Buying Experience Breakdowns Your Sales Team Has Missed
Explore how buyer experience breakdowns arise and stall deals, how great sellers prevent them, and how emerging AI tools like Intersight can help you detect and correct them earlier.
Most revenue teams focus on training sellers to “sell better”. But many stalled deals don’t come from execution errors – they come from buyer-side experience breakdowns. If the buying group can’t align on the problem, value, or the path to a decision, even great selling won’t move the deal.
All too often, a seller thinks they're making significant progress on a deal because someone on the buyer side has responded enthusiastically. In reality, the seller has been talking to several factions, not a united team.
Some telltale signs that the deal might be getting derailed due to a lack of internal alignment are:
Once-engaged champions become quiet, email replies slow, and enthusiasm fades after the initial excitement.
One contact says "ready," while another suddenly asks basic qualification questions.
The evaluation criteria keep expanding (e.g., “We also need it to do X….”).
The timeline or budget keeps moving.
Meetings get bigger, but no one seems empowered to decide. Champions start saying things like, “Let me get back to you after our internal sync.”
Your primary contact can't clearly explain who signs off or how.
Bruce Scheer, Co-Founder of ValuePros.io and author of “Inspire Your Buyers: Go to market with a story that sizzles” has identified ten recurring "buyer-side breakdowns" that derail complex (and not-so-complex) purchases. These issues stem from gaps in trust, clarity, alignment, or confidence—and each can be addressed through intentional steps from the seller and greater collaboration between the seller and the buyers.
Finance can’t defend the spend. The CFO is asking the budget owner, “Why do we need this now, and how does this help us meet our company objectives for the year?”. The budget owner wasn’t prepared to answer.
The buyer is fearful of messing up and making the wrong call (and possibly because they've been burned before). Doing nothing is the least risky option.
Expectations sold now determine revenue retained later. The product and post-sales teams don’t deliver on the promised value, putting renewal at risk.
Each can quietly stall or kill even the most promising opportunities. Below, we'll explore how they arise, how great sellers prevent them, and how emerging AI tools like Intersight can help you detect and correct them earlier. The recommendations we provide below draw on Bruce's work and our own field experience.
Note: I’ve chosen to highlight Bruce’s research and his best practices because I’ve experienced the impact of his work firsthand. More than a decade ago, I’d worked at Tableau Software (a market leader in data visualizations and business intelligence). Tableau had hired Bruce to help the company develop a new value narrative anchored on the theme of self-reliance – at a time when the sales team was in hypergrowth mode and getting ready to IPO. Bruce built the value narrative in collaboration with the full Go To Market Leadership Team, including sales, marketing, product, and success leaders. Once market validated and ready, Bruce trained the Tableau sales teams around the world to effectively utilize the new value narrative to increase buyer clarity, alignment, and confidence, resulting in faster buying decisions, greater win rates, and higher contract value in key segments (e.g, commercial and enterprise).
Tactical Guidance for Avoiding the Ten Buying Experience Pitfalls
1. Trust Gaps: When Buyers Sense Spin and Can’t Verify Claims
Buyers today can verify nearly everything — they read peer reviews, talk to references, and compare notes with industry peers. The moment your message feels exaggerated or inconsistent, they pull back.
Why trust gaps form: When buyers sense “spin,” a lack of proof or evidence, a mismatch between the sellers’ words and actions, or a lack of transparency about risks or fit, they’ll switch into defensive mode—asking more skeptical questions, looping in more evaluators, and slowing the process. Typical triggers include:
Overpromising outcomes (“You’ll double productivity in 2 weeks”)
Dodging questions about the implementation process, pricing, or security and compliance posture
Using vague claims (“We’re AI-powered”) without evidence or examples
Sellers say they will do X and Y by Z date, but fail to follow through
Dishonesty/dodginess about product limitations and fit. Pretending that your product is perfect is one of the fastest ways to lose trust. Mature buyers respect sellers who can say, "Here's where we are not the best fit."
How can sellers overcome trust gaps? The answer is to show up with credibility, consistency, and candor.
