Open source methodology
The Caritas Fit Call and Groundwork Playbook
Willing the good of the other
Transform sales conversations from transactions into partnerships through honest boundaries. One complimentary 30-minute fit call confirms mutual fit and readiness. Detailed discovery and custom work begin only in paid Groundwork.
The principle
Based on St. Thomas Aquinas's definition of charity: "Caritas": to will the good of the other. This means creating clarity without disguising unpaid consulting as generosity. The fit call produces a mutual decision. Accepted Groundwork funds the research, discovery, and solution design needed to create responsible value.
Core Philosophy
Will the Good of the Other
Prioritize the prospect's good through candor, care, and clear commercial boundaries. Do not imply that meaningful custom work is free.
Clarity Before Commitment
The complimentary fit call should leave both sides clear on fit and readiness. It is not a research, discovery, recommendation, or scoping session.
Come to Terms First
Deep discovery begins after explicit Groundwork acceptance, the $1,000 activation, and acknowledgment of the role-based rate card.
Fund Responsible Insight
Detailed research, stakeholder interviews, system and data review, ROI modeling, estimates, and solution design belong in paid Groundwork.
The Mindset Shift
This approach pairs generosity of spirit with disciplined boundaries. A candid no-fit decision can serve someone well. When deeper work is warranted, paid Groundwork gives it the time, access, and accountability it deserves.
Trust compounds when people know what is complimentary, what is paid, and what each stage can responsibly produce.
The Five Key Differentiators
Pattern recognition from fit calls reveals readiness for a responsible paid discovery process
Problem Framing: Single Point of Pain vs. Laundry List
Winning Pattern
Laser focus on one or two critical, interconnected problems that are:
- • Specific and quantifiable
- • Tied to revenue or strategic goals
- • Causing immediate business pain
- • Clear in scope and impact
Example: "Our inefficient recruiting process for 30,000+ annual hires is our biggest revenue risk"
Losing Pattern
Scattered list of potential improvements without prioritization:
- • Multiple "nice-to-have" improvements
- • No central urgent driver
- • Exploratory brainstorming mode
- • Unable to prioritize impact
Example: "We want to improve case management, mailroom, billing, intake, and reporting"
Urgency & Stakes: Bleeding Neck vs. Vitamin
Winning: High Stakes, Immediate Timeline
- Clear time-bound financial threat
- Risk of losing major customers
- Hard deadlines with consequences
Losing: Important but Not Urgent
- Long-term efficiency improvements
- Recurring inconveniences, not crises
- Future-state desires, not present pain
Prospect's Role: Decision-Maker vs. Information Gatherer
Winning: Direct Authority
Speaking directly to C-Suite, President, or Department Head with:
- • P&L responsibility
- • Budget authority
- • Mandate to solve the problem
Losing: Intermediary
Speaking with someone who:
- • Needs approval from others
- • Delegates next steps to subordinates
- • Is "looking into options"
Call Dynamics: Convergent vs. Divergent
Winning: Quick Convergence
Conversation narrows to one urgent problem and a clear decision about whether paid Groundwork is the right next step
Losing: Endless Exploration
Conversation remains broad, exploring many possibilities without landing on a concrete starting point
Mindset: Problem-Focused vs. Solution-Focused
Winning: Problem Obsessed
Describes the pain, business impact, and consequences of inaction. Ready to fund evidence-based Groundwork before choosing how to solve it.
Losing: Solution Shopping
Fixated on specific technical features. Gets stuck on "can AI do X?" rather than the business problem to solve.
The Rorschach Test: Your Hidden Qualification Filter
The Fit Signal
Analysis of successful calls reveals a powerful pattern: When you tell an illustrative story early in the conversation, the prospect's reaction helps reveal whether there may be mutual fit for Groundwork.
The story is the inkblot. Use the response to assess fit and readiness, then stop before diagnosis, recommendation, estimation, or solution design.
Winning Response Pattern
The prospect immediately:
- • Interrupts to ask about the workflow
- • Recognizes their own problem in your story
- • Reframes their situation in that context
- • Scales it to their larger challenge
"That's exactly our problem, but we have it at 10x the scale..."
