Persistence, grit, and experimentation

We’ve been conditioned to believe that saying less is safer. But playing it safe costs trust, influence, stronger negotiations, and deeper relationships because the line between “too much” and meaningful connection is further out than we think.

In the latest episode of Habits & Hustle, I’m joined by author Leslie John to break down the exact tipping point where leader vulnerability backfires, why holding your cards close in negotiation weakens your leverage, and how pushing slightly past your comfort zone builds real authority.

Leslie John is the James E. Burke Professor of Business Administration at Harvard Business School and author of Revealing: The Underrated Power of Oversharing. Her award-winning research appears in top academic journals and media including The New York Times, The Wall Street Journal, and The Economist.

What’s Discussed

• (04:00) Why oversharing feels risky but builds stronger relationships and influence

• (06:31) The difference between emotional dumping and strategic vulnerability

• (18:23) Disclosure flexibility and knowing when to reveal versus hold back

• (20:55) Why long term relationships erode when partners stop sharing

• (27:15) How strategic transparency increases trust and customer retention

• (28:50) The most common negotiation mistake: leading with concealment

• (34:03) Leader vulnerability and the tipping point where credibility drops

• (41:01) Authenticity versus impulse and why emotional intelligence matters

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Find more from Jen: 

Website: https://jennifercohen.com

Instagram: @therealjencohen

Books: https://jennifercohen.com/books

Speaking: https://jennifercohen.com/speaking-engagement

Find more from Leslie John:

Website: https://lesliekjohn.com

Instagram: @proflesliejohn

Youtube: @ProfLeslieJohn

X: @ProfLeslieJohn