Introduction

Modern revenue teams depend on deal intelligence to drive pipeline accuracy, forecast confidently, and coach reps more effectively. But with sales cycles growing more complex and data scattered across systems, even the most advanced teams find it hard to surface actionable insights in real time. Enter AI-driven deal intelligence—and with it, the power of targeted prompts. By asking the right questions of your AI-enabled platform, you can illuminate blind spots, identify risks, and accelerate deals. In this article, we explore the top 12 prompts to supercharge deal intelligence and how platforms like Proshort can operationalize them for maximum impact.

Why Prompts Matter for Deal Intelligence

Deal intelligence goes beyond basic activity tracking. It synthesizes information from CRM, meetings, emails, and more, turning static data into actionable recommendations. However, AI platforms are only as effective as the questions you ask them. Strategic prompts reveal hidden risks, surface coaching opportunities, and help teams prioritize effort where it matters most.

Let’s explore the 12 most powerful prompts to unlock full visibility into your pipeline and close more confidently.

1. "What are the key risks in my active deals this quarter?"

This prompt enables sales leaders to proactively identify where deals may be stalling or at risk. AI-powered platforms like Proshort cross-reference CRM fields, meeting transcripts, and email sentiment to flag risk signals—such as stakeholder silence, delayed responses, or gaps in MEDDICC/BANT coverage. Instead of relying on gut feel, managers get a prioritized risk list by deal, complete with actionable recommendations.

• Spot deals lacking clear next steps or decision-makers

• Detect negative sentiment in recent communications

• Highlight deals with overdue tasks or missing internal alignment

2. "Which deals have incomplete MEDDICC coverage?"

For enterprise teams, frameworks like MEDDICC are crucial for qualification. Asking for "incomplete MEDDICC coverage" surfaces deals missing key criteria—such as metrics, economic buyer engagement, or decision process clarity. Proshort’s Deal Agent can scan meeting notes, emails, and CRM fields, then map coverage gaps for each opportunity. This ensures reps focus on advancing qualification, not just activity volume.

• Quickly audit pipeline health against your chosen methodology

• Coach reps to fill gaps before deals progress

• Automate alerts for missing MEDDICC criteria

3. "Which opportunities lack recent executive engagement?"

Executive involvement often signals a higher likelihood of deal success, especially in complex sales. This prompt helps identify deals where C-level or VP stakeholders are absent from recent meetings or communications. Proshort can analyze calendar invites, email threads, and meeting transcripts to pinpoint such deals, helping teams re-engage buyers at the right level.

• Flag opportunities without executive sponsors

• Guide reps to secure top-down alignment

• Prevent late-stage surprises due to lack of senior buy-in

4. "Show me deals with negative or shifting sentiment in the last 30 days."

Sentiment analysis is a powerful AI capability for deal intelligence. By asking for deals exhibiting negative or changing sentiment, leaders can prioritize intervention. Proshort’s AI surfaces deals where buyer tone has cooled, objections are increasing, or enthusiasm is waning—often before these issues appear in the forecast.

• Act on early warnings before deals derail

• Correlate sentiment with win/loss outcomes

• Coach reps on addressing buyer concerns in real-time

5. "Which deals are most likely to slip this quarter based on historical patterns?"

This prompt leverages the predictive power of AI. By analyzing past deal cycles, activity cadence, and engagement signals, Proshort estimates which current deals are at risk of slipping. This allows managers to shift resources, escalate internally, or re-qualify deals proactively.

• Forecast with greater confidence and accuracy

• Minimize end-of-quarter surprises

• Drive accountability through data-driven nudges

6. "What are the common objections slowing down my pipeline?"

By aggregating objection themes across meeting transcripts and notes, this prompt reveals systemic blockers. Proshort’s Rep Intelligence module can tag and trend objections—whether about pricing, integration, or decision timing—enabling enablement teams to develop targeted objection-handling assets and training.

• Spot patterns that hinder deal velocity

• Empower reps with tailored objection-handling content

• Continuously refine battlecards and talk tracks

7. "Which deals had no follow-up activity after the last meeting?"

Lack of timely follow-up is a classic cause of deal stagnation. This prompt helps managers catch deals that are falling through the cracks. Proshort automatically maps meetings to opportunities and audits for follow-up emails, calls, or next steps, ensuring nothing is missed and deals stay on track.