Losing Response Pattern
The prospect:
- • Asks technical questions about HOW
- • Treats it as an interesting anecdote
- • Gets stuck on implementation details
- • Never connects it to their own pain
"What technology did you use? Is that ChatGPT? How does it integrate?"
Key Insight: You're not just telling stories for rapport. You're running a live qualification test. Winners see their world in your story. Losers just see an interesting story.
The Anchor-Story-Pivot Framework
Use this framework during the bounded fit call to identify one urgent priority and assess Groundwork readiness. Stop before custom diagnosis, recommendations, estimates, or solution design.
Anchor (Listen for the Domain)
First 2-3 minutes
Listen for the general business area of their pain. Don't let them give you a laundry list - just get a sense of the territory:
Sales/Growth
Pipeline, conversion, outreach
Operations
Efficiency, automation, quality
Talent/Hiring
Recruiting, training, retention
Story (Deploy the Rorschach Test)
Minutes 3-7
Interrupt their exploration with: "That reminds me of a situation with another client..." Then tell your most relevant, vivid success story for that domain:
If they mention growth:
Tell about analyzing 40,000 data points to drive word-of-mouth growth
If they mention operations:
Tell about solving a customer service crisis that risked major accounts
If they mention talent:
Tell about fixing a high-volume hiring process losing revenue
Focus on the business problem and outcome, not the technology.
Pivot (Ask The One Question)
Immediately after the story
The One Question:
"What is the single biggest, most expensive version of that problem in your world right now?"
This question is engineered to:
Force Prioritization
Compels them to identify their #1 pain
Frame for Value
"Most expensive" forces ROI thinking
Connect to Proof
Anchors to your proven success
Qualify Authority
Leaders answer instantly, others struggle
Critical: A strategic leader will answer immediately with specifics. An information gatherer will hesitate, deflect, or stay vague. Their response is your clearest qualification signal.
The Four-Phase Process
Clear boundaries protect the prospect, the practitioner, and the quality of the work
Phase 1: Bounded Preparation
Before the complimentary fit call
Prepare to assess fit without beginning unpaid discovery
Protect the Boundary
Reserve one 30-minute fit call and keep the conversation focused on mutual fit and readiness
Review the Intake
Read the submitted urgent problem, stakes, authority, and willingness to activate Groundwork
Avoid Premature Analysis
Do not research the company, model ROI, estimate value, inspect systems, or design a solution before activation
Request No Private Discovery
Do not add stakeholder interviews, private-data requests, or voice intake before paid Groundwork
Phase 2: The Fit Call
One complimentary 30-minute conversation
Confirm whether both sides are ready for a paid discovery engagement
State the Boundary
Confirm that the call covers mutual fit and readiness, not custom discovery, recommendations, or scoping
Hear One Priority
Understand the single urgent problem and why it matters now at a high level
Confirm the Stakes
Ask what happens if the priority remains unresolved and who owns the decision
Test Readiness
Confirm authority, access readiness, and willingness to accept the $1,000 activation and rate card
Make a Mutual Decision
Choose no fit, revisit later, or proceed to explicit Groundwork acceptance
Phase 3: Groundwork Activation
Before detailed work begins
Create an explicit paid engagement boundary
Accept Groundwork
Record explicit acceptance of the paid discovery engagement
Issue the Activation Invoice
Invoice the mandatory $1,000 one-time activation before discovery starts
Acknowledge the Rate Card
Confirm role-based hourly rates, prorated to the minute, plus the agreed monthly cap and NET 15 invoicing
Authorize the Work
Agree which stakeholders, systems, documents, and data can enter paid Groundwork
Phase 4: Paid Groundwork
Detailed discovery and design
Do the rigorous work required for defensible recommendations
Research and Interview
Conduct detailed research and stakeholder interviews inside the active engagement
Inspect Systems and Data
Review authorized workflows, documents, systems, and data to establish ground truth
Model and Design
Produce custom insights, ROI modeling, estimates, and solution design as paid Groundwork outputs
Clear the Underwriting Gate
Only then decide whether to propose separate value-based Quick Win terms
The Three Paths Forward
Pause
When there is no fit or readiness
End the fit call honestly when the problem, authority, urgency, or readiness is missing. Do not manufacture a paid next step.
Example: "I do not think Groundwork is the right next step based on what we heard today."
This builds immense trust and demonstrates true commitment to their success.
Self-Service
Use public resources without custom consulting
Point people to public frameworks, tools, or examples when they are not ready for Groundwork. Keep this distinct from a customized action plan.
- Share public resources available to everyone
- Use general examples without diagnosing their situation
- Let them decide if and when to act
- Invite them to consider paid Groundwork when one urgent problem is ready
Paid Groundwork
Formal discovery engagement
Begin detailed research, discovery, interviews, system and data review, modeling, estimates, and solution design only after activation.
Accept the Engagement
Record explicit Groundwork acceptance
Activate Groundwork
Issue the mandatory $1,000 one-time activation invoice
Confirm the Rate Card
Role-based hourly rates, prorated to the minute, under the agreed cap
Pricing & Terms Framework
Bound the Complimentary Call
Offer one 30-minute fit call for mutual fit and readiness. Research, diagnosis, recommendations, estimates, and design are outside its scope.
Activate Groundwork
Detailed discovery begins after explicit acceptance and the mandatory $1,000 one-time activation.
Use the Groundwork Rate Card
Bill live time and required compliance work at role-based hourly rates, prorated to the minute, under the agreed monthly cap.
Underwrite Only After Discovery
If paid Groundwork clears the gate, propose separate Quick Win terms based on the outcome's expected value.
Phase-Specific Commercial Terms
Paid Groundwork
- • $1,000 one-time activation
- • Role-based rate card
- • Live time prorated to the minute
- • Hard monthly cap and NET 15 invoicing
Quick Win in a Box
- • Offered only after Groundwork
- • Priced as a share of expected value
- • 50% on activation
- • 50% on verified success
Remember: System and data inspection occurs during paid Groundwork before Quick Win terms are proposed. The fit call does not produce a scope, estimate, roadmap, or underwriting decision.
Real-World Examples & Scenarios
The Pause Path: AI Trend Chaser
Scenario: A traditional manufacturing CEO wants to "put AI on everything" after a conference.
Fit Call: The CEO cannot identify one urgent workflow, an accountable owner, or readiness to fund Groundwork. Stop at the fit decision without diagnosing the business or estimating value.
Your Response: "I don't see enough focus or readiness for Groundwork today. I will point you to our AI Bottleneck Finder. If one material bottleneck becomes a priority with an owner, we can revisit paid discovery."
Result: The prospect gets an honest answer and no unpaid custom recommendation.
The Self-Service Path: Recruiter Exploring AI
Scenario: One recruiter is curious about improving notes but has no organizational sponsor or readiness to activate Groundwork.
Fit Call: Confirm that there is no current fit for paid discovery. Do not inspect their workflow or create a custom plan.
Self-Service: Point them to public, generally applicable resources. Do not provide a customized prompt, workflow, or implementation instructions.
Boundary: Any tailored analysis, recommendation, or implementation support requires accepted and activated Groundwork.
Result: They can learn independently without creating an unpaid consulting loop.
The Groundwork Path: Top-of-Funnel Crisis
Scenario: SaaS startup with 0.1% cold email response rate, burning $50K/month, 4 months runway remaining.
Fit Call: Confirm one urgent problem, an accountable sponsor, and readiness to activate Groundwork. Do not diagnose the cause or promise a result.
Activation: Record explicit Groundwork acceptance, issue the $1,000 activation invoice, and acknowledge the role-based rate card and monthly cap.
Paid Groundwork: Research the business, interview authorized stakeholders, inspect systems and data, test the bottleneck, model potential value, and design candidate solutions.
Quick Win Gate: If the evidence supports a specific outcome, propose separate value-based Quick Win terms with 50% on activation and 50% on verified success.
