So Why Aren't You Closing More Pipe? Your 15-Minute Diagnostic Questionnaire

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Beyond the Symptoms, Into Root Causes

You're in the post-mortem for a deal you thought you'd win.

The explanations sound familiar: 'The solution was too expensive.' 'Requirements changed halfway.' 'They went with the incumbent.' 'Budget got frozen.' 'Compliance/procurement killed it.' 'They decided to do nothing.'

These aren't reasons - they're symptoms.

When deals die from 'price,' the real breakdown happened weeks earlier - discovery failed to establish value. But most pipeline problems are more complex still. Slow solution response times, for instance, might stem from unclear deal prioritization (strategy), lost context in handoffs (execution), no reusable templates (process), and missing automations (technology). Multiple failures, compounding. This is why surface-level fixes rarely stick.

If you're a sales or presales leader tired of guessing why deals die, this diagnostic will help you pinpoint exactly where your pipeline is leaking - and more importantly, understand the structural failures causing it.

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Problems in Pipeline Qualification & Prioritization

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Interest, Not Intent

The customer shows some interest in modernizing their stack. They'd benefit, sure - but there's no 'burning platform'.

Sales ticks all the qualification fields in the CRM, providing estimates for budget and timeline. There is no commentary on the actual likelihood of closing the deal. Presales invests weeks in discovery and solution design. Spaced-out conversations follow. Eventually you realize: the customer just wanted to do some research and exploration.

It's a familiar pattern - studies from Forrester, HBR and others suggest that around 40% of B2B opportunities end up in 'no decision' rather than a competitive loss.

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Rewarding Quantity, Not Quality

It's subtle, but your culture may inadvertently reward pipeline creation, rather than pipeline quality. Everything stays 'warm.' Presales who push back are deemed difficult.

Poor conversion rates trigger the wrong response: instead of tightening qualification, leadership end up demanding bigger pipelines. More quantity, and even less quality. It’s a vicious cycle.

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Playing a Losing Game

You're pursuing deals in domains where you have no differentiation or spending months competing for business in crowded markets. You win occasionally, but on price. Meanwhile, deals where you have home ground advantage get under-resourced.

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Diagnostic Questions to Dive Deeper

• Pipeline Quality:
  • What % of your pipeline is older than 2× your average sales cycle?
  • What % of presales capacity goes to deals outside your ICP or to lower priority tiers?
  • What % of 'qualified' deals die as 'no decision' after proposals have been sent out?
• Strategic Alignment:
  • Can 5 random team members articulate your ICP and deal prioritization tiers consistently?
  • Does your pipeline review discuss quality (fit, competition, champion strength) or just total dollar value?
• Operational Discipline:
  • In your last 10 'qualified' deals, how many did sales document their conviction level and rationale for investing presales resources - or did they just tick the CRM qualification boxes?
  • Do you have guidelines for investing presales effort (e.g., 'Tier 3 deals get max 8 hours presales before validation')?

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The Impact on Your Team & Pipeline

Without qualification discipline, you chase everything. Presales gets stretched thin on low-probability work, and the deals you should win don't get the focus they deserve - a double hit to your conversion rate. Over time, your pipeline quality degrades, your team feels like they're working harder for less results, and every quarter starts with more pipe but the same win rate.

Also see The Presales Burnout Epidemic.

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Problems in Discovery & Requirements Gathering

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Thin, Technical, & One-Dimensional

The first 'discovery' call jumps straight into technical requirements - questions about servers, storage capacities, firewall rules. The conversation jumps past critical questions: 'Why now?', 'What happens if you don't fix this?', or 'What else does this compete with internally?' Discovery is a checklist to complete rather than strategic intelligence gathering. The opportunity to understand and build trust with broader business unit leaders gets missed. The proposal that follows is technically accurate but doesn't resonate because it never connected to the real business pain. You never uncover the multi-year strategic engagement opportunity.

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Methodology? What Methodology?

Each presales engineer approaches discovery differently. Some are thorough, others wing it. There's no standard framework, no discovery template, no consistent methodology. New hires shadow a few calls and figure it out as they go. The quality of your discovery depends entirely on who's running it, and you have no way to coach or scale best practices.

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Context & Intelligence Scattered

Discovery notes live in someone's head, scattered across emails, or buried in meeting transcripts. When the deal progresses, critical context - competitive intelligence, political dynamics, technical constraints never gets documented. All the nuance that is critical to closing that deal is lost. A different team member picks it up and has to start from scratch. Without documented intelligence, the proposal timeline bloats.

Also see Context Clarity: Your Edge to Winning Technical Deals in the AI Era.

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Diagnostic Questions to Dive Deeper

• Operational Discipline:
  • In your last 10 deals, how many would have: (a) a comprehensive 'Discovery Summary and Requirements List', and (b) a 'Stakeholder and Influence Map' so a new architect could pick up without re-running the meeting?
• Team Enablement:
  • Is presales trained to uncover customer objectives (cost vs. performance vs. speed vs. risk), or are requirements collected without understanding the trade-off priorities?
  • Is presales trained to come out of discovery with a point of view on how to win and proactively suggest future opportunities?
  • Do you have discovery playbooks for your top deal archetypes that guide the progression from high-level business context to technical depth?
• Technology & Automation:
  • How long does it take to transform messy discovery inputs (call transcripts, workshop notes, emails) into a structured requirements document?

