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How to ship like a startup

2025-03-25 20:03:48

👋 Welcome to a 🔒 subscriber-only edition 🔒 of my weekly newsletter. Each week I tackle reader questions about building product, driving growth, and accelerating your career. For more: Lennybot | Podcast | Courses | Hiring | Swag

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Mihika Kapoor is one of my all-time favorite podcast guests. Her passion, hustle, and ability to get sh*t done have inspired so many listeners and readers to think bigger and bring more joy to their work. In fact, her podcast episode is the most popular episode I’ve ever done with a non-founder or non-exec.

Mihika was one of the early leads on FigJam, Figma’s first-ever new product launch, and most recently, she pitched and launched Figma’s latest product, Figma Slides, which in my recent survey of readers is already ahead of Apple Keynote and tied with Canva as your most used presentation software. For something that launched less than a year ago (and just went GA last week), that is astounding.

Below, Mihika shares the seven biggest lessons she’s learned about successfully pitching big ideas, getting buy-in, rallying a team, and getting new products out the door—essentially, how to keep shipping like a startup as a company grows.

Check out Mihika on X and LinkedIn, and, if you’re interested in more, she recently launched a live cohort-based course on Maven—Product Storytelling: Pitch & Build 0-1 Products at Your Company—where she goes even deeper on this topic. Her next class starts March 31st, so get on it.


We often hear about companies trying to maintain a “startup” mindset as they grow. They want to build products rather than follow processes, assemble irrationally passionate teams, and empower every employee with a great idea to ship a blockbuster. But BigCo status quo often gets in the way. Based on my experiences building Figma Slides, FigJam, and a few others in development, I’ve learned a lot about how to actually keep teams scrappy while launching products on the ground.

Figma Slides was a bottom-up initiative that came to life through a mixture of prototyping, camaraderie, and optimism bordering on delusion. Evangelizing the idea at hackathons, vision pitches, and product reviews bought our team a small amount of headcount to “explore” the space. But that was all that we needed to sprint to the finish line.

When Figma Slides debuted at Config 2024, Figma’s annual user conference, it proved to be a huge hit. Since the launch, we’ve seen people create millions of Figma Slides decks, and, as of last week, it’s out of beta and available for all Figma users 🙌.

Announcing Figma Slides during the keynote at Config, Figma’s annual user conference

Below are seven strategies for replacing the BigCo status quo with a startup mindset. Regardless of whether you are pushing your own idea within a larger company, fleshing out a new product space, or expanding existing initiatives, these tips will accelerate you, your team, and your company.

1. Replace your PRDs with prototypes

🤨 BigCo status quo: A PM’s job is to write detailed PRDs to kick off projects and keep teams aligned.

🏃 Startup mindset: Speed and experimentation matter more than documentation. Anyone with an idea should be empowered to explore it through prototypes.

Learning how to write a PRD (product requirements document) constitutes one of the hallmarks of being baptized as a BigCo™ PM. But in fast-moving environments, PRDs often fail because:

1️⃣ They block valuable design and eng work.

2️⃣ They are almost never up-to-date, as specs change frequently.

3️⃣ Once a product exists, a PRD is just a watered-down version of the actual product being built.

At Figma, everyone is encouraged to design and prototype—PMs included. Additionally, with the rise of AI-assisted features to quickly get to a first draft, the barrier to getting started is plummeting even further, and PMs are much better off spending their time prototyping than writing docs. Conviction comes from prototyping, not paperwork.

Tips for working without PRDs:

Create a prototyping culture.

If I had written a PRD for every idea we explored for Figma Slides, I’d still be writing those docs. Instead we built, tested, and iterated—fast. Encourage engineers to code their “what-ifs.” Some of them might turn into flagship features.

Here are some of the very first prototypes of some of Figma Slides’ core features: slide grid, focused view, and design mode:

Align in lo-fi.

Use FigJam and quick wireframes to jam on ideas and explore solutions. Speed-run option spaces instead of spending weeks writing specs.

Let design files be the source of truth.

Once you align on a direction, don’t create a standalone PRD—annotate specs inside your designer’s mocks. A design file with notes is infinitely more useful (and accurate) than a text doc.

