Product Management 2 guests | 2 insights

Startup Pivoting

Startup pivoting is the skill of recognizing when to change direction and executing that change effectively. Most founders do incremental 10% pivots when they need dramatic 200% pivots. The key is maintaining rational distance from your current approach and honestly assessing whether you've exhausted the possibilities.

The Guide

3 key steps synthesized from 2 experts.

1

Ask if you've exhausted the possibilities

The core question when considering a pivot isn't whether things are going well - it's whether you've truly exhausted the possibilities with your current approach. If there are still promising paths unexplored, a pivot might be premature. If you've genuinely tried everything, it's time to change.

Featured guest perspectives
"The decision is about have you exhausted the possibilities?"
— Stewart Butterfield
2

Pivot 200%, not 10%

When founders finally decide to pivot, they often make changes that are too incremental. A tweak to the positioning or a new feature isn't a pivot - it's iteration. True pivots require dramatic change. If you're going to pivot, make it meaningful enough to actually test a new hypothesis.

Featured guest perspectives
"Most founders do a 10% pivot, and what they need to be doing is a 200% pivot."
— Todd Jackson
3

Maintain rational distance from your current approach

Founders get emotionally attached to their current product and approach, which clouds judgment about when to pivot. Cultivate rational distance - the ability to evaluate your startup as an outsider would. This emotional separation is essential for making clear-headed pivot decisions.

Featured guest perspectives
"The decision is about have you exhausted the possibilities?"
— Stewart Butterfield

Common Mistakes

  • Pivoting too early before exhausting possibilities with the current approach
  • Making incremental changes and calling them pivots
  • Being too emotionally attached to evaluate objectively
  • Pivoting to something equally unvalidated instead of learning from what didn't work

Signs You're Doing It Well

  • You can honestly say you've exhausted possibilities before pivoting
  • Your pivots are dramatic enough to test genuinely new hypotheses
  • You can evaluate your startup with rational distance, not emotional attachment
  • Post-pivot, you're seeing signals that were absent before

All Guest Perspectives

Deep dive into what all 2 guests shared about startup pivoting.

Stewart Butterfield 1 quote
Listen to episode →
"The decision is about have you exhausted the possibilities?"
View all skills from Stewart Butterfield →
Todd Jackson 1 quote
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"Most founders do a 10% pivot, and what they need to be doing is a 200% pivot."
View all skills from Todd Jackson →

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