When interviewing salespeople, the biggest red flag is blame. Strong candidates demonstrate humility and self-reflection by taking ownership of lost deals and analyzing their own shortcomings. Weaker candidates deflect, blaming the product, competition, or other external factors, signaling a lack of coachability.

To hire for traits over background, Mark Kosaglo suggests testing for coachability directly. Run a skill-based roleplay (e.g., discovery), provide specific feedback, and then run the exact same roleplay again. The key is to see if the candidate can actually implement the coaching, not just if they are open to receiving it.

Investors should view a founder's desire to learn skills like etiquette not as a weakness, but as a strong positive signal. It demonstrates humility, introspection, and a drive for self-improvement—key traits for a coachable and successful leader. The capacity for growth can be more valuable than pre-existing polish, identifying them as better long-term partners.

To build a culture of continuous improvement, prioritize hiring for coachability. Individuals with backgrounds in competitive athletics or music are often ideal because they have been heavily coached their whole lives. They view direct feedback not as criticism, but as an essential tool for getting better.

To gauge an expert's (human or AI) true depth, go beyond recall-based questions. Pose a complex problem with multiple constraints, like a skeptical audience, high anxiety, and a tight deadline. A genuine expert will synthesize concepts and address all layers of the problem, whereas a novice will give generic advice.

To simulate interview coaching, feed your written answers to case study questions into an LLM. Prompt it to score you on a specific rubric (structured thinking, user focus, etc.), identify exact weak phrases, explain why, and suggest a better approach for structured, actionable feedback.

For leadership roles, the interview itself is a critical test. If the candidate isn't teaching you something new about their function, it's a red flag. A true leader should bring expertise that elevates your understanding. If you have to teach them, they will consume your time rather than create leverage.

For high-level leadership roles, skip hypothetical case studies. Instead, present candidates with your company's actual, current problems. The worst-case scenario is free, high-quality consulting. The best case is finding someone who can not only devise a solution but also implement it, making the interview process far more valuable.

Ineffective interviews try to catch candidates failing. A better approach models a collaborative rally: see how they handle challenging questions and if they can return the ball effectively. The goal is to simulate real-world problem-solving, not just grill them under pressure.