership’s job to change a CEO’s personality or risk tolerance. It is our job to put critical accessibility information in front of executives before users, regulators, or the courts do. Sometimes, the best thing that can happen to an accessibility manager is for the organization to get sued, because nothing draws attention to an issue like huge legal bills and time away from product development to solve problems that could have been prevented.

If this sounds familiar, you are not alone.

Most senior accessibility professionals can name at least one demand letter or litigation disaster they have lived through that wouldn’t have happened if the recommendations in the email had been followed, the meeting containing the warning had actually happened, or the bug hadn’t been kicked into the next release.

The work continues anyway, because that’s who we are. We can’t solve the problems single-handedly; we can only raise awareness of the risks to decision-makers.