Masayoshi Son's bankers are taking a hard look at their most important client.

After the costly rescue of office-sharing startup WeWork and a series of other high-profile setbacks for Son, senior executives at two of Japan's biggest banking groups have said privately they've grown less comfortable with the eccentric billionaire's management of SoftBank Group Corp.'s $100 billion Vision Fund.

One executive, speaking in mid-November, said his firm wants to see a convincing turnaround plan for WeWork before lending more money to SoftBank.