How to build trust and buying decision confidence:
Lead with evidence from real customers, not claims with vague adjectives. Share case studies and metrics that match the buyer’s context (e.g., speak to their objectives, pain points, industry-specific challenges, etc.).
Acknowledge limitations. Be transparent about what your solution does and doesn't do (e.g., "We don't yet have the integration with X - would that affect your workflow?"). Furthermore, distinguish between what your product is today and what is on the roadmap.
Show you understand their world before they pitch. This step will help buyers feel seen and understood, and as a result, relax and open up. Tactically, this means demonstrating domain fluency by using the buyers' own language to show that you "get it.", and asking diagnostic questions that help you understand the buyers' motivations, objectives, and problems.
Don’t shy away from compliance: If you know that security, privacy, and compliance are important to the buyer, be upfront about the measures your company takes to ensure them and share key documents (e.g., a Trust Center).
Be reliable and consistent: Follow up exactly when you said you would. Recap meetings clearly and document mutual action plans.
Helpful resources
Sellers often default to cookie-cutter approaches and generic follow-ups because they lack sufficient time for thorough buyer research, meeting preparation, and the creation/curation of tailored materials. The quarterly (or monthly) performance cadence adds to the pressure. Even top-performing reps will feel pressured to “cut corners” from time to time.
Intersight recognizes time constraints as a key barrier to sellers taking a highly contextualized, tailored approach to serving buyers. Our AI revenue acceleration software is built to help B2B sellers engage with buyers in more contextually relevant ways in less time. Intersight:
Helps sellers identify key points to make to buyers and insightful questions to ask, tailored to their deal context. It also automatically flags relevant customer stories and value-oriented messages for the seller to cite to a buyer.
Helps sellers understand which features are most likely to interest each buyer role/type, and how to craft tailored demos.
Helps sellers follow up more promptly and professionally. Its AI helps sellers draft tailored follow-up messages, business cases, and mutual plans, all auto-populated with buyer context.
2. Clarity Gap: When Buyers Don’t Fully Understand the Stakes
Clarity Gaps occur when buyers don’t share a common understanding of the problem, the problem’s magnitude, the outcomes that define success, or the language used to describe these outcomes.
Why Clarity Gaps Occur:
Buyers are overwhelmed by complexity. When there are multiple departments, overlapping tools, and shifting organizational priorities, it becomes difficult for buyers to confidently define what success looks like. For instance, Marketing wants a system that unifies data; Sales wants better visibility. Finance wants cost reduction—yet no one has articulated how those pieces connect to a single business outcome.
The problem the buyers want to solve often isn’t quantified. If the buyer can’t measure the cost of the problem, the urgency evaporates.
The seller uses insider language, not the buyer’s language. Many sellers are so fluent in their product and category jargon that they forget buyers aren’t. The impact is that the buyer nods along but quietly tunes out, because they don’t understand the terms well enough to act.
No shared definition of success. Even when the buyer agrees there is a problem, the team may not agree on the right way to measure success. When the “why” is never clearly anchored, the project is likely to lose steam.
Seller frames value around features, not change. Features don’t create clarity – context does. When sellers emphasize what the tool does but skip why it matters now, the buyer merely leaves with more data, not more conviction.
How to Restore Clarity
Here are simple shifts to increase the educational value you deliver:
Make the problem tangible. Spend time upfront diagnosing the problem. Then work with the buyer to make the problem tangible. Ask them to quantify wasted time, lost revenue, inefficiency, etc. Ask questions like "Can you estimate how much time your team spends entering deal details into CRM each week?" and "If this amount of time were redirected towards selling, what would that mean in quarterly revenue increase?"
Teach buyers how to think about the problem, not just the product. Don't start by saying what your tool does. Explain why companies like theirs struggle with their issue and how performers approach it differently. Example: "Most teams don't have a visibility problem - they have a context problem. Data is everywhere, but disconnected. Here is how high-performing orgs fix that…"
Create a shared vocabulary. Use simple, consistent language that anyone in the buying group can understand. Define key terms early, summarize discussions in shared documents, and pause and reframe when you sense confusion. Try to end every call with a recap email that defines the agreed-upon goals and language, making it the "source of truth" for all stakeholders.
