Character Assessment

---
name: character-assessment
description: Evaluate the trustworthiness and reliability of individuals or organizations before entering business relationships, partnerships, or high-stakes agreements.
license: MIT
metadata:
  version: 1.0.3561
  author: sethmblack
repository: https://github.com/sethmblack/paks-skills
keywords:
- character-assessment
- writing
---

# Character Assessment

Evaluate the trustworthiness and reliability of individuals or organizations before entering business relationships, partnerships, or high-stakes agreements.

---

## When to Use

- Evaluating a potential business partner or co-founder
- Assessing a vendor or contractor before signing
- Hiring decisions for key positions
- Evaluating leadership teams (investment due diligence)
- Any situation where trust is foundational to the relationship
- Request for "Can I trust this person?" or "Should we do business with them?"

---

## Philosophy

As J.P. Morgan testified before Congress in 1912:

> "The first thing [in credit] is character... before money or anything else. Money cannot buy it... A man I do not trust could not get money from me on all the bonds in Christendom."

Numbers can be manufactured. Balance sheets can deceive. Character endures.

---

## Inputs

| Input | Required | Description |
|-------|----------|-------------|
| subject | Yes | The person, team, or organization to assess |
| context | Yes | The relationship being considered (partnership, hiring, vendor, etc.) |
| evidence | No | Available information: track record, references, interactions |
| stakes | No | What is at risk if trust is misplaced |

---

## Assessment Framework

### 1. Track Record Examination

What has this person done, not what have they said?

**Questions to answer:**
- Have they honored commitments in the past?
- Have they ever failed to deliver on an obligation?
- How did they behave when things went wrong?
- What do people who have worked with them say—not publicly, but privately?

**Red flags:**
- Broken commitments, even small ones
- Blaming others for failures
- Patterns of conflict with former partners
- Unexplained gaps or departures
- Excessive confidentiality about past dealings

**Green flags:**
- Long-term relationships maintained
- Acknowledgment of own mistakes
- References who would work with them again
- Consistent story from multiple sources
- Skin in the game in past ventures

### 2. Direct Engagement

Morgan insisted on meeting anyone seeking significant dealings. The character assessment happens face-to-face.

**What to observe:**
- Do they hold your gaze? (Avoidance suggests discomfort with scrutiny)
- Do they answer directly or deflect?
- How do they speak of former partners and competitors?
- Do they take responsibility or assign blame?
- What do they say when you ask hard questions?

**The pressure test:**
- Introduce difficulty into the conversation
- Ask about past failures directly
- Present a hypothetical ethical dilemma
- Observe reaction to unexpected challenges

**Morgan's insight:** The response to pressure reveals character that comfort conceals.

### 3. Reference Deep-Dive

Standard references are curated to be positive. Dig deeper.

**Questions for references:**
- "Would you do business with them again?" (Hesitation is telling)
- "What happened when things went wrong?"
- "How do they treat people who can't help them?"
- "What's the hardest thing about working with them?"
- "Is there anything you wish you'd known beforehand?"

**The backdoor check:**
- Find references they didn't provide
- Talk to former employees, not just peers
- Ask about specific situations, not general impressions
- Listen for what's not said as much as what is

### 4. Alignment Assessment

Character also means alignment of interests and values.

**Questions to answer:**
- What do they actually want from this relationship?
- Are their incentives aligned with yours?
- What would cause them to act against your interests?
- Do your values conflict in ways that will surface under pressure?

**Warning signs:**
- Overeager agreement without pushback
- Interests that diverge under stress
- Different definitions of success
- Conflicting ethical frameworks

### 5. The Final Question

Ask yourself: "If this person's character were the only collateral backing this relationship—no contracts, no legal recourse, just their word—would I proceed?"

If the answer is not an immediate yes, do not proceed.

---

## Workflow

### Step 1: Gather and Review Inputs

Collect all relevant information:
- Review the provided data and context
- Identify key parameters and constraints
- Clarify any ambiguities or missing information
- Establish success criteria

### Step 2: Analyze the Situation

Perform systematic analysis:
- Identify patterns and relationships
- Evaluate against established frameworks
- Consider multiple perspectives
- Document key findings

### Step 3: Generate Recommendations

Create actionable outputs:
- Synthesize insights from analysis
- Prioritize recommendations by impact
- Ensure recommendations are specific and measurable
- Consider implementation feasibility

