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Наталя ХандусенкоWork
4 September 2025, 13:51
2025-09-04
“I created a dialogue, not an interrogation, I hit a real pain point.” Senior Technical Product Manager shares how he got an offer thanks to one interview question
One interview question earned Senior Technical Product Manager Andriy Osypenko an offer in 10 seconds. He explained what needed to be done to make it work.
One interview question earned Senior Technical Product Manager Andriy Osypenko an offer in 10 seconds. He explained what needed to be done to make it work.
"I'm sitting in the final interview. Everything is going well, but I feel something is wrong. The hiring manager answers questions formally, clearly thinking about something of his own. And then it's my time to ask questions," Andriy wrote on LinkedIn.
So the Product Manager said the following: "Listen, I used to work in a similar domain. We had a problem with [specific technical problem]. I wonder how you handle it? Because we tried x and y, but it worked so-so."
According to Andriy, this immediately caught the person's attention: "For the next 15 minutes, she pours out all her pain on me. She tells me in detail how they tried to fix it, what didn't work, where they got stuck. At this point, I already know - the offer is mine."
Why it worked
The Product Manager believes this worked for three reasons:
he showed depth of expertise. "To ask a question like that, you have to really understand the specifics of the business. It's not 'tell me about your processes';
hit a real pain point. “Before the interview, I studied their product for 30 minutes, read the tech blog, and looked for similar cases in the industry;
created a dialogue, not an interrogation. "Shared how we solved this problem (even if I embellished the details a bit)."
Andriy also explained what not to do : “I read your article about the company culture, it’s very interesting!” It feels like flattery. The hiring manager can hear it a mile away.”
What to do before the interview
The specialist advises finding out additional information about the manager, namely:
find a manager on LinkedIn in advance;
see his background, projects;
understand what problems he/she has right now;
Prepare 2-3 questions that will demonstrate your expertise.
Question formulas
Andriy also shared his favorite question formulas:
"I see you're migrating to [technology]. How are you solving the problem with backward compatibility?";
“[Specific problem] is usually painful in your domain. I’m interested in your approach”;
"When working with [similar product], we encountered [problem]. Do you have this too?"
The Product Manager emphasized that it is important to understand that an interview is a professional dialogue with a potential colleague.
"If after your question a person starts sharing the team's pain, congratulations, you're practically on the team."
Andriy advises spending time on research, rather than searching Google for the most common interview questions.
"The best questions don't come from Googling 'top 10 interview questions', but from a real understanding of the company's business and technical challenges. Invest time in research — it will pay off," concludes the Product Manager.
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