Align early on success metrics. Have conversations with your buyer about what winning looks like for them, personally and for their team/department/org. For example, ask: What metrics would convince you this project was successful six months from now? If we were having a post-go-live review in a month, what outcomes would you want to report to your leadership team?
Create visuals to clarify concepts. Everyone grasps concepts more easily when they can visualize them. Create a simple visual of the problem you solve. Use frameworks, flow diagrams, and before-and-after snapshots to show the contrast between their current state and desired state. Example: "Here's what your workflow looks like today - 11 manual steps. Here's how it looks like with Intersight - 1 manual step and three automated ones.".
Keep teaching after the demo. Engagement and enthusiasm often fade after the demo meeting. Counter that by doing the following after the demo meeting:
Send short follow-up summaries that reinforce what was learned
Share customer stories that mirror their situation
Offer tools like ROI calculators they can use internally (e.g., ValuePros.io has a great one here)
Helpful resources
Intersight analyzes your past wins and losses to reveal which messages and outcomes resonated. It then helps sellers generate mutual action plans, ROI summaries, and business cases tied to each buyer's priorities — ensuring every stakeholder is working from the same definition of success. Further, it detects misalignment and risks early. Intersight analyzes activity, wording, and deal signals to flag instances where individuals in a buying group may not be aligned (e.g., due to hedging statements or skeptical questions). This app allows the seller to intervene sooner and keep the deal from going off track.
Bruce’s company, ValuePros.io, directly addresses the clarity gap by helping revenue teams develop clear, value-focused narratives and tools that articulate what success looks like for the buyer’s organization. Their “ValueEdge™” system offers a visual storytelling format, an AI-enhanced ROI calculator, and value proof, including ROI case studies that turn vague problem statements into quantified business cases and a shared language among stakeholders.
They also offer structured training, playbooks, and coaching to help sellers consistently engage decision-makers with clarity, relevance, and alignment across functions. By combining the power of storytelling, tools to quantify value, and coaching, ValuePros.io helps sales teams help their buyers align on "what's the value", "who cares", and "how we'll measure success."
3. Bond Breakdowns
Bond breakdowns can happen when the buyer senses that the experience is purely transactional and that the seller's questions are "extractive" rather than supportive. Buyers are just people, and all humans want to feel seen, listened to, and valued.
Behaviors that can lead to bond breakdowns:
The buyer senses that the seller is just going through the motions, not listening or trying to help.
There's a lack of understanding or genuine empathy for the buyer's concerns—fear of failure, career risks, internal politics—which means the seller may miss the emotional stakes.
The “first impression” or early rapport was weak (e.g., the seller came across as overly scripted, didn’t take time to build trust, or jumped straight into product features)
Communication is generic—the buyer doesn't feel valued as an individual with specific needs and concerns.
To avoid bond breakdowns and strengthen emotional connection, try:
Start with listening and empathy. Ask about the buyer's goals, challenges, and pressures. Reflect and reinstate.
Find common interests and points of common humanity (e.g., acknowledge how tough it can be to juggle work with two small children at home).
Acknowledge the feelings they share.
Find ways to be human. Provide personal, relatable comments and stories. Anticipate stakeholders' concerns before they voice them.
Frame the relationship as a partnership, not a transaction. Use language like "How can we help you succeed?" rather than "How can we get you to buy?"
4. Generic Journeys: When Every Buyer Gets the Same Story
When every demo looks the same, stakeholders stop listening. While a "Generic Journey" is efficient for the seller, it risks having buyer stakeholders mentally check out because they can't see themselves in the story.
The cookie-cutter journey is a tempting default because:
Most sellers are juggling multiple deals and feel pressured to work fast.
They may not have fully internalized the buyer context or know how to translate value to different stakeholders.
Fear of losing control of the conversation
“Enablement overload” - sellers are sent too much information and templates by their enablement team, but don’t receive practical guidance on when to use what.
