Generic discovery questions like "what's your pain point?" yield generic answers. A better question is, "If you hired someone to sit next to you, what would you have them do?" This reveals the tedious, unglamorous tasks that are ripe for an automation-focused product solution.

After probing a candidate's past, 'flip the table' and present them with a current, real-world problem your company faces. This reveals their curiosity, analytical skills, and ability to engage with a new challenge on the spot, shifting from their prepared stories to raw problem-solving.

Product managers excel at understanding users through empathy. However, they often abandon these core skills when communicating with executives. To be more effective, treat your executive as a key user whose needs, motivations, and context you must first understand.

During customer discovery, don't just ask about current problems. Frame the question as, 'If you had a magic wand, what would the perfect solution be?' This helps users articulate their ultimate desired outcome, revealing profound insights beyond tactical feature requests.

Asking a candidate when they first encountered the brand can reveal whether they are a true customer and believe in the mission. This question invites a conversation that helps suss out their level of preparation, empathy for the customer, and genuine interest beyond just seeking a job.

Product teams excel at using tools like empathy maps to understand customer feelings and behaviors. However, they often fail to apply this same rigorous curiosity to their internal peers and stakeholders. Using these tools internally can build stronger relationships, improve communication, and foster better collaboration.

To assess critical thinking, send C-level candidates your board deck under NDA before the interview. Use the conversation to gauge their feedback. A candidate who only offers praise is a red flag; the best candidates will challenge your thinking and provide constructive criticism.

Standard questions like 'What's your biggest pain point?' often yield poor results. Reframing the question to what work a customer would offload to a new hire bypasses their pride or inability to articulate problems, revealing the tedious, high-value tasks ripe for automation.

Instead of focusing on tactical issues, ask potential customers what they would wish for if they had a magic wand. This prompts them to describe their ideal, transformative solution, revealing the deeper, more valuable problem you should be solving.