The Manager's Playbook

“Can you give me a bit of your background?”

A common opening question to establish the guest's origin story before diving into their main career.

“How did you get your start in [a specific role, e.g., tour managing]?”

Used to transition the conversation to the guest's early career beginnings.

“What do you think it was that made [a mentor or boss] take a liking to you?”

This question seeks to uncover the personal qualities or actions that led to a key career breakthrough.

“How challenging was it being in a high-level role like co-president?”

Asks guests to reflect on the specific pressures and realities of a senior executive position.

“What made [a specific company] different from other places you've worked?”

This question explores the unique culture and operational model of notable companies in the industry.

“What was it like working under an industry leader like [e.g., Big Jon Platt]?”

Focuses on the lessons learned from working with legendary figures in music.

“How do you handle it when an artist loves a song you know isn't good?”

A situational question to understand how executives navigate difficult creative conversations with talent.

“How did you balance your executive duties with hands-on project work?”

Probes into the time management and focus of guests who held multiple high-stakes roles simultaneously.

“What were the initial goals and how did you structure the plan to hit them?”

Asks for specific details on business strategy and execution during a company's formation or a project's launch.

“What are your thoughts on artists constantly releasing music versus banking quality songs?”

This question addresses a key contemporary debate about release strategy in the streaming era.

“When is 'bad marketing' just an excuse for a song that isn't good enough?”

A pointed question designed to differentiate between a song's quality and its promotional support.

“How did you know a specific song was going to be a hit?”

This question delves into the A&R instincts and decision-making process of successful executives.