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From Layoff to OpenAI: Clarifying Questions, Improv, Better Interviews
SPOTLIGHT EPISODE: What happens when a senior engineer stops “faking it” and starts treating interviewers like partners? Eamonn sits down with James—now at OpenAI, with prior stops at Pinterest, Reddit, and Discord—to unpack how he managed imposter syndrome, learned to ask clarifying questions early, and used improv to become a clearer, more confident communicator on the job.
Along the way, we pause to analyze James’s mock coding interview on interviewing.io, tracing the exact habits that set him apart: writing while thinking, checking in for buy-in, and iterating toward better solutions under pressure. If you’re preparing for coding interviews, you’ll see how James navigates anagrams with letter-count tuples, weighs time/space tradeoffs, and engages with hints without losing the thread.
Watch James's Full Mock Here: https://start.interviewing.io/interview/Gw58xSkxBKqu/replayWatch Another of James's Full Mocks Here: https://www.youtube.com/watch?v=eHF6YxfOXy4
Watch replays & transcripts: https://start.interviewing.io/showcase
Book a mock interview: https://interviewing.io
Timestamps
00:00 Cold open — why “faking it” fails in interviews
01:00 James’s background and path to OpenAI
04:00 How improv rebuilt confidence and communication skills
07:00 Layoffs at Discord and finding upside in a reset
10:00 Structured prep: LeetCode, mocks, and recruiter advice
13:00 Why peer mocks matter more than grinding alone
16:00 Mock interview replay: the anagram challenge
24:00 Working through space vs. time tradeoffs under pressure
33:00 Staying unstuck: writing, asking, and engaging hints
58:57 Feedback clip: top-tier insight, senior-level signal
Disclaimer: All interviews are shared with explicit permission from the interviewer and the interviewee, and all interviews are anonymous. interviewing.io has the sole right to distribute this content.
View all episodes
By interviewing.ioSPOTLIGHT EPISODE: What happens when a senior engineer stops “faking it” and starts treating interviewers like partners? Eamonn sits down with James—now at OpenAI, with prior stops at Pinterest, Reddit, and Discord—to unpack how he managed imposter syndrome, learned to ask clarifying questions early, and used improv to become a clearer, more confident communicator on the job.
Along the way, we pause to analyze James’s mock coding interview on interviewing.io, tracing the exact habits that set him apart: writing while thinking, checking in for buy-in, and iterating toward better solutions under pressure. If you’re preparing for coding interviews, you’ll see how James navigates anagrams with letter-count tuples, weighs time/space tradeoffs, and engages with hints without losing the thread.
Watch James's Full Mock Here: https://start.interviewing.io/interview/Gw58xSkxBKqu/replayWatch Another of James's Full Mocks Here: https://www.youtube.com/watch?v=eHF6YxfOXy4
Watch replays & transcripts: https://start.interviewing.io/showcase
Book a mock interview: https://interviewing.io
Timestamps
00:00 Cold open — why “faking it” fails in interviews
01:00 James’s background and path to OpenAI
04:00 How improv rebuilt confidence and communication skills
07:00 Layoffs at Discord and finding upside in a reset
10:00 Structured prep: LeetCode, mocks, and recruiter advice
13:00 Why peer mocks matter more than grinding alone
16:00 Mock interview replay: the anagram challenge
24:00 Working through space vs. time tradeoffs under pressure
33:00 Staying unstuck: writing, asking, and engaging hints
58:57 Feedback clip: top-tier insight, senior-level signal
Disclaimer: All interviews are shared with explicit permission from the interviewer and the interviewee, and all interviews are anonymous. interviewing.io has the sole right to distribute this content.