Diligence sprint

When to use

Use this compound skill when:

• A deal is live and you have a hard decision deadline
• You need a clear risk burn-down plan and daily deliverables
• You want to coordinate multiple diligence workstreams with gates

Inputs you should request (only if missing)

• Deadline (term sheet / IC date)
• Intended role (lead/follow) and check size
• Top 3 "must be true" claims from first meeting
• Customer access constraints
• Sprint length: 3-day, 5-day, or 7-day

Outputs you must produce

• Day-by-day plan with owners and deliverables
• Ranked risk register (MAX 4 risks)
• Evidence pack with anti-confirmation
• Decision at each gate: kill, continue, or escalate
• Memo-ready findings or explicit kill decision

Every sprint ends with one of two outcomes:

1. Partner-ready memo + IC scheduled
2. Explicit kill with logged reason + "what would change our mind" + recheck date

5-day default sprint plan

Day 0: Setup (2-4 hours)

Deliverables:

• Aligned on top 4 risks + fastest tests
• Owners assigned and calls scheduled
• Salesforce Tasks created for each workstream

Day 0 Gate: Can we test the top 4 risks in the time available? If not, scope down or extend timeline.

Day 1: Customer diligence

Deliverables:

• 3 buyer calls completed
• 2 user calls completed
• 1 churned/lost deal call scheduled or completed (REQUIRED)
• Customer summary written

Day 1 Gate: Did customers validate or invalidate the core thesis? Any kill signals?

Risk	Before Day 1	After Day 1	Change
1
2

Decision: Kill / Continue / Escalate

Day 2: Product diligence

Deliverables:

• Hands-on demo completed
• Deployment reality assessed
• Integration blockers identified
• Time-to-value documented

Day 2 Gate: Does the product deliver on the promise? Any kill signals?

Risk	Before Day 2	After Day 2	Change
1
2

Decision: Kill / Continue / Escalate

Day 3: GTM + metrics diligence

Deliverables:

• Pipeline review completed
• Unit economics validated by segment
• Cycle time and pricing confirmed
• Competitor/alternative user call completed (REQUIRED)

Day 3 Gate: Is this repeatable? Are the economics real? Any kill signals?

Risk	Before Day 3	After Day 3	Change
1
2

Decision: Kill / Continue / Escalate

Day 4: Team + competition

Deliverables:

• Team learning rate assessed
• Decision rights clarity confirmed
• Competitive map updated
• "Incumbent build" threat evaluated

Day 4 Gate: Is this team credible? Can they win vs competition? Any kill signals?

Risk	Before Day 4	After Day 4	Change
1
2

Decision: Kill / Continue / Escalate

Day 5: Synthesis + decision

Deliverables:

• All evidence synthesized
• Memo sections drafted (market, product, traction, GTM, team, risks)
• Recommendation written (first line, no hedging)
• Steelman "best argument against" written
• IC readout prepared

Final Gate: One of two outcomes:

1. ADVANCE: Partner-ready memo + IC scheduled
2. KILL: Pass logged with reason + "what would change our mind" + recheck date

3-day sprint (urgent deal)

Day 0: Setup + risk alignment (2 hours)

• Align on top 2-3 risks (fewer risks, faster tests)
• Schedule all calls for Days 1-2

Gate: Are the tests achievable in 3 days?

Day 1: Customer + product

• 3-5 customer calls (buyers + users)
• Hands-on product eval
• Churned/lost deal call (REQUIRED)

Gate at end of Day 1: Kill or continue? No "need more time."

Day 2: GTM + team + competition

• Pipeline review
• Team assessment
• Competitor validation

Gate at end of Day 2: Kill or continue? All top risks tested?

Day 3: Synthesis + decision

• Evidence synthesis
• Memo draft
• IC decision

Final gate: Memo or kill. No limbo.

7-day sprint (deeper diligence)

Same structure as 5-day, with:

• Days 1-2: Customer diligence (more calls, deeper coverage)
• Day 3: Product diligence
• Days 4-5: GTM + metrics + competition
• Day 6: Team + synthesis
• Day 7: Memo + decision

Decision gates (mandatory checkpoints)

At each gate, you must answer:

1. Kill? Is there evidence that this deal should not proceed?
2. Continue? Is there enough positive signal to invest more time?
3. Escalate? Does a partner need to weigh in before Day X?

Kill criteria (stop immediately if any are true):

• Customer calls reveal fundamental misunderstanding of ICP
• Churned customer call reveals systemic product/service issue
• Metrics don't support the stated traction
• Competitive position is weaker than pitched
• Team shows inability to change mind with evidence

Continue criteria:

• Evidence supports core thesis
• Risks are testable and manageable
• No kill signals triggered

Escalate criteria:

• Risk requires partner relationship/expertise
• Deal dynamics require partner involvement
• Unclear whether to kill or continue

Anti-confirmation requirements (MANDATORY)

Every sprint must include:

1. Churned customer or lost deal call - What caused them to leave/not buy?
2. Competitor/alternative user - Why do they use something else?

If these calls are impossible, document why and flag the gap prominently in the memo.

Guardrails

• If you can't get a failed customer reference, discount retention claims.
• If the deadline compresses: do fewer risks, not more shallow work.
• Never extend a sprint without a partner decision. Time-box or kill.
• Every day must produce a decision-relevant deliverable.

Salesforce logging

• Create Tasks for each diligence workstream with owner and due date
• Log each call as Activity with notes
• Update Opportunity stage at each gate
• Attach final evidence pack and memo to Opportunity