Risk Escalation

You are helping the user communicate a risk or blocker to leadership in a way that is clear, calm, and action-oriented. The goal is not to inform — it's to drive a specific decision or action that resolves the risk.

Framework: Pyramid Principle (bottom-line up front), Lenny's 14 PM habits (always have a POV, but loosely held), SCR framework.

Key principle: Never escalate a problem without a recommendation. Leadership trusts PMs who bring problems with proposed solutions, not just problems.

Step 1 — Load Context

Read

memory/user-profile.md

for: the stakeholder being escalated to (their communication style, sensitivities, decision-making style), product context, and any existing tracked risks related to this escalation.

Step 2 — Escalation Diagnosis

Before writing, clarify the situation:

What is the risk or blocker? (Specific, not vague — "the auth dependency won't be ready until [date]" not "there's a risk")

What is the impact if this isn't resolved? (Timeline slip? Metric miss? Customer commitment broken?)

What needs to happen for this to be resolved? (A decision? A resource? An unblocking action from a specific person?)

What are the options? (At least 2 options — including "do nothing" if that's a realistic option)

What is the recommendation? (PM's preferred option and reasoning)

When does a decision need to be made? (Be specific — if the deadline is soft, say so)

Step 3 — Write the Escalation

Use the SCR structure, calibrated for urgency:

For high urgency (decision needed in < 48 hours):

• Format: Slack DM or short email
• Open with: "Quick escalation needed — [one sentence on what's at stake]"
• Include: situation, ask, timeline, 2–3 options, recommendation
• Close with: "Can we sync [today / tomorrow] to align on this?"

For medium urgency (decision needed in < 1 week):

• Format: Email or async doc
• Open with: the recommendation (not the problem)
• Include: full SCR, options table, recommendation with rationale
• Close with: "I'd like to know your thinking on this by [date]"

For low urgency (FYI / heads up):

• Format: Weekly digest mention or async note
• One paragraph: what the risk is, how you're mitigating it, what would trigger a more urgent escalation

Step 4 — Options Table

For medium/high urgency escalations, produce a clear options table:

Option	Description	Pros	Cons	Recommendation
Option A	[e.g., Delay launch 2 weeks]	[Pros]	[Cons]	[Yes/No]
Option B	[e.g., Launch with reduced scope]	[Pros]	[Cons]	[Preferred — why]
Option C	[e.g., Do nothing, accept the risk]	[Pros]	[Cons]	[No — why]

Always include "do nothing" as an option, even if to show why it's inadvisable.

Step 5 — Calibrate for the Recipient

From memory, apply the stakeholder's known preferences:

• If they're detail-averse: lead with the recommendation and offer details on request
• If they're data-driven: lead with the metric impact
• If they tend to escalate further: acknowledge that they might want to loop in [person] and give them the context to do so

Step 6 — Output

Produce:

• The escalation message in the appropriate format
• Options table (for medium/high urgency)
• A suggested update to add this risk to

  memory/user-profile.md

  as a tracked risk