Invest in evergreen, visual artifacts.

You still need to communicate why you’re building something, but don’t rewrite it for every feature. Instead:

  • 📌 Build a single vision artifact up front—so everyone understands the broader impact you’re aiming for. Think about this as your pitch deck.

  • 📌 Update a strategy artifact each quarter—so teams see how near-term work ladders up.

  • 📌 Invest in visuals—directional designs tell the story better than text ever could.

The first slide in the OG “Flides” vision pitch deck

Two prototypes from the original deck of some core features: AI tone dial and the alignment scale:

2. Build hype by working in the open

🤨 BigCo status quo: Sharing work in progress with colleagues leads to scrutiny of rough edges, depleted trust in the product, and an increased likelihood the project gets killed.

🏃 Startup mindset: Showing behind-the-scenes progress gets key stakeholders invested in the product’s success.

Think of your product as a small flame. Your job? Grow it into an unstoppable wildfire inside your company. Do that by sharing progress early and often. Here’s how:

Light the first spark with hackathons.

Hackathons aren’t just for fun—they’re a launchpad.

At Figma, previous attempts to get buy-in for Figma Slides through traditional pitches went nowhere. But when we built a working prototype at Maker Week, Figma’s company-wide hackathon, everything changed. The demo at our internal showcase took off because:

  1. It was big. Everyone expected small feature demos, not an entirely new product built in three days. One engineer even asked if we had 40 people working on it (in reality it was only eight).

    The Zoom chat when I demoed our “Flides” Maker Week project to the company
  2. It was funny. We held a live vote for the product name, with ridiculous contenders like “Feck” (Figma x Deck), “Sligma” (Slides x Figma), and my personal favorite, “Flides.” The absurdity of these suggestions made it an instant hit.

  3. It was relatable. To set the scene, I pretended I was a hackathon attendee late for submitting my demo video for Maker Week and used Flides to help me out. The demo mimicked a real-world scenario—being late on a presentation deadline. It resonated because it was exactly how we worked.

Share raw progress async.

Don’t wait for polished releases—share raw progress. One engineer on our team, Jon, posted over 70 prototype videos in Slack before launch. Soon everyone followed his lead. A steady drip of updates builds trust and keeps excitement high.

Turn your spark into a wildfire at the all-hands.

Figma Slides got the green light to launch in beta at Config after it was pressure tested in a real-world scenario—I advocated to use our minimum viable product (MVP) at the first company all-hands meeting of 2024. Though our IT team was wary of betting on unproven software, the team paused new feature development for two weeks to refine the MVP for that moment, addressing bugs as soon as they came up. The demo was the best possible showcase of progress and agility, and the team learned so much about user needs. The flawless presentation in front of the whole company sealed the deal.

Yuhki (our CPO) and Kris (our CTO) using Figma Slides for the first all-hands of 2024
The slide where we revealed to the company that Kris, Yuhki, and Dylan were presenting in Figma Slides
Speaker notes working for the first time ever! On the all-hands stage.

Bonus: Share beyond your company.

We launched Figma Slides in open beta at Config so we could gather as much feedback as possible before GA. The team shared some of our early WIP vision on platforms like X (with the GTM team’s blessing, of course), which proved to be an effective way to drive hype.

3. Build a cult(ure)

🤨 BigCo status quo: PMs are responsible for the product and the product alone.

🏃 Startup mindset: A product’s success depends on a team culture so strong it feels borderline religious.

Culture isn’t just a nice-to-have—it’s a cheat code for momentum, creativity, and execution. Here’s how to build one that people want to be part of:

Make it weird.

Inside jokes create attachment. The weirder, the better.

For Figma Slides, the absurd name “Flides” became an internal meme:

  • Slack emoji? ✅ [Make one for your team today if you don’t have one!]

  • Workstream names? ✅ [The animations sync? “Flanimations.”]

  • IRL team photo shoot . . . on actual slides? ✅

The more irrational the name, the stronger the inside joke—and the deeper the buy-in.