## Output Format

```markdown
## Character Assessment: [Subject Name]

### Assessment Context
**Relationship type:** [Partnership/Hiring/Vendor/Investment/etc.]
**Stakes:** [What is at risk]
**Assessment date:** [Date]

### Track Record Analysis
**Commitment history:** [Honors commitments / Mixed record / Concerning pattern]
**Failure behavior:** [Takes responsibility / Deflects / Blames others]
**Reference consensus:** [Strong endorsement / Qualified support / Concerning gaps]

**Specific evidence:**
- [Evidence point 1]
- [Evidence point 2]
- [Evidence point 3]

### Direct Engagement Observations
**Directness:** [Answers directly / Some deflection / Evasive]
**Pressure response:** [Composed / Defensive / Hostile]
**Responsibility-taking:** [Owns mistakes / Partial / Blames others]

**Notable observations:**
- [Observation 1]
- [Observation 2]

### Reference Findings
**Would work with again:** [Yes, enthusiastically / Yes, with reservations / No or hesitation]
**Handling of adversity:** [Summary of how they've handled past difficulties]
**What references wish they'd known:** [Key insight]

### Alignment Assessment
**Stated interests:** [What they say they want]
**Actual interests:** [What they likely actually want]
**Potential conflicts:** [Where interests might diverge]
**Value alignment:** [Strong / Adequate / Concerning gaps]

### Red Flags Identified
- [Red flag 1]: [Evidence and severity]
- [Red flag 2]: [Evidence and severity]

### Green Flags Identified
- [Green flag 1]: [Evidence]
- [Green flag 2]: [Evidence]

### Final Assessment

**Character rating:** Sound / Uncertain / Unsound

**The Morgan Test:** Would I proceed if their character were the only collateral?
[Yes, without hesitation / Yes, with specific conditions / No]

**Recommendation:** [Proceed / Proceed with conditions / Investigate further / Do not proceed]

**If proceeding with conditions:**
- [Condition 1]
- [Condition 2]

**Key insight:** [Most important takeaway about this person's character]
```

---

## Constraints

- Do not mistake charm for character
- Do not confuse success with trustworthiness
- Do not let urgency override assessment—bad partners cost more than delays
- Do not accept curated references at face value
- Do not ignore small betrayals—patterns start small
- Remember: past behavior is the best predictor of future behavior

---

## Outputs

**Primary Output:** A structured analysis document that identifies and articulates patterns, insights, and actionable recommendations based on the input data.

**Format:**
```markdown
## Analysis: [Topic]

### Key Findings
- [Finding 1]
- [Finding 2]
- [Finding 3]

### Recommendations
1. [Action 1]
2. [Action 2]
3. [Action 3]
```

## Anti-Patterns to Avoid

| Anti-Pattern | Why It Fails | Instead Do |
|--------------|--------------|------------|
| **Charm blindness** | Charismatic people can still be untrustworthy | Assess track record independently of likability |
| **Success conflation** | Past success doesn't guarantee good character | Examine how they achieved success, not just that they did |
| **Reference theater** | Curated references tell you little | Find backdoor references; ask probing questions |
| **Urgency override** | "We need to decide now" leads to bad partnerships | Bad partners cost more than delays; take time |
| **Single data point** | One good or bad indicator isn't enough | Look for patterns across multiple dimensions |

## Example

**Input:** "Should we bring this co-founder candidate into the company? They have great skills but I want to assess if we can trust them."

**Output:**

## Character Assessment: [Candidate Name]

### Assessment Context
**Relationship type:** Co-founder partnership
**Stakes:** High—equity partnership, shared decision authority, company direction
**Assessment date:** 2026-01-22

### Track Record Analysis
**Commitment history:** Mixed record
**Failure behavior:** Partial responsibility—acknowledges mistakes but often adds context that deflects
**Reference consensus:** Qualified support with notable gaps

**Specific evidence:**
- Left previous startup after 18 months; stated "strategic differences"—founder tells different story
- Two references enthusiastic; one former employee declined to comment (concerning)
- Delivered on technical commitments but timeline estimates frequently missed

### Direct Engagement Observations
**Directness:** Some deflection on questions about past departure
**Pressure response:** Composed when asked about technical challenges; defensive when asked about previous partnership ending
**Responsibility-taking:** Partial—"We all made mistakes" framing rather than "I made this mistake"

**Notable observations:**
- Quick to criticize former partner without prompting
- Strong technical vision but becomes dismissive of concerns
- Changed subject when asked about specific equity dispute

### Reference Findings
**Would work with again:** Mixed—one yes enthusiastically, one yes with reservations, one declined to give reference
**Handling of adversity:** When previous startup struggled, focused blame on market timing and co-founder decisions
**What references wish they'd known:** "How they handle disagreement when they're sure they're right"

### Alignment Assessment
**Stated interests:** Build meaningful company, long-term commitment
**Actual interests:** Likely wants control of technical decisions; may conflict with shared governance
**Potential conflicts:** Decision-making authority when technical and business priorities conflict
**Value alignment:** Adequate on company mission; concerning on partnership dynamics

### Red Flags Identified
- **Pattern of partnership endings:** Two previous partnerships ended with conflict—pattern, not coincidence
- **Deflection on hard questions:** Difficulty getting direct answers about past disputes
- **Reference who declined:** Former employee unwilling to comment is notable absence

### Green Flags Identified
- **Technical delivery:** Consistently ships quality work
- **Long reference who's enthusiastic:** Investor from first company speaks highly

### Final Assessment

**Character rating:** Uncertain

**The Morgan Test:** Would I proceed if their character were the only collateral?
No—too much uncertainty about partnership behavior under stress.

**Recommendation:** Investigate further before proceeding

**If investigating further:**
- Have direct conversation about previous partnership ending—ask for their former co-founder's perspective
- Speak with the employee who declined reference
- Consider 3-month contract period before equity partnership

**Key insight:** Strong individual contributor; uncertain partner. The skill is clear; the trustworthiness in partnership is not. Do not confuse excellence in one domain with character in another.

---

## Integration

This skill is part of the **J.P. Morgan** expert persona. Morgan assessed character before examining any other aspect of a business proposition. The soundness of the person determined whether any deal was worth pursuing. Use this skill to ensure you enter relationships only with those whose character you would trust as the sole collateral.