Cortana has struggled to find a place in the competitive corners of virtual assistants. Others in the game like Google Assistant, Alexa and Siri are winning better positions based on their satisfactory responses to questions. And there is one more challenge, Cortana doesn’t have smart speaker or mobile operating system, and it lacks native access to two of the most common devices people use to speak with AI assistants.

Microsoft is looking for ways to improve the functionality of Cortana, the focus is to make it part of its 365 productivity software for the workplace, which sees applications like Outlook, Word and Powerpoint currently being used by 180 million monthly active users. Microsoft Corporate VP, Andrew Shuman, said: “We are really focusing on this experience, embedding Cortana across M365. That’s really the message.”

The idea has been to find Cortana a place among its counterparts using the already existing number of Microsoft users. But that’s after some adjustments have been made and new features introduced to give users a new experience.

Cortana can now read your email summaries and send quick reply responses in Outlook. The AI assistant can now schedule meeting and deliver daily schedule and task rundown. Excel now supports natural language queries, enabling users to ask questions about Excel data, and Cortana can be used as coach. Email briefings from Cortana in Outlook can suggest focus time.

Apart from the choice of using Cortana as coach, there is a presenter coach launched last month by Microsoft, a PowerPoint service that listens to presentations and then provides feedback on pace, use of inclusive language, and repetitive use of mannerism like “basically” and “umm.”

Cortana can now transcribe meetings, perform voice email playback, find and automatically remind you about tasks in emails and schedule meetings.

At its Ignite conference, Microsoft announced a number of new features that help Cortana to become even more useful in your day-to-day work, all of which fit into the company’s overall vision of AI as a tool that is helpful and augments human intelligence. (TechCrunch)

But apart from any first-party hardware or mobile operating system of its own, that means, outside Windows 10, Cortana is likely going to live or die in a multi-assistant capacity, alongside the virtual assistants that are its direct competitors.

Despite the upgrades that give Cortana a chance to compete, there is still a challenge. The double-down on integration with Microsoft software doesn’t address the fact that the company missed its chance on hardware. This means, there is no first-party Microsoft smart speaker with Cortana, like, for example, the Google Nest or Amazon Echo. Harman Kardon Invoke was the only speakers that have Cortana inside, but it didn’t sell.

So speaker has been a hardware challenge that Cortana has found difficult to get around, even though Microsoft CTO, Kevin Scott told VentureBeat that Cortana doesn’t need a smart speaker to succeed as an AI assistant and can instead rely on legacy strongholds like Windows 10, reality disagrees.

A year ago, Microsoft released Surface headphones, and recently, earbuds too were released. But they are devices marketed to keep professionals busy, not home dedicated devices.

Shuman also told VentureBeat about Cortana’s focus on enterprise applications, Cortana’s future in hardware, and the new Voice Interoperability Initiative to make a multi-assistant world.

“I echo Kevin’s point about ambient devices, I think we are going to continue to work on our Amazon partnership and thinking a lot about how M365 users who have an Amazon speaker can get a great experience, as we have that in beta already today and we’ll do more there,” Shuman said.

There is also the challenge of less-than-clear hardware message by Cortana, and Shuman said Microsoft will find opportunities in mobile devices to fill the roles.

“We feel ever more convicted that getting ourselves into a great position on the mobile device you already have, you already trust with a lot of your data, but really being able to enhance that experience, because it is hard to do some stuff on the phone. That will be the way forward for us,” he said

Though there is rumor that AI assistant may be removed from the Microsoft Launcher for Android smartphones, Shuman said Microsoft is counting on mobile devices to move Cortana into viable position of competition.

But the success of an AI assistant may depend totally on existing market advantages, and it is believed to be the reason why Microsoft is focusing on leveraging mobile and PC use cases. The 180 million already existing users Powerpoint and Word is a huge market on its own, and Microsoft is trying to leverage on the numbers to put Cortana back on track.

SoftBank has inadvertently become a victim of WeWork’s predicament. In what it said to be its first loss in 14 years, the Japanese conglomerate suffered a surprising loss that got the CEO, Masayoshi Son, to a humble mood.

