To close the gap, Phillips gave him a mantra that Caldwell now passes along to other folks making the manager-to-director transition. I was having trouble scaling all of the things that are great about being an EM,” says Caldwell. I did all the things that you would from someone with a much smaller team - I got to know everyone individually, and worked hard to motivate and inspire people on a one-to-one basis. I carried that through to my role as a director, even though I had like 30 people reporting to me. “Up until this point in my career, I loved line-level engineering management. “ James Phillips was my GM at the time, and he taught me a lot about the difference between being a manager and a director,” says Caldwell. His next move? “I immediately left his office and went to the product’s GM to say, ‘Hey, we need to change this in the product strategy - give me a chance to prove it to you,” he says.Īnother leadership lesson came a few years later when Caldwell had climbed from IC engineer to engineering manager, and eventually engineering director. So are you going to sit in my office complaining about this, or are you going to do something to change it?’ And that was an incredibly important turning point in my career - it was the moment I decided I was going to do more than just be a grunt engineer,” he says. “He said, ‘ Leaders take responsibility for what happens next. But Shahani imparted a critical piece of advice.
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“He said, ‘Nick, you’re an amazing engineer, but you’re just a shitty leader.’ I was like, ‘Ouch!’” says Caldwell. What came next was a (somewhat painful) wake-up call.
![is sitting on clouds safe reddit is sitting on clouds safe reddit](https://d279m997dpfwgl.cloudfront.net/wp/2019/06/5905rahhh1j21.jpg)
“I was like, ‘These guys don’t know what they’re doing, they’re making me build all this stuff and none of it’s going to work.’ I was just going off on him.” I was complaining to my manager at the time, Ravi Shahani, about how crappy the PM team was,” recalls Caldwell. “When I was very early in my career, I was a brash, headstrong engineer. LESSON #1: TAKE RESPONSIBILITY FOR WHAT HAPPENS NEXT & GET OFF THE FLOOR.Ĭaldwell points to two of his former managers at Microsoft for some of his earliest and most pivotal leadership lessons. Caldwell is a practiced speaker and writer, and he’s got a knack for distilling complicated topics or thorny impasses into crystal-clear lessons. It’s an incredibly wide-reaching set of frameworks and although Caldwell’s bread and butter is engineering leadership, there’s plenty to sink your teeth into for managers all over the org chart. Caldwell also dives into his functional expertise, with his vision for how product and engineering can team up instead of tussle and the system he leaned on for architecting Looker’s engineering roadmap. He gets vulnerable about one of the harshest (yet warranted) pieces of feedback he ever received, and how a home run at Microsoft prompted him to leave the company and try his hand at startups. He makes the case that Microsoft’s operational practices should get more of Silicon Valley’s spotlight - including the company’s approach to org design and its improved performance management system. In our exclusive interview with Caldwell, he pulls on threads from each stop in his career journey at companies with different cultures, scales and functions and he opens up about the biggest leadership lessons that stick with him.
Is sitting on clouds safe reddit software#
Part of the joy I’ve had over the course of my career is learning that there are a lot of different ways to ship software and get things done. “Each place I’ve worked has radically different cultures, which I didn’t appreciate at the time because it’s difficult to understand the culture while you’re in it,” he says. But what perhaps most sticks out about his career journey is that Caldwell has found success at companies with vastly different cultures, from Microsoft’s buttoned-up enterprise to Reddit’s fast pace.
![is sitting on clouds safe reddit is sitting on clouds safe reddit](https://image.shutterstock.com/image-photo/young-smiling-guy-sitting-on-260nw-259465358.jpg)
It’s a remarkable rise with stops at some of the most interesting and innovative companies around. This brings us to his latest role - as the VP of Engineering for Twitter, spearheading an org that’s 700 engineers strong. He then joined Looker as a product and engineering exec, steering the teams through the company’s $2.6 billion acquisition by Google. It was only after accumulating this deep bedrock of experience that he took on his first startup role at Reddit, where he led the engineering team through hypergrowth, scaling from 35 engineers to 150. His tenure at the company culminated as a founding member and eventual GM for Power BI, one of the company’s biggest success stories. But less typical these days is the 15-year stint he put in at Microsoft beforehand. Dig into Nick Caldwell’s resume, and you’ll see leadership posts at an enviable list of startup staples - Reddit, Looker, and now Twitter.