Agent skill

High Stakes Decisions

by RefoundAI in RefoundAI/lenny-skills

Help users master the art of making high-stakes, irreversible decisions by using structured frameworks to reduce cognitive bias and maintain organizational momentum.

MITAuto-check passedMarketing & SEO

Install High Stakes Decisions

skills CLI
$ npx skills add RefoundAI/lenny-skills --skill high-stakes-decisions -a claude-code

Project install by default; add -g for ~/.claude/skills/.

GitHub CLI
$ gh skill install RefoundAI/lenny-skills high-stakes-decisions --agent claude-code

Project scope by default; add --scope user for a personal install. Needs GitHub CLI 2.90.0 or later (public preview).

Manual copy
$ git clone --depth 1 https://github.com/RefoundAI/lenny-skills.git skills-src && mkdir -p .claude/skills && cp -r skills-src/skills/high-stakes-decisions .claude/skills/high-stakes-decisions && rm -rf skills-src

Use ~/.claude/skills/ instead of .claude/skills for a personal install. The folder must contain SKILL.md.

Claude Code skills documentation · loads skills from .claude/skills/

Facts

Skill name
high-stakes-decisions
GitHub stars
1.4k
Token cost
~2k tokens
SKILL.md length
1,195 words
Files
3 (incl. references)
Skills in repo
76
Repo updated
First seen
Licence
MIT

At a glance

Help users master the art of making high-stakes, irreversible decisions by using structured frameworks to reduce cognitive bias and maintain organizational momentum.

  • Works in 4 steps: Categorize the stakes - Help the user… → Frame the core problem - Facilitate the… → Mitigate emotional bias - Use techniques… → …
  • Tasks that involve Marketing psychology
  • SKILL.md covers How to Help, Core Principles, Templates & Frameworks and Questions to Help Users, plus 3 more sections
  • Instructions only: no scripts, shell commands, URLs or credentials in SKILL.md

What it does

High Stakes Decisions is an agent skill from RefoundAI/lenny-skills. Help users master the art of making high-stakes, irreversible decisions by using structured frameworks to reduce cognitive bias and maintain organizational momentum.

Its SKILL.md is about 2k tokens, which your agent loads only when the skill is triggered. The skill folder holds 3 other files, including reference files (for example `references/artifacts.md` and `references/guest-insights.md`).

It sits in Marketing & SEO, covering Marketing psychology. The repository describes itself as: 86 product management skills from Lenny's Podcast for Claude Code and AI agents. Hiring, user research, strategy, shipping, and more. The licence is MIT.

When your agent uses it

  • Tasks that involve Marketing psychology

Example prompts

  • “/high-stakes-decisions”

Workflow steps

4 steps, taken from the first numbered list in SKILL.md.

  1. Categorize the stakes - Help the user determine if a decision is a one-way or two-way door to apply the appropriate level of rigor.
  2. Frame the core problem - Facilitate the identification of the 'Eigenquestion' or the single decisive reason that drives the choice.
  3. Mitigate emotional bias - Use techniques like pre-mortems and neutral third-party perspectives to identify where fear or sunk costs are…
  4. Drive to a conclusion - Transition from consensus-seeking to clear ownership, ensuring everyone is heard before a final call is made with…

What it can do on your machine

Read from SKILL.md and the folder at commit 13598cc. It shows what the files ask for, not the result of running them.

  • Tool permissions

    Pre-approves nothing: there is no allowed-tools line, so your agent's usual permission prompts apply.

    From allowed-tools in the SKILL.md frontmatter.

  • Runs code

    No scripts in the folder and no shell commands in SKILL.md.

    From the folder's file list and the shell code blocks in SKILL.md.

  • Network

    No URLs in SKILL.md.

    From URLs in SKILL.md, links to its own repository left out.

  • Credentials

    Names no API keys, tokens, secrets or passwords.

    From names ending in _API_KEY, _TOKEN, _SECRET, _KEY or _PASSWORD in SKILL.md.

Context cost

High Stakes Decisions loads about 2k tokens when it runs, and up to ~18k if it reads all its reference files. Until then it costs about 47 tokens; SKILL.md has 1,195 words of instructions outside code blocks.

Always · name and description, kept in context so the agent knows when to use it
~47
When it runs · the whole SKILL.md, loaded when a task matches
~2k
With references · SKILL.md plus every file in references/, read only if the agent opens them
~18k

Estimates: characters ÷ 4, the usual rule of thumb; real counts depend on the model's tokenizer. Scripts and assets cost tokens only if the agent reads them.

Safety

Auto-check passed

The automated check found no risky patterns in SKILL.md.

Automated static check — not a guarantee. Review scripts before installing. It scans the text of SKILL.md for risky patterns (piping downloads into a shell, reading credential files, hidden Unicode, destructive commands); files beside SKILL.md are not scanned.

SKILL.md

The full file from RefoundAI/lenny-skills at commit 13598cc, republished under its MIT licence (© RefoundAI). 1,195 words, ~2,040 tokens.

Download SKILL.mdSave it as .claude/skills/high-stakes-decisions/SKILL.md (or your agent's skills folder). This skill also uses 2 other files; get the full folder from GitHub.
name
high-stakes-decisions
description
Help users master the art of making high-stakes, irreversible decisions by using structured frameworks to reduce cognitive bias and maintain organizational momentum.

High Stakes Decision Making

Navigate irreversible choices and extreme uncertainty with speed and structural clarity.

Help the user with high stakes decision making using insights from 30 guests and posts across Lenny's Podcast and Newsletter.

How to Help

  1. Categorize the stakes - Help the user determine if a decision is a one-way or two-way door to apply the appropriate level of rigor.
  2. Frame the core problem - Facilitate the identification of the 'Eigenquestion' or the single decisive reason that drives the choice.
  3. Mitigate emotional bias - Use techniques like pre-mortems and neutral third-party perspectives to identify where fear or sunk costs are distorting reality.
  4. Drive to a conclusion - Transition from consensus-seeking to clear ownership, ensuring everyone is heard before a final call is made with 70 percent information.

Core Principles

Identify Leading Indicators

Annie Duke: "There is no such thing as a long feedback loop. And the way you choose to shorten the feedback loop is to say, what are the things that are correlated with the outcome that I eventually desire?"

Break down long-term goals into measurable intermediate signals to create shorter feedback loops for better decision-making.

Run Toward Necessary Pain

Ben Horowitz: "The biggest mistake that you make, the worst thing that you do as a leader, there's things in your control and there's things out of your control and hesitation, that's generally the most destructive. And I go through all the ways that it's destructive, but it's extremely bad. And the thing that causes you to hesitate is both decisions are horrible."

Trust your perception and act decisively when faced with two equally painful alternatives rather than avoiding the choice.

Build for Technological Trajectories

Kevin Weil: "Our general mindset is in two months, there's going to be a better model and it's going to blow away whatever the current set of limitations are. And we say this to developers too. If you're building and the product that you're building is kind of right on the edge of the capabilities of the models, keep going because you're doing something right. Give it another couple months and the models are going to be great, and suddenly the product that you have that just barely worked is really going to sing."

Design products and roadmaps based on where model capabilities will be in months rather than optimizing for current technical limitations.

Prioritize Existing Integrity

Laura Modi: "We are going to run out of product for the babies that are on Bobbie today. We have about six days before we get to a place where we won't be able to serve those who've already made a commitment to Bobbie. She's like, 'So we need to turn off our site and stop growing the business.'"

True customer-centricity requires prioritizing fulfillment for existing users over new acquisition during periods of severe supply or resource shortages.

Neutralize Fear-Based Predictions

Matt Mochary: "It's not because I'm magician or a genius, it's because when someone's in fear, they're gripped. They can't see reality, their brain is making very exaggerated predictions. Whereas when someone is not in fear, and I'm not because it's not my situation, I am not gripped and therefore, my brain isn't making exaggerated predictions. And so, we make this bet once I win, then all of a sudden the CEO realizes, oh my God, there's something to this, fear gives bad advice."

Use neutral third parties to identify when fear is causing you to make exaggerated negative predictions about a difficult choice.

Maintain Forward Momentum

Claire Hughes Johnson: "If you're not sure who the decision maker is, one, it's probably you. And I'd rather you act that way than not because you're going to like slow the whole company down. Follow a process and get it done, and don't forget to actually make a decision."