How to Create Personalized Buyer Experiences
Start with the buyer’s “why”. Anchor the meeting on their objectives.
Tailor examples, demos, and stories to mirror the buyer's real-world use cases
Let the buyer help shape the agenda. Co-ownership builds attention.
Call out relevance in real time. “You mentioned forecasting inaccuracies - here’s how we fix that.”
Personalize the debrief. After the call, send a recap email that restates the buyer's goals, what resonated, and proposed next steps tied to those outcomes.
Use the APROPOS framework to learn how to tailor the Buyer Experience. Bruce Scheer has invented the APROPOS sales conversation framework so sellers can ensure their conversation(s) are “APROPOS” to the specific buyer they are meeting with. As such, the framework is designed to help sellers tailor their conversations. For a quick rundown on the framework, here’s what each letter stands for with a short description:
A – Aspirations: Start by clarifying what success really looks like for this specific buyer – their business, operational, and personal wins.
P – Problem: Name the big problem (and related mini-challenges) standing in the way of those aspirations, in the buyer’s own context and language.
R – Risks of Inaction: Explore what’s at stake if they do nothing – the financial, operational, strategic, and even career risks of staying with the status quo.
O – Outcomes: Co-define the desired outcomes and benefits, making them as concrete and measurable as possible so everyone is aligned on “what good looks like.”
P – Path: Lay out the path forward, including your solution, how it will be delivered, and the key attributes and differentiators that make it the right choice.
O – Others: Bring in others to the conversation through social proof – customer stories, data, references, and competitive contrast that build conviction to change.
S – Steps: Close by prescribing clear next steps and buyer milestones, so the path from today’s conversation to a signed deal and realized value feels simple and doable.
Helpful resources
Intersight helps teams move beyond generic journeys by eliminating the guesswork and heavy preparation workload that causes sellers to default to generic meetings and cookie-cutter demos. Here's how:
Persona-Based Insights: Intersight highlights what each persona (finance, operations, enablement, IT) cared about in previous successful deals similar to each seller’s current deal, so sellers can tailor their talking points and adjust their story mid-meeting to keep everyone engaged.
Pinpoints Specific Individuals’ Concerns: After each meeting, Intersight summarizes what resonated and which objections surfaced (and from whom), so sellers can quickly course-correct and get ahead of potential deal blockers.
Demo agenda building: Intersight AI helps sellers develop tailored demos based on buyer context (e.g., priority focus areas, critical capabilities) captured in previous meetings and email threads.
5. Solution Confusion and Purchase Analysis: Too Many Options and No Clear Path
When buyers are presented with too many similar products that have overlapping features, their cognitive load increases. When a buyer faces five tools that 'all increase efficiency,' they get overwhelmed, and doing nothing feels the safest.
Or if the buyer group hasn't clearly defined what "success" means, they may struggle to pick among solutions because they lack unified evaluation criteria. Research from Corporate Vision shows that "buyers change their problem statement an average of 3.1 times during complex purchases."
Furthermore, if every vendor emphasizes the same benefits without clear context or differentiation, buyers will struggle to discern what makes any one solution truly better suited for their situation.
Additionally, each stakeholder may have their top use case or favor a different vendor. Without a unified view of the problem to solve and how the solution aligns, the buying group ends up comparing lenses rather than vendors. This phenomenon adds friction and confusion.
How to guide buyers through solution confusion:
Get the buyer to focus on and align with the problem. Help the buyer clarify: What exactly are we trying to solve—and what happens if we don't? Then map how different solution types compare.
Define and agree on evaluation criteria early. Ask directly: "What exactly will success look like? How will you judge these options?" Capturing shared criteria (cost, time-to-value, integration risk, scalability, and user adoption) allows you to frame your solution in that language.
Differentiate clearly and help the buyer compare apples to apples Construct comparison frameworks (yours vs. alternatives vs. status quo) oriented toward their stated criteria. Highlight what you do distinctly and how it aligns with their needs.
