Habits and Hustle

Episode 531: Leslie John: Oversharing as a Competitive Advantage in Leadership and Negotiation

February 24, 2026

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  • The fear of TMI (Too Much Information) often overshadows the benefits of sharing, but strategic vulnerability, especially positive sharing like genuine compliments, builds stronger relationships and influence. 
  • Long-term relationships erode when partners stop sharing due to an overconfidence bias that they know each other better than they actually do, leading to an 80% error rate in intuiting a partner's feelings. 
  • In professional contexts like leadership and negotiation, strategic sharing (revealing work-related weaknesses or values) enhances trust and leverage, provided it stays below the tipping point where it signals incompetence or panic. 
  • Authenticity and straight-shooting respect others by being honest, even when disagreeing, rather than nodding along to maintain a fake connection. 
  • Having extremely low expectations is a key life hack for happiness, as expecting others to act as you would leads to disappointment and vulnerability when they don't meet those expectations. 
  • Self-efficacy, built through hard work and experience, fosters a strong sense of self that prevents one from feeling threatened by the success or attributes of others, leading to a competitive focus on self-improvement rather than rivalry. 

Segments

Oversharing: Risk vs. Benefit
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(00:02:40)
  • Key Takeaway: Sharing embarrassing stories, despite the risk of a ‘disclosure hangover,’ can lead to closer friendships and stronger mentorships.
  • Summary: The term ‘oversharing’ carries shame, but opening up yields benefits like better relationships and influence. The key danger in early relationships is ’too much too soon’ disclosure without reciprocity, which can signal unavailability. Positive oversharing, such as genuine praise, is a safe way to start building connection.
Positive Oversharing Defined
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(00:05:52)
  • Key Takeaway: Positive oversharing primarily involves vocalizing genuine positive thoughts, such as direct compliments, which disarms others and fosters connection.
  • Summary: Positive oversharing is distinct from emotional dumping; it involves sharing positive observations like complimenting someone’s appearance or expressing liking them. This practice is safe because it is inherently positive and disarming, encouraging others to feel comfortable and reciprocate positive feelings. It is different from revealing deep, private vulnerabilities.
Academic Career Path and Reframing
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(00:08:43)
  • Key Takeaway: The initial frame used to approach a topic, such as viewing social media as negative, profoundly affects subsequent research and interpretation.
  • Summary: Leslie John’s career path involved an initial focus on the dangers of online oversharing before pivoting to its underrated power. Her early research framed social media negatively, leading her to study privacy risks. Reframing this perspective allowed her to see the positive aspects of disclosure, which became the basis for her current work.
Strategic Sharing in Negotiation
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(00:25:24)
  • Key Takeaway: The most common negotiation mistake is concealment, as strategic sharing of values and needs leads to better deals by revealing opportunities for trade-offs.
  • Summary: In negotiation, holding cards close often results in mutual concealment, creating a self-fulfilling prophecy of distrust. Being forthcoming about what one values (and what one values less) allows counterparts to find mutually beneficial trades. Data shows that more forthcoming negotiators often achieve better outcomes because they uncover shared interests.
Company Transparency and Trust
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(00:24:45)
  • Key Takeaway: Companies that strategically overshare by making downsides salient, like credit card fees, build greater customer trust and retention.
  • Summary: Experiments with banks showed that explicitly highlighting negative aspects, such as high fees, increased customer trust in the company. This transparency acts as a powerful tool for customer retention, counterintuitively building loyalty when downsides are openly disclosed. This relates to the broader theme that being known for who you truly are, warts and all, builds strong bonds.
Authenticity, Emotional Intelligence, and Success
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(00:38:27)
  • Key Takeaway: Authenticity is most effective when defined as being genuine and sincere within the appropriate context, heavily relying on high emotional intelligence (EQ) and situational awareness.
  • Summary: Authenticity is generally positive, but it must be tempered by context; simply saying everything on one’s mind can be detrimental if it lacks social intelligence. Success in life, well-being, and relationships is more strongly correlated with high EQ (street smarts) than with high IQ (school smarts). Emotional awareness allows individuals to navigate social situations effectively, unlike purely academic intelligence.
Creating Luck Through Savviness
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(00:44:16)
  • Key Takeaway: While inherent luck exists, individuals can actively create opportunities for success through strategic savviness, observational skills, and practicing in uncomfortable scenarios.
