Questions of feasibility: What are the odds of this endeavor succeeding, enduring and rebooting (if it crashes)? What changes those odds in favor of its success? What interference, opposition and conflicts is it likely to encounter? What momentum, consensus and prior experiences among participants are increasing the odds of success?
Questions of strategy: How does endeavor compare to other competing collaborations? What intrinsic value does this endeavor offer distinct from others? What differences will it make to participate in this endeavor that gives it advantages over others or leverage to attract essential participants? What approach does this endeavor take toward its rivals who could be provoked to become more competitive, to spend more on rivalries or to propagate false rumors?
Questions of adaptation: How many feedback loops are built in to report on a need for change? How much use will be made of the indicators of missed targets, undesirable outcomes or unexpected results? How much is likely to be learned from what happens and does not happen? How flexible, open and responsive are the internal process of listening, dialogue and rethinking previous assumptions?
Questions of efficiency: How much will get done by the endeavor? How quickly will it get done? How much involvement by how many people will it take to meet those targets? How vulnerable are the collaborative processes to breakdowns, rework and schedule slippage? How many resources need to be tied up and for how long -- by the work getting done?
Fragile collaborative endeavors cannot withstand this barrage of questions. This "thorough interview" could come across as disparaging, cynical and contrarian. Rather than being seen as supportive of more resilience and success, it could get framed as threatening to desired outcomes. However, when an endeavor is well-conceived, it would welcome this "cross examination" to uncover its blind spots, challenges its premises and refine it's approach before committing time, money and other resources.