Custom Slack emoji for our team that we created
Flides laptop stickers 🔥
Color-coordinated photo shoot with a bunch of slides the week we launched :D

Steal each other’s quirks.

Shared quirks = shared identity.

Our team leaned into this, hard. Everyone changed their Slack profile picture’s background to match. A Gen Z engineer always opened chats with “yoooooo”—so the whole team adopted it. Even small things, like entering a group chat, became dopamine hits.

Valentine’s Day card one of the engineers made for the team

Celebrate like it’s the Oscars.

On launch day, we threw an award ceremony. Red carpet, custom trophies, full production. What started as a joke turned into one of the most emotional moments of the entire project. The team was so hyped, we closed out the office at midnight.

Want maximum inside jokes with minimal effort? Crowdsource superlative awards from the team. P.S. Trophies are $20 on Amazon.

4. Find the believers instead of swaying the skeptics

🤨 BigCo status quo: People work on the products they are assigned to.

🏃 Startup mindset: Players who opt in to their teams build the most successful products.

The Figma Slides team was the most inspiring group I’ve worked with—not because they were assigned but because they wanted to be there. We pulled team members from across the org by spreading the word and empowering the most excited and invested folks we heard from to make the switch. Here’s how to build your dream team:

Find your early adopters.

A piece of feedback I was given early on, that to this day resonates with me, is: If you need to sell someone really really (like, really really) hard to join you, they are probably not the right fit. The best teammates are the ones begging their managers to work on your project. Make sure your project is known across your org (and ideally the whole company) so they can find you.

Look for “run with it” energy.

The best team isn’t always the most senior—it’s the one that can move forward without perfect specs. At Figma, we call this the “run with it” mentality. Find engineers and designers who thrive in ambiguity.

Recruit scrappily.

Don’t let org swimlanes prevent you from reaching out. I love working with engineers and designers both on and off my team. The best part is, if they like working with you, they’ll make the time to help out. If they love working with you, they’ll do whatever they can to join you.

Empower every team member to pitch.

Your team should be your biggest evangelists. The best pitches will actually come from the folks on your team. Ensure that they know when recruiting is a priority and that you are available as a resource.

5. Make every team member a product owner

🤨 BigCo status quo: Research hands off to Design, Design hands off to Engineering, and everyone stays in their lane.

🏃 Startup mindset: The best teams blur the boundaries. Everyone is a part-time PM.

Before Figma, I was told to stay in my lane. “That’s a designer’s job” or “This should be done by a data scientist” were constant refrains. Deviating from the original plan was considered “thrash.”

At Figma, it’s the opposite. Extreme collaboration isn’t just encouraged—it’s the norm. We’re able to improve decision-making and expand the solution space when we lean into the following practices:

Remove the black box around the product and design process.

Engineers shouldn’t be kept in the dark until handoff. Involving them early gives them better context, improves decision-making, and allows them to shape product behavior.

Engineers are often brought into design syncs where product decisions are being made. That way:

  • Design proposals are already informed by engineering feasibility.

  • Engineers can proactively contribute insights, not just execute specs.

Go from 0% to 100% together.

At Figma, teams don’t work in silos—they pair on solutions. PMs and designers jam together in a Figma file. Handoffs between design and engineering aren’t just “Here, build this”—they’re real-time pairing sessions, tweaking interactions and refining details together.

The result? A stronger product, fewer roadblocks, and a team that feels true ownership over what they’re building.

6. Remove the wall between your team and your users

🤨 BigCo status quo: Researchers are the only ones talking to users.

🏃 Startup mindset: Everyone on the team engages with users to demonstrate, deploy, and debug products.

One of the most fascinating phenomena I’ve witnessed is that if an employee hears a user directly express and elaborate on a pain point, they will be a bajillion times more likely to act on it than if they hear a secondhand summary. As a PM, your job is to engineer as many of these anecdote-driven crusades as possible.

How to get your team talking to users:

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Superhuman's secret to success: Ignoring most customer feedback, manually onboarding every new user, obsessing over every detail, and positioning around a single attribute: speed | Rahul Vohra (CEO)

2025-03-23 19:03:05

Listen now on Apple, Spotify, and YouTube.

