In tech’s heyday, you might’ve been asked in an interview why manhole covers are round or how many golf balls could fit in a school bus.

But now, big tech companies are trading in brain teasers for something far worse: labor-intensive interview processes that seem to never end.

Circuitous interviewing — oftentimes with a lot of waiting around, ghosting, and unpaid work — is something many have experienced.

We’re not just impatient, though. The time to hire has actually gotten longer, increasing across all industries to a 44-day average in 2023, up a full day from 2022.

And even interviews for technical jobs — often the highest paid positions aside from the C-suite — are getting grueling, per Wired.

• In 2023, ~263k workers were laid off from ~1.2k tech companies — with ~15k of those estimated to be engineers. In 2024, more than 42k tech employees have already been let go.
• On job site Interviewing.io, job seekers shell out $225+ for mock interviews with tech hiring managers. Scoring a “thumbs up” on a technical interview rose in difficulty by 22% since 2022, according to site data.

Plus, on anonymous apps like Reddit and Blind — popular with engineers — vent sessions have illuminated the growing trend of seemingly impossible tech interviews.

Falling from grace

Interviews for technical jobs are more than just an awkward Zoom call: candidates report extreme exercises like coding apps from scratch or crafting in-depth project evaluations — all on tight deadlines (and without compensation).

The experience is a far cry from the ping pong tables and kegs of yore, signaling the ways the industry is changing as companies recalibrate post-pandemic.

There’s also a new whiz kid to compete with: artificial intelligence. Generative AI is not only changing what positions companies are hiring for, but also how applicants apply and interview for jobs.

Like, um, this time a candidate used ChatGPT to generate a live script during a video interview for an engineering job.

Long before Microsoft’s investment in OpenAI or its AI chatbot Copilot, it offered a much cuter collection of digital assistants.

We’re talking about Bob, a short-lived and much-hated user interface with a surprisingly long-lasting impact.

What about Bob?

Bob launched in 1995 for a variety of Windows products, including Windows 95.

Instead of the standard Windows desktop, Bob offered a cartoon house where users could click on a letter to access an email client or a notebook to open a word processor.

Several cartoon assistants offered tips and personalization options including Rover, a cartoon dog, and William Shakespeare.

The idea…

… was that a familiar interface would be user-friendly and fun to use, but most people hated it.

Melinda French Gates — then Bill Gates’ fiancee and a Microsoft manager — helmed the project, and noted that it “needed a more powerful computer than most people had back then and a lot of critics found the visuals too cute.”

The New York Times lambasted it as clunky, inconsistent, irritating, and looking as though it’d been designed by “an esthetically challenged sixth-grader.”

Bob was discontinued in 1996.

But elements of Bob lived on

The software fueled Clippit, AKA Clippy, the cartoon paper clip that offered tips to Microsoft Word users, and Rover later appeared as a Windows XP search assistant.

Microsoft designer Vincent Connare also created Comic Sans to replace the more formal Times New Roman in Rover’s speech bubbles, but because it wasn’t ready at Bob’s launch, it appeared in a later font pack and in a movie maker program.

In many ways, Bob was ahead of its time. VR applications now frequently use pleasant home environments as interfaces, including Meta Quest and Apple’s Vision Pro, and AI-powered chatbot assistants are everywhere. They’re just a little more sophisticated.

Fun fact: Microsoft traded the domain name Bob.com to Bob Kerstein, who owned the domain Windows2000.com, in 1999.