  • Summary: Achieving high-level positions like a Harvard professorship involves both luck and the ability to create one’s own luck through strategic behavior. This includes learning the quirks of influential people (like reading the room) and practicing performance in environments harder than the actual event. Physical discipline, like ballet training, primes individuals with confidence and self-efficacy needed to persist through inevitable failures.
Canadian Niceness and Vulnerability
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(00:51:13)
  • Key Takeaway: Being perceived as overly nice or agreeable, often associated with Canadian stereotypes, can create vulnerability to being taken advantage of if not balanced with self-efficacy.
  • Summary: Confidence derived from experience allows one to be contrary without appearing arrogant. Being honest and straight-shooting is a sign of respect for the listener’s ability to handle the truth. Authenticity in conversation is crucial for real connection, but it must be delivered kindly, as being an ‘asshole’ is not required for honesty.
Comfort with Disagreement
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(00:53:16)
  • Key Takeaway: Being comfortable with not being liked by everyone is a key life hack, as universal approval suggests one is compromising their values or not pushing boundaries.
  • Summary: If everyone likes you, you might be doing something wrong, similar to how always succeeding in negotiation means you are not asking for enough. Growth requires failing sometimes, like not getting stronger if you never fail at push-ups. Disagreement should be treated as being a grown-up, not necessarily conflict, though society often polarizes simple disagreements.
Leading with Generosity
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(00:54:43)
  • Key Takeaway: Leading with a desire to help and give freely, even if reciprocity is low, is a core value that should be maintained, viewing occasional disappointment as the ‘price of admission’.
  • Summary: The speaker leads by giving help and contacts, even if reciprocation is only around 10% of the time. Maintaining this core value allows for meeting extraordinary people and opportunities. Grounding oneself by prioritizing family health helps keep minor disappointments in perspective.
Low Expectations and Authenticity
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(00:58:07)
  • Key Takeaway: Massively lowering expectations is key to happiness, preventing vulnerability that arises from doing things solely to please others.
  • Summary: Doing things to please someone makes one vulnerable because a negative reaction can be crushing. Helping or mentoring should be done because one enjoys the process and likes the person, not for external validation. Unrealistic expectations arise from implicitly assuming everyone acts like oneself, which is often untrue.
Zero-Sum Mentality vs. Collaboration
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(01:01:43)
  • Key Takeaway: The belief that achievement is a zero-sum game where one person’s success comes at another’s expense is a misguided mental model that hinders collective improvement.
  • Summary: The speaker observed a colleague hoarding ideas in teaching meetings, believing sharing would diminish their own evaluation, which is counterproductive. Sharing ideas with smart peers leads to better outcomes and reinforces one’s own understanding. Success begets success, and wanting others to win ultimately helps one win in the long game.
Self-Efficacy and Competition
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(01:05:56)
  • Key Takeaway: Competition should be directed inward—against one’s own past performance—rather than against others, especially when achievements stem from hard work rather than inherent advantage.
  • Summary: Achievements are attributed to hard work and optimization of existing capabilities, not exceptional innate traits. A strong sense of self allows one to appreciate others’ success without feeling threatened. Many women mistakenly view other successful women as competition due to fundamental insecurity, whereas true champions support others’ growth.
Boldness Over Perfectionism
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(01:11:39)
  • Key Takeaway: Bold individuals who make attempts win over the smartest people who suffer from analysis paralysis due to overthinking negative outcomes.
  • Summary: The speaker advocates making ten attempts at what one desires, as this process either yields the goal or presents a new opportunity. Students often persevere on their ‘core’ interests instead of brainstorming diverse ideas, leading to stagnation. Progress, even imperfect progress, is superior to analysis paralysis.
Disarming Naivete in Academia
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(01:14:03)
  • Key Takeaway: Appearing naive or non-threatening, even if it results in short-term loss (like in a Prisoner’s Dilemma), can disarm peers and foster necessary collaboration.
  • Summary: In a first-day grad school exercise, cooperating (playing ‘split’) when others defect (‘steal’) made the speaker look foolish but ultimately made them less of a threat. Being disarming meant classmates were willing to help the ‘dumb girl’ through difficult coursework. Seizing opportunities is beneficial as long as it is not done explicitly at someone else’s expense.
Confidence vs. Competence
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(01:22:00)
  • Key Takeaway: People often confuse high confidence with competence, overlooking genuinely smart but less outwardly assertive individuals.
  • Summary: True humility requires confidence, as it takes assurance to admit what one does not know. Overly confident speakers who deliver ‘word salad’ often enthrall audiences more than quiet, highly competent individuals. Likability is an underrated superpower that matters significantly in leadership, sometimes outweighing pure competence in areas like venture capital funding.