Empathy in Leadership

Kim Scott is the author of Radical Candor, currently the #1 most recommended book on this podcast. The book has sold over 1 million copies and has been translated into 23 languages. Before writing, Kim was a CEO coach at Dropbox, Qualtrics, Twitter, and other tech companies. She was also a member of the faculty at Apple University and before that led AdSense, YouTube, and DoubleClick teams at Google. This spring she’ll be launching Radical Respect, which she considers to be a prequel to Radical Candor. In today’s conversation, we go deep on Kim’s popular framework, including:

• What separates radical candor and obnoxious aggression

• Tactical advice on delivering constructive feedback

• How well-meaning empathy can become ruinous

• Strategies for effectively soliciting and responding to feedback

• The importance of having regular career conversations

• The false dichotomy of a good leader versus a kind person

• A sneak peek into Radical Respect

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Find the full transcript at: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice

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Where to find Kim Scott:

• X: https://twitter.com/kimballscott

• LinkedIn: https://www.linkedin.com/in/kimm4/

• Website: https://www.radicalcandor.com/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Kim’s background

(03:13) A brief overview of Radical Candor

(06:46) How people fail with ruinous empathy, manipulative insincerity, and obnoxious aggression

(08:37) The impact of radical candor on Kim’s life

(14:16) How to communicate feedback effectively

(20:34) A story illustrating the problem with ruinous empathy and manipulative insincerity

(27:50) How to get over the need to be liked

(31:31) How to have career conversations with your direct reports

(29:40) Reflections on how Kim handled an underperforming employee

(33:31) Best practices for soliciting feedback as a leader

(35:53) How to respond to feedback

(39:22) How often to ask for feedback

(41:48) Whether or not to accept “no feedback” as an answer

(50:48) Investing time in feedback

(54:04) How to ask for feedback as an employee

(57:42) Why obnoxious aggression is not the best way to deliver feedback

(1:01:23) A notable example of problematic management 

(1:03:43) Why context matters when diagnosing obnoxious aggression 

(1:07:39) Empathy is a good thing, but empathy can paralyze

(1:10:47) Reflections on the limitations of radical candor in a society riddled with biases 

(1:14:41) Kim’s new book, Radical Respect

(1:15:51) Tactical advice to get better at radical candor

(1:16:46) Lightning round

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Referenced:

• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509

• Radical Respect: How to Work Together Better: https://www.amazon.com/Radical-Respect-Work-Together-Better/dp/1250623766/

• The Office (American version) on Peacock: https://www.peacocktv.com/stream-tv/the-office

• Radical Candor diagram: https://www.radicalcandor.com/our-approach/

• Career conversation templates: https://review.firstround.com/the-power-of-performance-reviews-use-this-system-to-become-a-better-manager/

• A behavioral scientist explains why we should reacquaint ourselves with the telephone: https://news.uchicago.edu/story/nicholas-epley-explains-why-phone-calls-can-connect-us-better-zoom

• How to get promoted: https://www.lennysnewsletter.com/p/how-to-get-promoted

• When They Win, You Win: Being a Great Manager Is Simpler Than You Think: https://www.amazon.com/When-They-Win-You-Manager/dp/1250279666

• Peter Kazanjy on X: https://twitter.com/Kazanjy

• Christa Quarles on LinkedIn: https://www.linkedin.com/in/christaquarles/

• Jason Rosoff on LinkedIn: https://www.linkedin.com/in/jason-r-rosoff/

• Andrew Grove: https://en.wikipedia.org/wiki/Andrew_Grove

• Columbo on Prime Video: https://www.amazon.com/Columbo-Season-1/dp/B008SA89HA

• Squid Game on Netflix: https://www.netflix.com/title/81040344

• Leveraging mentors to uplevel your career | Jules Walter (YouTube, Slack): https://www.lennyspodcast.com/leveraging-mentors-to-uplevel-your-career-jules-walter-youtube-slack/

• Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://www.amazon.com/Poor-Charlies-Almanack-Essential-Charles/dp/1953953239

• Bridgewater: https://www.bridgewater.com/

• The Fund: Ray Dalio, Bridgewater Associates, and the Unraveling of a Wall Street Legend: https://www.amazon.com/Fund-Bridgewater-Associates-Unraveling-Street/dp/1250276934/

• Tim Cook on X: https://twitter.com/tim_cook

• Elon Musk: https://www.amazon.com/Elon-Musk-Walter-Isaacson/dp/1982181281

• Building high-performing teams | Melissa Tan (Webflow, Dropbox, Canva): https://www.lennyspodcast.com/building-high-performing-teams-melissa-tan-webflow-dropbox-canva/

• Middlemarch: https://www.amazon.com/Middlemarch-Penguin-Classics-George-Eliot/dp/0141439548

• The Bluest Eye: https://www.amazon.com/Bluest-Eye-Vintage-International/dp/0307278441

• Song of Solomon: https://www.amazon.com/Song-Solomon-Toni-Morrison/dp/140003342X

• Orlando: https://www.amazon.com/Orlando-Biography-Virginia-Woolf/dp/015670160X

• The Color Purple: https://www.amazon.com/Color-Purple-Novel-Alice-Walker/dp/0143135694

• The Deptford Trilogy: Fifth Business; The Manticore; World of Wonders: https://www.amazon.com/Deptford-Trilogy-Business-Manticore-Wonders/dp/0140147551

• Grey’s Anatomy on Netflix: https://www.netflix.com/title/70140391

• My year of saying yes to everything: https://www.ted.com/talks/shonda_rhimes_my_year_of_saying_yes_to_everything

• Attitude: https://attitudeliving.com/collections/adult-hair-care

• Dostoevsky books: https://www.amazon.com/Fyodor-Dostoevsky-Books/s?k=Fyodor+Dostoevsky

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.

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