• Reduce pipeline leakage due to missed follow-ups

• Automate reminders and task assignments

• Drive rep accountability and process adherence

8. "Which reps are excelling at deal progression, and what can we learn from them?"

Deal intelligence isn’t just about risk—it’s also about replicating success. This prompt highlights top-performing reps based on deal velocity, conversion rates, and ability to advance deals through stages. Proshort curates video snippets and conversation patterns from star reps, making it easy to share best practices across the team.

• Identify and disseminate winning behaviors

• Fuel peer learning and enablement initiatives

• Benchmark reps on metrics that matter

9. "Show me deals with inconsistent or conflicting CRM data."

Data hygiene is foundational to deal intelligence. This prompt surfaces opportunities where CRM records don’t align with meeting notes, emails, or other interaction data. Proshort’s CRM Agent automatically flags discrepancies—such as mismatched contacts, stage inaccuracies, or missing fields—helping teams correct errors before they impact forecasting.

• Boost trust in forecasting and reporting

• Automatically sync notes and update CRM fields

• Minimize manual data entry and errors

10. "Which deals have stalled for more than X days without meaningful progress?"

Stalled deals represent both risk and opportunity. By defining what constitutes “meaningful progress”—such as advancing stages, securing a new stakeholder, or completing a key deliverable—teams can use this prompt to surface at-risk deals. Proshort visualizes pipeline health and automates nudges to reinvigorate stalled accounts.

• Get proactive alerts on stagnating pipeline

• Equip managers with context to unblock deals

• Refine sales process to minimize stalling patterns

11. "What buyer signals have we observed in high-probability deals?"

Not all buyer signals are created equal. This prompt analyzes historical wins to identify which signals—such as multi-threading, technical validation, or executive involvement—most often correlate with closed-won outcomes. Proshort surfaces these signals in real-time, helping teams double down on what works.

• Turn qualitative signals into quantitative insights

• Refine ideal customer profile and qualification criteria

• Coach reps to prioritize high-value engagement

12. "Which deals require immediate enablement intervention?"

Enablement and RevOps leaders need to know where to focus their efforts. This prompt synthesizes risk, rep skill gaps, objection themes, and stalled opportunities to recommend where enablement resources—such as training, bespoke assets, or deal strategy sessions—will have the highest impact. Proshort’s contextual AI agents can even auto-assign interventions based on deal context.

• Pinpoint enablement impact in real time

• Maximize ROI of coaching and content investments

• Close skill gaps before they affect revenue

How to Operationalize These Prompts with Proshort

While these prompts are powerful on their own, their true value emerges when integrated into daily workflows. Proshort’s contextual AI agents (Deal Agent, Rep Agent, CRM Agent) make it easy to transform insights into action. Here’s how:

1. Automate Prompt Responses: Set up scheduled alerts for your top prompts—delivered via Slack, email, or within your CRM.

2. Surface Insights In-Workflow: Embed deal intelligence directly into your pipeline views, 1:1s, and forecast calls.

3. Drive Rep Accountability: Assign follow-up tasks, update CRM fields, or trigger enablement assets based on prompt responses.

4. Track Impact Over Time: Measure improvements in deal velocity, win rates, and forecast accuracy as you deploy prompt-driven workflows.

Best Practices for Prompt-Driven Deal Intelligence

• Customize prompts to your GTM motion: Tailor language and criteria to reflect your unique sales process, vertical, and buyer personas.

• Review and iterate: Regularly audit which prompts deliver the most actionable insights, and refine them as your business evolves.

• Integrate with enablement: Pair prompt-driven insights with training, peer learning, and coaching for maximum impact.

• Foster a data-driven culture: Encourage reps and managers to act on insights—not just observe them.

Conclusion

The era of static pipeline reviews is over. Today’s high-performing teams use AI-driven deal intelligence—powered by strategic prompts—to achieve unprecedented pipeline visibility, risk management, and revenue growth. Platforms like Proshort make it easy to operationalize these prompts, turning insights into sustained competitive advantage. Start with these 12 prompts to unlock the full potential of your revenue organization.

Ready to transform your deal intelligence?

Learn how Proshort can help you deploy prompt-driven deal intelligence and accelerate your path to quota.