Move beyond surface-level discovery questions. Asking 'What do you value most in a partner?' forces prospects to articulate their core needs for a relationship (e.g., responsiveness, consultation). Their answer quickly reveals if there is a fundamental values alignment, a better predictor of success than technical fit.

Transactional questions get transactional answers. A "story-worthy" question, like "Tell me about the moment you first sensed trouble with your supplier?", prompts a narrative. This approach extracts the emotion, context, and deeper story behind an issue, leading to more authentic connection and insight.

In a complex field like ad tech, curiosity is as critical as experience. Interviewers should assess this by seeing if candidates drive the conversation with insightful questions. A lack of curiosity is a major red flag, suggesting they won't thrive in a dynamic environment.

Ditch standard FANG interview questions. Instead, ask candidates to describe a messy but valuable project they shipped. The best candidates will tell an authentic, automatic story with personal anecdotes. Their fluency and detail reveal true experience, whereas hesitation or generic answers expose a lack of depth.

The chaotic, underdog nature of a startup is a binary filter. Frame this reality honestly during interviews. The right candidate will be energized by the challenge, while the wrong fit will be stressed. This question quickly reveals cultural suitability.

The first step to humanizing a brand is not internal brainstorming, but conducting deep-dive interviews with recent customers. The goal is to understand precisely what problem they were solving and why they chose your solution over others, grounding your brand messaging in real-world validation.

Early-stage founders often make the mistake of grilling candidates in the first interview. Instead, the entire first hour should be dedicated to selling the company, the vision, and the opportunity. You can't evaluate someone who isn't excited to join your mission yet.

Instead of generic interview questions, ask what truly motivates a candidate and what they'd do for a hobby if money weren't an issue. The way they describe these passions reveals their energy, personality, and core drivers far more effectively than rehearsed answers about work experience.

When interviewing, ask founders about their perspective on long-term brand investments versus short-term pipeline goals. Their answer reveals if they understand marketing's true value beyond being a sales support function, indicating the strategic role you'll be allowed to play.