Airbnb CEO Brian Chesky's assistant shares the main reason why his schedule is so difficult to manage and how she broke into Big Tech

• In an episode of the podcast "Reach," host Jessica Vann interviewed Jordan Sugar-Carlsgaard.
• Sugar-Carlsgaard is the senior executive assistant to the cofounder and CEO of Airbnb.

Brian Chesky founded Airbnb with Nathan Blecharczyk and Joe Gebbia in 2008. Since then, the company has grown to a valuation of more than $76 billion and become one of the top-200 most valuable companies in the world. It's also attracted criticism for affecting housing affordability and for its intense lobbying efforts to stave off regulation.

Jordan Sugar-Carlsgaard worked in Washington, DC, as the director of scheduling for the office of Rep. Steny Hoyer, the House Democratic whip and then the House majority leader, from 2017 to 2019. She was headhunted to join Airbnb as the senior-executive assistant to Chesky, the CEO, in 2019, and she describes the company as "captivating."

Sugar-Carlsgaard spoke to Jessica Vann, the CEO of Maven Recruiting Group and the host of the podcast "Reach," on an episode about the challenges of transitioning from politics to the tech giant and how she manages Chesky's schedule.

At first, she felt intimidated

"Starting anything new, it's always intimidating," Sugar-Carlsgaard told Vann.

One challenge she faced was not knowing anyone in the company, much less "who the heavy hitters were." After a couple of months, she said she had to take a step back and remind herself that she was in a transition.

"I thought I would come in, bring all my scheduling wisdom from DC, and just change Brian's life," she said.

Sugar-Carlsgaard admitted that it took one year to feel comfortable in the role. One way she dealt with the pressure was being more patient with herself and more humble.

How she got up to speed

Getting up to speed in the demanding role required asking everyone a lot of questions and doing research. She said asking vulnerable questions is also "a great way to create bonds with your teammates."

Before Sugar-Carlsgaard started, Chesky's team was beginning to transition into having "a lot of eyes" on them as Airbnb grew bigger. With big plans for the next 12 months, the team didn't have a consistent method of collaborating with other teams within the company.

"One of the things we wanted to try to work on was fostering these relationships with our internal-communications teams, external-communications teams, the executive team, and all of the different companies within Airbnb," she said.

Consistency, transparency, and trust were critical

When asked to name the keys to offering good support, Sugar-Carlsgaard said it comes down to communication, transparency, and consistency. But, she said, "not consistency in the sense of every day needs to look the same, because that's completely unrealistic."

To her, consistency means establishing how you want to work together. Transparency is establishing trust and authenticity so that your principal is comfortable letting you into their life to handle confidential matters and to problem solve together.

When an executive assistant is on the front lines supporting their boss, they need to represent them appropriately. This should create "a good, honest image of who this person is, and how they would want to be received," Sugar-Carlsgaard said.

On especially hard days, whether she's talking to a VIP or to a new intern, she returns to a philosophy of "be nice, be honest, and be helpful" to represent Chesky as he wants to be known and seen.

Keeping the CEO's schedule organized

Sugar-Carlsgaard described Chesky as "very much a creative."

"His approach to how he uses his time and how he communicates with his company and his team is very different than what I had been used to on the political side," she said.

Staff in the company were already used to asking for his time when she started, and it was Sugar-Carlsgaard's role to establish a standard of what his priorities would look like.

"The last year and a half has been a really eye-opening experience for me and Brian to work together to figure out how we use his time best, because he does really want to be available to everyone," she said.

At the same time, Chesky's approach also "makes it really hard to keep things moving on track and on time, to set some boundaries, and to have some consistency in how he communicates and what he does every day."

This is an ongoing challenge for the pair, with Sugar-Carlsgaard noting that they don't have a set way of handling specific situations, and they address things on case-by-case basis to "dissect" his priorities and focus.

It's the way Airbnb functions, she said. "Everyone has Brian's email; he talks to the company every week. He really wants to be visible and open."

Working out rhythms

A key part of her role became trying to align on protocol and expectations for meetings with Chesky. She also became a point person for "fleshing out details about how Brian likes to work best on certain things," she said.

Giving herself a break and not being afraid to seek guidance helped her handle difficult days.

She told Vann that she learned it was OK to tell Chesky: "I don't know, but let me find that answer for you." He realized, she said, that "I'm human, and I'm not always going to have everything out there ready, but I will come back to you, and we can figure it out."

Sugar-Carlsgaard added that Chesky is approachable, which is important for building a relationship with a CEO. Sometimes this means having a quick get-together, where she asks him questions about what he thinks, what he needs, or what's the plan, she said.

Advice for others

Sugar-Carlsgaard's advice for starting in a new industry is simply: "Take the risk." Even if it doesn't work out, it can be an "enlightening experiment" that helps you work out what you want.

Breaking into Big Tech was about "trusting myself and being able to sell myself and my experiences," she said. Activating a network of mentors that she respects and relies on has made a big difference.

When it gets really hard, she suggests stepping back and reevaluating by asking yourself questions like: "How should I do this?" and "Why are they not receptive to me wanting to do it this way?"

"Risk-taking, trusting yourself, and having a network — I think these can really create a path professionally that helps you identify what your strengths are and where you want to go," she said.