Reduce the number of viable options. Where possible, help the buyer narrow the field: "Given your primary metric is 'forecast accuracy' and you value integration with XYZ CRM, you only really need to compare X and Y vendors—here's how we stack up." By curating the options, you reduce overwhelm and help steer toward a decision.
Translate features into outcomes and risk mitigation Don't just say "we have automation"; say "this automation will reduce manual input by 30% and save your team 8 hours/week, which means you can push 20% more deals without hiring." Additionally, be sure to address risk: "Here's where this may not be the right fit given your current architecture—and here's how we mitigate it."
Guide the process and keep momentum. Offer frameworks such as decision trees, ROI calculators, pilots, or proof-of-concepts. These tactics will prevent the buyer from drifting into "we'll circle back later." You can also ask for small commitments: "If I summarize what we've discussed in the last two meetings into a business case you can share with your CFO, will you review it and comment on it?"
Helpful Resources:
Intersight cuts through buyer confusion by surfacing what works—drawing from your own closed-won deals to show sellers precisely how other sellers have guided buyers towards decisions, including the tactics, differentiation positioning, and messages they've used. Furthermore, since Intersight tracks buyer interactions and rep activity, it utilizes AI to help you identify patterns of indecision, redundant option exploration, or stalled momentum. These insights give sellers and sales leadership early warning to step in and simplify the buyer's path.
6. Vague Value: Finance can’t defend the spend.
Deals often die in the CFO’s office because sellers didn’t equip their champion to answer tough questions about ROI, consolidation, and total cost.
According to OnlyCFO (and other CFOs I've directly worked with before), all spending goes into four buckets:
Increases revenue
Increases efficiencies
Mission critical (e.g., cybersecurity)
“Candy” (the nice-to-haves)
OnlyCFO wants its budget owners to be able to answer the following questions:
Tool Need:
Why do we need this tool now? What has changed?
Is the spending in the budget? If not, how will you make up the difference?
How does this tool help us meet our company objectives for the year?
How urgently do we need to tool? Do we need it now?
How does (or will AI) impact the decision?
With AI, does the build vs. buy decision change?
Will the tool add more or less value over time?
Choosing Vendors:
Can we consolidate vendors?
If similar tools exist, why can’t we consolidate and use those?
Does the vendor we are considering also provide other modules/features where we can consolidate?
How big and stable is the vendor?
What risk are we taking on if this vendor were to shut down in the future?
How long will the vendor’s tool be able to scale with the company? Will we have to replace it in 12 months?
How confident are we in the vendor? Will they still be the best tool for us in 6-12 months?
Hidden Costs:
What are the people's time requirements?
Does it require hiring more people to implement and maintain?
Can it help reduce headcount or help maintain the current headcount for longer?
What are the direct and indirect implementation costs?
Will we need to upgrade our plans to the enterprise tier soon?
Are there other overages or other hidden fees?
Pricing:
What's the current price, and what will it be next year?
COFs want transparent pricing at a reasonable price that can be accurately forecasted.
Build vs. Buy:
With AI advancements, the "build vs. buy" discussion has more substance today than it did before. While most companies do not want to be in the business of building and maintaining all their software needs, if the price is very high for what they need or the tool is in a low-impact area, organizations of a certain scale will consider building internally.
Tactics and tools for overcoming vague value
Successful sellers are those who can help their champions answer the questions above. Deals get approved when CFOs (and other leaders) trust that the internal champion has done their homework and that the vendor's product and roadmap are a good bet. Below are some steps on how to do so.
Ask Value-Oriented Discovery Questions to Get Real Customer Input
Salespeople often don't ask buyers enough questions about the business consequences of the buyers' pain points and the time-sensitive factors that create urgency for the buyer to act now. If these customer inputs aren't provided, sellers cannot build compelling value cases.
Sellers shy away from such questions for many valid reasons. Most often, it's because time pressures are real, some sellers lack training and confidence in their ability to add value (so they stick to scripted questions), or sellers haven't yet established a bond with buyers that prompts the buyers to open up. This underscores why building a bond, overcoming trust gaps, and personalizing the buyer experience are critical areas of focus.
