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When Reddit VP Nick Caldwell groused to his mentor at Microsoft, he learned a lesson that altered his career

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About two years ago, Nick Caldwell was poached from his long-time career at Microsoft to become the new VP of engineering at Reddit.

It was a pivotal moment for Caldwell. He had started as an intern at Microsoft in 2001, working his way up to general manager of one of the company’s most promising new products in the reign of CEO Satya Nadella: Power BI. Power BI is a cloud-based data analysis tool that takes information stored in spreadsheets, Office documents and hundreds of other sources and turns it into charts and graphs.

Caldwell had led the 150-person engineering team that worked on Power BI before and was later promoted to the GM of the unit, responsible for the whole shebang, he told Business Insider. The product was launched in mid-2015 and a year later had 5 million users and was (and still is) a source of pride for Nadella, who talks about it regularly.

It put Caldwell into the league where he was sought after by other companies, eventually taking on the role of VP of engineering position at Reddit, managing that team of about 200 people and growing.

Nick Caldwell
Nick Caldwell

But none of it would have happened if he hadn’t had a moment of frustration when it seemed like his career at Microsoft was stuck and going nowhere.

Caldwell had been working on a machine learning/AI project at Microsoft back in the years when ML/AI wasn’t cool, but was considered a dusty, academic technology, not for the commercial world. Microsoft has a massive R&D operation and has been developing ML/AI tech for decades.

Caldwell had been one of those genius kids: taught himself to code as a kid, landed an internship at NASA when he was 13 (writing software for satellites), earning his undergraduate degree from MIT.

He never imagined his career could languish. But, “the group I was in was struggling,” Caldwell told us. “It was one of what I call my ‘leadership moments.’ I was complaining to one of my mentors, Ravi Shahani, about a lack of product vision, that we didn’t have a roadmap, even though the team was full of smart engineers in machine learning.”

And Shahani told him, “All you are doing is complaining. What are you going to do about it?”

That advice caused Caldwell to shift his thinking. “I switched from going along with whatever came my way, to being an active participant on what happens next,” he said.

Caldwell booked a meeting with the general manager of his unit and told him he “wasn’t satisfied with the direction of the team.” The boss “believed in me and gave me 10 engineers to work for 3 months,” Caldwell says. They came up with a product idea, and a roadmap for it.

In an instant, he went from an engineer to a boss of his own team on a project that lasted two years.

The product was called Huddle, a team collaboration tool that used software bots, which he describes “like an early version of Slack,” Caldwell said. Microsoft never shipped it as a product but did use parts of it in its other products.

And internally, Caldwell grew a reputation as a skilled engineer, good at creating products out of unproven technologies.

Working with Bill Gates

Soon after, Bill Gates had an idea for a project called InfoNavigator that let regular business people ask databases questions using regular language, no coding required. Gates asked around for the top people capable of developing this tool and Caldwell’s name came up.

The team started with two people, Caldwell and another engineer, grew to 30 people and shipped its first version in eight months. This team would eventually be folded into the Power BI project.

As part of this project, Caldwell had to meet with Gates every couple of months and present a progress report. These meetings were “really intimidating,” Caldwell recalls. Gates wasn’t just the richest person on earth, “he was basically my childhood hero.”

He and his team spent hours preparing for those meetings. It wasn’t just Gates in the room. He was briefing Satya Nadella, who would become CEO but was at that time running server and tools division and later Microsoft’s cloud projects. The heads of other divisions were there, too.

Bill Gates (left) and Microsoft CEO Satya Nadella
Microsoft

“I got to present, 15 minutes,” Caldwell recalls. “The things I remember is … it was terrifying. Bill Gates was asking me questions.” But then he realized that this was a great position to be in, that he was the person who knew more about this machine learning stuff, and this project, than Gates, or the others did.

And he took stock of how Gates handled those meetings.

“Bill doesn’t talk a lot. He listens a lot. He says one or two words, and nods, and even the slightest indication of his happiness or not, the other execs were watching him, writing it down,” Caldwell said.

The lesson Caldwell took from that: leaders don’t need to be the expert. They need to listen, learn and gently guide, rather than impose and dictate.

Plans for Reddit

In his two years at Reddit, he’s hit the ground running, organizing a redesign, a reorganization, adding a bunch of technology to the site and hiring like mad. He’ll add 80 more people to his 150 person team this year, he said.

And, he’s got plans to add machine learning tech that helps users create more personalized experiences on Reddit, too, he says.

And all of it because he stopped complaining about things, and leaned in.

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