Take the initiative to drive a decision when authority is ambiguous to prevent organizational paralysis and maintain career velocity.

Decide with 70 Percent Information

From "Five habits of highly annoying product managers": "Try this next time you’re stuck on a decision: Ask your team if they’d rather keep hashing it out or for you to just make a call. I bet you they’d rather just move on."

Aim for approximately 70 percent of the information needed before making a call to maintain team momentum rather than seeking perfect consensus.

Show full SKILL.md (473 more words)Show less

Templates & Frameworks

  • Eigenquestions: The Art of Framing Problems (My favorite product management templates) - A framework for identifying the single most important question that, when answered, will answer all subsequent questions
  • S.P.A.D.E. Decision-Making Framework (My favorite decision-making frameworks) - A structured decision-making framework that replaces consensus with accountability by assigning a single responsible decision-maker. SPADE stands for Setting, P
  • RAPID Decision-Making Framework (Hari Srinivasan) - A model to clarify roles in complex decisions to ensure speed and accountability.
  • Kombucha Scale (My favorite decision-making frameworks) - A quick mental model from Square for determining whether a decision warrants a formal framework, based on two variables: importance and urgency.
  • Type-1 and Type-2 Decisions (How to get into product management) - Jeff Bezos's framework for categorizing decisions as irreversible (Type-1) or reversible (Type-2) to determine how much deliberation is warranted
  • Pre-mortem with Tigers, Paper Tigers, and Elephants (Shreyas Doshi) - A structured pre-mortem meeting framework where you imagine the project has failed, then categorize risks into three types: Tigers (real threats that will kill
  • Single Decisive Reason (SDR) (Rahul Vohra) - A decision-making tool learned from Reid Hoffman where you must identify one reason that alone justifies a decision, preventing collections of weak reasons from
  • Scenario Planning for Crisis (Three Scenarios) (Leading your company through a pandemic - Issue 20) - Framework for modeling business outcomes under three severity levels during an economic crisis
  • Framework Selection Guide (Structured to Least Structured) (My favorite decision-making frameworks) - Lenny's ranking of decision-making frameworks from most structured to least structured, with guidance on when to use each.

See references/artifacts.md for the full list with details.

Questions to Help Users

  • "Is this a one-way door or a two-way door decision in terms of cost to reverse?"
  • "What is the single decisive reason for this proposal that stands alone without a laundry list of arguments?"
  • "What are the leading indicators we will monitor to validate this path before we reach the final outcome?"
  • "Who are the key detractors and have you met with them individually to understand their concerns?"
  • "What are the pre-defined kill criteria that would trigger us to stop this project objectively?"
  • "If you had to decide with only 70 percent of the data you want, what direction would you take right now?"

Common Mistakes to Flag

  • Seeking Consensus over Alignment - Aiming for total agreement often leads to watered-down decisions or organizational paralysis.
  • Misapplying the Two-Way Door - Using reversibility as an excuse to bypass deep thinking on strategic features that consume significant resources.
  • Avoiding the Painful Choice - Leaders often delay decisions because all available options are undesirable, which only increases the eventual cost.
  • Ignoring Sunk Cost Bias - Persisting in a failing project because of the emotional identity attached to it rather than its future utility.

Deep Dive

For all 24 sourced insights from 30 guests, see references/guest-insights.md

  • Roadmap Prioritization
  • Goal Setting Okrs
  • Planning Cadence
  • Evaluating Trade Offs

© RefoundAI, MIT. Rendered from Markdown: HTML in the file is shown as text, images as links, and headings moved down two levels. Raw file

Files

SKILL.md and 2 other files (references) in skills/high-stakes-decisions of RefoundAI/lenny-skills.

  • SKILL.md
  • references/artifacts.md
  • references/guest-insights.md

Open the folder on GitHubat commit 13598cc

Compare with similar skills

High Stakes Decisions next to the 5 skills that share the most tags, products or categories with it. Stars are the repository's; “used in” counts other GitHub owners with a copy.