To ask better, value-oriented discovery questions, try the SPICED framework developed by Winning by Design. SPICED is a customer-centric approach designed to help sales teams deeply understand a buyer's needs, goals, and the context of their business to provide more relevant solutions, especially in recurring revenue model businesses. By focusing on the customer's desired impact, it encourages a diagnostic, collaborative approach rather than a simple product pitch.
Situation:
This step involves understanding the buyer's current environment, context, and organization.
Pain:
Focuses on identifying the specific challenges, inefficiencies, or frustrations the buyer is experiencing.
The goal is to uncover the root cause of their pain, whether it's financial, operational, or people-related
Impact:
Quantify the business consequences of the pain points
and detail what happens if the challenges aren't solved, and what the potential benefits of a solution will be.
Critical Event:
This step identifies the time-sensitive factors that create urgency for the buyer to act now. It involves identifying the "compelling event" that forces a decision within a given timeframe.
Decision:
This step involves understanding the buyer's decision-making process, including their criteria, the people involved, the timeline, and the paper process.
Understanding this is critical to navigating the rest of the sales cycle and determining what to focus on.
Develop a value narrative.
Developing a value narrative is an effective way to help the buyer answer their CFO (and other leaders’) questions about the need for a tool/solution.
A value narrative is a structured story that connects the pain, impact, outcome, and solution, so it's easy for buyers to recall and share internally. In other words, it draws attention to the buyer's aspirations and objectives, what's getting in the way, the business consequences of not solving the challenges, and communicates the specific ways in which the vendor solution can help the buyer achieve its desired outcomes. It has been proven effective in building consensus among buyer stakeholders, improving time-to-alignment, increasing the sense of urgency to act, and increasing deal size.
Quantify Results with an ROI calculator using real customer inputs and industry benchmarks.
Once a seller uncovers the buyer's objectives, aligns on the value drivers, helps them quantify their current state and the expected value they'll achieve with the solution, they can plug these customer inputs into compelling personalized business cases. Providing industry benchmarks adds even more credibility to the business case by putting the metrics into context.
Helpful Tools and Services:
ValuePros.io and Intersight.ai both have AI-powered templates for building business cases and value stories. Sellers walk in with finance- and executive-ready documents, and champions can sell to their internal stakeholders.
7. Confidence Crunch
Buyers are more likely to freeze making high-cost, high-visibility, or mission-critical purchases. Fears is more likely to the one in control when:
The buyer is on an insecure footing (e.g., new to the org, boss recently left, recently shifted to a new role).
They haven’t secured alignment or buy-in from key stakeholders
They face too many options
Have doubts about the product/solution fit and their readiness
There are concerns that the solution won't be ready in time to make an impact on meeting a time-sensitive business event.
They fear internal pushback from end users, leadership, or their own team disliking the change. There's a perceived lack of resources on effective change management.
How to build confidence
The key is to instill confidence by helping buyers alleviate the perceived and real risks.
Diagnose the fear early. Ask, “If you moved forward and it didn’t work, what would your biggest concern be?”
Highlight risk mitigation
Don't just discuss the upside of your solution. Demonstrate how to minimize potential issues and plan for implementation and change management.
Addressing adoption and time-to-value concerns:
Showcase how your company has helped similar companies implement this in 90 days with minimal disruptions.
Bring the customer success manager to calls with the buyer to develop an implementation plan with them if they were to become a customer.
Provide a change management workshop to equip your champion and other members of the buying team with solid skills to drive adoption.
Addressing product fit/roadmap concerns:
Invite the product manager/technical resources on your team to address buyers’ questions directly
Be candid with prospects when your product doesn't do something, or does it in a way that doesn't meet the prospect's desire: "here's where we are a great fit, here's where we might not be a good fit."
Share your short-term roadmap (the one provided by your product leadership team), but don't promise any delivery dates.
Discuss your process for intake of customer product requests and demonstrate how your team has delivered enhancements based on customer feedback.
Provide a structured, time-bound product trial.
Clarify decision-rights
Help your primary point of contact or champion map out who needs to be involved, who needs to approve, what success looks like, and how you'll demonstrate it. Understand who the key decision influencers are early on and involve them from the start.
