To get past a founder's polished pitch, ask about their core motivations (like ambition) multiple times throughout the diligence process, using different phrasing. This repeated, layered approach can reveal inconsistencies and expose their genuine life goals versus what they think investors want to hear.

Sales candidates easily handle generic 'how would you' questions. To get a true assessment, persistently ask for specifics: 'Tell me about a specific situation when...' If they give a general answer, repeat the question. This forces them beyond rehearsed responses to reveal actual experience.

When asked about their sales process, weak candidates brainstorm a long list of activities. Strong candidates have a concise checklist for the key "moments of truth" in a deal, like discovery or proposal calls. The brevity and clarity of their answer signal true process discipline.

To understand a candidate's true drivers, ask them to walk through every major career decision they've made, from college choice to job changes. This narrative reveals patterns and motivations—such as status-chasing, financial incentives, or problem-solving focus—far more effectively than direct questions.

Top salespeople know their numbers precisely. When interviewing, demand specific dollar amounts for their quota and actual performance. Resistance, vagueness, or answers like "100-plus percent" are strong signals they are either hiding underperformance or lack discipline.

To genuinely test for mission alignment, avoid asking direct questions like "Why do you care about our mission?". Instead, listen for two signals: the candidate bringing up the mission unprompted, and them sharing a personal story about the problem you solve. This reveals authentic motivation, not a rehearsed answer.

To understand a candidate's perspective and definition of excellence, ask what criteria they would use to hire someone for the same position. This meta-question reveals their priorities, uncovers nuanced aspects of the role you may have missed, and improves your own hiring criteria.

Don't ask if a candidate *can* do the job; ask them to envision a scenario in 90 days where they have failed to meet expectations. This forces them to honestly assess if they *want* the daily realities of the role, leading to better self-selection and preventing costly mis-hires.

To assess an SDR candidate's strategic thinking, challenge them to narrow a large TAM (e.g., 40,000 companies) down to 25 weekly targets by verbally applying filters. Pushing them past their initial ideas until they get stuck reveals their resourcefulness and problem-solving abilities under pressure.