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Rahul Vohra is the founder and CEO of Superhuman. Prior to Superhuman, Rahul founded Rapportive, the first Gmail plug-in to scale to millions of users, which he sold to LinkedIn in 2012. He is also a prominent angel investor, and his fund has invested $50 million in over 120 companies, including Placer, Supabase, Mercury, Zip, ClassDojo, and Writer.

What you’ll learn:

  1. The unexpected insight about virality Rahul gained from LinkedIn’s head of growth.

  2. Why Rahul restructured his entire executive team to spend 60% to 70% of his time on product, design, and marketing instead of the typical CEO responsibilities.

  3. The counterintuitive approach to finding product-market fit using a methodical system inspired by Sean Ellis, and how this algorithmically determines your roadmap.

  4. How manually onboarding every user (Superhuman had 20 full-time people doing this at peak) created superfans and allowed engineers to focus on product rather than onboarding flows.

  5. The “Single Decisive Reason” framework for making better decisions by avoiding collections of weak justifications.

  6. How Superhuman’s AI features have evolved to create a truly intelligent email experience that works while you sleep.

Some takeaways:

  1. The secret to true virality isn’t viral mechanics but word of mouth. LinkedIn’s head of growth revealed to Rahul that no app has sustained a viral factor above 1 for long periods—even Facebook peaked at 0.7. What drives growth is when users spontaneously tell others about products they love.

  2. Ignore feedback from users who don’t love your product’s core value—focus on the “somewhat disappointed” users for whom your main benefit resonates.

  3. Tracking his time revealed that Rahul was spending only 6% to 7% on product, design, and marketing—areas where he excels. By hiring a president to handle operations and restructuring his role, he increased this to 60% to 70%, dramatically accelerating Superhuman’s product velocity.

  4. Manual onboarding scaled further than you’d think. At its peak, Superhuman had only 20 people manually onboarding new users, creating superfans who drove word-of-mouth growth while allowing engineering resources to focus on product rather than self-service flows.

  5. Typography matters more than you think. After testing 15 different fonts and finding none adequate, Rahul spent six months perfecting Superhuman’s typography, selecting and modifying Adelle Sans because it’s beautiful, conveys any sentiment appropriately, optimizes reading speed, and makes email addresses look natural.

  6. Before setting pricing, establish positioning—Superhuman chose $30 a month by asking at what price the product “starts to feel expensive but isn’t out of the question.”

  7. The “Single Decisive Reason” framework prevents justifying decisions with collections of weak reasons. Learned from Reid Hoffman, this approach asks: “If only one reason were true and you’re still advocating for this decision, what would it be?” This creates clarity and prevents rationalization.

  8. Superhuman’s “Write with AI” feature is used 37 times per week per user—far more than expected—while features Rahul anticipated would be popular have seen less adoption, highlighting the challenge of predicting which AI capabilities will resonate.

  9. When selling to enterprise, understand that user needs (like calendar integration for Outlook users) and institutional requirements (like security controls) create a multi-threaded sale with different stakeholders. Superhuman spent a year piloting with a major consulting firm before full deployment.

  10. Most B2B software slows down because companies shift from “solution deepening” (improving product) to “market widening” (expanding platform support).

  11. Hiring a president freed Rahul to focus on his “zone of genius.” This operational leader manages the executive team and serves as a thought partner on strategy—effectively functioning as a “grown-up co-founder” for a 10-year-old company where the original co-founders have departed.

  12. Working with a TM meditation coach transformed Rahul’s performance. After four years of practice (30 minutes in the morning and afternoon), he experiences increased focus, creativity, and expressiveness that has become essential to his effectiveness as a founder.

