Cool product, great mission, typically exasperating on-site interview. I didn’t have a hellacious experience like some others on Glassdoor. Sure, the recruiters were a bit flaky, but they didn’t string me along for months or anything like that. The main problem was that the interviewers didn’t seem to know how to interview a writer. The one that did know how was a product manager. He asked tough but fair questions about my previous tech writing experience and how I interact with those outside my team (PMs like him, engineers, etc). Then we looked at one of my writing samples from a previous job and I explained my thought process to him, paragraph by paragraph. It felt natural, and useful. Two of the interviewers were engineers. One readily admitted he didn’t know how to interview a tech writer, so we just got to know each other. We mused about different working styles, the company’s mission, and about how maddening the writing and editing process can be. The other engineer was similarly relaxed. Two very friendly, sharp guys—no ego. I wanted to work with them. That leaves the two bad cops. Both interviewed me as if I had applied to a software engineering role. First was the architecture interview. Straightaway the interviewer ordered me up to the whiteboard to start writing/diagramming... something about docs. Anything. He didn’t say what, really. He might as well have said, “Design me a system.” First I pushed back on the whiteboarding thing, but he *really* wanted me to be a whiteboard person. I said the questions were vague. “That is deliberate,” he grinned. God. We spitballed some general ideas about how to write docs, how to think about different reader archetypes, etc. Any time I said something he liked, he’d say “Write that down,” like he was teaching me the wonders of the whiteboard. Then there was the coding interview. It was with the hiring manager, a nice guy whom I had already had spoken with for the phone screen. He cut to the chase: “I don’t like to just fire questions at candidates. I like to use the interview time to see what it’s actually like working with them.” Sounded good in theory. In practice, it was as contrived as the whiteboard interview. He wheeled around shoulder-to-shoulder with me and brought up some existing docs for me to rewrite. He told me to take my time reading through them (they weren’t short), and as I started, he awkwardly turned away, still by my side. I couldn’t bear to read in silence for minutes on end, so I started to think out loud, pointing out bad writing and bad design as I noticed it. When I lingered over one paragraph, he told me to rewrite it. Again he awkwardly stared out the window. I did my best in the short time, but I was flustered. Only a non-writer could expect a writer to write well on command and under supervision—and have it come out sparkling in short order. All the non-engineer interviewers were really hung up on the reader archetypes thing. When one mentioned something about “Enterprise Erin” or “Developer Dan,” alarm bells went off in my head. I’d heard that somewhere before, and moments later, I remembered where: in tech journalist Dan Lyons’s book “Disrupted,” a sardonic tell-all about his time employed at the cultish and groupthink-prone marketing startup HubSpot. Then I remembered that one of my interviewers had come from HubSpot. And a few days later, one of Cloudflare’s founders shared some cheesy platitude on LinkedIn from HubSpot’s CTO, who (according to Lyons) used to bring a teddy bear into meetings as a surrogate for the customer. In some companies, tech writers fall under the Engineering org. I wish that had been the case with this role; the engineers at Cloudflare seemed like a really great bunch. But the Product org spooked me out. I knew I wasn’t going to get an offer. I followed up with the recruiter a day or two later, and he got back to me the following Monday, asking me for a 15-minute window for a phone call. (Honestly, 5 minutes is enough for a thumbs down.) I invited him to call me any day, any time. No need to schedule it. But like the calendar-obsessed HubSpotters in “Disrupted,” he scheduled it anyway—for Thursday. What nonsense. I politely requested a simple Yes/No by email, and a day later he emailed me the rejection.

The process was speedy and clearly laid out. First I had to submit samples of my work and from there my first interview was with the person who would be my first manager. After that I had an on-site, then a couple of chats with a very engaged recruiter. The final step (after an informal offer) was a call with the CEO.