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Ratna | @jobwhisperer

The question that almost cost me the interview


I was recently halfway through my interview rounds and got this curveball question that threw me off...

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"What's something your boss might say about you that you disagree with?"

This is tricky for two reasons.

1️⃣ It's like the cousin of "What's your greatest weakness?"

2️⃣ .... but it's putting you in an awkward spot to politely say "yeah, they've said this, but I don't think it's true" without sounding defensive.

What they're really asking...

Not just “are you self-aware” but... can you take a perceived flaw, disagree respectfully, and flip it into a positive story that reassures us you’d be a strong hire?

🧠 Yes, this question is annoying. Another variation is “If I asked your manager what it’s like to work with you, what would they say?” For this one, you want to anchor to positive traits, but layer in something that shows you’re self-aware.

Do two things...

1️⃣ Share the misconception directly (don’t dodge), but don't pick something that could raise red flags like, "my boss thinks I struggle with time management."

2️⃣ Flip the narrative with a story that shows why it’s actually a strength for the role.

Script 1: For the "overly opinionated change agents"

“I haven’t necessarily gotten this feedback directly, but one misconception that comes to mind is that I can be too much of a ‘change agent.’ The reality is I know transformation can be uncomfortable, so I’m intentional about phasing it in and respecting existing systems, even if they aren’t perfect. For example, I revamped our forecasting process by introducing new steps gradually over two quarters, which took us from last place to first in forecast accuracy. At the end of the day, I see myself as a change agent, but an effective one only when the environment is ready for change — and I make it a point to bring people along so they feel ownership rather than resistance.”

Script 2: For the people who "struggle to delegate"

“I've gotten feedback that I need to delegate more. I see it differently - I’ve worked on under-resourced teams where rolling up my sleeves was the fastest way to get things done. Over time, especially as I’ve grown into people management roles, I’ve learned to balance that with delegation. I am conscious of pairing being hands-on with empowering my team, and I make sure I understand the work well enough to set them up for success. I generally don’t just assign work without fully understanding what it takes to complete it.”

What's an interview question that recently stumped you, or you're struggling to answer well? Reply and tell me! I read every email.
P.S. Not sure how your interview answers are landing? I offer 1-hour sessions to help you get clear, confident, and out of your own head.

The lesson here

This is a hard question to answer on the spot if you haven't already given it some thought.

It's really testing for your ability to reframe something without getting defensive.

How would you answer this questions?

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Ratna | @jobwhisperer

Get weekly-ish tips on interviews, resumes, networking, salary negotiation, and how to break through the noise in a crowded market. I’ve worked in product, GTM, strategy and ops roles at Google, Microsoft, and Salesforce, hired and developed high-performing teams, coached 100s of job seekers (without insider connections) into roles that changed their lives. The problem is that most career advice is outdated and comes from folks who’ve never hired, survived an 11-round interview loop, or worked in the roles you’re applying to. I write the advice I needed, but couldn’t find. 👉🏾 Not another boring newsletter. 2,000+ job seekers are already reading, so join our community. Subscribe now.

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