- Ted Rogers
- Reading Time: 4 minutes
Issuing an RFP should be a strategic act. This is the moment your organization asserts control, aligns expectations, and signals to your vendors: We’re serious.
But too often, RFPs do the opposite. They expose uncertainty, invite vendor manipulation, and surrender leverage before negotiations even begin. And now, in the era of AI-powered deal strategy, vendors are analyzing your RFPs at a level of speed and sophistication most clients aren’t prepared for.
If your RFP shows any of the following red flags, it’s not just underperforming. It’s putting your transformation at risk.
Red Flag 1: It’s All IT, No Business
Many RFPs are driven entirely by IT. This is especially the case when the trigger is technical, like SAP ECC end-of-maintenance or upgrading to Oracle Fusion only for the hope of reducing cost. In these cases, the project is framed as an infrastructure shift, not a transformation opportunity.
Similarly, moving to Workday from legacy HR or finance systems can be positioned as a tech upgrade rather than a business reinvention, which misses the broader opportunity to drive operational agility and employee experience.
Warning signs:
- No one in the kickoff meeting can say who speaks for the business.
- Procurement is the only non-IT stakeholder involved.
- Business leaders are brought in only after vendor responses are submitted.
Why it matters: Vendors notice this immediately. It tells them that compliance, not business value, is the goal, and that no one will hold them accountable for outcomes like adoption, productivity, or process improvement.
What UpperEdge does: We realign the effort around business priorities, ensure early business involvement, and structure the RFP to demand cross-functional ownership from vendors.
Red Flag 2: You Recycled the RFP and Vendors Can Tell
Under pressure to launch, many organizations reuse an old internal template or pull an RFP from the internet. The result is often a document that appears comprehensive but is riddled with vague assumptions, misaligned requirements, or legacy content.
And today’s vendors are using AI tools to exploit that. They:
- Identify inconsistencies and outdated language
- Cross-reference your RFP against a database of prior wins
- And generate responses designed to look tailored while avoiding accountability
This is particularly risky when sourcing enterprise solutions from strategic vendors like Salesforce, Oracle and Workday, where product lines are evolving rapidly and RFPs need to reflect current platform capabilities.
Consequences:
- You get polished marketing decks, not actionable proposals.
- Pricing is either padded for risk or strategically low with missing scope intended for future Change Orders.
- Evaluation becomes impossible due to wildly inconsistent response formats.
Even worse: one of those prices becomes a psychological anchor with executives, regardless of its validity.
What UpperEdge does: We eliminate ambiguity with tailored, scenario-driven RFPs that force vendors to show their cards early and commit to realistic, structured responses.
Red Flag 3: You’re Scoring What Can’t Be Scored
Scoring models are designed to bring structure. However, when these models are misused, they create the illusion of objectivity while masking confusion and misalignment.
Typical pitfalls:
- Qualitative factors like “approach” or “fit” are scored numerically with no shared definitions.
- Stakeholders score inconsistently or guess due to response overload.
- Important soft signals, like chemistry, integrity, and confidence, go unmeasured, yet drive decisions behind the scenes.
Now multiply this by five vendors, hundreds of pages, spreadsheets, and non-standard formats, and the scoring process becomes unmanageable and meaningless.
These challenges are amplified when evaluating platform-based solutions like Workday, where architectural limitations or integration nuances may not surface clearly without deliberate structuring of vendor responses.
What UpperEdge does: We design scoring systems that match reality. These systems are domain-specific, role-aligned, and anchored to your business priorities. We enforce response structures that make true comparison possible.
Red Flag 4: Your RFP Lists Features But Not Outcomes
Most RFPs are functionally detailed, but strategically empty. They specify what a system should do, but not why it matters or how it ties to business success.
This becomes especially dangerous in cloud platform evaluations like Salesforce, Workday or Oracle Cloud, where out-of-the-box functionality can mask critical differences in implementation complexity, integration requirements, and user enablement.
Result:
- Vendors comply with the feature list, but don’t drive innovation or value.
- SOWs become task-based, not outcome-based.
- No one owns the connection between delivery and the business case.
What UpperEdge does: We connect requirements to measurable business outcomes, push vendors to align their methods to those outcomes, and ensure contracts reflect both effort and impact.
Red Flag 5: The Vendors Set the Rules Because You Didn’t
If your RFP doesn’t control how vendors respond, they will take that freedom and use it to their advantage.
What that looks like:
- One vendor submits a deck, another sends spreadsheets, and a third ignores your structure entirely.
- Pricing is inconsistent and based on untraceable assumptions.
- Workstreams are presented differently, making evaluation impossible.
This creates confusion and decision fatigue. Eventually, internal teams gravitate toward the vendor that simply seems easiest to understand or most familiar, often to the benefit of established players like Oracle or Salesforce, who know how to work the process in their favor.
What UpperEdge does: We create structured flexibility. Innovation is welcome, but within a format that supports clear comparison, preserves leverage, and accelerates confident decision-making.
Final Word: Who Has the Advantage?
You may be leading one major ERP or cloud transformation, but your vendor has led hundreds.
They know where the risks are buried, where to price in defensively, and how to turn assumptions into margins. They’ve seen every concession, clause, and scenario. They know exactly how to steer the process, unless someone stops them.
That’s why third-party advisors exist. UpperEdge brings:
- Deal-tested RFPs and SOWs aligned to real outcomes
- Commercial leverage designed into the sourcing process
- Strategic vendor insights based on actual deal behavior, not just sales decks
- And the experience to challenge assumptions before they cost you
Because once your RFP is issued, you’re already negotiating whether you realize it or not.
And let’s not forget what is at stake. The ultimate output of this RFP isn’t a shortlist or a pricing sheet. It’s a Statement of Work that will shape how your business runs, what it pays, and who owns the risk for years to come.
