Carrie Olesen Drives Change with Meaning at GitHub

A self-styled “change addict,” Carrie Olesen is helping GitHub become a destination employer for those looking to do things a little differently

Carrie Olesen digitally arrives for her interview with her video turned on. It’s not accidental. “There were behaviors and habits that were baked into GitHub’s culture because it was born as a distributed company working remote,” Olesen explained. “I had to figure some of it out, and I can tell that being on a Zoom meeting with the video means that I can’t multitask, and you have my full attention. We have nine centers in the brain to process visual information and one for auditory, and this will help our brains imprint this as a meeting.”

Carrie Olesen GitHub
Carrie Olesen, GitHubPhoto: Chad Salvador

It’s a small sidebar in a long conversation, but it sends home the amount of thought and care that Olesen brings to her role as chief human resources officer at GitHub, whose workforce is 70 percent remote.

This focus on the small details that gives way to obvious reflection and thought processes is what sets Olesen apart. The CHRO, who also amassed nearly four dozen successful mergers and acquisitions at Microsoft prior to coming to GitHub (one of those successful acquisitions), describes herself as addicted to partnering in effective cultural change.

Driving change in an already successful organization presented some interesting challenges. “How do you take a company like GitHub that would remain a wholly owned subsidiary and separate company but also achieve the value that’s intended from the acquisition?” Olesen posits. “Change is so hard, and I thought this would be an amazing way to test myself and see if I could actually do the job of driving that change instead of just supporting it.”

Green, Blue, and Red

One of the models Olesen used at Microsoft is the perfect encapsulation of how she is able to culturally move companies ahead. “No matter what the change is, you’re going to see people divided into three different buckets: green, blue, and red,” Olesen explains. In short, those who are on board, those who are reticent, and those who don’t want the change.” It seems natural to work to engage those most opposed, but not for Olesen.

“When you engage the red dots, you amplify all the things that may be wrong about the idea, and all of a sudden those blue dots are listening to those arguments,” Olesen says. “It increases your resistance, and so the trick as a leader is to engage those green dots and to just put those blinders on for a short period of time.”

It’s not blind leadership; it’s allowing the positive momentum to bring those who may have been unsure along. “There’s only 66 percent that are ever going to agree with what I’m doing at any given time,” Olesen says with a laugh. “That’s all I need.”

The additional challenge in coming to GitHub, Olesen says, is also what makes the company so special. “This is an online platform that was born to support open source software development,” Olesen says. “The spirit of open source is to create something and put it out for anyone to use. That core is very much part of how this company operates.”

That means a workforce much more given to independent thinking, which can add further challenges when one factors in the 70 percent remote workforce. “Initially, I thought it was an HR nightmare,” Olesen says, laughing again. “I couldn’t imagine not being able to drive change without being in the room.”

Baking Through Quarantine

Working from home wasn’t something new for Carrie Olesen, but not being able to engage in her regular outdoor activities during the COVID-19 quarantine certainly was. The CHRO responded by engaging in an all-out culinary assault. Olesen is a pie baker extraordinaire. “Whatever fruit is fresh at the time, that’s what I’ll use,” Olesen says. Her strawberry rhubarb is her scene stealer, but she has yet to meet a blueberry or peach that also hasn’t found its way into a dessert.

As often happens, necessity became its own drive for ingenuity. Every meeting at company headquarters includes a display wall gallery view of those who are calling in. Meetings are recorded automatically and sent out to those who were not in attendance. But it’s more than that. “The rule is you start everybody on Zoom so there is equality,” Olesen explains. “You don’t have five people in a conference room with everyone else on Zoom, because that’s when you get the ‘us versus them’ dynamic and some voices may not feel heard.”

Retain and Recruit with Purpose, Not Foosball

Just eighteen months into her tenure, retaining and recruiting top talent has been a major focus point, and she’s noticed a change. “There was an era where it was about being hip and cool and kind of collecting company logos on your résumé,” Olesen says. “I think we’ve come out on the other side of that and it feels like people are being much more driven by purpose and social responsibility. How is your company contributing to the greater good?

“GitHub kind of has that anarchist mentality where it’s not necessarily about IP ownership; it’s about making things that are free and accessible for everyone,” she continues. It’s a major selling point for talent, both current and future. “We’re making it easier and easier and easier for people to have the advantages of technology everywhere in the world and a utopian belief in the outcome of technology being positive for the world, particularly if it’s community created.”

There’s another important consideration for future talent at GitHub, Olesen says.

“There are people that move from company to company every two or three years and hope to eventually have someone bringing them coffee and those little Silicon Valley niceties, and that’s OK. Facebook has it. Google has it. But please don’t come to my start-up,” she says. “I want you to roll up your sleeve and contribute. There’s probably some food here too, but you’re going to have to find it.”

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