Where to find Rahul Vohra:

• X: https://x.com/rahulvohra

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

• Email: [email protected]

In this episode, we cover:

(00:00) Introduction to Rahul and Superhuman

(05:00) The most pivotal moment in Rahul's career

(07:01) The secret to virality

(11:02) Superhuman’s product evolution and core values

(13:32) Overcoming slowdowns at scale

(18:06) Time management and meditation

(27:35) The role of a president

(30:56) Attention to detail

(43:00) Finding your unique position

(47:32) The power of manual onboarding

(52:37) Mastering product-market fit

(59:33) Game design in business software

(01:05:35) Contrarian pricing strategies

(01:09:29) Leveraging AI

(01:15:40) Transitioning to enterprise solutions

(01:19:08) The Single Decisive Reason framework

(01:22:32) Conclusion and final thoughts

Referenced:

• Superhuman: https://superhuman.com/

• Rapportive: https://techcrunch.com/2012/02/22/rapportive-linkedin-acquisition/

• Elliot Shmukler on LinkedIn: https://www.linkedin.com/in/eshmu/

• What Are ‘Whales’ in Video Games: https://gamerant.com/video-games-whales-concept-term-explained/

• Figma: https://www.figma.com/

• Notion: https://www.notion.com/

• Loom: https://www.loom.com/

• How to use Team Comments to reimagine email collaboration: https://blog.superhuman.com/how-to-use-team-comments-to-reimagine-email-collaboration/

• Rajiv Ayyangar’s post on X about Superhuman: https://x.com/rajivayyangar/status/1816176308130570385

• Transcendental Meditation: https://www.tm.org/

• Laurent Valosek on LinkedIn: https://www.linkedin.com/in/laurent-valosek-18708b5a/

• Peak Leadership Institute: https://www.peakleadershipinstitute.com/

• Ed Sim’s website: https://edsim.net/

• Adelle Sans: https://fonts.adobe.com/fonts/adelle-sans

• Comic Sans: https://en.wikipedia.org/wiki/Comic_Sans

• Greenfield project: https://en.wikipedia.org/wiki/Greenfield_project

• Why Mailbox died: https://www.theverge.com/2015/12/8/9873268/why-dropbox-mailbox-shutdown

• Bill Trenchard on X: https://x.com/btrenchard

• How Superhuman Built an Engine to Find Product-Market Fit: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit/

• Using the Sean Ellis Test for Measuring Your Product-Market Fit: https://medium.productcoalition.com/using-sean-ellis-test-for-measuring-your-product-market-fit-c8ac98053c2c

• Sean Ellis on LinkedIn: https://www.linkedin.com/in/seanellis/

• The original growth hacker reveals his secrets | Sean Ellis (author of “Hacking Growth”): https://www.lennysnewsletter.com/p/the-original-growth-hacker-sean-ellis

• The Trouble with Rewards: https://www.kornferry.com/insights/briefings-magazine/issue-13/519-the-trouble-with-rewards

• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan

•  Van Westendorp Price Sensitivity Meter: https://en.wikipedia.org/wiki/Van_Westendorp%27s_Price_Sensitivity_Meter

• AI-powered email for high-performing teams: https://superhuman.com/ai

• Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu

• Single Decisive Reason: decision-making for fast-scaling startups: https://blog.superhuman.com/single-decisive-reason-decision-making-for-fast-scaling-startups/

• Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/

Recommended books:

• Positioning: The Battle for Your Mind: https://www.amazon.com/Positioning-Battle-Your-Al-Ries/dp/0071373586

Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

Lenny may be an investor in the companies discussed.

🧠 Community Wisdom: 225th issue + balancing child care and career transitions, pregnancy disclosure in new roles, measuring retention effectively, discount strategies, and more

2025-03-23 00:01:43

👋 Hello and welcome to this week’s edition of ✨ Community Wisdom ✨ a subscriber-only email, delivered every Saturday, highlighting the most helpful conversations in our members-only Slack community.

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Which companies produce the best product managers

2025-03-18 20:01:17

👋 Welcome to a 🔒 subscriber-only edition 🔒 of my weekly newsletter. Each week I tackle reader questions about building product, driving growth, and accelerating your career. Annual subscribers now get a free year of Perplexity Pro, Notion Plus, Superhuman, Linear, and Granola.

Subscribe now

For more: Lennybot | Podcast | Courses | Hiring | Swag


My first-ever deep dive a few months ago into which companies accelerate PM careers most led to a lot of great feedback and ideas, so I’m back with a follow-up, going one level deeper into the question: Which companies produce the best product managers? We arrived at the answer by triangulating a bunch of juicy data.

