The Decision Helper skill guides you through structured decision-making processes using proven frameworks, mental models, and de-biasing techniques. Rather than relying on gut feel alone or getting paralyzed by analysis, this skill helps you think clearly about choices that matter.
This skill applies decision science, behavioral economics, and strategic thinking frameworks to help you evaluate options systematically, identify hidden biases, consider long-term consequences, and make choices you'll be confident about. It recognizes different decision types—reversible vs. irreversible, urgent vs. important, personal vs. professional—and provides appropriate frameworks for each.
The tool doesn't make decisions for you—it clarifies your thinking, surfaces assumptions, and ensures you've considered what matters most before committing to a path.
Core Workflows
Workflow 1: Decision Framing
Clarify what you're actually deciding:
Question Definition
What exactly are you choosing between?
Stakes Assessment
How important is this? How reversible?
Timeline
When must you decide? Can you wait for more information?
Stakeholders
Who else is affected? Who should have input?
Context
What constraints or requirements apply?
True Question
Often the initial framing isn't the real decision
Workflow 2: Options Generation
Expand your choice set:
List Obvious Options
The choices you're already considering
Explore Alternatives
Are there other possibilities?
Challenge Constraints
What if X weren't a factor?
Hybrid Options
Can you combine approaches?
Do Nothing
Is staying put an option?
Third Alternative
Beyond binary choices
Workflow 3: Criteria Definition
Identify what matters:
Values Alignment
What principles matter here?
Success Definition
What does a good outcome look like?
Trade-offs
What are you willing to sacrifice for what?
Weighted Importance
Not all criteria are equal
Deal-breakers
Non-negotiable requirements
Workflow 4: Systematic Evaluation
Assess options against criteria:
Score Options
Rate each option on each criterion
Weight Criteria
Apply importance multipliers
Compare Trade-offs
Where does each option excel/fail?
Test Assumptions
What must be true for each option to work?
Consider Consequences
Second and third-order effects
Workflow 5: Decision Validation
Pressure-test your choice:
10/10/10 Analysis
How will you feel in 10 mins/months/years?
Regret Minimization
Which choice minimizes future regret?
Reversibility Check
Can you undo this if it doesn't work?
Advice to Friend
What would you tell someone else in this situation?
Pre-mortem
If this fails, what will be the reason?
Decision Frameworks
The Eisenhower Matrix
For prioritization and urgency decisions:
Urgent
Not Urgent
Important
DO NOW
SCHEDULE
Not Important
DELEGATE
ELIMINATE
The WRAP Framework (Chip & Dan Heath)
W
iden your options
Avoid "whether or not" framing
Consider multiple alternatives simultaneously
R
eality-test your assumptions
Ask disconfirming questions
Seek outside perspectives
A
ttain distance before deciding
10/10/10: How will you feel in 10 mins/months/years?
What would you advise a friend?
P
repare to be wrong
Set tripwires to reconsider
Plan for both success and failure
The Regret Minimization Framework (Jeff Bezos)
Project yourself to age 80 and ask:
Will I regret not doing this?
Will I regret the safe choice?
What minimizes future regret?
Best for: Life-changing decisions, risk-taking, career choices
The Weighted Decision Matrix
Option
Criterion 1 (weight: 5)
Criterion 2 (weight: 3)
Criterion 3 (weight: 2)
Total
Option A
4 × 5 = 20
3 × 3 = 9
5 × 2 = 10
39
Option B
5 × 5 = 25
2 × 3 = 6
3 × 2 = 6
37
Best for: Complex decisions with multiple factors
Two-Way vs. One-Way Doors (Jeff Bezos)
Two-Way Doors
(Reversible)
Decide quickly with limited information
You can walk back through if wrong
Examples: Hiring, new feature, process change
One-Way Doors
(Irreversible)
Take time, gather data, consult widely
Very difficult or impossible to reverse
Examples: Marriage, major career change, selling company
Second-Order Thinking
Don't just ask "What happens next?"
Ask "And then what?"
