6 Questions To Ask In Every Deal Inspection

Published on December 7, 2023 by Sawyer Middeleer

6 Questions To Ask In Every Deal Inspection

Deal inspections are a critical component of any effective sales management process, but often, they are conducted in a procedural or checkbox fashion that fails to unearth underlying issues or opportunities. When executed with depth and focus, a deal inspection can be a turning point in the sales cycle - providing clarity, guidance, and strategy to best position the deal for closure.

To elevate deal inspections beyond surface-level checkpoints, here are six essential questions reps and managers should ask. These questions not only aim to provide a clearer understanding of the deal's health but also serve to align strategy, uncover potential obstacles, and solidify the path to a successful close.

1. What are the customer’s critical business issues and how does our solution align?

Understanding the precise nature of the customer’s pain points is foundational. It allows you to tailor your value proposition so that it resonates deeply with the customer's needs. Inquire about the strategic business objectives of the customer and how these tie into the issues they're currently facing.

Take a deep dive by asking:

  • How well do we understand the customer's business landscape and the external pressures they face?
  • Have we identified their specific business pain points and can we articulate how our solution directly addresses these concerns?
  • Does the customer perceive our solution as critical to their success or as a nice-to-have?

This question ensures the sales team remains customer-centric and ties the product's capabilities directly to resolving the customer's issues.

2. Who are the decision-makers and how engaged are they?

Identifying and engaging with the right stakeholders is a make-or-break aspect of any deal. It’s vital to have a granular understanding of the decision-making unit for each opportunity.

The key aspects to explore include:

  • Have we mapped out the decision-making unit thoroughly?
  • What do we know about each decision-maker's priorities, preferences, and the problems they seek to solve?
  • How engaged are these individuals with our solution, and have we influenced their perception effectively?
  • How can we increase our engagement with less enthusiastic decision-makers?

Engagement isn’t binary - it’s a spectrum. A deal inspection should quantify this engagement and strategize ways to elevate it.

3. What evidence do we have that the customer is committed to moving forward?

A promising dialogue doesn't necessarily indicate a serious intent to buy. It's vital to look for tangible actions taken by the prospect that indicate a commitment to proceed.

Consider the following:

  • What specific actions (e.g., sharing proprietary information, scheduling follow-up meetings, involving procurement) has the customer undertaken that hint at a move forward?
  • Have we established a mutual action plan that aligns the sales process with the customer's buying process?
  • Are there deadlines, budgets, and formal RFPs at play which signal true commitment?

This line of questioning validates the deal's progression and pinpoints the necessary steps to maintain momentum.

4. What competitive threats exist, and how are we differentiating ourselves?

Even when a customer’s need aligns perfectly with your solution, competition cannot be ignored. A thorough deal inspection assesses both known and potential competitive threats and how you stand out.

Ask yourself:

  • Have we accurately identified direct and indirect competitors for this deal?
  • How is the customer perceiving our differentiating factors against competitive offerings?
  • What strategies have we implemented to address competitor moves and ensure our offer remains top of the customer’s mind?

This question is about reaffirming your value proposition and ensuring it's perceived as superior within the client's specific context.

5. Do we understand the customer’s buying process and timeline?

Every customer has a particular journey they follow to purchase. This becomes even more complex in B2B environments with longer sales cycles.

The relevant insights to gather include:

  • Have we mapped out the customer's procurement process in detail?
  • Are we aligned with their timeline and what are the potential bottlenecks?
  • Is there clarity on legal, compliance, and operational requirements to avoid last-minute surprises?

Ensuring your sales strategy mirrors the customer’s buying process can be crucial in avoiding misalignments and unexpected setbacks.

6. What potential risks could derail this deal and what’s our mitigation plan?

Every sale comes with its set of risks. Proactively identifying and mitigating them can be the difference between a won or lost deal.

Reflection should be given to:

  • What possible internal or external factors could impact the deal negatively?
  • Have we developed effective risk mitigation strategies for these factors?
  • Is there a clear plan of action for critical risks such as changes in decision-makers, budget cuts, or shifts in strategic direction at the customer’s end?

Adequate risk management sets a safety net, ensuring the deal has the resilience to withstand unforeseeable challenges.


A rigorous deal inspection is not a mere formality but a strategic necessity in the sales process. It necessitates asking probing questions and requiring evidence-based responses. When you dissect a deal with these questions, you go beyond the surface level, gauging the deal’s real status, foreseeing possible challenges, and shaping a strategy that maximizes the chances of success. It’s also essential to rely on efficient tools and technologies like Aomni that can streamline deal inspections by providing real-time insights and actionable data, further enhancing the sales strategy.

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