Former Microsoft CEO Steve Ballmer. (GeekWire File Photo)

Former Microsoft CEO Steve Ballmer and former Windows president Steven Sinofsky met for a surprising chat on Thursday night when they appeared together on the invite-only conversation app Clubhouse.

The two tech leaders, who didn’t exactly have the most amicable split, joked and reminisced together as guests on “The Good Time Show,” which is hosted by the tech wife and husband team of Aarthi Ramamurthy and Sriram Krishnan.

Because it’s 2021, Ballmer had to be instructed to unmute at one point, even though he wasn’t using a computer.

“One of the great things about Clubhouse, you don’t have to be in front of the computer, you can be on your phone, you can be relaxed,” Ballmer said. “Well, I’ve been in a hot tub during our whole Clubhouse session … and I don’t know if you can hear the water splashing, but I gotta say, it’s a pretty good way to do a discussion.”

Beyond that, Ballmer shared a lot about his time at Microsoft, what he’s learned and what he’s working on as owner of the Los Angeles Clippers NBA franchise, some big-tech insights and more. Here are a few highlights from the conversation, edited for length and clarity:

On becoming a meme

Sinofsky: “One of the things that aside from being [at Micosoft] for a long time that we both have in common is memes, and the idea that stuff we’ve done turns into memes. And so, I still can’t live down this Clippy thing. It’s funny how it was embarrassing and humiliating and then really disappointing. And then all of a sudden it’s kind of cool. And I think what’s happening is a lot of the things that have meme’d for you have happened that way. And so one of the ones I want to ask about, because I know folks want to hear about, is ‘developers, developers, developers.'”

Krishnan: “Steve, you have to say the words.”

Ballmer: “You sound like a guy doing an interrogation. ‘Say the words!'”

Sinofsky: “I was there. Just explain to people these meetings that we had, and what it’s like when you have to lead, you know, 30, 40, 50,000 salespeople or employees, once a year and get them going, and that context gets lost when all you see is the stage.”

Ballmer: “There will always be questions about how you galvanize organizations around mission, that’s a hard thing to do. It’s hard when you’re 20 or 30 people, but at least you can walk into everybody’s office and talk about it. When you get to be about 300 or 400 people you need to have some notion of how to do it and still think you’re going to have the regular weekly pizza event on Friday. But when you get larger, you can write memos, you can do lots of communications. But you’ve got to try to make things simple enough for people to get it in their head. ‘Developers, developers, developers,’ yeah, people got it, we’re only going to exist if we can get application support behind our platform. There was no question the thing that established the PC was the set of work that developers did on top of the platform.

“I actually don’t even remember when I first said this ‘developers, developers, developers’ thing. I probably said it 1,000 times. I thought the first time I said it was actually an event for developers trying to show the developers love. But it’s possible I did it first internally.”

Sinofsky: “It’s so fascinating to try to get people to understand the context of, ‘I love this company.’ That was all very real at the moment. It is just what you have to do for so many people.”

Ballmer: “Whether you’re doing a product launch, whether you’re doing a sales meeting, you have to make sure that you can instill understanding, confidence and excitement in your people. I wasn’t scripted. Sometimes I’d actually be up on stage and some new plot would come into my head, and I blurted out — I don’t think that’s a bad thing. I think that’s an honest and real thing. … That’s part of the role of leadership and part of my techniques. were some of the speeches you can see online now, that as Steven said, out of context they kind of look buffoonish, but they had a value at the time.”

On customers, and the cloud

Sinofsky: “You did this speech in like 2010 or something, [saying] “we’re all in on the cloud.” And customers and industry analysts were like, what? No.”

Ballmer: “You gotta listen to your customers. But you also have to understand enough about what your customers may need that they don’t know about yet. You could blow it — you can give them something they’ll never need. But unless you’re thinking about what are the pain points that they’re expressing — not just how do I patch up a pain point, but how do I fundamentally redo it — you’re not going to get there.”

“I was told by customers for 15 years, at least — ‘Microsoft’s never going to be right for the enterprise.’ Okay, well, now Microsoft seems to be known as an enterprise company. Same thing on the cloud. It was clear that you could reduce complexity, you can help standardize things, you could take out labor costs, you could attack new workloads, if we can get things to the cloud.

“The company did a great job getting out in front of that on Office. With Azure, I wish we probably started two years earlier. And we started actually with Platform as a Service, instead of Infrastructure as a Service. Probably would do that a little bit differently. It cost us a little bit of time in the eventual battle with AWS.”

On big companies

Steve Ballmer at the 2019 GeekWire Summit in Seattle. (Photo by Dan DeLong for GeekWire)

Ramamurthy: In the context of current technology companies, especially the big, super successful ones … how do you think they should think about either developing new products or [keeping] existing customers happy? What tradeoffs do you think you make?

Ballmer: “If you’re a big company, you sort of have to avoid getting caught in that trap. Steven and I [had] many conversations: Do you start a parallel team to essentially do the same thing and in a different way? Do you have a team that’s responsible for building next week’s product? Build a product for three years from now? Those are complicated things. But if you don’t do them, you’re going to stop being a big company. If you view this as a question of ‘or’ instead of ‘and’ then you just have to figure out the best way for ‘and.’ There are companies who have navigated that well. Apple has navigated that well. They continue to push their products forward, and to some degree, I won’t say abandoned their customers because they don’t do that. But you either take big leaps with them or you’re not going to be as happy as they would have you be.

“For big companies, the things that are most likely to trip you up is how you see yourself. If Microsoft had not chosen to see itself as a cloud company, Microsoft wouldn’t exist in the same form that it does today. IBM did not, in the old days, choose to see itself in certain way. Amazon has chosen to see itself as a full service delivery company. It could have viewed itself just as a retailer. But the incredible effort and energy they put into that backend distribution system is amazing. And were they supposed to compete with UPS effectively? Well, no. They said, ‘look, we’re going to continue to see ourselves in in different ways.’

“If you get preconceived notions about what your company does, and those get too deeply embedded in the culture, and they need to change, that’s where you get, I think, into bad trouble. And the great companies don’t get afflicted by that. …You see companies that have been more dynamic and those are the companies that either started with new propositions, like Facebook, that have developed, or companies that have evolved, like Apple, like Amazon, like Microsoft. And that’s where you get three largest market cap companies in the world.”

On NBA lessons

Los Angeles Clippers owner Steve Ballmer (center) at a game inside Staples Center in 2018. (GeekWire Photo / Kevin Lisota)

Ballmer: “The NBA, the business of the NBA probably was actually quite a bit more complicated than I thought it was going to be when I bought the [Los Angeles Clippers]. When you work in the software tech business, you essentially have an inexhaustible supply of your product, particularly software of the old days, but to some extent also, internet services today. And with a basketball team, that’s not what you have. You have an inexhaustible supply of tickets that disappear at the end of each game. And if you didn’t sell one it’s like an airline, you never get any revenue.

“How do you think about that problem? Where’s the money gonna come from? Sponsorship is a whole different set of set of issues. Big licensor of intellectual property — I had no idea how to value TV rights. So the business was more complicated, but the cool thing was, I’ve learned so much owning the Clippers that would have made me a better CEO of Microsoft than I ever could have imagined. And that’s not the business side. that’s the basketball side.

“In business, what’s the one thing they’ll say? We’re accountable, we’re results focused, we’re all about our outcomes. In basketball, every game you won, you lost, it’s completely accountable. It’s gone. You can’t ever recover it. You can’t say I’ll make it back up in sales next quarter. Every 24 seconds, actually, you know if you won or lost. Did you score a basket? Did the other guy score a basket?

“People talk about accountability and transparency in business. Well, I don’t know anything about the Los Angeles Clippers that you can’t know. You can watch our team, you can read all the statistics, you can follow all the video. You can read about matchups, you can watch the players. That kind of transparency and performance and accountability … teamwork gets a lot of talk in business. But [with basketball] you can see teamwork, you can see how people have to come together. There’s no time for random crap, you really have to be together on the floor, and everybody can see it if you’re not. I would say those were good lessons for me.”

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