Red Flag Pattern Library

This library contains copy-paste detection patterns for scanning outbound emails before they reach clients. Each pattern includes regex expressions, keyword lists, and context rules you can implement in your email review workflow.

Use these patterns to catch four critical errors: internal pricing leaks, forgotten placeholders, wrong client names, and unprofessional language. Every pattern includes detection logic and real examples.

Accidentally sending internal rate cards, cost breakdowns, or margin calculations destroys negotiating position and violates confidentiality protocols.

Numeric Pattern Detection

Dollar amounts with context:

• Regex: \$\d{1,3}(,\d{3})*(\.\d{2})?(?=\s*(per|/|hourly|hr|hour|rate|cost|fee))
• Catches: "$250/hr", "$1,500 per day", "$85.00 hourly rate"

Price ranges:

• Regex: \$\d{1,3}(,\d{3})*\s*(-|to|through)\s*\$\d{1,3}(,\d{3})*
• Catches: "$15,000 - $20,000", "$500 to $750", "$2,000 through $3,500"

Percentage margins:

• Regex: \d{1,3}%\s*(margin|markup|profit|discount|overhead)
• Catches: "35% margin", "20% markup", "15% overhead allocation"

Keyword Trigger Lists

High-risk pricing terms:

internal rate
standard rate
our cost
blended rate
loaded rate
fully burdened
cost-plus
margin
markup percentage
discount from list
partner rate vs associate rate
realization rate
write-down
write-off
budgeted hours
actual vs budget

Dangerous phrase combinations:

• "Don't share this with [client name]"
• "Internal only"
• "For pricing purposes"
• "Our actual cost is"
• "We're billing X but paying Y"

Detection Example

Flagged email:

Subject: Re: Q4 Engagement Scope

Hi Sarah,

Based on our discussion, here's the breakdown:

Partner time: 40 hours @ $450/hr = $18,000
Senior Associate: 80 hours @ $275/hr = $22,000
Staff: 120 hours @ $150/hr = $18,000

Total: $58,000 (our internal budget is $52,000, so we have 
10% margin built in)

Let me know if this works.

Why it's flagged:

• Explicit hourly rates with role titles
• Line-item cost breakdown
• Internal budget reference
• Margin calculation visible to client

Corrected version:

Subject: Re: Q4 Engagement Scope

Hi Sarah,

Based on our discussion, the fixed fee for this engagement 
is $58,000. This includes all partner oversight, research, 
analysis, and deliverable preparation.

I'll send the formal engagement letter by end of day.

Placeholder text signals rushed work and destroys credibility. Clients notice "[INSERT NAME]" immediately.

Standard Placeholder Patterns

Bracket placeholders:

• Regex: \[(CLIENT|COMPANY|NAME|DATE|PROJECT|DELIVERABLE|INSERT|TBD|PENDING|XXX|TODO)\]
• Case-insensitive matching
• Catches: "[Client Name]", "[insert date]", "[TBD]", "[XXX]"

Angle bracket placeholders:

• Regex: <(client|company|name|date|project|your|insert).*?>
• Catches: "<client name>", "<your company>", "<insert details>"

Lorem ipsum variants:

• Exact match: "Lorem ipsum", "dolor sit amet", "consectetur adipiscing"
• Catches partial lorem ipsum blocks

Template-Specific Patterns

Proposal templates:

[Scope of Work]
[Timeline]
[Deliverables]
[Assumptions]
[Out of Scope]
[Pricing]
[Terms and Conditions]

Email templates:

[Client First Name]
[Company Name]
[Project Reference]
[Specific Detail]
[Next Steps]
[Meeting Date/Time]

Document references:

See attached [document name]
As discussed on [date]
Per our conversation with [name]

Detection Example

Flagged email:

Dear [Client Name],

Thank you for the opportunity to work with [Company] on 
the [Project Name] engagement.

Our team will deliver:
- [Deliverable 1]
- [Deliverable 2]  
- [Deliverable 3]

We'll complete this work by [Date]. The total investment 
is [Price].

Please let me know if you have questions.

Best regards,
[Your Name]

Why it's flagged:

• Six separate placeholder fields
• Zero personalization
• Template structure completely visible

Corrected version:

Dear Marcus,

Thank you for the opportunity to work with Apex Industries 
on the supply chain optimization project.

Our team will deliver:
- Current state process maps (15 workflows)
- Bottleneck analysis with cost impact
- Implementation roadmap with quick wins

We'll complete this work by March 15. The total investment 
is $47,500.

I'll call you Thursday at 2pm to walk through the proposal.

Best regards,
Jennifer

Using the wrong client name is unrecoverable. One instance destroys months of relationship building.

