E08: Flipping the script: Evaluating your boss as they evaluate you | Prashant Singh

Episode 8 of the My Best Hire podcast, hosted by Rajeev Soni, titled "E08: Flipping the script: Evaluating your boss as they evaluate you | Prashant Singh" was published on April 22, 2025 and runs 37 minutes.

April 22, 2025 ·37m · My Best Hire

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Summary

In this thought-provoking episode of "My Best Hire," host Rajeev Soni flips the script with product veteran Prashant Singh. Instead of discussing someone he hired, Prashant reveals how he "hired his boss" – a refreshing perspective on career advancement that puts leadership selection at the center of professional growth. Currently heading product at fintech startup Jar, Prashant shares his unconventional strategies for evaluating potential leaders, from morning walks to pointed questions about decision-making frameworks. With insights from 15+ years building products that have reached over 50 million users, he reveals why 60% of his initial impressions proved wrong and the critical difference between leaders who delegate from trust versus those who delegate from overwhelm. Whether you're building teams or advancing your career, this episode offers a masterclass in choosing the right leadership environment for sustainable success.Key MomentsThe Walking Interview (13:45): Prashant's unconventional strategy of requesting a morning walk with potential bosses to assess their leadership style outside formal settings.The 60% Revelation (20:41): The surprising admission that 60% of Prashant's initial assessments of colleagues proved wrong after working together.The Competency vs. Capacity Question (15:34): Prashant's direct question to potential employers about whether they view product management as a competency or capacity role.The Customer Insight Gap (35:09): Identification of the three roles closest to customers whose feedback rarely reaches product teams.Must-Listen Quotes"People join companies and leave managers." (10:12)"Whether the ability to delegate or trust is a person's inherent nature or it's a side effect of organizational growth... If you're on a rocket ship, a lot of projects will be delegated to you and you will be king. But the moment you hit choppy weather, everything will be folded back." (29:19)"Do you see product as a competency decision or a capacity decision? If it is competency, you are more tolerant. If it is capacity, you think 'my time is more important, so that's why I'm hiring you.'" (15:34)"I believe there are three people in organizations who are very close to customers and they are never listened to: customer support, sales people, and researchers who go out and talk to people." (35:09)Key TakeawaysEvaluate the Boss, Not Just the Role: Look beyond compensation and company prestige to assess the leadership style of your potential manager.Test Decision-Making Frameworks: Ask specific questions about how decisions are made to understand company culture and leadership approach.Identify Delegation Motives: Determine if leaders delegate out of trust or necessity, as this reveals how your autonomy might change when growth slows.Recognize First Impressions Are Often Wrong: Be aware that interview behavior may not accurately reflect day-to-day working relationships.Build Empathy Through Multiple Perspectives: Regularly engage with customer-facing teams to develop true product empathy.Make Yourself Redundant: True leadership involves creating frameworks that empower your team to make decisions without you.Hard Work Complements Smart Work: Even for the most talented individuals, success requires putting in the hours.Chapters00:00 - Introduction to Prashant Singh02:55 - Prashant's Product Leadership Journey06:58 - The Best Hire Philosophy: Hiring Your Boss08:17 - The Job Hunt Decision Framework13:45 - The Walking Interview Strategy16:35 - Product Management: Competency vs. Capacity20:00 - Evaluating Company Culture During Interviews22:14 - First Impressions vs. Reality24:40 - The Path to Jar26:11 - Remote Work Challenges28:06 - Understanding True Delegation30:33 - Leadership Values That Matter32:33 - Making Yourself Redundant35:44 - The Customer Feedback Loop

Episode Description

Key Moments

The Walking Interview (13:45): Prashant's unconventional strategy of requesting a morning walk with potential bosses to assess their leadership style outside formal settings.
The 60% Revelation (20:41): The surprising admission that 60% of Prashant's initial assessments of colleagues proved wrong after working together.
The Competency vs. Capacity Question (15:34): Prashant's direct question to potential employers about whether they view product management as a competency or capacity role.
The Customer Insight Gap (35:09): Identification of the three roles closest to customers whose feedback rarely reaches product teams.

Must-Listen Quotes

"People join companies and leave managers." (10:12)
"Whether the ability to delegate or trust is a person's inherent nature or it's a side effect of organizational growth... If you're on a rocket ship, a lot of projects will be delegated to you and you will be king. But the moment you hit choppy weather, everything will be folded back." (29:19)
"Do you see product as a competency decision or a capacity decision? If it is competency, you are more tolerant. If it is capacity, you think 'my time is more important, so that's why I'm hiring you.'" (15:34)
"I believe there are three people in organizations who are very close to customers and they are never listened to: customer support, sales people, and researchers who go out and talk to people." (35:09)

Key Takeaways

Evaluate the Boss, Not Just the Role: Look beyond compensation and company prestige to assess the leadership style of your potential manager.
Test Decision-Making Frameworks: Ask specific questions about how decisions are made to understand company culture and leadership approach.
Identify Delegation Motives: Determine if leaders delegate out of trust or necessity, as this reveals how your autonomy might change when growth slows.
Recognize First Impressions Are Often Wrong: Be aware that interview behavior may not accurately reflect day-to-day working relationships.
Build Empathy Through Multiple Perspectives: Regularly engage with customer-facing teams to develop true product empathy.
Make Yourself Redundant: True leadership involves creating frameworks that empower your team to make decisions without you.
Hard Work Complements Smart Work: Even for the most talented individuals, success requires putting in the hours.

Chapters00:00 - Introduction to Prashant Singh02:55 - Prashant's Product Leadership Journey06:58 - The Best Hire Philosophy: Hiring Your Boss08:17 - The Job Hunt Decision Framework13:45 - The Walking Interview Strategy16:35 - Product Management: Competency vs. Capacity20:00 - Evaluating Company Culture During Interviews22:14 - First Impressions vs. Reality24:40 - The Path to Jar26:11 - Remote Work Challenges28:06 - Understanding True Delegation30:33 - Leadership Values That Matter32:33 - Making Yourself Redundant35:44 - The Customer Feedback Loop