How to Diagnose Why Your Sales Are Actually Failing

There's a version of sales advice that sounds something like this: "Post more often. Run better ads. Fix your pricing." Again, not wrong, but rarely the actual problem.

When sales stall, most entrepreneurs reach for tactics. They tweak their Instagram strategy, rewrite their website copy, or launch another promotion. Busy work that feels productive but doesn't solve anything. Because tactics can't fix a problem you haven't properly diagnosed.

I learned this during a quarter when I was posting consistently, getting engagement, and hearing "I love this!" in the DMs. But the sales? Silent. I kept adjusting surface-level things, convinced the next tweak would be the one. Spoiler: it wasn't.

The breakthrough came when I stopped trying to fix the sales and started examining what was actually happening at every point in the buyer's journey. Turned out, my offer was clear to me but confusing to everyone else. They loved the content but couldn't connect it to what I was selling. No amount of better posting was going to solve that.

Sales problems hide. They disguise themselves as marketing problems, pricing problems, or timing problems. But when you dig into what's really happening, you usually find something more specific and fixable.

Why Sales Diagnostics Matter More Than Sales Tactics

Most sales advice assumes you know where the breakdown is. It tells you to "optimize your funnel" or "improve your close rate" without first asking whether people even understand what you're offering or if they're the right people in the first place.

Running tactics on top of a misdiagnosed problem just amplifies the wrong thing. I've watched entrepreneurs spend thousands on ads driving traffic to offers nobody wanted. I've seen beautiful sales pages that converted zero people because the targeting was completely off. I've been that entrepreneur.

A diagnostic approach means you pause before you fix. You look at the data, the patterns, and the actual behavior of the people you're trying to reach. You identify where the system is breaking down so you can address the real issue, not just the loudest symptom.

Sales diagnostics aren't glamorous, but they're what separate entrepreneurs who are guessing from entrepreneurs who are building something sustainable.

The Five Places Sales Actually Break Down

When I work through a sales problem, I look at five specific points where things tend to fall apart. Not every business struggles with all five, but almost every stalled sale can be traced back to at least one.

01: Targeting

You could have the best offer in the world, but if you're showing it to people who don't need it, care about it, or have the capacity to buy it, nothing else matters.

Targeting problems show up as lots of interest but no conversions. People engage with your content, they ask questions, but they don't buy. Or they buy and immediately request refunds because they didn't understand what they were getting into.

I worked with a client who was getting strong engagement on her content but zero sales. When we examined who was actually following her, we discovered her audience was earlier in their journey than she realized. They liked her ideas but weren't in a position to implement them. Once she shifted her targeting to match the actual readiness of her market, the sales followed.

02: Offer Clarity

If someone has to work hard to understand what you're selling, they won't buy it. Offer clarity means a potential buyer can land on your page and within 30 seconds know exactly what they're getting, who it's for, and what problem it solves.

Vague offers don't convert. "Strategic consulting" doesn't tell me anything. "A 90-day framework to scale your service business to $250K without hiring a team" tells me everything.

During my years managing a travel insurance line of business, we tested two approaches to selling annual plans. The first listed features: "Comprehensive coverage, 24/7 support, global network." Conversion was flat. The second made the value concrete: "Save money on multiple trips. Save time making travel plans instead of filing claims. Get peace of mind knowing you're covered anywhere." That shift to clear, tangible benefits drove a 30% increase in annual plan purchases.

The offer hadn't changed. The clarity had.

03: Positioning

Positioning is how you sit in the market relative to alternatives. If you sound like everyone else, you're competing on price. If your positioning is sharp, you're competing on value.

A positioning problem looks like prospects constantly comparing you to cheaper options or asking "What makes you different?" If you can't answer that question in one clear sentence, your sales will reflect it.

I've watched businesses reposition their work multiple times before finding the angle that resonated. Positioning takes iteration, feedback, and the willingness to be more specific than feels comfortable. I've made my share of positioning missteps too, thinking I was being clear when the market was telling me otherwise.

04: Pricing

Pricing problems are tricky because they rarely show up as "your price is too high." They show up as hesitation, long decision cycles, or people who love your work but keep saying "not right now."

Sometimes the price genuinely doesn't match the value. But more often, the price is fine and the perceived value is low. You haven't made a strong enough case for why this investment makes sense.

I once audited a service business where clients consistently called the pricing "aspirational." That wasn't a pricing problem. That was a positioning problem disguised as a pricing conversation. Once the business repositioned the value and the transformation being offered, the price stopped being an issue.