Result: The client underwrites discovery before Caritas underwrites the outcome.
The Tire Kicker: "Just Exploring Options"
Red Flags: Vague about budget, no specific pain point, "just want to learn about AI," multiple stakeholders but no decision maker present.
Your Response: End the one complimentary fit call with a no-fit or revisit-later decision. Share public resources without adding unpaid discovery meetings.
Script: "Based on what you've shared, you're in exploration mode. Here's my AI Bottleneck Finder. If one urgent priority emerges and you are prepared to activate Groundwork, contact us about paid discovery."
Lesson: Clear boundaries protect the prospect, the practitioner, and the quality of the work.
Tools by Engagement Phase
Paid Groundwork Research
- ChatGPT/Claude: Authorized research and evidence synthesis
- Perplexity: Sourced market intelligence to validate hypotheses
- Clay.com: Data enrichment within the accepted Groundwork scope
Fit Call and Capture
- Qualification form: Bounded fit and readiness inputs
- Fireflies.ai: Call transcription with participant consent
- Calendly: Scheduling after qualification
Decision and Follow-Up
- Fit record: Document no fit, revisit later, or Groundwork offered
- Shortwave/Superhuman: Send the decision and next-step summary
- Groundwork terms: Share activation and rate-card details when offered
Paid Groundwork Interview Setup
Boundary: Use stakeholder interview tools only after explicit Groundwork acceptance, the $1,000 activation, acknowledgment of the rate card, and client authorization. This is not an extra complimentary intake call.
Sample Stakeholder Interview Frame
"We are working within your active Groundwork engagement to understand [workflow]. With your permission, I would like to document the evidence behind the current process.
Where does the workflow break down today?
What evidence shows the scale and consequences of that bottleneck?
Which systems, documents, and data sources reflect ground truth?
What would a verifiable improvement look like?"
Implementation Steps
- 1.Confirm Groundwork activation and the authorized interview scope
- 2.Obtain participant consent and approved access before recording
- 3.Conduct interviews as paid Groundwork activities
- 4.Validate interview evidence against authorized systems and data
- 5.Produce recommendations, estimates, and solution designs as Groundwork outputs
Practical Tools & Templates
Paid Groundwork Research Prompt
Use only after Groundwork is accepted, the $1,000 activation is invoiced, and the rate card is acknowledged.
PAID GROUNDWORK ONLY Use this prompt only after explicit Groundwork acceptance, the $1,000 activation, and acknowledgment of the rate card. Do not run it for the complimentary fit call. Draft a dossier on [Person's Name], [Title] at [Company]. Groundwork has been activated to investigate [Context]. Focus on: 1. Professional background and recent activity 2. The organization's business model and customer experience 3. Financial metrics: - Revenue & profit estimates - Growth trajectory - Peer comparison 4. Potential value and ROI hypotheses to validate 5. Strategic initiatives they may be pursuing 6. Challenges they're likely facing Separate sourced facts from hypotheses. Do not recommend or scope a solution until the relevant stakeholders, systems, and data have been reviewed.
Groundwork Validation Questions
Use these during paid Groundwork to test a candidate outcome:
- "If I could snap my fingers and guarantee you'd have 10 qualified meetings with LPs booked by the conference, how would that feel?"
- "If we could guarantee your team would save 20 hours per week on repetitive tasks starting next month, what would that mean for you?"
- "If you knew with certainty that your conversion rate would double in 90 days, how would that change your planning?"
Treat the answers as hypotheses. Validate them against stakeholder evidence, systems, and data before producing recommendations or Quick Win terms.