In this post, well look at:

  1. Which companies create the most successful PM alumni founders

  2. Which companies accelerate PM careers most—with four new data points since the last deep dive

  3. Why Stripe PMs didn’t score higher—this one is fascinating

Across the board, here are the top companies that seem to produce the best PMs:

The big change we made in this updated edition was zeroing in on just the past 10 years vs. the company’s entire history. We also went deeper into the founder data, looking at not just the raw number of founders but also how they’ve done. And we added a few companies to the list (e.g. Airbnb, DoorDash, Salesforce, Dropbox) that people pointed out we missed.

A big thank-you to Live Data Technologies (Jason Saltzman and Ethan Elias) for sharing this data with us and for helping with the analysis.

Caveats:

  1. We are looking only at companies that have enough data (i.e. enough PM alumni) to draw meaningful conclusions from. Your startup may be producing the best PMs ever—we just won’t know this yet.

  2. A confounding variable is the quality of PMs these companies hire. If a company hires only amazing senior PMs, they will naturally go on to do amazing things—and that doesn’t mean the company made these PMs great. However, if the goal of this post is to help you figure out where to work, getting a gig at one of the companies on this list will put you on a good track either way.

1. Which companies create the most founders—and the most successful founders?

First, we looked into which companies’ PM alumni go on to start the most companies, irrespective of how these companies do. Palantir dominates. Over a third of their PMs have started a company. 🤯

Intercom comes in second, at over 18% (almost one in every five alumni PMs!), followed by Dropbox, Plaid, N26, Revolut, Duolingo, Uber, LinkedIn, and Coinbase.

I’ll also give props to Ramp, Airbnb, and Notion, which came in just below the top 10 but all have 10% of alumni PMs who start a company. That’s impressive as hell.

Go work at one of these companies if your goal is to start your own company: Palantir, Intercom, Dropbox, Plaid, N26, Revolut, Duolingo, Uber, LinkedIn, Coinbase, Ramp, Airbnb, or Notion. But keep reading. . .

Next, we looked more closely at which companies create the most successful founders. It’s one thing to start a company—it’s another to start something that works.

Based on the data we have available to us, the best proxy we found for measuring “successful” was to look at which companies have gone on to raise a Series A. Yes, some founders choose to stay bootstrapped and never raise money, and raising a Series A doesn’t mean you’re successful, but it’s a simple way to zero in on founders aiming to build large venture-scale companies.

The headline is Chime. Wow. Over 20% (one in five) of Chime’s PM alumni go on to not just start a company but also raise a Series A.

Scale, Palantir, and Faire aren’t too far behind, at around 15%. And then we have Dropbox, Robinhood, Stripe, Block/Square, Coinbase, and Salesforce rounding out the top 10.

Go work at one of these places if you want to build a venture-scale company: Chime, Scale, Palantir, Faire, Dropbox, Robinhood, Stripe, Block/Square, Coinbase, Salesforce.

Which companies accelerate PM careers most?

Building on our analysis in the previous edition and adding four new data points, below we’ve triangulated which companies’ alumni PMs create the biggest inflection in the career of their PMs by looking at:

  1. Rate of PMs getting promoted within the company

  2. Rate of alumni PMs getting promoted after leaving

  3. The average time to promotion after leaving

  4. The average time to reach a leadership position (e.g. VP of Product, Head of, CPO)

Takeaways:

  1. Intercom dominates. It’s the only company to rank in the top 10 on all four dimensions (1st in promotions internally, 5th in promotions externally, 7th in fastest to promotion, and 9th in fastest rise to leadership). 👏

  2. Revolut and Nubank are tied for second place, both ranking in the top 10 in three different categories. Fintech? More like Win-tech. 🤣

  3. N26 comes in fourth, ranking in the top 10 in two categories: rate of promotion externally and fastest rise to leadership. Nice.

  4. A special mention to Palantir, Deel, HubSpot, Discord, Block/Square, Faire, Chime, and Cruise for ranking highly in at least one of the categories.

