Uber's CEO search reaches new degree of difficulty

SoftBank investment offer complicating an effort with an unprecedented array of obstacles

Five weeks after Travis Kalanick’s surprise resignation as chief executive of Uber Technologies Inc., the board of the now-leaderless company is wrestling with a thorny question.

Should it negotiate with SoftBank Group Corp., which has in recent weeks approached Uber with a multi-billion-dollar investment offer that could alter the course of the ride-sharing powerhouse? Or should it wait until after it hires a new chief executive to consider the offer?

The puzzle points up the delicate situation Uber’s eight-member board is in as it rushes to find a chief executive to head a depleted executive suite and help navigate a litany of