Example:
Decision: Take on more clients
First-order: More revenue
Second-order: Less time for existing clients, quality drops
Would you take this option if it required 10x the effort/cost?
If yes → genuine priorities
If no → probably not that important
Quick Reference
Action
Command/Trigger
Start decision process
"help me decide" or "making a decision"
Binary choice
"should I [option A] or [option B]"
Generate options
"what are my options for [situation]"
Evaluate trade-offs
"compare [option A] vs [option B]"
Pressure test
"help me validate my decision"
Remove bias
"am I thinking clearly about [decision]"
Long-term view
"future implications of [decision]"
Risk assessment
"what could go wrong with [decision]"
Decision Types & Approaches
Type 1: Career Decisions
Framework: Regret Minimization + Values Alignment
Questions:
What does success look like in 10 years?
What am I optimizing for? (Money, impact, growth, balance)
What's irreversible vs. what can I change later?
Type 2: Financial Decisions
Framework: Expected Value + Risk Assessment
Questions:
What's the downside if this goes wrong?
Can I afford to lose this?
What's the opportunity cost?
Is this speculation or investment?
Type 3: Relationship Decisions
Framework: Values Alignment + Long-term Impact
Questions:
Are core values aligned?
What patterns am I seeing?
What would I advise a friend in this situation?
Am I making excuses or seeing reality?
Type 4: Time Allocation Decisions
Framework: Eisenhower Matrix + Opportunity Cost
Questions:
Is this urgent, important, both, or neither?
What am I NOT doing if I do this?
Does this align with my goals?
Can someone else do this?
Type 5: Strategic Business Decisions
Framework: WRAP + Pre-mortem
Questions:
What are we really trying to achieve?
What must be true for this to work?
What would make this fail?
Is this reversible?
Decision Templates
Standard Decision Template
DECISION: [What am I deciding?]
TIMELINE: [When must I decide?]
STAKES: [How important/reversible is this?]
OPTIONS:
A. [Option 1]
B. [Option 2]
C. [Option 3]
D. Do nothing / stay the course
WHAT MATTERS MOST (Criteria):
1. [Criterion 1] - Weight: [1-10]
2. [Criterion 2] - Weight: [1-10]
3. [Criterion 3] - Weight: [1-10]
EVALUATION:
| Criterion 1 | Criterion 2 | Criterion 3 | Total
Option A | | | |
Option B | | | |
Option C | | | |
ASSUMPTIONS I'M MAKING:
-
-
WHAT COULD GO WRONG:
Option A risks:
Option B risks:
10/10/10:
In 10 minutes, I'll feel...
In 10 months, I'll feel...
In 10 years, I'll feel...
DECISION: [Choice]
WHY: [Rationale]
REVERSIBILITY: [ ] Can undo [ ] Hard to reverse [ ] Irreversible
REVIEW DATE: [When to reassess this decision]
Quick Decision Template
DECIDING: [Question]
OPTIONS:
A. [Option A]
B. [Option B]
PROS/CONS:
Option A:
✓ Pro
✓ Pro
✗ Con
✗ Con
Option B:
✓ Pro
✓ Pro
✗ Con
✗ Con
GUT FEELING: [What does intuition say?]
LOGICAL CHOICE: [What does analysis say?]
IF THEY DISAGREE: [Explore the tension]
CHOICE: [Decision]
Values-Based Decision Template
DECISION: [What I'm deciding]
MY CORE VALUES (in order):
1. [Value 1]
2. [Value 2]
3. [Value 3]
OPTION A:
How it aligns with Value 1:
How it aligns with Value 2:
How it aligns with Value 3:
OPTION B:
How it aligns with Value 1:
How it aligns with Value 2:
How it aligns with Value 3:
WHICH OPTION BEST HONORS WHO I WANT TO BE?
DECISION: [Choice]
Best Practices
Define the real question
- "Should I take this job?" might really be "Am I ready to leave my current job?"
