Podcast Summary: The Learning Leader Show with Ryan Hawk

Episode 654: Jake Tapper – The Most Important Leadership Skill, Handling Criticism, Chasing Your Curiosity, Understanding Tradeoffs, Responding to Rejection, and Being So Good They Can't Ignore You
Release Date: September 21, 2025
Guest: Jake Tapper (CNN Anchor & Award-Winning Author)

Overview and Main Theme

In this episode, Ryan Hawk interviews Jake Tapper, CNN Chief Washington Correspondent and bestselling author, about leadership lessons learned from decades covering presidents and world leaders, handling public criticism, harnessing curiosity, making tough tradeoffs, and building a career that stands out. The conversation blends practical strategies for improvement with stories illustrating humility, relentless learning, and the crucial role of honest feedback in leadership.

Key Discussion Points and Insights

1. Lessons from Legendary Journalists

• Jake’s Dedications: Tapper dedicated his book to mentors such as Diane Sawyer, Ted Koppel, Charlie Gibson, and Peter Jennings, expressing gratitude for their influence.
• Notable Lessons:
  • Ted Koppel’s advice: “Remember, you can always tell them no.” (03:20)
  • Negotiate for vacation days—people don’t realize their value, and it’s easier to get than money. (03:40)
• Work-Life Realities: Jake admitted it’s hard to unplug, especially in relentless news cycles, but emphasizes it's okay to miss a “news emergency” since there will always be another. (04:24)

2. Passion and Purpose in Journalism

• Both Ryan and Jake discussed the rarity and privilege of being in careers they love, despite public criticism.
  • “It’s just such a thrill to be able to cover this stuff ... I have the best seat in the world.” – Jake Tapper (06:00)
• Peak moments (moderating the 2015 GOP debate) highlight fulfillment from being in the heart of history. (06:00)

3. Interview Process and Tradeoffs

• Preparation: Success relies on a strong team—Tapper credits CNN’s producers and writers for helping frame “the most important thing” in each interview or debate. (07:20)
• On-the-Spot Judgments: Always a tension between following up or moving to the next crucial topic; sometimes you get it wrong, and that’s okay. (08:00)
• Fact vs. Opinion: Balancing when to push back, what to fact-check, and recognizing subjective viewpoints are imperfect but essential tasks. (08:30)

4. Handling Criticism

• Critique Dynamics:
  • Filters out personal attacks but listens to constructive criticism, even from strangers online.
  • Example: Writer Elon Green’s repeated criticism about Tapper’s lack of climate coverage led to Jake changing and informing Green when he addressed the topic. (11:15)
  • “Constructive criticism actually can be effective in the social media age ... you can theoretically reach anybody.” (11:40)
• Personal Touch: Most harsh critics are not people he cares about; genuine feedback from respected peers matters more. (09:45)

5. Staying Grounded: The Power of Observation

• Tapper’s long-pinned tweet (Orwell quote: “To see what is in front of one's nose needs a constant struggle”) serves as a daily reminder to observe and not ignore obvious truths, even when it is uncomfortable. (12:05)
  • Used as a lesson about noticing cognitive decline among leaders despite political “gaslighting.” (12:29)

6. Chasing Curiosity Relentlessly

• The origin story for his new book, Race Against Terror, began at a paintball party—a chance encounter leading to years of reporting and writing. (14:15)
• Tapper illustrates the intensity of his curiosity—researching topics obsessively, even on microfiche as a child, and now as a journalist.
• “You actually end up being the expert on this whole thing because you know enough of all of the stories...” (18:46)

7. The Role of Hard Work & Steve Martin’s Principle

• "Be so good they can't ignore you" (Steve Martin; 22:01)
  • Not about being the prettiest or smoothest, but about working harder and breaking more stories than peers.
  • “The main thing in my career has been hard work.” (21:27)
• Sacrifices: Missed family time, possible friction with colleagues, but the goal was to reach a level where it was irrational not to pick him for top jobs. (24:04)

8. Responding to Rejection

• Every major project met early discouragement—being told “don’t do it,” even by respected peers.
• Emphasizes humility: sending works-in-progress to experts for “unrelenting” criticism, eager for feedback so he could fix issues before public release.
  • “Having the humility to accept that I am not an expert… is an important part of the process.” (26:42)

9. The Superpower of Being a Beginner

• Willingness to admit "I don't know" and learning from scratch is presented as an under-appreciated leadership skill.
  • “I think this willingness to be a beginner...is a superpower.” – Ryan Hawk (28:48)

10. Key Leadership Lesson: Avoiding Yes-Men

• Repeatedly witnessed that powerful leaders often remove critical voices from their inner circle, which leads to blind spots (“the Jar Jar Binks theory”). (29:47)
  • Surrounding oneself with honest truth-tellers—who care and offer reality checks—produces better decisions and protects against self-sabotage.
  • Example: Senior leadership insulating Biden from honest feedback. (31:39)
• Importance of creating a team culture where debate is normal, even if true candor is hard for junior staff due to power dynamics. (34:13)
• “I don’t want a yes person. I want somebody...where it’s a healthy tension.” (34:18)

11. Empathy and Perspective Taking

• Leadership requires imagining oneself in others’ shoes, especially under relentless scrutiny or criticism.
  • “My point isn’t that the criticism makes me a better person. My point is that it makes me a better journalist.” (39:10)
• Acknowledgment that everyone, even leaders, faces “unrelenting” rejection and adversity.

