Why Sales Assets Fail (And the 3-step Fix)
Your assets don't suck because of design. They fail because product, marketing, and sales aren't telling the same story about what buyers actually care about.
Quick Answer: The Real Reason Sales Assets Die in the Field
Sales assets fail when product, marketing, and sales aren't aligned on what buyers actually care about. Marketing creates decks based on internal assumptions. Sales rewrites them because they don't match real conversations. Champions can't multi-thread because the story only works for one person. The fix isn't better design or more workshops—it's 3 strategic conversations that diagnose the root cause and rebuild from buyer truth.
Key Takeaway: If your sales team doesn't use your assets, you have an alignment problem, not a design problem.
The Pattern You Keep Seeing
Marketing ships the "perfect" deck
You spent 6 weeks on it. Stakeholder reviews. Multiple revisions. Beautiful design. Launch meeting goes great—everyone nods along.
Two weeks later, sales isn't using it.
When you ask why, you get:
"It doesn't land in real conversations"
"Customers don't talk like that"
"It's too focused on features they don't care about"
"I made my own version that actually works"
Sales goes rogue
Now you've got 12 different versions of the deck floating around. Each rep telling a slightly different story. Nobody can answer "what makes us different?" the same way twice.
Leadership asks: "What does marketing even do?"
Deals stall in multi-threading
Your champion loves you. But when they try to sell internally to Finance, Ops, or the CTO, everything falls apart.
Your one-pagers speak to your champion's pain, not the buying committee's. Your champion walks into internal meetings without a story that works for everyone else.
Deal dies quietly. You never find out it was a positioning problem.
Key Takeaway: These aren't three separate problems. They're symptoms of the same root cause—misalignment about what buyers actually care about.
Why This Keeps Happening
You're building assets from internal mythology, not buyer truth
Here's what usually happens:
Product says: "We need to lead with our technical architecture—that's what makes us different"
Marketing says: "Our research shows buyers care about ease of use and fast implementation"
Sales says: "Customers keep asking about security and compliance—that's what's blocking deals"
Everyone's right. And everyone's wrong.
Because nobody actually knows:
That the boring stuff is sometimes what buyers care about most (but you're not mentioning)
Which capabilities win deals and which are just table stakes
Why you beat Competitor A but lose to Competitor B
What your champions need to say to Finance, Ops, and Engineering
So marketing builds assets based on best guesses and flashy product releases. Sales ignores them because they don't match reality. And the cycle repeats.
The workshop trap
Many companies try to fix this with workshops.
"Let's get everyone in a room and align on messaging!"
What happens:
Week 1: Kick-off meeting (2 hours, everyone agrees this is important)
Week 2: Research review (another 2 hours, findings are "interesting")
Week 3: Positioning workshop (3 hours, positioning by committee meaning the loudest voices dictates direction. Hint: no clear decisions)
Week 4: Message framework workshop (another 3 hours, still debating language)
Week 5: Stakeholder review (people who weren't in workshops have opinions)
Week 6: Revision workshop (because stakeholders disagreed)
Week 7: "Let's schedule a follow-up to finalize"
Three months later, you have a 47-slide deck nobody uses and a message framework document sitting in Google Drive or a custom GPT.
Why workshops fail: They're designed to build consensus, not uncover truth. Everyone leaves feeling heard, but nobody leaves with clarity about what buyers actually care about.
Key Takeaway: You can't workshop your way to buyer truth. You need diagnostic conversations that uncover what's actually broken.
What Actually Fixes This: The 3-Conversation Diagnostic
I've diagnosed misalignment problems at HP (enterprise scale), in military intelligence (high-stakes environments), and across a dozen startups. The pattern is always the same.
Here's how it works:
Step 1: Diagnose Where Alignment Breaks
Who I talk to: Product leader, Sales leader (or top rep and/or sales engineer), Customer Success.
What I'm listening for:
Where do their answers diverge?
What are they avoiding saying out loud?
What assumptions are they making about buyers?
What are they noticing about prospects and customers who get the most value out of the product?
Questions I ask:
What do prospects that tend to close have in common?
What do the most successful customers have in common?
How can you tell during implementation/onboarding a customer is going to succeed (get the most value)?
What things do prospects always ask about?
Which competitor do you avoid, and why?
What I learn in 90 minutes:
Product thinks the differentiator is X
Marketing is messaging Y
Sales is pitching Z
Nobody knows what actually wins deals
But also:
You’re not talking about half the things buyers care about
What your best customers really have in common (not firmographics - pains, internal dynamics, buy-in)
Where is the gap between champion’s excitement and their CFO and head of IT’s concerns
Key Takeaway: Three different people telling three different stories isn't a communication problem—it's an alignment problem.
