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    Startups & Entrepreneurship

    Why This Startup CEO Interviews Candidates on Sundays

    adminBy adminApril 22, 2026No Comments4 Mins Read
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    Why This Startup CEO Interviews Candidates on Sundays
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    Key Takeaways

    • Work trials are short-term recruitment assessments where candidates perform real job tasks.
    • Crosby, a legal services startup, started offering multi-hour work trials on Sundays and found that candidates were relieved rather than annoyed.
    • Candidates were grateful that they didn’t have to use up precious vacation days at their current jobs to stay in the running for a role.

    Ryan Daniels expected pushback when he started asking job seekers to interview on Sundays. What the founder and CEO of legal services startup Crosby got instead were sighs of relief. 

    Crosby, a startup that offers basic legal services to other startups, is one of many employers that are leaning into “work trials,” or short-term recruitment assessments where a candidate performs real job tasks, Business Insider recently reported. 

    Daniels sought to interview candidates thoroughly, but didn’t want to disrupt their schedules with mid-week, on-site auditions. He realized that these interviews were forcing candidates to choose between their current jobs and a shot at Crosby. His solution was simple: offer Sunday as an interview and trial day. 

    He found that many people responded to a Sunday interview with “huge relief” rather than annoyance. A Sunday visit meant that they could participate in a demanding, multi-hour work trial without sacrificing paid time off or tipping off their current employer. 

    How the Sunday trials work

    Daniels told Business Insider that the company uses Sunday sessions to simulate real work, not just to ask theoretical questions. For software engineer positions, for example, Crosby may drop a candidate into a live project so the team can assess their coding and AI skills in practice. 

    For business roles, candidates come in on Sundays for panel interviews with Crosby’s executive team. Executives have more uninterrupted time on Sunday to probe how candidates think, communicate and solve problems, Daniels explained. 

    The trial does not end with the formal interview block. Candidates also join the team for lunch or dinner, which gives hiring managers and prospective colleagues a chance to observe how employees interact when they are off-script. Daniels said that this social window can be crucial in convincing top candidates, those with multiple offers, that Crosby is the place they want to be. 

    “If people vibe with the team, we never lose them,” he told Business Insider. “If they don’t, it’s a good lesson for all of us.”

    Other companies with work trials

    Work trials can vary in intensity. At the remote-first startup Linear, a work trial consists of co-working with existing employees on the real codebase, creating something the company will use. 

    “It’s challenging to assess in interviews if someone is truly a builder, has good taste and judgment, can take initiative, and approaches problems productively,” Linear CEO Karri Saarinen told Lenny’s Podcast in 2023. “The goal with the work trial is to simulate a normal working environment as much as possible.”

    Linear pays candidates across two to five days to complete a real project, with access to internal tools and resources. 

    Sahil Lavingia, CEO of e-commerce platform Gumroad, takes things one step further by hiring candidates as contractors for four to six weeks. In general, the candidates work on small bug fixes and other simple tasks. 

    “It’s so very hard a priori to know if someone can do the job,” Lavingia told Lenny’s Podcast in 2024. “So we just pay them to do it!”

    Key Takeaways

    • Work trials are short-term recruitment assessments where candidates perform real job tasks.
    • Crosby, a legal services startup, started offering multi-hour work trials on Sundays and found that candidates were relieved rather than annoyed.
    • Candidates were grateful that they didn’t have to use up precious vacation days at their current jobs to stay in the running for a role.

    Ryan Daniels expected pushback when he started asking job seekers to interview on Sundays. What the founder and CEO of legal services startup Crosby got instead were sighs of relief. 

    Crosby, a startup that offers basic legal services to other startups, is one of many employers that are leaning into “work trials,” or short-term recruitment assessments where a candidate performs real job tasks, Business Insider recently reported. 

    Daniels sought to interview candidates thoroughly, but didn’t want to disrupt their schedules with mid-week, on-site auditions. He realized that these interviews were forcing candidates to choose between their current jobs and a shot at Crosby. His solution was simple: offer Sunday as an interview and trial day. 

    candidates CEO interviews Startup Sundays
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