On Wednesday, SoftBank posted figures that indicated loss of $4.7 billion out of the $6 billion it invested in WeWork, and its Vision fund lost $3 billion out of the $4 billion it put into the troubled giant.

So the week offered SoftBank news of losses, $6.4 billion in all, denting its Vision Fund which now looks like a drag on its parent company because of poorly performing investments in WeWork, Uber and Slack. The Vision Fund lost nearly $9 billion in the quarter.

“SoftBank Group Corp. is a Japan-based company principally engaged in the communication and Internet related business. The Company operates in six business segments. Softbank segment is involved in the sale of mobile terminals, the provision of mobile communication services and fixed communication services in Japan. The Segment also sells mobile terminal accessories, PC software and peripherals. Sprint segment is involved in the provision of mobile communication services and others in the US. Yahoo segment conducts advertising business on the Internet, e-commerce business and membership service business. ARM segment is involved in the design of IP and related technologies for microprocessors, and the sale of software tools. Softbank Vision Fund and Delta Fund segment conducts investment activities in the technology area. Bright Star segment conducts distribution of mobile terminals overseas. The Company is also involved in Fortress and Fukuoka Softbank Hawks related business.”

Though the loss broke a 14 years old record and opened the way for other possibilities, Son said it is part of the process, it’s not all about winning. “We can’t win every time, but our return is twice the average industry return,” he said.

Son admitted a poor investment strategy as a reason for the huge loss. Throwing huge sums around for startups was a risk that its price comes in billions.

SoftBank is trying to restore confidence in its big bets, after its backing of WeWork has drawn months of scrutiny. That means shoring up the corporate governance at some of the companies it backs and restrictions on dual-class shares, moves designed to restrict the nearly free reign enjoyed by some founders—like WeWork founder Adam Neumann, who departed his company with a $1.7 billion payout. (Fortune newsletter)

WeWork’s ordeal brought questions about Son’s commitment to unconventional tech founders which have necessitated it to spend extra cash to keep them in business.

A month ago, SoftBank paid $10 billion bailout fund to keep WeWork in existence, it includes $5 billion in new financing, a tender offer of up to $3 billion for existing WeWork shareholders and an acceleration of an earlier promise of $1.5 billion in funding. It’s a huge bailout that investors considered avoidable if SoftBank has done its homework before venturing into WeWork.

Questionable corporate governance practices are believed to be responsible for the troubles of WeWork.

Initially, Son appeared defiant and said he was not going to change anything or do things differently due to the recent losses. But in a sudden change of tone, he acknowledged in a news conference that such corporate challenges exist, and he regrets taking some steps.

“Various negative media reports about WeWork were true in some sense,” he said.

“The perception is that Softbank is being dragged down into the quagmire of Wework. I am looking back with true regret about the mistaken investment moves that I have made.”

Although SoftBank has been mainly at the receiving end of these poor decisions, Son said that investors are still reaping profits from their total investments and the Vision Fund’s value for shareholders has not fallen despite the latest losses because of gains from other stock holdings of SoftBank.

SoftBank has series of investments cuts across array of companies like Alibaba, Uber, Didi and Grab, Yahoo, Internet of Things (IoT), British based company Arm. So SoftBank has relied on its investment in these companies to keep its shareholders away from losses incurred in WeWork.

Although some of its investment companies like Uber and Slack have been suffering its own losses recently, SoftBank said it’s not that bad. Son also said that though Uber is losing money, SoftBank’s investment with the ridesharing company has kept it from becoming worse.

One of the concerns raised by the media is that SoftBank is more a real estate company than it is a tech company, and demanded to know why Wework is viewed as technology investment. Son said it is due to the internet technology used by the company, which offers office spaces to startups.

Though it all seems gloomy, Son said “it’s not a sinking ship.” It’s a common thing that happens with new companies, even those considered successes. “But there is no storm, and things are under control,” he assured.

SoftBank is counting on the good performances of its other various investments to keep the sinking ones afloat, a method that appears so practical as long as the majority of the investments stay on top of their game.