Time Management
Fit Call (30 min)
- • State the fit and readiness boundary
- • Hear one urgent problem and its stakes
- • Confirm authority and activation readiness
- • Decide no fit, revisit, or Groundwork
Groundwork Activation
- • Record explicit acceptance
- • Issue the $1,000 activation invoice
- • Confirm the role-based rate card
- • Confirm the monthly cap and NET 15 terms
Paid Groundwork
- • Research and interview stakeholders
- • Review authorized systems and data
- • Model ROI and create estimates
- • Develop scoped opportunities and solution designs
Stage-Appropriate Follow-Up
Fit Call Follow-Up
- Thank them for their time
- Record the mutual fit decision
- Restate only the priority and stakes they shared
- Send public resources when appropriate
- If offered, send Groundwork activation and rate-card details
- Do not include custom recommendations, estimates, or a roadmap
Paid Groundwork Output
- Document evidence from research and interviews
- Map authorized systems and data access
- Quantify potential value and uncertainty
- Present estimates and scoped opportunities
- Recommend a path based on verified evidence
- Propose Quick Win terms only if the gate clears
Profile of a Winning vs. Losing Prospect
The Strategic Firefighter
Role
C-Suite, President, or Department Head with P&L or critical KPI responsibility
Problem
Articulates a single, specific, urgent business problem using phrases like "revenue risk," "losing customers," or "bottleneck to growth"
Urgency
Can point to clear negative consequences that will occur this quarter or half if unaddressed
Mindset
Problem-fluent and solution-agnostic. Willing to fund evidence-based discovery before choosing an approach
Action
Has authority to accept Groundwork, fund the $1,000 activation, and acknowledge the role-based rate card
Key Signal: When you tell a relevant story, they immediately interrupt to relate it to their bigger problem
The Curious Explorer
Role
Can be a leader, but often an intermediary or manager tasked with "looking into AI"
Problem
Presents a broad list of potential improvements or general "inefficiencies" without a single priority
Urgency
Pain is chronic but not acute. Focused on being "better" or "more efficient" with no immediate driver
Mindset
Solution-focused, asking "can AI do X?" and getting stuck on technical features vs business outcomes
Action
Unwilling or unable to activate paid Groundwork, while suggesting more free meetings or delegating the decision to others
Key Signal: When you tell a story, they ask about the technology instead of connecting it to their pain
Fit Call Qualification Techniques
Red Flags to Watch For
- Laundry list problems: Multiple unconnected pain points
- Solution shopping: "Can your AI do X, Y, Z?"
- Delegates follow-up: "I'll have my team reach out"
- Technical fixation: Gets stuck on HOW vs WHAT
- No quantification: Can't articulate financial impact
- Vitamin problems: "Would be nice to improve"
Green Flags of Quality Prospects
- Single burning issue: One critical problem to solve
- Revenue impact: "This is our biggest revenue risk"
- Pattern matching: Relates your story to their problem
- Personal urgency: Decision maker feels the pain
- Quick convergence: Narrows to one urgent problem without designing a solution
- Groundwork authority: Can accept Groundwork and fund activation
Power Questions for Qualification
Questions to Force Prioritization
"Of all the things you mentioned, which one is causing the most tangible pain right now?"
"If we could only solve one of these in the next 90 days, which would have the biggest impact on your key business goals?"
"What happens if none of these get addressed in the next six months?"
Questions to Reframe Efficiency as Opportunity
"If your top performers got 10 hours back each week, what high-value activities could they focus on?"
"What revenue opportunities are you missing because your team is stuck in manual processes?"
Questions to Sidestep Solution Shoppers
"Setting the technology aside for a moment, if we could save your team X hours per week, what would the value of that be?"
"Before we talk about HOW, help me understand WHAT success looks like for you in 3 months?"
Updated Disqualification Scripts
For the Explorer (Multiple Problems, No Priority):
"You've mentioned several areas for improvement, which tells me you're in exploration mode. Start by identifying one urgent bottleneck with a clear owner and meaningful stakes. If you become ready to fund a responsible investigation, Groundwork is where we can research the evidence and design a solution."
For the Solution Shopper (Technology Focused):
"I can see you're focused on technical capabilities. A responsible recommendation requires evidence from the workflow, stakeholders, systems, and data. If you are ready to fund that investigation, we can do it inside paid Groundwork."
For the Delegator (Not the Decision Maker):
"It sounds like the real decision sits with [decision maker]. They should join the single complimentary fit call. If they cannot, let's reschedule this call rather than add another unpaid discovery meeting."
