Coaching practices for Why a Good Strategy Feels Wrong
Describe almost anything you are working through and IX Coach finds the practices whose real-world fit is closest. For Why a Good Strategy Feels Wrong, these are the strongest matches in the current practice library.
Does this sound like the set of challenges you might be facing?
- Everyone swears this approach is the right one and on paper it clearly is, but it just feels subtly off when I do it, like it’s cut against my grain
- I made a call that turned out badly and now I feel like an idiot for it
- I’ve decided the lesson from this success is “focus narrow” or “go big”
- I beat myself up over a call that went badly even though it was the right move with what I knew, and I let myself off the hook for reckless ones that happened to work out
- A rule of thumb that served me brilliantly in one area keeps failing me somewhere else, and I can’t figure out why
Practices that may help
- Align your strategy with your regulatory focus for "regulatory fit"
When your strategy matches your regulatory focus, the task feels more right and performance improves.
Regulatory Focus Theory: Promotion vs Prevention Thinking - Judge decisions by the process, not the result
A good decision that produces a bad outcome is still a good decision.
Expected Value Thinking: Deciding Under Uncertainty - 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 - Separate the quality of the decision from the outcome
A good decision can produce a bad outcome, and a bad decision can produce a good outcome — do not confuse them.
Thinking in Bets - Match your heuristic to the structure of the environment
A good rule works because it matches the statistical regularities of the environment — wrong environment, wrong rule.
Simple Heuristics: Gerd Gigerenzer’s Case for Fast and Frugal Thinking - Identify whether defensive pessimism or optimism fits your anxiety profile
Defensive pessimism works best for high-anxiety people — applying it to low-anxiety people, or optimism to high-anxiety people, tends to backfire.
Defensive Pessimism, Made Practical - Prefer positions with optionality over positions with precision
In uncertain environments, prioritize options to pivot over optimized fixed positions.
The Ludic Fallacy: When You Mistake Real Life for a Game - Ask the workability question
Ask "is what I am doing working?" — not "is it right?" but whether it is moving you toward the life you want.
Emotional Agility, Made Practical - Check whether your judgment is tracking affect, not the target attribute
When a decision "just feels right," ask whether the feeling is about the actual question or about your current emotional state.
Attribute Substitution: When Your Brain Answers a Different Question - Simulate the adversary’s response to your move
Assign someone to genuinely think and plan as your competitor, not just describe them.
Red Teaming: Stress-Testing Plans Before They Fail
Related concerns
- Needs Vs Strategies
Choose the study method that matches the type of knowledge you are building, not the one that feels most comfortable.
Deliberate strategy selection
- Both Sides Of A Strategy
Assign someone to genuinely think and plan as your competitor, not just describe them.
Simulate the adversary’s response to your move
- Oblique Strategies Error
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.
- Resulting Bias Decisions
Judge a decision by the quality of the reasoning at the time, not by what happened.
Evaluate decisions by process, not outcome
- Barbell Strategy Taleb
Before adopting a lesson from a success story, build the best possible case for the opposite approach.
Steelman the strategy opposite to the successful one
- Cognitive Flexibility Pessimism
Choose optimism where the cost of error is low, and sober realism where the stakes are high.
Practice flexible optimism, not blind optimism
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