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The Impact on Your Team & Pipeline

Discovery is your critical window to build trust and shape the deal. When the buyer experience here is weak, every downstream stage sits on shaky foundations. Solutions need rework, proposals miss the mark, margins erode, and strong-looking deals die late when real decision criteria finally surface. Worse, without uncovering the customer's broader roadmap, you miss the multi-year opportunities that should be building your future pipeline.

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Problems in Solution Design & Proposal Development

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No Validation Before the Big Reveal

You spend weeks building what you believe is the perfect solution, then present it in a formal proposal review. That's when you discover: they preferred a different primary vendor, your pricing model doesn't fit their procurement process, or the technical approach conflicts with an undisclosed IT standard. There was no lightweight checkpoint to pressure-test direction before investing in detailed design. Now you're scrambling for those last-minute changes.

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Vendor Drag Instead of Velocity

New designs trigger a fresh round of vendor validations and special pricing requests. But customers don't wait - and neither do competitors. The longer you're stuck in vendor queues, the wider the window opens for someone else. If they've already pre-validated stacks and aligned rebates, they’ll win on speed, not just price.

Also see Vendor Expert Bottlenecks & Cycle Time Bloat.

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No Playbooks, No Patterns

For your top deal types, there are no standard patterns, no reusable SOW blocks, no agreed 'good/better/best' configurations. Every opportunity triggers a blank-page moment. Presales engineers have their own templates, and pricing models - knowledge is not institutionalized. A backup and DR solution gets architected completely differently by 3 different engineers. What should take hours takes days because there's no foundation to build from.

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Commodity Supplier, Not Solution Partner

There's no clear story: 'Given what you told us in discovery, here's the path we recommend, why, and how it sets up your future roadmap.' You don't frame the strategic trade-offs early - are we optimizing for cost, performance/resilience, or speed/flexibility, and what does each path mean for risk, support and future upgrades/adjacent projects? Without that discussion, it simply collapses to line-item pricing. The customer sees a quote, not a strategic investment plan.

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Diagnostic Questions to Dive Deeper

• Solution Response Time:
  • What is your typical time from 'discovery complete' to the first high-level solution, then to a customer-ready proposal?
  • What % of that is 'waiting time' on internal approvals or vendor validation?
  • Is it standard deal process to have a lightweight checkpoints or customer calls to pressure-test direction before full proposal build-out?
• Accelerators:
  • For your top 5-10 recurring deal archetypes, do you have reference architectures, configuration patterns, and proposal/SOW templates that are up-to-date?
  • What % of proposals are built on repeatable frameworks vs. one-offs?
• Positioning:
  • Is there a clear proposal structure that leads with business outcomes and then supports them with technical design?
  • Are presales engineers empowered to translate infrastructure choices into executive-level impact and a future-state roadmap?
• Technology & Automation:
  • How much of your proposal development process is automated or AI augmented?
  • Do you have tools that accelerate diagram creation, compliance documentation, or technical narrative writing?

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The Impact on Your Team & Pipeline

Without a systemized approach to solution design and proposal development, even winnable deals slip away. Competitors win on speed - and in sales, velocity equals revenue (Hubspot). Without strategic positioning, deals tend toward smaller, transactional wins. And worse, you quietly limit your own future pipeline as you aren’t brought to the table for your customers' future opportunities.

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Problems in Proposal Defense & Stakeholder Management

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Comprehensive, Not Compelling

Your deck has everything - diagrams, specifications, timelines, RACI charts. The team walks through it methodically, slide by slide. But instead of a sharp narrative - 'Here's the problem, here's the path, here's what it means for you' - it feels like a project status update. 10 minutes in, the executive sponsor is on their phone. The proposal is thorough, but it's not compelling.

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No Objection Handling Playbook

Every proposal faces predictable friction points - pricing comparisons, vendor concerns, timeline misalignment with fiscal cycles. The difference between won and lost deals often comes down to how these moments get handled. Without preparation frameworks and response strategies, teams struggle to transform objections into value conversations.

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Single-Thread Dependency

Your entire deal depends on one champion. When they leave, go quiet, or lose an internal battle, the deal dies - because you never built relationships with the CFO, CIO, or business sponsor who actually controls the budget.

Diagnostic Questions to Dive Deeper

• Stakeholder Engagement:
  • For deals above a certain threshold, do you require documented engagement with multiple stakeholder types - technical buyers, economic buyers, executive sponsors?
  • Can you articulate each stakeholder's win criteria, concerns, and influence level?
• Team Enablement:
  • Are your presales engineers equipped to deliver compelling presentations and tailor to the audience - executive summaries for sponsors, technical depth for delivery?
  • Before important customer meetings, do sales and presales run a structured prep session (objections, roles, red flags, 'no-go' positions)?

