Week 24 Day 1: Every Great Leader Has Questions Only They Ask

Standard interview questions produce standard answers. Every candidate has rehearsed 'Tell me about yourself,' 'What is your greatest weakness,' and 'Where do you see yourself in five years.' These questions are so predictable that entire industries exist to help candidates prepare scripted responses. The leaders who consistently hire well have moved beyond the standard set. They have developed questions that are uniquely theirs -- questions they have refined through years of interviewing, calibrated against the outcomes of their hires, and sharpened to reveal the specific traits they value most.

Here is how I developed my signature question, and what it taught me about interview craft. Early in my career, I asked textbook questions and got textbook answers. I could not distinguish between candidates who were genuinely thoughtful and candidates who were well-prepared. Then I started experimenting. I would invent a new question, use it for ten interviews, and track which candidates it differentiated. Most invented questions failed -- they produced interesting conversation but did not predict job performance. After years of this iteration, I landed on a question that became my signature: 'What is the most important thing you have learned in your career that you could not have learned from a book or a class?' This question works because it requires genuine reflection. There is no rehearsed answer because no interview prep guide includes it. It reveals multiple things simultaneously: intellectual curiosity (do they learn from experience or just accumulate experience?), self-awareness (can they identify what they did not know?), and communication skill (can they articulate a complex insight concisely?). The best answers I have heard include: 'That being right is not the same as being effective' -- from an engineer who learned that technical correctness does not matter if you cannot bring others along. 'That the person who asks for help gets further than the person who refuses it' -- from a designer who overcame a chronic independence problem. 'That urgency is not importance, and confusing them will ruin your career' -- from a project manager who burned out once before learning to distinguish the two. Every one of these hires turned out to be excellent.

The signature question methodology reflects the iterative refinement process that Ericsson, Krampe, and Tesch-Romer (1993) define as 'deliberate practice' -- the systematic improvement of performance through structured feedback loops. Applying deliberate practice to interview question design means treating each interview as data and each hiring outcome as feedback, gradually calibrating questions against validated outcomes. Research by Cortina, Goldstein, Payne, Davison, and Gilliland (2000) found that the validity of individual interview questions varies enormously -- from near-zero to 0.60 -- and that the most valid questions are those that have been empirically refined against performance criteria, supporting the iterative development approach. The 'could not have learned from a book' question targets what Polanyi (1966) calls 'tacit knowledge' -- knowledge that is acquired through experience and cannot be fully articulated or transmitted through formal instruction. Research by Wagner and Sternberg (1985) demonstrated that tacit knowledge is a stronger predictor of managerial effectiveness than IQ, personality, or formal education, with validity coefficients of 0.30-0.40 for predicting management performance. The multi-dimensional reveal -- curiosity, self-awareness, and communication -- exemplifies what Campion, Campion, and Hudson (1994) call 'construct breadth' in interview design, where a single question measures multiple job-relevant constructs simultaneously, increasing efficiency without sacrificing validity.