10 Critical Marketing Questions To Help Fix What’s Not Working
Executive Summary
If your marketing and sales are not delivering the way you expected, the issue is usually a few blind spots you cannot see from the inside. This article gives you ten honest questions to ask about your website, your content, your transparency around pricing, your use of video, your data, and how well your teams work together. They are not about pointing fingers, they are about creating clarity. Work through them and you will know exactly where the gaps are and what to fix first.
If you’re a business leader, you already know how hard it is to juggle priorities. You’re focused on driving results, but maybe you’re feeling stuck or unsure why your marketing and sales efforts aren’t delivering as expected.
The truth is, most businesses have blind spots in their strategy—and addressing them is the key to unlocking growth.
That’s where these 10 questions come in.
They’re designed to help you reflect on what’s working, where you might be falling short, and what you can do to fix it.
Let’s dig in.
1. Do your potential customers know what it’s like to work with you before they even pick up the phone?
Think about whether your website and content help them feel confident and informed before a conversation.
Or are you finding that customers come to you confused or hesitant because they don’t fully understand what you offer?
Why this matters: First impressions are everything. Your content needs to set the stage by answering basic questions, building trust, and reducing hesitation. If they don’t feel informed or assured, they might not engage at all. First impressions often determine whether a potential customer trusts you enough to move forward. If your content leaves them guessing, you’re likely losing opportunities.
2. Can your team confidently explain what makes your business the right choice—and back it up with content that answers buyer questions?
Are you addressing their concerns about pricing, comparisons, or even competitors?
Or are you relying on vague messaging and hoping buyers figure it out themselves?
Why this matters: Buyers crave clarity and assurance. When your team has the tools and messaging to answer questions confidently, you position yourself as the obvious choice and build trust. Buyers want clarity and honesty. If your team can’t articulate your value, it’s hard to stand out in a crowded market.
3. When a potential customer lands on your website, can they easily find what they need to make a decision?
Is your site clear and user-friendly, with answers to questions like pricing and next steps?
Or are they leaving frustrated because the information they need isn’t there?
Why this matters: It’s not about the graphics, theme, or look and feel—despite what many agencies might tell you. What truly matters is the purpose of your site, its ease of use, the value of the content, and how well it serves your customer’s needs. If your site doesn’t provide clarity and value, the most beautiful design won’t keep prospects from walking away.
4. Are you consistently creating content that directly addresses what your customers ask during sales conversations?
If not, what would it take to turn those conversations into tools that help you close deals faster?
Or are you repeating yourself in every sales call because those answers aren’t available elsewhere?
Why this matters: Answering recurring questions through content saves time for both your team and your prospects. It helps your sales team close faster and positions you as a thoughtful, customer-focused business. Great content isn’t just for marketing—it should support your sales team, saving time and building trust with prospects.
5. Does your team use content—like articles or videos—to educate prospects before meetings?
This can save time and make sales conversations more productive.
Or are your sales calls starting from scratch, spending valuable time covering the basics?
Why this matters: Educated prospects are more confident and prepared, which means faster decisions and smoother sales conversations. Providing this content ahead of time sets a professional tone and respects everyone’s time. Educated buyers make better decisions faster. Content that informs them upfront leads to more productive conversations.
6. Are you addressing the topics most businesses avoid, like pricing or honest comparisons to competitors?
Being upfront can set you apart and build trust with potential buyers.
Or are you avoiding these conversations, using terms like “contact us for pricing” , and leaving buyers to guess or look elsewhere for answers?
Why this matters: Transparency isn’t just about honesty; it’s a competitive advantage. When you tackle these topics head-on, you establish credibility and reduce friction in the buying process. Transparency builds trust. Avoiding these topics makes you seem less credible and pushes buyers to your competition.
7. Do your customers see and hear from your team before they meet them?
Videos, like team bios or product demos, can make your business feel more approachable and real.
Or are you relying on cold calls and emails to make a first impression?
Why this matters: Video builds familiarity and trust before prospects even talk to you. It humanizes your business and reduces the anxiety of the unknown, creating a smoother start to the relationship. People buy from people they trust. Video humanizes your business and builds that trust before the first conversation.
8. Are you confident that your relationship with outside agencies is productive, aligned with your goals, and keeps you in control?
Do you feel they’re helping you build internal capabilities and drive results?
Or is the relationship fostering greater dependence and unclear ROI?
Why this matters: Agencies should empower your team, not create reliance. If they’re not building your internal capabilities, you’re missing opportunities for long-term success.
9. Are you tracking how your content impacts leads and sales?
If you’re not looking at the data, how do you know if it’s working?
Or are you making decisions based on guesswork and gut feelings?
Why this matters: Without data, it’s impossible to know if your efforts are paying off or where to improve. Tracking helps you spend your time and resources where they’ll have the most impact. Data tells the real story. Without it, you’re flying blind and risking wasted time and resources.
10. Is everyone on your team aligned on how marketing and sales should work together?
Misalignment is one of the biggest reasons efforts don’t deliver results.
Or are your teams working in silos, missing opportunities to collaborate and drive results?
Why this matters: Alignment means better communication, fewer dropped leads, and a shared focus on revenue. When teams are in sync, the results are more consistent and impactful. When marketing and sales work as one team, the results are exponentially better. Misalignment leads to missed opportunities and wasted effort.
Why These Questions Matter
These questions aren’t about pointing fingers; they’re about creating clarity. If you’re not seeing the results you want, it’s worth asking yourself: Are we focused on the right things? More importantly, are we doing them well?
By reflecting on these areas, you can uncover gaps and start making meaningful changes. You don’t have to tackle this alone—sometimes, an outside perspective can help you see what’s not working and create a plan to fix it.
Let’s Talk
If these questions got you thinking about areas where your business could improve, let’s have a conversation. Together, we’ll identify what’s working, address what’s not, and create a strategy that gets your marketing and sales efforts moving in the right direction.
Common Questions
There are ten questions here. Where do I start?
You do not have to tackle all ten at once. Read through them, notice which ones make you pause or feel a little uncomfortable, and start there. Those are usually pointing at your real blind spots. The goal is clarity, not a perfect score, so pick the gap that would make the biggest difference and work on that first.
Do I really need to put pricing on my website?
Being upfront about the topics most businesses avoid, like pricing and honest comparisons, is a competitive advantage. When you tackle these head-on, you build credibility and reduce friction in the buying process. Hiding behind “contact us for pricing” tends to make you seem less credible and pushes buyers to go look for answers elsewhere.
What if answering these makes me feel behind?
That feeling is common and it is not a reason to worry. These questions are meant to create clarity, not to make you feel like you are failing. Most businesses have gaps in their strategy, and simply seeing them is the first step to closing them. You also do not have to figure it all out alone, since an outside perspective often spots what is hard to see from inside.
My website looks great. Is that enough?
Not on its own. As Cary puts it, it is not about the graphics, theme, or look and feel, despite what many agencies might tell you. What matters is whether your site is clear, easy to use, and genuinely helpful in answering the questions a buyer has, like pricing and next steps. The most beautiful design will not keep prospects from leaving if they cannot find what they need.
Related Resources
Defining Your Marketing Priorities – Cary’s Clarity Circles
Once these questions surface the gaps, this helps you decide which to tackle first.
10 Simplified Rules of Marketing
If you want a simple yardstick alongside the questions, these rules give you one.
Business Leaders – You Know More About Marketing Than You Think
If answering these makes you feel behind, this is a reminder you know more than you think.