“It would pour more cold water on the office market, which is struggling direly,” he said, noting that WeWork rents nearly 20 million square feet of office space, more than any other company in the United States.

Until recently, Mr. Mathrani appeared committed to turning WeWork around. But he had grown exhausted by the challenges of the business and was frustrated by what he perceived as a lack of engagement from SoftBank, according to four people familiar with his leadership who spoke on the condition of anonymity. He told colleagues that he was particularly annoyed that it did not move more quickly to wrap up the debt restructuring, three people familiar with his conversations said.

The transaction could not be done quickly because it was complex and required sign-off by numerous parties, according to a person familiar with SoftBank’s thinking.

Mr. Mathrani declined to comment.

As WeWork and SoftBank discussed a restructuring, other parties suggested deals aimed at steadying the company.

Last fall, Mr. Neumann, the co-founder, who holds a small stake in the company, started telling friends and associates that he was thinking about getting involved in WeWork again and buying back some of its stock, according to three people familiar with his conversations. He scheduled a meeting with Mr. Mathrani in October to discuss a large investment and other strategic initiatives that could bolster the company, four people familiar with the plans said.