05: Friction

Friction is everything that makes buying harder than it should be. Complicated checkout processes, unclear next steps, too many options, or a lack of urgency.

Sometimes friction is invisible until you map out the entire buyer journey. I once discovered during an audit that a required field in a checkout form was causing 40% of prospects to abandon their purchase. One field. That's friction.

But friction lives in more places than just your checkout page. The multichannel nature of how people buy creates friction you might not see. A prospect discovers you on Instagram, clicks to your website on mobile, gets interrupted, comes back later on desktop but can't find what they were looking at. They receive your email on their phone but can't complete the purchase until they're at their laptop. They visit your physical location but can't find product details that were clear online.

Friction isn't just what happens on your website. It's what happens across every platform and space where your prospect interacts with your business.

Each platform shift, each device change, each move between digital and physical spaces introduces potential drop-off points. If your branding, messaging, or buying process feels disjointed across these touchpoints, you're creating friction without realizing it.

How to Run Your Own Sales Diagnostic

You don't need a consultant to figure out where your sales are breaking down. You need honesty, data, and a structured way to examine what's happening.

Start by looking at your numbers. How many people are seeing your offer? How many are clicking through to learn more? How many are starting the checkout process, and how many are completing it? Those numbers tell you exactly where the drop-off is happening.

Then talk to the people who didn't buy. Not in a "What would make you buy?" way, but in a "Help me understand what happened when you were considering this" way. You'll learn whether they didn't understand the offer, didn't see the value, or just weren't ready.

Pay close attention when they describe their experience. Did they start on mobile and switch to desktop? Did they bounce between your Instagram, your website, and your email trying to piece together what you actually do? Did they visit a physical location but couldn't find the information they saw online? These cross-platform and cross-space experiences reveal friction you can't see from analytics alone. When someone has to work too hard to buy from you, whether that's navigating between devices, platforms, or physical and digital spaces, they often don't.

Look at the people who did buy. What do they have in common? What were they experiencing when they made the decision? That pattern is your actual target, not the aspirational one you thought you were going for.

Finally, walk through your own sales process as if you were a stranger. Read the copy with fresh eyes. Click through every step. Notice where you hesitate, where you feel confused, or where the momentum drops. That's where your buyers are hesitating too.

When the Diagnosis Reveals Something Uncomfortable

Sometimes the diagnosis points to something you don't want to hear. Maybe your offer isn't as strong as you thought. Maybe you're targeting the wrong people because you're afraid to niche down. Maybe your positioning is safe instead of sharp.

I remember the moment I realized my original business model wasn't working. Not because I was bad at sales, but because I was trying to sell something the market didn't need in the way I was packaging it. That was a hard pill. But once I faced it, I could actually fix it.

Sales problems are fixable, but only after you stop avoiding the real issue. You can't tactic your way out of a misaligned offer or unclear positioning. You have to go back to the foundation and rebuild from there.

What Changes After You Diagnose Correctly

Once you know where the breakdown is, the path forward gets clearer. You're not guessing anymore. You're making targeted adjustments based on actual data.

If targeting is the issue, you refine who you're talking to. If offer clarity is the problem, you rewrite your sales page with precision. If friction is slowing people down, you simplify the process.

The relief that comes with a proper diagnosis can't be overstated. You stop spinning. You stop second-guessing every marketing decision. You focus your energy on the thing that will actually move the needle.

A Tool for Strategic Thinking

Sales diagnostics aren't something you do once and forget. Markets shift. Your business evolves. What worked last quarter might not work now.

I keep a running record of where my sales breakdowns happen because patterns reveal themselves over time. Maybe every few months I notice friction creeping back in. Maybe positioning drifts when I'm not paying attention. The diagnostic becomes a regular practice, not a one-time fix.

If you want a structured way to work through this, I built something specifically for that. The Keep Going: Solve What's Slowing You Down journal has an entire section dedicated to diagnosing bad sales with 25 prompts designed to help you think through what's really happening at each stage of your process. You can grab it here.

Because here's the truth: you don't need more sales tactics. You need to understand why the ones you're using aren't working. And that starts with asking better questions.

Understanding what's stalling your sales is only part of building a sustainable business. Your unique strengths shape how you approach everything from client relationships to how you structure your offers. If you're curious how your natural edge influences the way you sell and serve, take the Entrepreneurial Edge Quiz →.