Should leaders adapt their approach to each individual, or apply one consistent leadership style to everyone?

Harry Stebbings · Nov 1, 2023

A leader's job is to know how each individual internalizes feedback and to tailor their leadership style to the employees they have, rather than picking one style and sticking with it

He defaulted to being direct and truth-seeking, but some people need more hand-holding and nurturing

28:15 20Product: Why You Should Not Go Into Product Management, Why the CEO is Always the CPO, How to Build the Best Product Teams & Why You Should Hire People Who Aren't In Product Already with Databricks SVP Product, David Meyer

Max Levchin · Feb 5, 2025

Leaders should stop projecting their own drive onto employees and instead identify each person's actual motivation and invest against it; if someone's motivation is fundamentally incompatible with the work, that was a hiring mistake

Telling a new hire 'we're all working weekends because I want to succeed' does nothing for them; motivations are often not relatable to the founder, so you have to work out what they're actually looking for — e.g. someone motivated by craft quality should be given the time to make work they're proud of

Scope: hardest part is deciding when someone is irredeemable, after giving second, third and fourth chances

9:48 20VC: Affirm Max Levchin on Why Grading Talent by Letter (A or B) is Total BS | How to Create a Culture of Post Mortems and Writing | Why You Should Only Study Failure Not Success & The Biggest Surprises Scaling to $18.7BN Market Cap

Harry Stebbings · Mar 21, 2025

Culture isn't homogenous — some people respond to the carrot and some to the stick, so a leader must change who they are to get the best out of different people

That's what he has learned from leading

27:41 20VC: Selling Drift for $1.2BN is the Biggest Failure: What No One Tells You About Selling Your Company | Why Incumbents Are Slower & Worse Than Ever | Why the Most Valuable Companies in a World of AI Will Not Have More Than 100 People with Elias Torres

Harry Stebbings · Jun 6, 2025

Leaders should adapt their leadership style to each individual — some people need a carrot, some a stick — rather than applying one blanket approach

He used to lead one blanket way and found changing his style per person gets the most out of them

66:59 20VC: The Science of Storytelling: Three Steps to Master the Perfect Story | From Near Death Experience to Unicorn Startup: The Untold Story of Omaze with Matt Pohlson

Ophelia Brown · Mar 17, 2023

You cannot fundamentally change your own nature, so an intense leader should own their intensity while consciously respecting that colleagues are not like them

Your intensity is what got you where you are; you can improve and moderate behaviour (e.g. not sending the Sunday morning message) but not become a different person

40:33 20VC: Why Growth Investors Ruined the Venture Market, Why Marketing in Venture Has No Substance, Why Follow-On Investing Can Damage Returns and The Mistakes VCs Made in the Last 18 Months with Ophelia Brown, Founder @ Blossom Capital

Matt Pohlson · Jun 6, 2025

All relationships are just between two people and each person is different, so leaders must create systemic messaging true to themselves but adjust to individuals

Zinni ran NATO troops across services and national cultures and said this was how he handled the leadership challenge

67:17 20VC: The Science of Storytelling: Three Steps to Master the Perfect Story | From Near Death Experience to Unicorn Startup: The Untold Story of Omaze with Matt Pohlson