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The hidden power of introverts: How to thrive without changing who you are | Susan Cain (author of "Quiet")

2025-03-16 19:03:13

Listen now on Apple, Spotify, and YouTube.

Brought to you by:

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Susan Cain, author of the groundbreaking bestseller Quiet: The Power of Introverts in a World That Can’t Stop Talking, shares a guide for how introverts can thrive in the workplace without sacrificing their authentic selves. Drawing from her extensive research and personal experience, Cain offers a powerful reframing: success doesn’t require becoming more extroverted—it demands becoming more fully yourself.

What you’ll learn:

  1. A simple definition of introversion and how it differs from shyness—plus a simple two-question test to determine where you fall on the spectrum

  2. Five practical tactics introverts can use to be more successful in business while staying true to their natural temperament

  3. How to handle challenging workplace scenarios like meetings dominated by loud voices and networking events that drain your energy

  4. Specific strategies for managers and founders to create environments where introverted team members can contribute their best work

  5. Practical techniques for saying no to energy-draining commitments

  6. Strategies for managers to better support and leverage introverted team members

  7. Practical advice for raising introverted children to help them develop confidence while honoring their natural temperament

  8. Why seeking to become “more extroverted” is the wrong goal—and what to focus on instead to achieve professional success

Some takeaways:

  1. A simple test for introversion: after two hours at a party with people you enjoy, do you feel energized and want more (extrovert) or drained and ready to leave (introvert)?

  2. About 30% to 50% of people are introverts—far more than most realize.

  3. Many high-profile people are closet introverts. Presenting as confident doesn’t mean someone isn’t an introvert.

  4. Most people become more introverted with age, not less.

  5. Introversion is a temperament to leverage, not overcome. The most successful introverts become more of who they truly are rather than trying to be extroverts.

  6. Look for successful introverted role models in your field to see how they’ve succeeded while being true to themselves.

  7. Introversion and shyness are different traits that often overlap.

  8. Public speaking fear can be conquered through desensitization—start with very small, low-stakes speaking opportunities and gradually build up.

  9. Connect one-on-one with people rather than trying to dominate group settings—this builds deeper relationships that compound over time.

  10. Create content to showcase your expertise instead of relying on spontaneous verbal communication—blogs, newsletters, or written analysis.

  11. Introverts are often misunderstood as unambitious—make your goals known to mentors who can advocate for you.

  12. In meetings, prepare points in advance and speak up early to establish presence—people pay more attention to ideas shared first.

  13. Managers should structure meetings to hear from everyone, not just the loudest voices—try round-robin formats or collecting written ideas.

  14. Create “deep work” time with no meetings so introverts can work in flow state without interruptions.

  15. For introverted children, understand they need a “longer runway” before taking off—gradually expose them to new situations with patient support.

  16. Most successful teams include both introverts and extroverts—their complementary strengths create balance.

  17. When designing your career, focus on work that aligns with your natural temperament—you should generally look forward to your days.

  18. As Gandhi (a shy introvert) said, “In a gentle way, you can shake the world.”

Where to find Susan Cain:

• Substack: https://thequietlife.net/

• X: https://x.com/susancain

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

• Website: https://susancain.net/

• Instagram: https://www.instagram.com/susancainauthor/#

• Facebook: https://www.facebook.com/authorsusancain

In this episode, we cover:

(00:00) Introduction to Susan Cain

(05:07) Understanding introversion

(08:55) The spectrum of introversion and extroversion

(13:27) Overcoming public speaking anxiety

(17:13) Learning to embrace your introverted self

(23:16) The power of leaning into your strengths

(24:36) Strategies for introverts to thrive in their career

(34:06) The importance of saying no

(38:35) What to do instead of networking

(41:59) Effective meeting participation for introverts

(47:31) Creating a productive work environment

(51:14) Raising an introverted child

(57:58) Finding the right career fit

(01:08:09) Lightning round and final thoughts

Referenced:

• The power of introverts: https://www.ted.com/talks/susan_cain_the_power_of_introverts

• The hidden power of sad songs and rainy days: https://www.ted.com/talks/susan_cain_and_min_kym_the_hidden_power_of_sad_songs_and_rainy_days

