Is Your Content Answering the Wrong Questions?

Your content says one thing. Their questions say another. The gap costs you conversions.

Your prospects have questions. Real ones. The kind they type into Perplexity (Google on Steroids without the ads) at 2 a.m. or ask on sales calls if prompted. But here's the thing: Most content answers the questions you wish they'd ask instead.

That gap? It's killing your conversions.

It happens because teams are scared of being boxed in. So they stretch their message to cover everything, creating content that helps exactly nobody. Meanwhile, your prospects aren't searching for "which brand can help me." They're typing specific problems into Google. Problem resolution at the expertise level. Not your brand story.

The Three-Minute Reality Check

Try this right now:

• Pull your three most-visited content pieces.

• List the questions they answer.

• Compare those with the last five questions real prospects actually asked you.

Found a mismatch? You're not alone.

Why This Matters (With Numbers That Sting)

Content gaps aren't just annoying. They're expensive. The Content Marketing Institute found that misaligned content ranks as a top reason marketers fail to connect with buyers. Think about that. All those hours writing. All that budget. Wasted because you're answering phantom questions.

Here's the price tag: Nearly half of CMOs say marketing is viewed as an expense rather than a strategic investment, according to Gartner's 2024 research. When your content answers phantom questions, even your own C-suite stops believing in what you do.

But fix it? Different story.

I worked with an enterprise software client who wanted more inbound leads. So I asked their top sales guy to tell me the 10 most frequently asked questions he gets when talking to prospects.

It was like pulling teeth.

But after repeated requests – framed around a new sales deck we were building and reverse engineering it (writing the questions from the presentation’s bullet points) – we published a 10-question FAQ that’s generated some calls for a company that only needs a few new clients per year.

Why is this so important? Marcus Sheridan’s research (author of Endless Customers, an evolution of They Ask You Answer) shows 70% of buying decisions happen before prospects ever talk to sales. If you don’t answer their questions, someone else will.

Providing thorough, transparent answers, covering topics such as cost, potential drawbacks, comparisons, reviews, and the best options, empowers customers to complete their pre-purchase research on their own terms. In today’s marketplace, people want to arrive at the first conversation feeling fully informed and confident in their decision.

I see far too many companies touting product features and benefits when their prospects want implementation timelines, integration headaches, and ROI. Are you publishing methodology content? It doesn’t matter how well written it is, your prospects want clear answers about how they’re going to sell the investment to the CFO and CEO.

Where do you start? Ask your sales and marketing teams what questions they get. I’ll bet the sales guys have different answers than the marketers.

The LinkedIn Version of This Problem

This problem isn’t just on your website. Pull up your LinkedIn profile right now. You're showcasing strategic vision and technical prowess. Meanwhile, recruiters scan for concrete achievements and measurable impact, not a job description or a marketing description of your previous employer (assuming you’re even filling out the experience section. If your profile reads like a capabilities deck instead of a results scorecard, you're invisible to the people who matter.

At Bank of America, we were asked to focus our year-end reviews on WHAT an employee accomplished (results, KPIs, and objectives) and HOW those results were achieved (behaviors, teamwork, and qualitative factors).

I’ve adopted this approach to helping clients with their LinkedIn profiles. We cover the HOW in the About section and focus on impact. The WHAT goes in the Experience section.

When applying for a job, I urge these clients to research the problems their target employer has and make sure their resume includes specific examples, where possible, of the hiring manager’s pain points and how the client can resolve them.

Remember: People don't search for visionaries. They search for someone who solved their exact problem before.

The Fix: Listen, Audit, Align

• Listen first. Not to what you think they need. To what they actually ask. Sales calls. Support tickets. Social media complaints. That's your content goldmine. Your prospects are literally telling you what to write.

• Audit regularly. Monthly, compare your top content with real customer questions. Use Search Console to see what people type before they find you (or don't). Check your site search logs. Those queries? They're your content roadmap.

• Align ruthlessly. Kill content that doesn't answer real questions. Yes, even that piece you love. Update what's salvageable. Create what's missing. Your LinkedIn profile needs the same surgery. Replace vision statements with victory stories.

The Uncomfortable Truth

Most content exists because someone thought it should exist. Not because anyone asked for it. That white paper about your company values? Nobody's downloading it. The blog post about industry trends from 2019? It's brand garbage now.

Your audience doesn't care about your mission statement. They truly do not. They care about their problems. Their deadlines. Their budgets. Their bosses breathing down their necks.

Good content answers the question behind the question. When someone asks about price, they're really asking about value. When they ask about features, they want to know about their specific problem. Answer what they mean, not just what they say.

The Bottom Line

Every piece of content should pass this test: Did a real human actually ask for this answer? If not, why does it exist?

Need help finding those real questions and clearing out your content closet? That's where a communication audit starts. No assumptions. Just what your audience actually wants to know.

If You Want to Go It Alone on AI:

Prompt 1: Question Mining from Sales Calls "I'm going to paste a transcript from a sales call. Identify every question the prospect asks (both explicit and implied). Then categorize them as: Technical, Timeline, Budget, ROI, or Implementation. Finally, tell me which questions reveal the deepest concerns. Here's the transcript: [PASTE]"

Prompt 2: Content Gap Analyzer "Compare these two lists. List A contains the titles of my top 10 blog posts. List B contains actual customer questions from the past month. Identify: (1) Which blog posts answer no actual questions, (2) Which questions have no corresponding content, (3) What new content I should create first based on question frequency.

List A: [PASTE TITLES] List B: [PASTE QUESTIONS]"

If this hits close to home, let's talk. I help experienced executives cut through the Brand Garbage and get seen for the value they actually bring. And if you’re interested in a one-page summary of my From Brand Garbage to Communications Windex tips, just hit the Contact button above and ask.