Nick Caldwell on the engineering cultures that power Microsoft, Reddit, Looker & Twitter

Today’s episode is with Nick Caldwell, VP of Engineering at Twitter. Previously, Nick was at Microsoft for 15 years, eventually becoming GM of Power BI. Nick has also held roles as Reddit’s VP of Engineering and Looker’s Chief Product and Engineering Officer.   Between Microsoft, Reddit, Looker, and now Twitter, Nick’s worked for companies with vastly different cultures. And in today’s conversations, we comb through the biggest lessons from each of these orgs.    With Microsoft, we unpack what Nick believes is a massively underrated approach to organizational design. He explains the company’s rigorously approach to regular pruning and shaping the org chart. He also gives us an inside look at their management training and talent development, as well as what Nick calls the fairest performance review system he’s seen.   As Nick tells it, there was a steep learning curve when he pivoted from 15 years at Microsoft to Reddit. He doles out advice for other folks getting their bearings after a big career move. He also explains how Reddit’s mission-driven culture informs his approach to leadership at Twitter.    Finally, with Looker, Nick unpacks his biggest lessons from leading both the product and engineering teams, which offered him a unique perspective on how these two orgs that are often at odds can properly team up.   It’s an incredibly wide-reaching conversation, so there’s something for pretty much everyone. Whether you’re interested in the cultural practices that power some of the world’s biggest companies, or you’re a manager looking to level up, or you’re an engineer with goals to take on leadership, Nick’s got plenty of advice and insider stories to share.    You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson