Radical Candor: Communication at Work
Episode: The Wild Courage to Get What You Want, With Jenny Wood
Date: March 26, 2025
Hosts: Kim Scott, Jason Rosoff & Amy Sandler
Guest: Jenny Wood
Episode Overview
In this episode, Amy Sandler and Kim Scott have a lively conversation with Jenny Wood, former Google executive and author of the forthcoming book “Wild: Go After What You Want and Get It.” The discussion explores Jenny's provocative thesis: the very traits we’re conditioned to suppress—like being weird, shameless, or even a bit manipulative—are the traits most critical for advancing our careers and leading fearlessly. The trio digs into practical stories, memorable tactics, and tangible advice to help professionals unlock their own “wild courage,” overcome self-doubt, and achieve audacious goals without compromising authenticity.
Key Discussion Points & Insights
1. Challenging Career Stereotypes: Jenny’s Nine “Dangerous” Traits
[03:07]
- Jenny introduces the nine traits her book advocates: Weird, Selfish, Shameless, Obsessed, Nosy, Manipulative, Brutal, Reckless, and Bossy.
- These words are often used to box people in, but Jenny encourages dialing up these traits (with care) to gain confidence and assertiveness.
- "These words can create the bars of an invisible cage that keep you small, that keep you quiet, that keep you following instead of leading. But I find that more people need to dial these traits up just a little bit." — Jenny Wood [03:21]
Memorable Moment:
On “manipulative,” Jenny emphasizes reframing:
"To be manipulative is the courage to build lasting relationships, to build influence through empathy... It's all about mutual benefit. And essentially you have to figure out what people want and get it for them."
— Jenny Wood [04:34]
2. The Subway Story: Practicing “Wild Courage” in Life
[05:42]
- Jenny recounts approaching a stranger (now her husband) on the NYC subway—a pivotal moment where she challenged her own cautious nature and acted on instinct.
- This act was uncharacteristic for Jenny who is highly analytical, underlining the importance of sometimes overriding our left-brain scripts in favor of gutsy action.
"Serendipity isn't found. It's made. It's made. And I made my own serendipity that day."
— Jenny Wood [08:41]
[09:05]
- The act led to marriage, underscoring her book's title—knowing what you want and taking bold action to get it.
3. Overriding Societal & Self-Imposed Limitations
[09:10–10:00]
- Discussion about how societal expectations and rigid personal systems (like Jenny’s “first date spreadsheet”) can limit our openness to opportunity.
- Kim highlights the challenge of actually knowing what you want as the hardest part.
[13:14]
- Jenny contrasts two relationships to illustrate the “weird” trait: embracing quirks and authentic self-presentation attracts the right people and opportunities.
"Within your so called weirdness lie your greatest strength. So I say hone every ounce of weirdness you've got."
— Jenny Wood [14:05]
4. How Google Shaped Authentic Leadership (& the Value of “Weird”)
[15:15–19:12]
- Both Kim and Jenny reflect on how Google fostered an environment where being unconventional was embraced, building confidence and willingness to take risks.
- Not all organizations are as welcoming, leading Jenny and Amy to discuss strategies for cultivating self-confidence and “permission” to be authentic, especially outside supportive environments.
"A success mindset must precede success itself... the ability to be yourself [and] to ask for what you want are tied." — Jenny Wood [20:02]
5. Dealing with Rejection and Building Resilience
[21:59]
- Jenny shares her struggles with promoting her book and facing “ghosting” or nonresponses—a vulnerable, relatable window into the emotional labor of self-advocacy.
- Kim adds advice: sometimes, “you have to beg”—and it’s okay.
"It's so hard for me to send those last hundred [emails] having the rejection of the first 200...But it's a labor of love."
— Jenny Wood [22:14]
6. Embracing Strategic Self-Promotion (“Shameless” and Authentic)
[24:44]
- Jenny introduces the concept of a “power portfolio”—knowing and owning your key strengths (both hard and soft skills).
- Actionable advice: Schedule regular meetings not just with your boss (“managing up”) but your boss’s boss (“manage higher”), and key cross-functional peers (“manage diagonally”).
Tactic:
“Whether it's knowing your power assets that make up your power portfolio and starting there and talking about those with your boss, or every six months setting up time with your boss's boss... manage higher, right? Maybe manage diagonally... That’s the start.”
— Jenny Wood [28:02]
- Kim reframes strategic relationship building as a smart investment, not politicking.
[29:34–32:46]
- Jenny defends “playing politics” in the positive sense: understanding influence, building relationships, and learning how power actually works in organizations.
7. Navigating Bias, Identity, and the Double Bind
[33:00–36:57]
- Kim shares a concept from Mecca, another Googler: for underrepresented people, “difficulty anchors” and strategic alliances with respected leaders can counteract implicit bias.
- Amy & Jenny discuss the particular social cost of self-promotion for women and minorities; Jenny acknowledges the “boys’ club” aspect of authorship and entrepreneurship compared to Google.
"I'm not saying this stuff is easy, folks. That's why it takes wild courage."
— Jenny Wood [35:01]
- Kim’s advice: “Be fucking funny” or self-promote anyway, because silence will not protect you.
8. Practical Tools: How to Say “No” Without Guilt
[39:03–43:56]
- Jenny introduces three tactics for rejecting requests without drama:
- Let’s Drink to Async: Propose email collaboration instead of a meeting.
- Power Postpone: Suggest revisiting later, often letting the problem resolve itself.
- Agenda Avenger: Ask for a detailed agenda before agreeing to a meeting.
- [41:40]: The “Sisyphus No” (named on the spot by Amy) is saying a clear, firm no and why that clarity commands respect.
“People pleasing pleases no one. And it keeps you small. And so no, you know, this is what I call brutal. It is the courage to protect your time and energy.”
— Jenny Wood [39:29]
9. Tactics for Respectful, High-Impact Communication
[47:38–50:36]
- The "Pull it and Bullet" method for emails:
- Pull out 50% of the text.
- Use concise bullet points, with bolded keywords.
- Jenny credits this for impressing Kim and opening doors.
"Pull it and bullet. Pull 50% [of the text] and write in bullets, not prose."
— Jenny Wood [50:13]
Notable Quotes & Memorable Moments
- "Within your so-called weirdness lie your greatest strength. So I say hone every ounce of weirdness you've got." — Jenny Wood [14:05]
- "Serendipity isn't found. It's made." — Jenny Wood [08:41]
- "Be fucking funny... Your silence will not protect you." — Kim Scott [36:41]
- "People pleasing pleases no one." — Jenny Wood [39:29]
- "If cauliflower can be pizza, you can be anything." — Amy Sandler [50:02]
- "Pull it and bullet." — Jenny Wood [52:54]
Timestamps for Important Segments
- 03:07 – Jenny introduces the nine “wild” traits.
- 05:42 – Jenny’s subway story of wild courage.
- 08:41 – The role of serendipity and following your gut.
- 15:15 – The impact of Google’s culture on confidence and authenticity.
- 20:02 – Cultivating a success mindset outside supportive cultures.
- 24:44 – Building a “power portfolio” and managing “higher and diagonally.”
- 28:02 – Practical tactics for self-promotion and relationship-building.
- 32:46 – How bias and identity shape the reception of ambition.
- 39:29 – Saying no, and the “Let’s drink to Async” tactic.
- 47:38 – Office hours and lowering the barrier for communication as a leader.
- 50:13 – “Pull it and bullet” email technique.
- 52:54 – Closing and book details.
Actionable Takeaways
- Embrace your “dangerous” traits: Being a little weird, shameless, or obsessed may be the very thing that unlocks your next level.
- Strategically expand your influence: Meet regularly not just up, but higher and diagonally in your organization.
- Reframe self-promotion: It’s not shameful—it’s about pride in your contribution and helping the organization.
- Master the art of saying “no”: Use concrete tactics like requesting agendas, async collaboration, or honest, brief explanations.
- Communicate efficiently: Use the “Pull it and Bullet” approach for stakeholder emails.
- Be brave with feedback and authenticity: The real risk is in being invisible—not in being memorable.
For more, get Jenny Wood’s Wild: Go After What You Want and Get It (preferably the hardcover, as Jenny shamelessly and strategically recommends in week one), subscribe to her newsletter at itsjennywood.com, and visit radicalcandor.com/podcast for show notes and more resources.
Remember: Pull it and bullet! And go make your own serendipity.