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The Impact on Your Team & Pipeline

Nothing damages morale like losing a deal at the finish line. High-stakes opportunities that collapse in the final room rarely fail for a single reason - they reveal compounding gaps in preparation, stakeholder coverage, and objection readiness. But when losses get chalked up to 'price' or 'incumbent,' the real failures stay hidden. The same patterns repeat quarter after quarter.

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Problems in Sales Engine Foundations (Data, Operating Model, & People Enablement)

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Missing the Metrics That Matter

How long would it take to pull win rates by ICP segment, deal type, and domain? What about average time to first solution, or proposal turnaround time?

Most teams can’t - the data is scattered, manual to compile, or simply not captured in sufficient granularity. Pipeline reviews obsess over dollar totals while ignoring quality indicators that actually predict success. But the data dividend pays - McKinsey research shows companies with data-driven sales engines are 1.5× more likely to achieve above-market growth.

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Cowboy Culture, Not Collaboration

When revenue is climbing, nobody notices the teams' missing collaboration protocol. Growth has masked a critical gap: sales and presales never established how to work together at scale. Without clear ownership, handoff points, or rules of engagement, individuals default to their own approaches and incentives. The foundational elements - RACI (Responsible, Accountable, Consulted, Informed) for deal stages, shared accountability metrics, cross-training between teams - continuously gets deprioritized. Teams compensate through heroics - exhausting at small scale, impossible at large. Deals quietly slip through organizational gaps because no one owns the full customer journey.

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No System for Scaling Expertise

When deals are lost, someone picks a one-word loss reason and moves on. There's no debrief on fit, discovery quality, stakeholder dynamics, competitive position or commercial design. The truth of why you won or lost stays in the heads of the people who ran the deal. Without systematic capture, there's no pattern recognition, no playbook evolution, no knowledge transfer. When a top performer leaves, years of hard-won knowledge walk out the door. When new macro-market opportunities emerge, teams can't pivot quickly.

Also see Knowledge Lives in Heads, Not Systems.

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Diagnostic Questions to Dive Deeper

• Sales Engine Metrics:
  • Can you pull these metrics within a week: stage-by-stage conversion, no-decision rate, and win rate by ICP segment, deal type and domain (e.g., cloud, workplace, security, professional services, managed services), average sales cycle, proposal turnaround time?
  • Can you pull these reports: deal loss reasons by stage, win/loss by competitive position (competitor present, incumbent advantage, existing relationship), and fastest-growing deal type or domain in the last quarter?
  • Do you trust these numbers enough to reallocate resources or change strategy based on them?
• Knowledge Capture:
  • What percentage of deals get a structured post-mortem within 2 weeks of closure?
  • How often are your reference architectures and proposal templates updated - and is there an owner responsible for keeping them current?
• Team Enablement:
  • Is there a clearly defined sales-presales workflow and when was the last discussion or training on collaboration protocols - not just tools, but actual ways of working together?
  • Is knowledge contribution part of performance reviews, or just encouraged in principle?
• Technology & Automation:
  • Do your core tools (CRM, deal rooms, knowledge base, AI assistants) support your sales engine - making it easy to tag deals, surface patterns, and find prior solutions at the moment of need?

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The Impact on Your Team & Pipeline

When structural foundations are weak, the entire sales engine runs with hidden friction, eroding conversion rates at every stage. Every issue upstream - qualification, discovery, solution design - is quietly amplified because you're not measuring it properly or institutionalizing what works. Your pipeline looks healthy on paper while conversion steadily deteriorates. Working harder doesn’t actually produce better results. These structural gaps are the invisible reasons why you aren't closing more pipe.

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Next Steps: Focus Your Energy on the Big Rocks

You can't address everything at once - but if you focus on solving the big structural issues, a lot of the noise may just disappear.

Start With Clarity, Together With Your Team

Your team lives these problems every day. Run this diagnostic together and ask them directly: Where do deals really die? What friction slows us down? Their answers will reveal both problems and solutions you hadn't considered.

Yes, you'll see issues everywhere. But consider where your biggest leverage might be:

• Could a more systemized buyer experience transform your win rates? What if sales and presales collaborated seamlessly instead of lobbing handoffs over the fence? (Also see The Sales-to-Presales Handshake Gap).
• Would upskilling sales to run credible technical qualification free up presales for deeper strategic work?
• Is your team fighting battles they can't win? What if sharper focus on winnable deals gave you back 30% capacity?
• Could technology be your unlock - automating the mundane, surfacing past solutions, generating first drafts - so presales can focus more on spending time with customers?

Build Momentum Through Alignment

Structural changes take time to show in the numbers, and you'll never prove direct causation - was it the new process, better tools, or market timing? This complexity is exactly why your team needs clarity and alignment on the journey.

Share your strategy and roadmap: what you're changing, how you'll work differently, and which metrics should improve first. Use early indicators - faster response times, fewer rework cycles, better discovery notes - to build belief before win rates and pipeline metrics catch up. When people understand the full journey, they commit to the process, not just the next checkpoint.

Your team wants to win. When you fix foundational issues collaboratively - involving them in solutions, explaining the why, celebrating progress - you're not just improving conversion rates. You're building a sales engine where excellence becomes systematic and success becomes repeatable.

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