According to Business Insider, Ayumi Nakajima, a senior director at Pinterest heading Asia-Pacific content partnerships, has a defining interview strategy honed over hundreds of candidate meetings. Having started at Nielsen before a leadership role at Meta in 2013 and joining Pinterest in 2015, she now leads a team of about 20. Her critical interview question is: “What are some failures you have experienced?” She specifically watches for candidates who own their mistakes, saying “This was when I messed up,” instead of spinning a failure into a hidden success story. Nakajima values this adaptability and growth mindset over specific experience, arguing the tech landscape changes too fast. She also advises hirers not to rush, thinking of a hire as a four-to-five year commitment, even if it means delaying an offer by a month.
The Failure Test
Here’s the thing: everyone preps for the “greatest weakness” question. But Nakajima is digging for something more raw. She’s not looking for a rehearsed tale of being “too much of a perfectionist.” She wants the real, unvarnished “I screwed this up” moment. And that’s brutally hard to fake in an interview. When someone can genuinely dissect a failure, take real ownership, and articulate what they learned, it signals a level of self-awareness and psychological safety that’s pure gold for a team. It tells you they can handle feedback without getting defensive. In a fast-paced environment, that’s the difference between a project that stalls with blame and one that pivots and adapts quickly.
Skills vs. Mindset
Her point about valuing versatility over a checked box is so relevant right now. Tech stacks and project scopes evolve constantly. Hiring someone who’s a perfect fit for today’s specific task is a short-term win. But what about in six months? You need people who can learn, not just people who already know. This is basically a bet on curiosity and intellectual agility over a static resume. It’s a reminder that we should be interviewing for trajectory, not just for a snapshot. Can this person grow with the role, or will they be obsolete when the first big shift happens?
The Rush-To-Hire Trap
Now, her advice to slow down is the counterintuitive part we all ignore. A one-month delay feels like an eternity when you have a burning need on your team. But she’s right. Thinking in four-to-five year terms completely reframes the cost of that delay. A bad hire is monumentally more expensive and disruptive than waiting a few more weeks to find the right person. How many times have we seen a team rush to fill a seat for a project, only to be stuck with a mismatch for years? Her willingness to change her mind on a near-offer, even if it annoys the recruiting team, shows a disciplined long-game focus. That’s hard, but it’s probably what separates good managers from great builders of teams.
Beyond the Interview Room
This philosophy isn’t just for hiring, though. It’s a cultural blueprint. If a leader prioritizes this growth mindset in interviews, it likely means they foster that same environment for their existing team. It signals that it’s okay to take calculated risks and sometimes fail, as long as you learn. That’s the kind of culture that retains top talent. So maybe the real lesson isn’t just “ask about failure.” It’s to build a company where giving an honest answer to that question doesn’t feel dangerous. Because let’s be honest, in a lot of places, it still does.