Step 2: Map What Buyers Actually Care About
What I review:
Win/loss interview notes (if they exist)
Sales call recordings (the real conversations, not the polished demos)
Competitive deal data (who you beat, who beats you, and why)
CRM notes from stalled deals
Customer emails asking questions, NPS scores and surveys
What I'm looking for:
Pattern recognition: When you win, why? When you lose, why?
The boring stuff: What do buyers keep asking about that you're not highlighting?
What I add:
Competitive research: How buyers are solving for the pain; how competitors and competing approaches provide
Market research: What trends, shifts and pressures are happening in the market
Persona research: Who is involved in the buying decision, what are their pains, goals, and KPIs
What I’m looking for:
Competitive reality: Which capabilities actually matter in deals?
Multi-threading gaps: Where do deals stall when champions try to sell internally?
What I build:
Capability map: What you're actually good at vs. what competitors do
Buyer pain map: What each persona in the buying committee cares about
Competitive positioning: When to fight which battles, and what to lead with
Example from a recent client:
They thought their differentiator was "AI-powered insights."
After reviewing 20 competitive deals, the pattern was clear:
They won when implementation speed mattered (2 weeks vs. competitor's 12 weeks)
They lost when enterprise security was a top-3 criterion
“AI-powered" was table stakes—everyone claimed it
The boring thing buyers cared about: Implementation speed and not needing a dedicated admin.
They weren't talking about either one.
Key Takeaway: They care about the specific pain your capabilities solve—and you're probably not talking about the right ones. Features are secondary - it’s the “how you do it”. But first, show them what you can do (capabilities in their use case)
Step 3: Build the Defensible Narrative
What I do: Synthesize steps 1 and 2 into The Win Map™.
The Win Map™ is:
Your single source of truth
Built in Notion (so it's connected, not a static doc)
Maps buyer research → competitive intel → positioning → sales assets
Shows what you say, why it works, and where to use it
What goes in The Win Map:
Buyer Truth: What each persona actually cares about (from the data, not assumptions)
Capability Map: Your strengths vs. competitors, tied to buyer pains
Defensible Narrative: The story that holds up in real conversations
Asset Blueprint: What sales needs (decks, one-pagers, champion materials)
Competitive Playbook: When levers to pull in each competitive situation
Why this works:
Instead of another positioning doc, you have a living system that:
Product uses to prioritize roadmap (based on competitive gaps that matter)
Marketing uses to build campaigns (based on capabilities that win)
Sales uses to know what to say (based on what actually lands)
So instead of claiming “AI-powered analytics platform with advanced ML capabilities” like all your competitors, you can start being specific. Naming real pains, at the use case level and at the persona level.
Your sales reps have a valid asset to share with the champion. Both the CFO and IT care about implementation time, but for different reasons. Now you can create assets that tell the same story from each persona’s POV.
Why 3 conversations, audit and research Work Better Than 7 Workshops
| Approach | 3 Steps | 7 Workshops |
|---|---|---|
| Focus | Uncover truth | Build consensus |
| Output | Buyer-validated narrative | Internal agreement document |
| Diagnostic depth | Root cause analysis | Surface symptoms |
| Sales adoption | High (built from their reality) | Low (built from committee compromise) |
| What you learn | Why deals are actually won/lost | What internal stakeholders think |
The difference:
Workshops optimize for making everyone feel heard. Diagnostic conversations optimize for finding out what's actually broken.
You don't need consensus before you have clarity.
Key Takeaway: Speed matters because every week of misalignment costs you deals. Three weeks to clarity beats three hours to consensus.
What This Looks Like in Practice
Before the 3-conversation diagnostic:
Product: "Our technical architecture is the differentiator"
Marketing: "We should lead with AI"
Sales: "We lose deals because of security"
Reality: Nobody knows what actually wins deals
Assets created:
40-slide pitch deck covering everything
12 different one-pagers (one per feature group)
Competitive battlecards nobody opens
**
Sales adoption: 15%
Win rate: Declining
Leadership: "Why marketing isn’t working?"
After the 3-step diagnostic:
Buyer truth discovered:
Deals are won on implementation speed (2 weeks vs. 12 weeks because CS has a plan, templates, and 1:1 guidance)
Deals are lost when security is missing (SOC 2 gap)
Champions struggle to explain value to Finance (no ROI story)
The "boring stuff" buyers care about: no dedicated admin needed
Win Map™ built:
Capability map showing implementation speed as true differentiator
Narrative: Why speed matters
Competitive positioning: speed battles, avoid security-first deals (until SOC 2 done)
Multi-threading playbook: what Finance, Ops, and Engineering need to hear
New assets (built from Win Map™):
12-slide pitch deck leading with speed + no-admin-needed
Champion deck with business case outlining cost of “the old way”
Persona-specific infographics for multi-threading
Competitive talking points embedded (not separate battlecard)
Outcome:
Sales adoption: 87% in 6 weeks
Win rate: Up 23% in first quarter
Leadership reaction: "Now we know what to say"
Key Takeaway: The difference isn't better slides. It's alignment around what buyers actually care about—discovered through diagnosis, not guesswork.