• Why bittersweet emotions underscore life’s beauty: https://www.ted.com/talks/susan_cain_why_bittersweet_emotions_underscore_life_s_beauty

• Desensitization: https://en.wikipedia.org/wiki/Desensitization_(psychology)

• Malcolm Gladwell’s website: https://www.gladwellbooks.com/

• Warren Buffett on X: https://x.com/warrenbuffett

• Dale Carnegie speaking courses: https://www.dalecarnegie.com/en/presentation-skills-public-speaking-training

• Bill Gates on X: https://x.com/billgates

• Kathy Fish on LinkedIn: https://www.linkedin.com/in/kathy-fish-23b5777/

• Why most public speaking advice is wrong—and how to finally overcome your speaking anxiety | Tristan de Montebello (CEO & co-founder of Ultraspeaking): https://www.lennysnewsletter.com/p/master-public-speaking-tristan-de-montebello

• Ultraspeaking: https://ultraspeaking.com/lenny/

• Rethinking the Extraverted Sales Ideal: The Ambivert Advantage: https://faculty.wharton.upenn.edu/wp-content/uploads/2013/06/Grant_PsychScience2013.pdf

• Cutco: https://www.cutco.com/

• Tim Ferriss’s post about his new book: https://x.com/tferriss/status/1878936085033791817

•  Mihaly Csikszentmihalyi: https://en.wikipedia.org/wiki/Mihaly_Csikszentmihalyi

• Naval on X: https://x.com/naval

• On saying no: https://www.lennysnewsletter.com/p/how-to-say-no

• Susan Cain—How to Overcome Fear and Embrace Creativity: https://tim.blog/2019/01/24/susan-cain/

• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building

• Renee Wood on LinkedIn: https://www.linkedin.com/in/recoale/

The Sopranos on Max: https://play.max.com/show/818c3d9d-1831-48a6-9583-0364a7f98453

The Talented Mr. Ripley on Prime Video: https://www.primevideo.com/detail/The-Talented-Mr-Ripley/0HA0GNFQ4ZXYPDNJHQEENK2Q6Q

• Tugboat Institute: https://www.tugboatinstitute.com/

• Leonard Cohen quote: https://www.goodreads.com/quotes/4484-there-is-a-crack-in-everything-that-s-how-the-light

Recommended books:

Quiet: The Power of Introverts in a World That Can’t Stop Talking: https://www.amazon.com/Quiet-Power-Introverts-World-Talking/dp/0307352153

Creativity: Flow and the Psychology of Discovery and Invention: https://www.amazon.com/Creativity-Flow-Psychology-Discovery-Invention/dp/0062283251

Quiet Power: The Secret Strengths of Introverted Kids: https://www.amazon.com/Quiet-Power-Secret-Strengths-Introverted/dp/0147509920

Gandhi: An Autobiography—The Story of My Experiments with Truth: https://www.amazon.com/Gandhi-Autobiography-Story-Experiments-Truth/dp/0807059099

• Flow: The Psychology of Optimal Experience: https://www.amazon.com/Flow-Psychology-Experience-Perennial-Classics/dp/0061339202

The Power of Myth: https://www.amazon.com/Power-Myth-Joseph-Campbell/dp/0385418868/

Bittersweet: How Sorrow and Longing Make Us Whole: https://www.amazon.com/Bittersweet-Oprahs-Book-Club-Longing/dp/0451499794

Good Energy: The Surprising Connection Between Metabolism and Limitless Health: https://www.amazon.com/Good-Energy-Surprising-Connection-Metabolism/dp/0593712641

The 5 Types of Wealth: A Transformative Guide to Design Your Dream Life: https://www.amazon.com/Types-Wealth-Transformative-Guide-Design/dp/059372318X

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

Lenny may be an investor in the companies discussed.

🧠 Community Wisdom: Job search burnout, prioritizing features with many stakeholders, boosting product velocity, and more

2025-03-16 01:01:32

👋 Hello and welcome to this week’s edition of ✨ Community Wisdom ✨ a subscriber-only email, delivered every Saturday, highlighting the most helpful conversations in our members-only Slack community.

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