Why It’s Worth It | Remember The Giving Tree? That childhood classic about generosity? Here’s what’s fascinating: when we reread it as adults, it’s actually disturbing. The tree gives everything until she’s literally a stump, and we’re told “the tree was happy.” Really? She barely exists. The boy isn’t happy either, constantly returning for more, never satisfied. It’s not an allegory for maternal love; it’s a cautionary tale about toxic people-pleasing. 

In this episode of WorkLife, Adam Grant explores why we struggle to say no and how mastering this skill can transform our work and relationships. Adam starts out speaking with playwright Topher Payne, who rewrites broken children’s books. Topher’s take on The Giving Tree reveals the core problem: the tree confuses giving with self-sacrifice, becoming “the most extreme people-pleaser you could possibly imagine.” This resonates with Adam’s own journey. After being featured as “the generosity guy” in the New York Times, he got flooded with thousands of requests. He realized he’d been saying yes not because he cared about helping, but because he craved approval. Research shows chronic people-pleasing isn’t about others; it’s about needing their validation.

Cornell professor Vanessa Bohns then joins the conversation to explain why saying no feels so hard. When someone makes a request, they’re extending their hand for cooperation. Refusing feels like rejecting that outstretched hand, violating everything evolution and society taught us about working together. Her research shows we wildly underestimate how often people say yes: New Yorkers agreed to walk strangers to destinations or lend phones nearly half the time, twice what people predicted. We’re especially vulnerable to the “acquaintance trap”: with close friends, relationships are secure; with strangers, there’s no relationship to protect; but with acquaintances, we fear damaging uncertain connections.

The pressure intensifies for certain groups. Sherry Liu, founder of the Eldest Daughter Club, embodies multiple pressures: female, eldest child, immigrant family. As an Asian woman in corporate America, colleagues expected her to handle secretarial work nobody wanted. Her breakthrough came when her manager delivered tough love: “All your projects, you’re helping other people. You need something you own.” The manager helped Sherry see that being overly selfless wouldn’t advance her career. Everyone would like her, but liking doesn’t lead to job satisfaction or promotions.

Research confirms these gendered dynamics. Women do most office housework (taking notes, planning events) but get less credit. When men help, it’s rewarded as unexpected generosity. Versus when women decline to help, they are viewed as not meeting expectations. For women of color, these pressures compound. But saying no strategically can work. Sherry started explaining her priorities to her manager, who then helped deflect inappropriate requests. She learned most requests aren’t life-or-death; people often just say “okay, I’ll ask someone else.”

Adam shares three strategies that consistently work. First, explain your personal policies. Instead of treating each request separately, create guidelines: “I don’t give career advice to strangers” or “I don’t write book forewords.” This shows you’re not rejecting them personally. Second, convey care while declining. Say “my plate is beyond full,” then offer something costless but helpful, like a list of resources. Third, make referrals. We fear looking incompetent or damaging relationships, but research shows people aren’t as disappointed by referrals as we imagine.

The responsibility isn’t just on those saying no. When making requests, we should ask non-coercively: “Would you or someone you know be willing to…?” Give people the words to refuse: “No pressure, no obligation, no repercussions.” Allow time to process rather than demanding immediate answers. Face-to-face requests generate 34 times more yeses than emails, so consider the medium carefully.

Background | In this episode, Adam Grant hosts Vanessa Bohns, professor of organizational behavior at Cornell and the author of You Have More Influence Than You Think and stories from recovering people-pleasers Topher Payne and Sherry Liu, who’ve learned that setting boundaries isn’t selfish but essential. Key insights include:

• Giving versus giving in: People-pleasing isn’t generosity; it’s approval-seeking. We say yes because we need validation, not because we care about helping. True giving requires boundaries to sustain itself.
• The acquaintance trap hits hardest: We struggle most with mid-distance relationships where connections feel uncertain. Close friends understand refusals; strangers expect nothing; acquaintances trigger our deepest fears of rejection.
• Create personal policies: Instead of agonizing over each request, establish guidelines. “I don’t work for companies for free” removes decision fatigue and depersonalizes refusals.
• Women face double binds: Expected to say yes but penalized for it. Office “housework” is mandatory yet unrecognized. Saying no violates gender norms but paradoxically may be necessary for career advancement.
• Convey care while declining: Trying to offer ideas for other resources or solutions shows concern without overcommitting. Teaching boundaries helps others learn appropriate requests.
• Make requests less coercive: Offer exit ramps (“or someone you know”), give processing time, use email over face-to-face. Each yes reinforces that such requests are acceptable.
• Boundaries create respect: Like cats who are selective with affection, clear boundaries can increase rather than decrease how much others value our eventual yeses. Scarcity creates appreciation.

Source | WorkLife: How to Say No (April 29, 2025)

About | Adam Grant is a well-known organizational psychologist and wildly popular Wharton professor. He is an accomplished writer, a profound thinker, and a thorough researcher, covering various subjects to help people discover purpose and motivation and lead more creative and generous lives. Adam’s content includes New York Times bestsellers, TED podcasts and talks, columns in various publications and GRANTED, a free email newsletter (sign up on his website!). Adam encourages us to constantly question our ideas and rethink our beliefs.