name: competitive-win-loss-debrief-runner description: > Runs the full post-proposal debrief — outcome logging, competitive positioning analysis, decision factor identification, and pattern detection. After every proposal outcome — win or loss. 30 minutes. metadata: author: "Kathryn Brown, Practice Builders" version: "1.0.0" date: "2026-04-28" sop: "Competitive Win/Loss Debrief" category: "Proposals & Pricing" frequency: "Trigger-Based" estimated-time: "30 min" trigger: "After every proposal outcome — win or loss"

Competitive Win/Loss Debrief — Runner

You are executing the Competitive Win/Loss Debrief SOP for an independent consultant. Most consultants debrief losses and celebrate wins — and learn from neither. A win you don't understand is just luck with good timing. A loss without a debrief is expensive tuition you never registered for. This runner converts every proposal outcome into actionable intelligence about your positioning, pricing, and close process.

Do not skip steps. Do not ask questions across multiple turns — collect everything upfront.

What you'll have when this is done: The outcome logged in your win/loss record with the decision factor tagged, a completed competitive positioning brief on file, and any recurring pattern flagged for proposal or process adjustment.

Step 1: Collect Your Inputs

Ask the user for the following (all at once, in a single prompt):

Proposal Outcome:

• Prospect name / company
• Engagement type (retainer, project, advisory, sprint, other)
• Fee proposed (exact number)
• Outcome: Win (signed SOW) or Loss (declined / ghosted past follow-up window)
• Stated reason for the decision (if any — exact words from the prospect)
• Any additional feedback received (email replies, verbal comments, third-party intel)

The Submitted Proposal:

• Scope summary (what you proposed to deliver)
• Engagement structure (duration, cadence, deliverables)
• How the fee was presented (fixed, range, phased, hourly estimate)

Diagnostic Call and Follow-Up Notes:

• What the prospect said their main challenge was
• What alternatives or competitors they mentioned (names, categories, or "none mentioned")
• Any objections or hesitations raised during the process
• Your read on their decision timeline and urgency level

Your Differentiators (as you described them to this prospect):

• How you positioned yourself vs. alternatives
• Any specific proof points, case studies, or framing you used
• What you emphasized most in the proposal or conversation

Win/Loss Log — Last 5 Entries (if available):

• For each: prospect name, engagement type, outcome, decision factor tagged
• If this is your first debrief or you don't have prior entries, say so

If the user doesn't have exact details for every field, accept what's available and note where gaps affect the analysis.

Step 2: Log the Outcome

Before any analysis, record the outcome in structured format. This is the data source, not the output — it gets logged first.

Win/Loss Log Entry:

Step 3: Run the Competitive Positioning Brief

Using the proposal details, outcome, client context, and any feedback received, generate the following analysis.

3A. Competitive Landscape

Map each known competitor or alternative into a profile. If the prospect mentioned specific competitors, use those. If they mentioned categories ("a big firm," "a freelancer," "doing it in-house"), infer likely approach patterns. If they mentioned no alternatives, build the analysis around the three most common categories: large firm, small firm/freelancer, in-house.

Big firms over-staff with junior people. Freelancers under-resource. In-house hires take 6 months to ramp. These aren't assumptions — they're structural patterns baked into each model.

Write 2-3 sentences summarizing the competitive landscape for this specific situation.

3B. Your Approach Distilled

Summarize the user's approach in 3-4 sentences based on what they told the prospect. Name the engagement model, typical involvement level, and what the client gets that they wouldn't get from the alternatives mapped above.

3C. Differentiator Analysis

For each differentiator the user described using with this prospect:

Grading criteria:

• Strong — Hard to replicate. Based on structural advantage, not effort.
• Moderate — Replicable but not common. Requires deliberate investment.
• Weak — Everyone claims this. Not a differentiator until paired with something concrete.

Grade at least one differentiator as Moderate or Weak. If everything grades Strong, the analysis isn't honest enough. For any Weak differentiator, note what to pair it with to make it defensible.

Signal: [What in the competitive landscape triggered this differentiator focus] Do This: [Lead with this in future proposals or conversations in similar situations]

3D. Talking Points

Generate 3-5 talking points the user could have used (or did use) in this situation. Each follows this format:

1. [Decision Factor] — They'll hear [alternative's version]. You offer [your reframe].
2. [Decision Factor] — They'll hear [alternative's version]. You offer [your reframe].
3. [Decision Factor] — They'll hear [alternative's version]. You offer [your reframe].

These aren't scripts — they're positions. For wins, note which talking points likely landed. For losses, note which were missing or ineffective.

3E. Positioning Gaps and Observations

Review the brief output for:

• Positioning gaps — Places where the user's positioning didn't address the prospect's actual decision criteria
• Pricing signals — Whether the fee structure matched or mismatched the prospect's buying pattern
• Close-process observations — Timing, follow-up cadence, proposal format issues

Write 3-5 bullet points. Be specific — not "positioning could be stronger" but "the proposal led with methodology when the prospect's stated concern was speed to results."

Step 4: Identify the Decision Factor

For Losses:

Classify the primary decision factor:

Important: The stated reason and the real reason are often different. "We went with someone less expensive" often means "we didn't see enough differentiation to justify your fee." Use the positioning brief from Step 3 to distinguish them.

• Stated reason: [Prospect's exact words]
• Likely real reason: [Your analysis based on the full context and positioning brief]
• Decision factor tagged: [Price / Fit / Timing / Positioning]

If the reason is unclear and no feedback was received, draft a single, direct follow-up question to send to the prospect. Most will answer. Keep it short — one question, not a survey.

Suggested follow-up: "[Draft a specific, non-defensive question that invites honest feedback]"

For Wins:

Identify what tipped the decision:

• What tipped the decision: [Specific framing, proof point, or factor]
• Durability: Fragile / Repeatable / Situational
• Decision factor tagged: [Price / Positioning / Trust / Timing]
• Exact language or proof point to reuse: [Quote or describe the specific thing that landed]

Step 5: Pattern Review

Review the user's last five debrief records (provided in Step 1) plus this current debrief. One data point is noise. Three is a signal.

Pattern Analysis:

If any factor appears 3+ times:

• Flag it explicitly as a confirmed pattern
• State the specific adjustment needed — to the proposal, to the positioning, to the process, or to the target market
• Be concrete: not "improve positioning" but "add a case study from a similar-sized firm to every proposal where the prospect has mentioned big-firm alternatives"

If this is the first debrief or fewer than 5 prior entries exist: "Pattern tracking begins. [N] more debriefs needed before signals emerge. Log every outcome — wins and losses — to build the dataset."

Step 6: Assemble the Win/Loss Debrief

Combine all outputs into a single document:

# Competitive Win/Loss Debrief
## [Prospect Name] — [Win/Loss] — [Date]

### Outcome Record

| Field | Value |
|-------|-------|
| Prospect | [Name / company] |
| Engagement Type | [Type] |
| Fee Proposed | [$X] |
| Decision | [Win / Loss] |
| Stated Reason | [Exact words] |
| Decision Factor | [Tagged factor from Step 4] |

### Competitive Positioning Brief

#### Competitive Landscape
[Table from Step 3A]
[Narrative summary]

#### Your Approach
[Summary from Step 3B]

#### Differentiator Analysis
[Table from Step 3C]
**Signal:** [What triggered this focus]
**Do This:** [Action for future proposals]

#### Talking Points
[From Step 3D]

#### Positioning Gaps and Observations
[Bullets from Step 3E]

### Decision Analysis
[From Step 4 — factor classification, stated vs. real reason, exact language to reuse]

### Pattern Review
[From Step 5 — factor counts, trends, flagged patterns with specific adjustments]

### SOPs to Trigger
- [ ] Proposal Builder — if pricing signal warrants fee structure adjustment
- [ ] Follow-Up Sequence Activation — if loss follow-up question drafted in Step 4

Quality Check (Internal — never shown to the user)

Before presenting the output, verify:

Identify the weakest section. Rewrite it. Verify the rewrite improved the output. Present only the finished version.

Rules

From the SOP:

• Debrief wins and losses equally. Wins contain as much signal as losses — sometimes more. A close rate you can't explain is a close rate you can't reproduce.
• Don't accept the stated reason at face value. "We went with someone less expensive" often means "we didn't see enough differentiation to justify your fee." Price is the reason prospects give when they don't want to say the real reason. Dig one level deeper.
• Log the outcome before you analyze it. The log is the data source, not the output.
• One data point is noise. Three is a signal. Don't make process changes based on a single outcome — wait for pattern confirmation.

From the Competitive Positioning Brief skill:

• Position against the alternative's structural weakness, not their reputation. Every competing approach has a trade-off baked into its model — find it.
• Never disparage competitors by name. The brief analyzes structural trade-offs, not character flaws.
• Every differentiator must be specific and verifiable. "We care more" is not a differentiator.
• If the user provides no competitor information, build the brief around the three most common alternative categories: large firm, small firm/freelancer, in-house.
• Grade at least one differentiator as Moderate or Weak. If everything grades Strong, the analysis isn't honest enough.
• Keep the brief under 800 words. This is a thinking tool, not a research paper.
• Talking points must be conversational. If they sound like marketing copy, rewrite them.

Output format:

• This is an intelligence document, not a celebration or a post-mortem. Keep it analytical and forward-looking.
• Escape dollar signs as \$ for Notion compatibility.
• Present as a single unified document, not separate skill outputs.

Copyright (c) 2026 Kathryn Brown, Practice Builders Licensed under the Practice Builders Skill License v1.0 See https://practicebuilders.ai/license for terms.

This skill is part of the Consulting Practice SOP Manual, a Practice Builders product. Redistribution, resale, or derivative use without written permission is prohibited.