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Red Flags

This page identifies warning signs that a deal should not proceed. When you see these, pause and escalate.

Critical Red Flags​

These should stop a deal immediately:

Requests for Things We Don't Do​

If a prospect keeps asking for things we've explicitly said we don't provide (managed services, 24/7 support), they either don't understand our model or are hoping we'll bend. Neither is a good foundation.

Unwillingness to Take Ownership​

If a prospect resists the idea that they'll operate and maintain their own systems, our model won't work for them. We enable self-sufficiency; we don't create dependency.

Unrealistic Expectations Despite Clear Communication​

If you've explained trade-offs and constraints clearly but the prospect continues to express unrealistic expectations, they're not listening. This predicts future conflict.

Budget-Scope-Timeline Triangle Violations​

If they want high scope, low budget, and fast timeline, something has to give. Refusal to acknowledge this predicts project failure.

Pressure to Skip Process​

If a prospect pushes to skip requirements analysis, bypass evaluation, or rush past normal steps, they're either inexperienced or hoping to exploit ambiguity later.

Serious Red Flags​

These warrant escalation and careful evaluation:

History of Failed Vendor Relationships​

If they've gone through multiple vendors and blame all of them, consider whether the common factor is them.

Vague or Shifting Requirements​

If they can't articulate what they need, or requirements change significantly between conversations, scope management will be extremely difficult.

Key Decision-Makers Unavailable​

If the people who will actually make decisions are never in conversations, you may be building a proposal for someone who doesn't know about it.

Internal Politics Evident​

If you sense significant internal disagreement about the project, the project may stall or fail regardless of your work quality.

Price-Shopping Behavior​

If they're clearly shopping multiple vendors primarily on price, they may not value what we specifically offer.

Requesting Free Work​

If they want significant scoping, analysis, or proposal work before committing, they may be harvesting free consulting.

Yellow Flags​

These warrant attention and extra qualification:

Aggressive Timelines​

Not always a problem, but warrants understanding why and whether the timeline is realistic.

Limited Budget​

Not disqualifying, but requires honest scope conversation.

No Current IT Capability​

Workable if they're willing to build capability, problematic if they're not.

Previous Bad Experience with Open Source​

May indicate unrealistic expectations or may indicate they learned from a poorly-run project.

Highly Regulated Industry​

Not a problem, but requires confirming we understand the compliance requirements.

How to Use This List​

  1. During qualification: Check prospects against these flags
  2. Before proposal: Review whether any flags appeared
  3. When feeling uneasy: Use this list to articulate concerns
  4. In escalation: Reference specific flags when escalating

Responding to Red Flags​

When You Spot a Critical Flag​

"I want to pause here. Based on our conversation, I'm concerned we may not be the right fit. [Explain specific concern.] I'd rather be direct about this now than have it become a problem later."

When You Spot a Serious Flag​

"Before we go further, I want to address something. [Raise the concern.] How do you see that working with the engagement we're discussing?"

When You're Unsure​

Escalate internally before proceeding. Document the specific flags you observed.

Documentation​

When declining a prospect or escalating concerns, document:

  1. Which specific flags you observed
  2. What evidence led to that assessment
  3. What (if anything) the prospect said when you raised concerns
  4. Your recommendation on whether to proceed

This creates institutional memory and helps refine our qualification process.