The best strategic decisions often look questionable at the time they’re made.
Netflix mailing DVDs when everyone was building streaming. Amazon losing money for years while investors screamed for profitability. Apple killing the iPod that had made them successful. Intel exiting memory chips (the business that built the company) to focus on processors.
In retrospect, these decisions look brilliant. At the time, they looked somewhere between bold and insane. Critics were loud. Shareholders were nervous. Even insiders had doubts.
This is the paradox of strategy: the moves that create the most differentiation are often the moves that generate the most skepticism. A strategy everyone immediately agrees with is probably a strategy that doesn’t change much.
Why good strategy looks wrong
Strategic differentiation requires doing something different from competitors. But “different” triggers discomfort:
Different contradicts conventional wisdom. If an approach were obviously right, everyone would already be doing it. Good strategy often requires believing something the market doesn’t believe yet: that customers will pay for this, that technology will enable that, that competitors are wrong about the other thing. Contrarian bets feel contrarian.
Different abandons proven models. Strategies that worked got the organization where it is. Changing them feels like throwing away success. “Why would we stop doing what made us successful?” is a reasonable question with an uncomfortable answer: because what made you successful may not keep you successful.
Different cannibalizes existing business. Often the right strategic move threatens current revenue. Building the thing that competes with your cash cow feels like self-destruction, even when the alternative is waiting for someone else to destroy you.
Different requires patience. Strategic bets take time to prove out. Results may not be visible for quarters or years. In the meantime, the strategy just looks like money being spent on something unproven while critics point to the absence of returns.
Different is hard to explain. Complex strategic logic doesn’t fit in a sound bite. When the strategy depends on a chain of reasoning (“if we do X, then competitors will respond with Y, which positions us for Z”), communication becomes difficult. Stakeholders hear the bet; they don’t see the logic.
Distinguishing good-strange from bad-strange
Of course, not every unconventional strategy is brilliant. Some strategies that look wrong are wrong. The challenge is distinguishing between them.
Good-strange has clear logic. The strategy can be explained in terms of cause and effect, even if the explanation is complex. There’s a theory of why this will work: what customer need it serves, what competitive dynamic it exploits, what capability it builds. “This feels right” isn’t a strategy; “this positions us to win because X, Y, Z” is.
Good-strange acknowledges trade-offs. Real strategy involves choosing to not do things. If the strategy claims to have no downsides, it’s probably marketing rather than strategy. Good-strange strategies are clear about what they give up, and why the trade-off is worth making.
Good-strange has testable assumptions. The strategy depends on certain things being true. Those assumptions should be explicit and, ideally, testable. “We believe customers will pay a premium for this feature” is an assumption that can be validated. Strategies built on untestable assumptions are faith, not strategy.
Good-strange connects to reality. Even visionary strategy must connect to present circumstances. There should be a plausible path from here to there, not just a picture of the destination. Good-strange strategies explain the first steps, not just the end state.
Good-strange acknowledges uncertainty. The strategist should be able to articulate what could prove them wrong. Absolute certainty about an unconventional strategy is a red flag. Honest strategists hold their conclusions with appropriate confidence: strong enough to act, humble enough to adapt.
Bad-strange lacks these features. It’s unconventional without clear logic. It claims no trade-offs. Its assumptions are vague or unfalsifiable. The path from here to there is hand-waved. Certainty is absolute. Bad-strange is often conventional strategy dressed up in unconventional language, or wishful thinking without analytical foundation.
The leader’s dilemma
Strategic leaders face an asymmetric challenge:
If the strategy is conventional and succeeds, the leader gets modest credit. After all, they did what everyone expected.
If the strategy is conventional and fails, the leader is criticized for not being bold enough, for missing the shift that others saw coming.
If the strategy is unconventional and fails, the leader is blamed for reckless decisions that ignored conventional wisdom.
If the strategy is unconventional and succeeds, the leader is celebrated as a visionary who saw what others missed.
The rewards for being right-and-different are large; the penalties for being wrong-and-different are also large. This asymmetry explains why so many leaders default to conventional strategies: the personal risk is lower, even when the organizational risk is higher.
Breaking this pattern requires either leaders secure enough to bet their reputation on unconventional moves, or governance that evaluates strategic decisions on their logic at the time rather than their outcomes in hindsight.
Supporting unconventional strategy
Organizations that want good-strange strategies need to create conditions that support them:
Evaluate logic, not just outcomes. A strategic decision can be right based on available information and still fail due to factors that couldn’t be predicted. Judge strategies on the quality of the thinking, not just the result. A bad strategy that got lucky is still bad strategy; a good strategy that met unexpected obstacles is still good strategy.
Tolerate early ambiguity. Unconventional strategies often have uncertain early results. Demanding immediate validation kills strategies that would have succeeded with patience. Build in time for the strategy to develop before judging it.
Protect strategic experiments. If every initiative is held to immediate ROI standards, no one will pursue the unconventional. Create space for strategic bets that might not pay off, with appropriate scale limits and learning objectives.
Encourage constructive dissent. The best test of a strategy is serious challenge. If leadership can’t defend the strategy against intelligent skeptics, that’s a problem. If skeptics are silenced rather than engaged, that’s a different problem.
Distinguish skepticism from rejection. Pushback on unconventional strategy should trigger explanation, not abandonment. The goal is to refine the strategy through challenge, not to retreat to safety whenever someone objects.
When to hold and when to fold
Even good-strange strategies sometimes prove wrong. How do you know when to persist and when to pivot?
The original logic should still hold. Has something changed that invalidates the reasoning behind the strategy? If the assumptions were wrong, or if circumstances have shifted dramatically, reconsideration is warranted. If the logic still holds but results are slow, patience may be appropriate.
Leading indicators matter. What early signals were supposed to indicate the strategy is working? Are those signals appearing, even if final results aren’t? Strategies often show progress in leading indicators before financial outcomes arrive.
Adapt, don’t just persist. Holding a strategic direction doesn’t mean rigidly executing the original plan. The core bet might be right while the execution approach needs refinement. Persistence with learning beats both abandonment and stubbornness.
Set honest decision points. Before launching unconventional strategy, agree on what would cause reconsideration. This pre-commitment prevents both premature abandonment and endless continuation of failing approaches.
The line between strategic patience and strategic stubbornness is real but not always clear. The best leaders revisit their reasoning regularly, update based on new information, and maintain honest assessment of whether the strategy is working, while resisting the pressure to abandon bold moves simply because they generate discomfort.
Strategic Advisory helps organizations develop and evaluate unconventional strategies, building the analytical foundation that distinguishes good-strange from bad-strange.