For the Vitamin Seeker (No Urgency):
"Based on what you've shared, this sounds like a 'nice to have' rather than a 'must solve now.' In my experience, these projects rarely get the resources and attention they need to succeed. When this becomes a burning priority with an accountable owner, we can revisit whether paid Groundwork is the right next step."
Critical Best Practices
End With a Clear Fit Decision
The complimentary call should end with no fit, revisit later, or an offer to activate Groundwork. Do not use the call to pressure a commitment or invent extra unpaid meetings.
Let Clarity Create Goodwill
A candid fit decision can leave someone better off without opening an unpaid consulting loop. Share a public resource when useful, then let trust and referrals develop without making either a condition of the call.
Use Technology as Force Multiplier
Use the qualification form and scheduling tools before the fit call. Use Fireflies with consent for the call record. Deploy research agents, stakeholder interview tools, and detailed synthesis only after Groundwork activation.
Use Examples Without Diagnosing
A relevant story can help assess fit, but it is not a custom recommendation. Reserve tailored insights and advice for paid Groundwork, where they can be supported by evidence.
Model Economics in Groundwork
The fit call may confirm that the stakes are material. Detailed revenue analysis, cost modeling, ROI estimates, and CFO-level validation begin only after paid Groundwork is active.
The Goodwill Flywheel
When you consistently apply this methodology, something magical happens:
You Create Genuine Clarity
The fit call leaves both sides clear on fit and next steps
Goodwill Accumulates
People remember and share their experience
Private Networks Activate
Your name spreads in decision-maker circles
Quality Opportunities Flow
The right clients find you naturally
You can't measure this channel, but it has no ceiling.
Trust the process. Will the good. The rest follows.
Track Fit Calls and Paid Groundwork Separately
Fit Call and Groundwork Tracker
Use the CSV as a starting point, then keep the complimentary fit decision separate from any evidence or deliverables produced in paid Groundwork.
- Track prospect details and company info
- Record the fit decision and readiness signal
- Record Groundwork acceptance, activation, and rate-card acknowledgment
- Add estimates or value models only after Groundwork activation
- Link to recordings only when participants consent
Ready to take the next step? Complete 3+ disciplined fit-call decisions and activated Groundwork engagements, then apply to become a Caritas Associate.
Licensed under Apache 2.0 with GSD at Work LLC copyright. Free to use, modify, and distribute with attribution.
How This Connects to Other Caritas Methodologies
Fit Call → Paid Groundwork
The fit call confirms only mutual fit and readiness. Detailed discovery starts after Groundwork is accepted and activated.
Fit Call Output
No fit, revisit later, or Groundwork offered
Groundwork Activation
Explicit acceptance, $1,000 activation, and rate card
Paid Groundwork → Quick Win
Groundwork researches, interviews, inspects systems and data, models value, and designs candidate solutions before any Quick Win is proposed.
Groundwork Output
Evidence-backed outcome, access map, value model, and estimate
Separate Quick Win Terms
Value-based price only after the underwriting gate clears
Fit Call and Groundwork → Associate Program
Demonstrate disciplined fit decisions and responsible paid discovery to qualify for the Caritas Associate Program.
- Complete 3+ fit-call decisions and activated Groundwork engagements
- Demonstrate mastery of the three paths
- Build reputation for creating genuine value
Groundwork → Oracle and Strategy Methods
When appropriate, paid Groundwork can use Oracle and strategy methods for authorized research, stakeholder alignment, and verification planning.
Inside Groundwork
Interview authorized stakeholders and analyze evidence
Before Quick Win Terms
Define the verifier and evidence only after system and data review
The Two-Stage Foundation
The bounded fit call is the entry gate. Activated, paid Groundwork is the discovery foundation where custom research, recommendations, estimates, and solution design occur.
Create Trust Through Clear Boundaries
Willing the good means giving a candid fit decision and reserving custom work for paid Groundwork. That clarity protects both sides and gives responsible discovery the time, access, and accountability it deserves.