Designing Teams That Push Back

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The Learning Leader Show with Ryan Hawk

Guest: Jake Tapper is an award-winning broadcaster and chief Washington correspondent, currently anchoring The Lead with Jake Tapper every day on CNN. He's also the #1 New York Times best-selling author of 7 books, including The Outpost (which was later made into a movie), Original Sin, and most recently Race Against Terror.

Notes:

• Be So Good They Can't Ignore You. Jake: I'm in control of how hard I work. It is our responsibility to work so hard that we become the obvious choice for the job or the promotion. Be So Good They Can't Ignore You. "I had to be so good that even though maybe on a broadcasting level I wouldn't be the number one pick... they had to give it to me."
• The one leadership skill that is massively important to develop… Don't insulate yourself with "yes" people. You have to have truth tellers in your life. Who are your foxhole friends? Who are the people who are willing and able to tell you the truth? Who are the ones who love you and care about you enough to let you know when you've messed up? Those people are gold. We all need them.
• Rejection: Dr. Seuss was rejected by 47 publishers. Rejection is part of life. You have to stay in the game for a chance to win it. Keep going. And nobody will give you a job to be nice. What value do you bring to a company? How will you make your boss's life better? You get hired to solve a problem, not because someone wants to be nice.
• Pinned tweet since 2017 – "To see what is in front of one's nose needs a constant struggle." -- George Orwell. A reminder to see obvious truths being obscured by spin or wishful thinking.
• "You Can Always Tell Them No" - Ted Koppel's crucial advice to young Jake about maintaining journalistic integrity and not compromising values for opportunities. This became a career-defining principle that Jake still follows 20 years later.
• The Jar Jar Binks Theory of Leadership - Successful leaders often remove critics from their inner circle, creating dangerous echo chambers. "Great people often achieve as much as they can to the point that they are able to remove from their inner circle anyone who tells them they're being an asshole or making a wrong decision."
• Constructive vs. Destructive Criticism - Jake learned to distinguish between useful feedback and personal attacks: "Very few of my critics are people that I actually care what they think... folks who understand I'm just trying to be a good faith operative here."
• Curiosity as Career Driver - Deep curiosity drove Jake from reading microfiche about MASH as a kid to investigating complex stories as an adult: "I find something interesting and I wanna find out everything I can about it."
• Rejection as Constant Reality - Even at his career peak, Jake faces daily rejection: "I get rejected every day... it doesn't matter that I've had New York Times bestsellers before... it's part of life."
• Humility Enables Learning - Accepting expertise gaps allows growth: "Having the humility to accept that I am not an expert on any particular thing... I'm a journalist, which means I try to be an expert on whatever I'm covering at that moment."
• Leadership Lessons From Powerful People
  • The Inner Circle Problem: Leaders systematically remove critics until surrounded only by yes-people, creating dangerous blind spots. Jake witnessed this pattern with Joe Biden (surrounded by aides and family who weren't honest about his declining acuity) and across industries.
  • The Solution: Intentionally maintain truth-tellers in your inner circle who care about you personally but will challenge you professionally.
  • Creating Truth-Telling Environments: Jake encourages healthy disagreement with executive producers, acknowledges power imbalances that make criticism harder for junior staff, and creates indirect channels for feedback ("some people on the staff think...").
  • The Criticism Paradox: Public leaders face constant harsh criticism, making them naturally defensive. Understanding this context helps leaders distinguish between constructive feedback that improves performance versus personal attacks that serve no purpose.
• Following Curiosity Despite Opposition
  • Jake's major works were all advised against by professionals:
    • The Outpost (no military expertise)
    • The Atlantic story of freeing a wrongly imprisoned man
    • Biden book (started the day after the election, despite uncertainty)
  • Key Insight: "Every single one of them, people were telling me not to do it... It's been following my curiosities even when people told me I'm not interested in that."
• The Hard Work Advantage: Jake couldn't compete on appearance or natural broadcasting ability, so he outworked everyone: broke stories constantly, used blogs when he couldn't get on air, and made himself impossible to ignore through sheer output.
• Dealing with Rejection
  • Expect constant rejection even at a career peak
  • Don't take rejection personally unless there's constructive feedback
  • Use rejection as data, not judgment of worth
  • Keep creating regardless of immediate acceptance
• The Wave Metaphor: Like Tom Hanks in Cast Away, timing the waves - "every code can be cracked" if you persist and find the right timing.
• Key Elements for Writers:
  • Strong structure: "Act one, chase your hero up a tree. Act two: throw rocks at your hero. Act three, get your hero out of the tree."
  • Good editor who pushes back - be willing to "kill your darlings"
• Life Philosophy
  • The Acceleration Mindset: At 56, Jake is speeding up output: "I don't know how much longer I have this window where people are paying attention... relevance is ephemeral... when it leaves, it looks fucking brutal."
  • For Young People: "So much of life is rejection... You cannot stop it... don't take it personally." Focus on developing skills and delivering value: "Nobody will give you a job to be nice... They'll do it because you have something they want."
  • Time Sacrifice Awareness: Success requires acknowledging costs: "What I cried about is the stuff I missed that I wasn't there for because I was chasing a story or on assignment."

Time Stamps:

02:46 Jake's Dedication to Influential Figures

05:05 Hot Mic Moment in Alaska

06:59 Preparing for Big Interviews & When to Follow Up

09:01 Dealing with Criticism

12:07 The Story Behind Jake's Pinned Tweet

13:48 Race Against Terror: The New Book

18:29 Balancing Multiple Roles

20:47 Chasing Your Own Curiosity

23:58 Sacrifices for Career Success

29:00 The Importance of Humility in Leadership

31:08 Surrounding Yourself with Truth Tellers

34:18 Healthy Tension in Team Dynamics

37:15 Understanding the Pressure on Public Figures

40:09 Empathy in Leadership

45:17 Balancing Career and Family

49:00 Advice for Aspiring Journalists and Writers

52:01 The Reality of Rejection and Hard Work

57:26 The Importance of Structure and Editing in Writing

01:01:16 End of the Podcast Club