12. Work-Life Balance and Sacrifice

• Real about tradeoffs—missing parts of parenthood due to career demands, yet trying to maximize support in other ways. (46:24)
  • Cites daughter Alice’s book and the values behind “raising your hand.”
  • “One of the parts of my weeping was about everything I missed...” (46:39)

13. Advice for Aspiring Leaders and Journalists

• Core advice:
  • Be a reporter, not just a pundit—focus on telling others’ stories, not just your own (49:49)
  • Expect and accept rejection; learn and move on.
  • Nobody will give you a job to be nice. You must provide value. (53:49)
  • Hard work often beats innate brilliance in most fields, including journalism.
  • “If you work hard enough, you can sneak past the wave on the seventh time. Every code can be cracked.” (50:25)
• Resilience: Sticking with projects through uncertainty—both the Biden book and Race Against Terror were almost self-published after publisher rejections, yet succeeded when finished. (54:27)
  • “I get rejected every day, every day. And it doesn’t matter that I’ve had New York Times bestsellers before. It’s part of life...” (56:35)

14. On Sustaining Momentum

• Even at career highs, Jake sees the importance of “speeding up” rather than coasting, acknowledging the ephemeral nature of relevance and wanting to maximize his window of opportunity. (59:27)
  • “Relevance is ephemeral. And when it leaves, it looks brutal… I just want to make sure that I’m producing as much as possible while I still can.” (59:37)

Notable Quotes & Memorable Moments

• On Value of Feedback:
  “Constructive criticism actually can be effective in the social media age... much more effective than ‘you suck.’” – Jake Tapper (11:40)
• On Work Ethic:
  “I could work harder than all of them, and I could break more stories than all of them...” – Jake Tapper (22:05)
• On Leadership Pitfalls:
  “They often remove any critic from their inner circle... You need people around you, not just to keep you humble, but to protect you from yourself.” – Jake Tapper (29:47)
• On Enduring Rejection:
  “I get rejected every day, every day. And it doesn’t matter that I’ve had New York Times bestsellers before... It’s part of life...” – Jake Tapper (56:35)
• Steve Martin’s Advice:
  “Be so good they can’t ignore you.” – Jake Tapper quoting Steve Martin (22:01)
• On Being a Beginner:
  “Having the humility to accept that I am not an expert...is an important part of the process.” – Jake Tapper (28:48)
• On Leadership & Empathy:
  “A good leadership skill is to try to understand the world through somebody else’s eyes.” – Ryan Hawk (40:58)

Timestamps for Key Segments

• 03:00 – Lessons from legendary TV journalists and mentors
• 04:24 – The draw and challenges of daily news work
• 07:20 – Debate and interview preparation
• 09:01 – Handling criticism and learning from feedback
• 12:05 – The meaning behind Jake’s pinned George Orwell tweet
• 14:15 – Origin of Race Against Terror and Jake’s research process
• 18:46 – Balancing writing, reporting, and personal life
• 21:27 – The role of hard work, Steve Martin’s advice
• 24:04 – Sacrifices made for success
• 29:47 – Leadership lesson: avoiding yes-men
• 34:18 – Creating a culture of candor on his teams
• 39:10 – Empathy and the reality of public criticism
• 46:24 – Reflections on parenthood and work-life tradeoffs
• 49:49 – Advice for aspiring journalists and leaders
• 53:49 – The reality of rejection and value-driven careers
• 56:35 – Even at the top, rejection continues
• 59:27 – On speeding up instead of coasting late in career

Conclusion: Actionable Takeaways

• Work so hard you’re impossible to ignore.
• Don’t shield yourself from honest feedback—actively seek out truth-tellers.
• Resilience and curiosity, not credentials, are the foundation of sustained excellence.
• Expect rejection; embrace it as part of growth.
• Empathy, humility, and beginner’s mindset are critical leadership assets.

This episode provides a masterclass in leadership and personal growth, illustrated through Jake Tapper’s hard-won experiences. For aspiring leaders—inside or outside of journalism—the episode underscores that grit, openness to feedback, the willingness to always learn, and valuing honest relationships are timeless keys to success.