Expand your options
- Most decisions aren't binary
Separate deciding from doing
- Make the choice, then create the plan
Set decision deadlines
- Avoid perpetual analysis
Gather just enough information
- More data doesn't always improve decisions
Identify your biases
- We all have them
Sleep on big decisions
- Your unconscious processes information
Write it down
- External thinking clarifies internal confusion
Imagine explaining your choice
- To someone you respect
Consider opportunity cost
- Every yes is a no to something else
Run a pre-mortem
- Assume it failed, work backward to why
Make reversible decisions quickly
- Don't overthink two-way doors
Consult selectively
- Too many opinions create noise
Trust your gut (sometimes)
- Intuition is pattern recognition
Commit fully once decided
- Second-guessing wastes energy
Common Decision Biases
Status Quo Bias
What it is
Preferring things to stay the same
Counter
Imagine you're starting fresh—would you choose current state?
Sunk Cost Fallacy
What it is
Continuing because you've already invested
Counter
Would you start this today knowing what you know?
Confirmation Bias
What it is
Seeking evidence that supports what you already believe
Counter
Actively seek disconfirming evidence
Anchoring Effect
What it is
Over-relying on first piece of information
Counter
Generate options before hearing others' opinions
Availability Bias
What it is
Overweighting recent or vivid information
Counter
Look at base rates and statistics, not just stories
Optimism Bias
What it is
Overestimating chances of success
Counter
Run a pre-mortem, consider downside scenarios
Analysis Paralysis
What it is
Overthinking to avoid deciding
Counter
Set information cutoff, recognize diminishing returns
Integration Points
This skill works well with:
Goal Setter
Ensure decisions align with goals
Journal Prompter
Reflect on decision outcomes
Learning Path Creator
Decide what to learn next
Daily Planner
Decide how to allocate time
Time Blocker
Decide what deserves calendar space
Example Decision Session
User
"help me decide"
Skill Response
:
"I'll help you think through this clearly. Decision-making is a skill, and structure beats wishful thinking.
First, tell me: What are you deciding?
Be as specific as you can. For example:
"Should I take the new job offer?" (career decision)
"Should I invest in this opportunity?" (financial decision)
"Should I end this relationship?" (personal decision)
"Should we build feature A or feature B?" (strategic decision)
What's your decision?"
User
"Should I take the new job offer or stay at my current company?"
Skill Response
:
"Classic career crossroads. This is a high-stakes, somewhat reversible decision (you could change jobs again, but there are costs).
Let's structure this properly. I have some clarifying questions:
Context Questions:
Timeline
When do you need to decide?
What's driving this?
Actively unhappy at current job?
Excited about new opportunity?
Just exploring?
The offers
:
What does the new job offer (role, comp, growth)?
What does staying look like (trajectory, changes possible)?
What matters most to you in a job?
(Top 3)
Compensation?
Growth/learning?
Work-life balance?
Impact/mission?
Team/culture?
Location/flexibility?
Take your time—clarity here shapes everything else."
User
"Need to decide by Friday. Not actively unhappy but feeling stagnant. New job is 20% raise, more senior role, but longer commute. Most important to me: growth, work-life balance, compensation (in that order)"
Skill Response
:
"Got it. Growth is #1, balance #2, money #3. The new role offers more growth and money but potentially threatens balance (longer commute).
Let's use a structured framework: Weighted Decision Matrix
Here's how we'll score each option (1-10) on your criteria:
CRITERION 1: Growth/Learning Opportunity
(Weight: 10 - your top priority)
Current job: How would you rate growth potential? [1-10]
New job: How would you rate growth potential? [1-10]
CRITERION 2: Work-Life Balance
(Weight: 8 - second priority)
Current job: [1-10]
New job: [1-10] (consider that commute)
CRITERION 3: Compensation
(Weight: 6 - third priority)
Current job: [1-10]
New job: [1-10]
Give me your honest ratings for each. Then we'll run the math and validate with other frameworks."
[Continues with evaluation, 10/10/10 test, regret minimization, and final recommendation based on user's values]