Name Mismatch Patterns

Salutation vs body inconsistency:

• Extract name from "Dear [Name]" or "Hi [Name]"
• Scan body for different name references
• Flag if names don't match

Company name inconsistency:

• Extract company from signature block or previous emails
• Scan for different company references
• Flag variations: "ABC Corp" vs "ABC Corporation" vs "XYZ Inc"

Pronoun mismatch:

• Track gender pronouns used
• Flag switches: "he" to "she" or vice versa
• Flag "they" switching to gendered pronouns

Context Clues for Detection

Email thread analysis:

• Compare current draft to previous thread
• Flag if recipient name changed but content didn't
• Check if "Reply All" includes people not mentioned

Signature block comparison:

• Extract client name from their signature
• Compare to name used in salutation
• Flag spelling variations

Project name verification:

• Check if project name matches client
• Flag: "Smith Project" in email to Jones Company

Detection Example

Flagged email:

Dear Jennifer,

Thank you for your patience as we finalized the Anderson 
Manufacturing analysis. 

Sarah, I wanted to update you on our progress. The team 
has completed the initial assessment and identified three 
priority areas for improvement.

I'll send the full report to Jennifer by Friday.

Best regards,
Michael

Why it's flagged:

• Salutation says "Jennifer"
• Body addresses "Sarah"
• Closing references "Jennifer" again
• Project name is "Anderson Manufacturing" (neither Jennifer nor Sarah)

Likely scenario: Email drafted for Sarah Anderson, then copied for Jennifer at different company, names not fully updated.

Unprofessional language in client emails creates HR issues, damages reputation, and provides evidence in disputes.

Profanity and Explicit Terms

Direct profanity list:

damn
hell (context-dependent)
crap
ass (except in "assessment", "class", etc.)
pissed
screw/screwed (in negative context)
bullshit

Masked profanity:

• Regex: \b\w*\*+\w*\b (catches "f***", "sh*t")
• Catches: "What the f***", "This is bs"

Unprofessional Tone Markers

Overly casual language:

Hey (instead of Hi or Hello)
Yeah/Yep/Nope
Gonna/Wanna/Gotta
LOL/LMAO
Cheers (in US business context)
Dude
Guys (when addressing mixed groups)

Passive-aggressive phrases:

As I already mentioned
Per my last email
Not sure if you saw my previous message
Just following up again
Circling back on this
I'm still waiting for
Friendly reminder (third+ time)

Emotional escalation:

This is unacceptable
I'm extremely disappointed
This is ridiculous
I can't believe
You need to understand
Frankly
To be honest (implies previous dishonesty)

Discriminatory Language Patterns

Protected class references:

• Age: "old-school", "dinosaur", "millennial approach"
• Gender: "you guys", "manpower", "chairman"
• Disability: "crazy", "insane", "lame", "blind to"
• Religion: religious holiday assumptions
• National origin: "foreign", "exotic", "articulate"

Microaggression patterns:

• "You're so articulate"
• "I don't see color"
• "That's so gay"
• "Spirit animal"
• "Powwow" (for meetings)

Detection Example

Flagged email:

Hey Marcus,

Just circling back on this again. Per my last three emails, 
we really need to get this wrapped up. 

I can't believe we're still dealing with this. Your team 
needs to understand that this is unacceptable. We've been 
busting our asses to hit your crazy deadlines.

Frankly, if we don't get answers by EOD, this whole thing 
is going to be a total shitshow.

Let me know.

Cheers,
Brad

Why it's flagged:

• "Hey" (too casual)
• "Just circling back" (passive-aggressive)
• "Per my last three emails" (aggressive)
• "I can't believe" (emotional)
• "needs to understand" (condescending)
• "busting our asses" (profanity)
• "crazy deadlines" (ableist language)
• "Frankly" (aggressive)
• "total shitshow" (explicit profanity)
• "Cheers" (inappropriately casual for tense situation)

Corrected version:

Hi Marcus,

Following up on the outstanding items from our last call. 
We need the following by end of day Thursday to maintain 
the project schedule:

1. Approval on revised scope (sent Monday)
2. Access credentials for the staging environment
3. Confirmation of the March 15 delivery date

Our team has the analysis complete and ready to deliver 
once we receive these items.

I'm available for a call this afternoon if that helps 
move things forward.

Best regards,
Brad

Set up detection rules:

1. Add regex patterns to your email client or review tool
2. Create keyword lists in your spam filter or compliance system
3. Configure alerts for high-risk pattern matches
4. Test patterns against last 50 sent emails to calibrate

Create review workflow:

1. Run detection scan before sending any client email
2. Flag emails with 2+ pattern matches for human review
3. Require partner approval for emails with pricing references
4. Archive flagged emails for training purposes

Train your team:

1. Share this library with all client-facing staff
2. Review flagged examples in monthly team meetings
3. Update patterns based on new incidents
4. Celebrate catches that prevented client issues