Helmsley Charitable Trust Interview Questions
& Process

The interview process was very long, aiming to include everyone in the org, but it ended up being repetitive and messy. It felt like it hurt both the candidate and the org over time because it was clear there wasn't a solid agreement on goals, and the role's actual needs weren't based on a realistic view of what the org might need. This was also seen in how they talked to candidates. Even though it was slow, they didn't give any feedback even in the second-to-last round (after 6 months), which was rude to the candidate's time and the team's, but it also showed a lack of internal direction. The hiring manager even said they didn't remember the first meeting during the in-person because it had been so long ago. It's a bummer because the org does good work but it really holds itself back from making a real impact publicly.

The process was really long and messy, taking more than four months. It started with an HR screening, then a Zoom call with the hiring manager, followed by another meeting with two team members. After that, I had a third interview with four colleagues from different parts of the organization. The last step was an in-person interview with the whole team. The interviews felt like they were asking the same things over and over. It was weird because I had to meet the hiring manager again, months later, and it seemed like they totally forgot we'd already talked.

I got an email a week after applying for a phone interview. The first interview was a phone screen with an HR associate. The second interview was a Zoom video call with 2 Program Officers and 2 members of the HR team. There were more people to meet with after the second, but I didn't make it past this stage.

So, this place calls their interview process "the gauntlet" - which, like, says a lot. It was a whole bunch of interviews. First HR, then a Zoom with the General Counsel, then I met with the hiring manager two times, and also had meetings with two different sets of coworkers. The whole thing clocked in at about 6 hours. And after all that, they hit me with a "no longer moving forward." The weirdest part is they asked me the exact same questions in every single chat, so I felt like I was just saying the same things over and over. They also made it seem like things were going well, which was a bummer.