Equip the buyer to sell internally.
Provide them with clear, executive-ready materials (business case, ROI model, success metrics) so they can defend the decision to their leadership or peers. When they feel supported in their role, their fear of being blamed or held accountable drops.
Show reliability and social proof.
Use case stories from companies similar to theirs. Emphasize how you helped other teams deliver on their promises and earned their trust.
8. Alignment Abyss: When Stakeholders Disagree.
If there's no consensus, the process ends in a no-decision.
Lack of alignment can occur when buyers don't share a common understanding of the problem, its magnitude, the outcomes that define success, or the language used to describe these outcomes. Or the decision-making process could be unclear—who needs to sign off, what questions they'll ask, or how value is being measured.
Great sellers see it as their job to collaborate with the buyer to help them achieve internal consensus. Concrete steps to take to build alignment include:
Map the buying committee early. Use calls to ask: "Who else needs to agree for this to move forward?" and "What will each stakeholder need to say 'yes'?" Then, create a shared document mapping roles, objectives, concern areas, and decision rights.
Establish a shared definition of the problem and success. Lead or co-lead a session with the buyer champion where you confirm the problem statement and define success metrics. Get the champion's input on which language and metrics to include based on their stakeholders' language.
Use mutual action plans. Develop a mutual action plan together with the buyer champion. Include: stakeholder names, decision checkpoints, required internal reviews, task deadlines, and what each group must contribute.
Facilitate internal alignment workshops or briefings. Offer to host a short "internal alignment call" where you, the buyer champion, and other key stakeholders review: the problem, the chosen solution, alternative options, timeline, and next steps.
This move helps the seller become the facilitator (gain influence), and the buyer's internal team sees you supporting their work. Meanwhile, the seller gains an opportunity to surface hidden questions or objections that haven't been voiced yet.
Furthermore, be sure to monitor engagement to identify potential alignment risks. Keep an eye on deal activities. For instance, are new stakeholders joining? Are responses getting slower? These are signals that alignment may be shifting, and you need to step in.
Helpful resources:
Alignment takes time—something most sellers are short on. Intersight solves the time crunch by helping sellers quickly create alignment artifacts that buyers can share internally.
Intersight provides templates for mutual action plans and business case documents that are auto-populated with buyer-specific context. Furthermore, it provides persona-tailored guidance, enabling sellers to effectively engage with IT, Finance, Ops, and other departments using relevant language and concerns. Finally, it analyzes past engagement trends and alignment patterns, allowing sellers to identify which stakeholders are most challenging and how alignment can slip.
9. Purchase Paralysis
Time kills deals. And sequential process kills time.
When a deal drags out over time, the buyer has more opportunities not to purchase, and deal-killing environmental factors (e.g., an acquisition or a budget freeze) are more likely to materialize.
Sequentially completing tasks (e.g., discovery, demo, technical proof of concept, then pricing/scope agreement, and contracting) takes longer than running them in parallel.
Sellers often spend multiple meetings with a single person instead of involving all stakeholders early in the process. Yet research has shown that B2B sales teams using streamlined, multi-threaded approaches (engaging all stakeholders early in the sales cycle) achieve a 42% higher close rate.
At one of my past companies, we began by operating a linear/sequential sales process. However, we soon shifted to a dual-track process in which product evaluation and commercial negotiations occurred concurrently, resulting in deals closing 2-6 weeks faster.
The parallel process looked like this:
Discovery call
Demo and continued qualification
Define Proof of Concept Criteria, Commercial Expectations, and Decision Process. This step happens before a PoC begins: both parties agree on clear success criteria, a timeline for evaluating the product, and the resource requirements. At the same time, the seller ensures the buyer accepts the initial proposal, pricing, and MSA terms to align both teams on the commercial front.
POC and commercial/legal work proceed in parallel.
Track 1: Product Evaluation (POC)
Track 2: Commercial alignment
With both tracks advancing in parallel, the deal is primed to close as soon as the POC wraps up. When the buyer has validated the product's value, most of the commercial and legal work is also complete. This duo-track process has proven faster, more efficient, and less prone to stalling than the traditional linear approach.
10. Renewal Risk: When Overpromising Today Hurts Retention Tomorrow
Keeping a customer (and expanding with them) is usually much less costly than acquiring a new account. But when sellers oversell, and the product (or service or support) underwhelms, customers soon enter the trough of disillusionment, and churn risk increases significantly.
Other factors that put renewal at risk:
The solution is not being fully adopted internally due to insufficient user training and ineffective change management.
Implementation is significantly delayed, or the product fails to go live on time, resulting in a missed critical business event. So buyer patience and confidence erode.
Internal stakeholders and priorities changed. When a customer’s internal champion leaves or priorities shift, what seemed urgent at the time of sale is no longer so.
Competitive pressure and pricing pressure have increased
Lack renewal process discipline. The organization ignored the customer until renewal time. They could have had a series of conversations around value delivery throughout the year.
Here are actionable steps your sales and post-sales teams can take together to reduce the likelihood of churn:
Set realistic promises & milestones up front. During the sale, clearly map what success looks like, by when, and who is accountable. Avoid over-hyping. Instead, build in early "quick wins" that can be achieved in the first 30-60-90 days to build momentum.
Embed a value realization cadence. Schedule regular check-ins post-go-live (30, 60, 90 days) to ensure the customer is measuring progress against the success criteria defined before signing. Monitor usage, stakeholder engagement, and incremental business impact. These signals help you spot early disillusionment.
Share adoption and health metrics proactively. Develop health scores or dashboards (feature usage, login frequency, key KPI changes) to monitor the account’s “health”. Low scores should trigger action.
Keep the internal champion engaged and aligned. Ensure your buyer champion remains in the role, is still aligned with the initiative, and maintains internal visibility. If priorities shift, recalibrate. Provide the champion with internal-facing assets (an executive summary, an ROI update, an adoption report) so they can defend the investment when renewal time comes.
Make renewal a value discussion, not a checkbox. As renewal approaches, don't treat it simply as "will they sign again?" but rather as "what value have we delivered, what's next, and how can we expand?" Show progression: "Since launch, you've achieved X. Next year, let's aim for Y, and here's how." This step positions the renewal as the logical next step.
Align service/CS and sales teams on renewal from the start. At hand-off, sales should pass clear success criteria, risk flags, and customer expectations to CS. CS should be equipped to track those criteria and escalate if things go off track. Shared ownership of renewal helps avoid the "post-sales drop" of commitment.
Offer upgrade/expansion pathways tied to value achieved. When the customer has realized part of the value, propose next steps (such as upselling or cross-selling) tied to their next set of goals. This step turns renewal conversations into growth conversations.
Automate reminders and streamline renewal logistics. Use your systems to trigger reminders, send renewal documentation early, provide transparent terms, and simplify administrative burdens. This action reduces friction.
The takeaway
The biggest threat to complex B2B deals isn’t competition — it’s confusion. Most opportunities stall not because the product falls short, but because the buying experience breaks down: stakeholders aren’t aligned, the value story is unclear, and fear outweighs confidence.
Bruce Scheer’s research and the work of ValuePros.io shine a light on these human and organizational factors. His frameworks help revenue teams develop value narratives that connect emotionally and logically — showing buyers what’s at stake, what success looks like, and how to build consensus internally. By teaching sellers to facilitate clarity and confidence, not just persuasion, ValuePros enables organizations to close the “empathy gap” that derails so many high-consideration purchases.
At the same time, Intersight equips sellers with the AI-powered infrastructure to operationalize those principles at scale — automatically surfacing relevant proof points, generating deal-specific documents, flagging misalignment, and keeping CRM data clean. Where ValuePros strengthens your message, Intersight streamlines the mechanics of delivering it consistently and contextually across every deal.
Together, these approaches turn selling from a performance into a partnership. They help buyers reach clarity faster, align their teams, and make confident decisions that lead to successful outcomes — not just purchases, but lasting relationships.
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