/pivot-decision

Help founders decide whether to pivot and, if so, how to execute the transition.

Tone: Thoughtful and structured. Pivots are existential decisions that deserve rigor.

Process:

1. Understand where they are:

   • "What's driving the pivot consideration?"
   • "How long have you been working on the current direction?"
   • "What have you learned about why it's not working?"

2. Load context:

   • Check .claude/metrics.local.md for runway, growth metrics
   • Understanding cash position is critical for pivot timing

Part 1: Should You Pivot?

3. Distinguish pivot from iteration:

   Iteration	Pivot
   Improving what exists	Fundamental change in direction
   Same target customer	Different customer or problem
   Optimizing product	Different product or model
   Normal startup evolution	Strategic reset

   "Is this really a pivot, or is it iteration that feels dramatic because it's hard?"

4. Apply the pivot decision framework:

   Signals it might be time to pivot:

   • Consistent negative feedback from target customers
   • Can't find product-market fit after significant effort
   • Market turned out smaller than expected
   • Unsustainable unit economics that won't improve
   • Team has lost conviction in the direction
   • Discovered a bigger opportunity through current work

   Signals to persevere instead:

   • Some customers love it, just not enough yet
   • Haven't truly tested the core hypothesis
   • Execution issues rather than strategy issues
   • Giving up too early due to impatience
   • Running from hard problems rather than toward better opportunities

5. The pivot or persevere questions:

   Question	Pivot Signal	Persevere Signal
   Do any customers love this?	No strong advocates	Yes, even if few
   Is the problem real?	Problem doesn't resonate	Problem is real, solution is off
   Can you reach customers?	Distribution is impossible	Distribution is hard but possible
   Can economics ever work?	Fundamentally broken	Need scale to work
   Does team believe?	Lost conviction	Still believe, frustrated
   Is there a bigger opportunity?	Clear better path	Grass-is-greener thinking

6. Assess your runway:

   • How many months of runway do you have?
   • How long would a pivot take to show results?
   • Do you need to raise? Can you raise in current state vs. pivoted state?

   Rule of thumb: You need 12+ months of runway to pivot effectively. Less than that and you're probably better off raising first or winding down.

Part 2: Deciding Where to Pivot

7. Identify pivot options:

   Types of pivots:

   Type	What Changes	Example
   Customer segment	Who you serve	SMB to Enterprise
   Problem	What you solve	Scheduling → Communication
   Solution	How you solve it	Software → Services
   Channel	How you reach customers	Direct → Partner
   Revenue model	How you make money	Subscription → Transaction
   Technology	Core tech platform	Build → Buy
   Zoom in	Focus on one feature	Full suite → One tool
   Zoom out	Feature becomes platform	Tool → Platform

8. Evaluate pivot directions:

   For each option, assess:

   • What evidence do we have that this will work?
   • What's our unfair advantage in this direction?
   • How much of what we've built carries over?
   • How does the team feel about this direction?
   • What's the market size and competition?

9. Make the pivot decision:

   Decision framework:

   If you have strong evidence AND team conviction AND runway → Pivot to best option
   If you have weak evidence but strong hypothesis → Test before full pivot
   If team has lost all conviction → Pivot or wind down
   If runway is short → Raise first or wind down
   

Part 3: Executing the Pivot

10. Plan the pivot:

    Key decisions:

    • Hard pivot (stop everything) vs. soft pivot (parallel path)?
    • What do we keep vs. abandon?
    • How do we handle existing customers?
    • What does the team look like post-pivot?

11. Communicate the pivot:

    To the team:

    • Be honest about what's not working
    • Share the reasoning behind the new direction
    • Acknowledge this is hard
    • Get buy-in vs. just announcing
    • Allow questions and concerns

    Script:

    "I want to talk about where we're headed. [Current direction] isn't working as we hoped. Here's what we've learned... Based on that, we're going to [new direction]. This is why we believe it's the right move... I know this is a big change. Here's what it means for the team..."

    To investors/board:

    • Inform before you tell the team (they should hear from you)
    • Share the data and reasoning
    • Present the new plan
    • Ask for their support
    • Be prepared for hard questions

    To existing customers:

    • If you're discontinuing their product, give notice
    • Help them transition
    • Honor commitments where possible
    • Maintain relationships for the future

12. Execute the transition:

    Week 1-2:

    • Announce internally
    • Begin winding down old work
    • Define new priorities
    • Identify what carries over

    Week 3-4:

    • Ship something in new direction (momentum matters)
    • Release team members who don't fit new direction
    • Communicate externally as needed

    Month 2-3:

    • Full focus on new direction
    • Set new milestones
    • Regular check-ins on whether it's working

13. Create the pivot plan:

    # Pivot Decision & Plan
    Date: [YYYY-MM-DD]
    Status: [Evaluating/Decided/Executing]
    
    ## Current State
    - Direction: [Current product/market]
    - Why it's not working: [Specific reasons]
    - Runway: [X months]
    
    ## Decision
    - [ ] Persevere with current direction
    - [ ] Pivot to: [New direction]
    - [ ] Wind down
    
    ## If Pivoting
    
    ### New Direction
    - Target customer: [Who]
    - Problem: [What]
    - Solution: [How]
    - Why we believe: [Evidence]
    
    ### What We Keep
    - [Technology, relationships, learnings that carry over]
    
    ### What We Stop
    - [Products, features, efforts to abandon]
    
    ### Timeline
    | Week | Actions |
    |------|---------|
    | 1 | Announce, begin transition |
    | 2 | Wind down old, spin up new |
    | 3-4 | First delivery in new direction |
    | 8 | Checkpoint - is this working? |
    
    ### Communication Plan
    - Team: [When, how]
    - Board: [When, how]
    - Investors: [When, how]
    - Customers: [When, how]
    
    ### Success Criteria
    - By [date], we will know this is working if: [Specific metrics]
    - If not working by [date], we will: [Next action]
    

14. Close with perspective:

    • "Many great companies pivoted - Slack, Instagram, YouTube. A pivot isn't failure."
    • "The hardest part is the decision. Execution is just work."
    • "Trust your judgment. You know more about this than anyone."

Key principles:

• Pivot toward something, not just away from something
• One decisive pivot is better than many small ones
• Preserve what's working even as you change direction
• Communication is as important as strategy
• Give the new direction a real chance before evaluating