High Stakes Decisions compared with similar skills
SkillStarsUsed inTokensAuto-checkLicenceRepo updated
High Stakes Decisions this skillRefoundAI/lenny-skills1.4k—~2kAutomated safety check: PassMIT
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Cold Email Sequence Generatornicepkg/auto-company1953 repos~4.9kAutomated safety check: PassNone
Ugcfal-ai-community/skills251—~1.5kAutomated safety check: PassNone
Landing Optimizeraaron-he-zhu/aaron-marketing-skills2.9k—~3.3kAutomated safety check: PassApache-2.0
Social Proof Architectsickn33/agentic-awesome-skills47k2 repos~1.4kAutomated safety check: PassMIT

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Categories

Questions about High Stakes Decisions

What does High Stakes Decisions do?

Help users master the art of making high-stakes, irreversible decisions by using structured frameworks to reduce cognitive bias and maintain organizational momentum. High Stakes Decisions is an agent skill from RefoundAI/lenny-skills. Help users master the art of making high-stakes, irreversible decisions by using structured frameworks to reduce cognitive bias and maintain organizational momentum.

When should I use High Stakes Decisions?

High Stakes Decisions fits situations like: tasks that involve Marketing psychology.

How do I install High Stakes Decisions in Claude Code?

Run `npx skills add RefoundAI/lenny-skills --skill high-stakes-decisions -a claude-code`. Or copy the skill folder (skills/high-stakes-decisions in RefoundAI/lenny-skills) into .claude/skills/high-stakes-decisions in your project. Claude Code loads it when a task matches its description.

How do I install High Stakes Decisions in Codex?

Run `npx skills add RefoundAI/lenny-skills --skill high-stakes-decisions -a codex`. Or copy the skill folder (skills/high-stakes-decisions in RefoundAI/lenny-skills) into .agents/skills/high-stakes-decisions in your project. Codex loads it when a task matches its description.

Can I use High Stakes Decisions in Cursor, Gemini CLI or GitHub Copilot?

Cursor, Gemini CLI, GitHub Copilot and OpenCode also load SKILL.md folders. With the skills CLI, run `npx skills add RefoundAI/lenny-skills --skill high-stakes-decisions -a cursor` (or -a gemini-cli, github-copilot or opencode for the others). To copy it by hand, put the folder in .cursor/skills/high-stakes-decisions, .gemini/skills/high-stakes-decisions, .github/skills/high-stakes-decisions and .opencode/skills/high-stakes-decisions in your project.

What does High Stakes Decisions need to run?

SKILL.md names no scripts, command-line tools or credentials: High Stakes Decisions is instructions for the agent only.

Does High Stakes Decisions access the network?

SKILL.md contains no URLs. Any network use would come from the scripts or tools the agent runs. This is read from the text; nothing was executed.

Is High Stakes Decisions safe to install?

Our automated static check of SKILL.md found no risky patterns, such as piping downloads into a shell, reading credential files or hidden Unicode. It is not a guarantee. Review the folder before installing.

What licence does High Stakes Decisions use?

High Stakes Decisions is published under the MIT licence (the repository's licence). It allows redistribution, so the full SKILL.md is shown on this page.

How many tokens does High Stakes Decisions use?

About 2k tokens (SKILL.md is roughly 8.2k characters). Agents keep only the skill's name and description in context until a task matches; then they load SKILL.md in full. Its references folder adds about 16k tokens, read only when the agent opens those files.

What are the alternatives to High Stakes Decisions?

Skills that share tags, products or a category with High Stakes Decisions: Marketing Psychology (freekmurze/dotfiles, 1k stars), Cold Email Sequence Generator (nicepkg/auto-company, 195 stars), Ugc (fal-ai-community/skills, 251 stars) and Landing Optimizer (aaron-he-zhu/aaron-marketing-skills, 2.9k stars). The comparison table on this page puts their stars, adoption, token cost, safety result and licence side by side.

Who maintains High Stakes Decisions?

RefoundAI (a GitHub organization) maintains it in RefoundAI/lenny-skills, which has 1,382 GitHub stars. The repository holds 76 skills in this directory. The repository was last updated on July 16, 2026.

Source: RefoundAI/lenny-skills on GitHub. Facts on this page come from the repository at the commit we read; the author's words are quoted as theirs.