Did a Wayfair onsite for a Senior SWE role in March 2026, coming back after a two-year career gap. I was nervous the behavioral rounds would be brutal given the gap. Sharing what happened.
How many behavioral rounds? Two. One with the hiring manager, one with a cross-functional partner (in my case a PM on the team). Each was 45 minutes.
Questions that actually came up:
With the hiring manager: Tell me about a time you disagreed with a technical direction and how you handled it Describe a project that didn't go as planned. What was your role in the failure? How do you approach working with ambiguous requirements? Give a specific example.
With the PM: Tell me about a time you had to explain a complex technical constraint to a non-technical stakeholder Give an example of when you pushed back on a product requirement and the outcome How do you prioritize when you have two equally urgent problems?
Wayfair's values angle. The recruiter mentioned that Wayfair cares about "customer obsession, collaboration, and bias for action" (classic corporate triad, I know). In practice, the behavioral questions seemed to specifically probe for: do you take ownership of failure, and do you communicate across functions.
The career gap question. The hiring manager did ask about it. Directly but not adversarially. I gave a straightforward answer (caregiving situation) and explained what I'd done to stay current: a couple of online courses, some open-source contributions. They moved on quickly. It was not a dealbreaker moment.
What worked in my prep. Writing out 6-8 STAR stories before the loop, specifically ones that covered failure, disagreement, and cross-functional work. The questions aren't that unpredictable if you think about what a senior IC needs to demonstrate. I also made sure at least two of my stories had messy outcomes where I owned the mess, because the "what went wrong" questions are real.
Tone in the room. Pretty conversational. Not gotcha, not pressure-test. The hiring manager was clearly looking for self-awareness more than perfect outcomes.