Coaching practices for How to Use Oblique Strategies

Describe almost anything you are working through and IX Coach finds the practices whose real-world fit is closest. For How to Use Oblique Strategies, these are the strongest matches in the current practice library.

Does this sound like the set of challenges you might be facing?

• I’ve decided the lesson from this success is “focus narrow” or “go big”
• Something’s off in this piece but I can’t tell what, and every time I get frustrated I tear the whole thing down and rebuild from scratch
• Every approach I come up with sounds like me, because I keep ruling out anything that doesn’t feel like something I’d do
• When I ask my team how to make this succeed they just reinforce the direction we’re already pointed, but I have a hunch that if I flipped it and asked how we’d deliberately sabotage this thing, the risks they’re too polite to raise would come pouring out.
• I’ve tried this dreaming-and-planning thing in bits and pieces in my head and it never takes

Practices that may help

1. Oblique Strategies, Made Practical
   Oblique Strategies is a deck of constraint-based prompts created by Brian Eno and Peter Schmidt to interrupt habitual thinking during creative blocks. The prompts work by forcing an indirect, unexpected approach to a problem rather than attacking it head-on. Evidence for constraint-based creativity is solid in cognitive research; the specific deck is widely used in music, design, and writing with strong anecdotal support.
2. Steelman the strategy opposite to the successful one
   Before adopting a lesson from a success story, build the best possible case for the opposite approach.
   Survivorship Bias: Learning from What You Can’t See
3. Change exactly one element and observe what shifts
   Alter a single variable at a time to see how the rest of the system responds.
   Oblique Strategies, Made Practical
4. Ask what a specific other person would do
   Step into a named other’s perspective to access approaches you would not generate as yourself.
   Oblique Strategies, Made Practical
5. WOOP: Wish, Outcome, Obstacle, Plan
   WOOP — Wish, Outcome, Obstacle, Plan — is Gabriele Oettingen’s science-based goal strategy: you picture the best outcome, then deliberately confront the inner obstacle in your way, and pair it with an if-then plan. Unlike pure positive thinking, WOOP combines mental contrasting with implementation intentions, and both halves have genuine support from randomized trials.
6. Use reverse brainstorming to find failure modes
   Ask "how would we make this fail?" instead of "how do we make this succeed?"
   Red Teaming: Stress-Testing Plans Before They Fail
7. Run the full WOOP sequence — not just parts of it
   WOOP works as a sequence; running only the wish and outcome steps (pure positive visualization) is not WOOP and may be counterproductive.
   Mental Contrasting and WOOP
8. Use the decoy structure to guide others toward better options
   If you’re structuring choices for a team or organization, include a dominated option to help people recognize and choose the best option.
   The Decoy Effect — How an Irrelevant Option Changes Your Choice
9. Mental Contrasting and WOOP
   Mental contrasting — Gabriele Oettingen’s technique of vividly imagining your desired future and then confronting it with the specific obstacles standing in the way — activates the motivational and planning systems simultaneously. When combined with implementation intentions (WOOP: Wish, Outcome, Obstacle, Plan), multiple RCTs find improved goal achievement across health, academic, and professional domains — though effect sizes are moderate and the full WOOP sequence matters more than any single step.
10. Form an if-then plan linking the obstacle to a specific response
    "If [obstacle occurs], then I will [specific action]" — this plan is what converts mental contrasting into behavior change.
    Mental Contrasting and WOOP

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