Common Questions About the 3-step Fix
Q: Do we really need to pay a consultant for 3 conversations and audits? Can't we just do this internally?
A: You can. But here's why most teams don't:
Three problems with DIY diagnosis:
Politics: Your product leader won't tell your marketing leader "your messaging is wrong" directly
Assumptions: You're all too close to see your own blind spots
Pattern recognition: You need someone who's seen this 50 times to spot the patterns in 3 conversations
The value isn't the conversations—it's knowing what to listen for and connecting dots across 20 deals that your team sees as separate events.
Q: What if we don't have win/loss data or sales call recordings?
A: Then we start there. I might need to talk to a few more people about recent deals instead of reviewing recordings. If needed, we can also conduct an external buyer research instead of reviewing win/loss data.
You learn the same patterns—just takes slightly longer.
Q: How do we know the narrative you build will actually work?
A: Because it's built from what's already working in the field. I'm not inventing positioning—I'm finding the version of your story that's already winning deals and making it repeatable.
If a rep is closing at 40% win rate while everyone else is at 15%, I figure out what they're saying differently.
Q: What if our sales team still doesn't use the assets after this?
A: Then the problem isn't positioning—it's something else (enablement, trust, process). But in 18 years, I've never had sales reject assets built from their own competitive intel and win patterns.
When you build from their reality, they use it.
Q: How is this different from hiring a positioning consultant?
A: Most positioning consultants give you a positioning document. I give you The Win Map™—a system that connects positioning to assets reps line up to use.
Positioning is the foundation. But a foundation without walls and a roof isn't a house.
Q: What happens after? Do you disappear?
A: No. The 3 conversations are the diagnostic. Then we build The Win Map™ (2-3 weeks) and create your core sales assets (another 3-4 weeks).
Total engagement: 6-12 weeks depending on scope. After then, I’m still available for 60-day email support, or for enablement assistance and coaching through advisory.
The 3 conversations aren't the whole fix—they're how we find out what's actually broken so we don't waste time fixing the wrong thing.
The "Oh Shoot" Moment
Every client has this moment during the diagnostic.
It's when we're reviewing initial findings and they suddenly see the pattern:
“Oh shoot. We JUST lost a deal because of that”
It's not that the information was hidden. It's that nobody connected the dots.
The rep said it was "timing"
CRM notes said "went with competitor"
Leadership assumed it was pricing
But when you ask customer-facing teams the right questions, and cross it with customer data and market insights, the real reason becomes obvious:
You were selling implementation ease to buyers who cared about security compliance.
Or selling technical features to buyers who cared about not needing a dedicated admin.
Or selling "AI-powered" when the competitor's 2-week implementation beat your 12-week timeline.
The pattern was always there. You just needed someone to see it.
That's what the 3-conversation diagnostic does. It surfaces the pattern you're living but can't see from the inside.
Key Takeaway: You don't have a sales asset problem. You have a clarity problem. And clarity comes from diagnosis, not design.
What to Do Next
If you're seeing these symptoms:
Sales isn't using the decks you create
Everyone tells a different story about differentiation
Deals stall when champions try to sell internally
You keep losing to the same competitor and don't know why
Leadership asks "why are conversion rates low?”
Start here:
Option 1: Run your own mini-diagnostic
Ask these 3 questions to Product, Customer Success, and Sales:
When we lose deals, what's the actual reason?
What's the boring thing buyers care about that we're not talking about?
Which competitor do we avoid, and why?
If you get three different answers, you have an alignment problem.
Option 2: Book a diagnostic call
I'll walk through your current assets, ask the hard questions, and tell you where alignment is breaking.
30-minute call. No pitch. Just diagnosis.
Option 3: Read how The Win Map™ works
Learn about the system that turns diagnosis into repeatable sales assets.
Related Resources
The Win Map System: How to align product, marketing, and sales in a living Notion system - coming soon
3 Conversations vs. 7 Workshops: Why diagnostic speed matters more than stakeholder consensus - coming soon
Alignment Problem Self-Assessment: 10-point diagnostic to see if you have misalignment - coming soon
About This Framework
Context: This diagnostic approach emerged from 18 years of fixing sales asset problems at HP (enterprise scale), Israeli military intelligence (high-stakes diagnosis under pressure), and a dozen B2B SaaS startups (resource-constrained teams that couldn't afford to guess).
Why it works: Because it finds what's actually broken (through diagnosis) rather than what people think is broken (through consensus). And it builds from buyer truth, not internal mythology.
Last Updated: January 2026
Author: Talya Heller, Down to a T
