Seven Leadership Lessons I Wish I'd Known Sooner

Author

Charlene Li
March 25, 2025

Before we begin, a quick note:

This marks the final "Big Gulp" newsletter in its current form. The next newsletter you'll receive from me will be called "Leading Disruption"—the title of my LinkedIn Newsletter which goes out to 100,000 subscribers each week and offers insights on how leaders set strategy, build culture, and manage uncertainty to drive transformative growth.

I've long been wanting to create one central home for my two newsletters, and I'm excited to blend them into a single, cohesive conversation. I'll be publishing these insights across Beehiiv, LinkedIn, and Medium—big changes coming soon!

By staying subscribed here on Beehiiv, you remain in my inner circle as these two worlds come together. You'll continue to receive the same quality insights, just under a unified banner.

Perhaps most exciting? I'm looking to transform The Big Gulp into a podcast launching this fall. As a loyal subscriber, you'll be the first to hear about development milestones and have exclusive opportunities to shape the topics we'll explore together.

Whether you follow me on LinkedIn, Medium, or here on Beehiiv, you'll receive the same content. This isn't a goodbye—it's an evolution of our conversation about navigating change and embracing disruption.

I'm excited for this next chapter and grateful to have you along for the journey. 

In my newspaper days, I had no chairs in my office.

When someone needed to talk, they'd walk in and we'd handle it right there. No scheduling, no emails, just quick conversations that got things done.

Speaking at a startup conference in San Diego recently, I realized I've collected quite a few unconventional leadership practices over the years—from running large teams at Forrester to founding Altimeter to my current role. While these insights emerged from conversations with founders, they're just as valuable for leaders in established organizations.

Here's what I've learned about building strong organizations through seemingly small leadership choices:

1️⃣ Find Your Blue Ocean

When I founded Altimeter after a decade at Forrester, I faced a challenge. How could a four-person analyst firm compete with industry giants? The answer came from a simple insight: while everyone else charged $20-30,000 for research access, we could give our research away for free and monetize through consulting.

It's harder to compete against free. This "Blue Ocean Strategy"—going where others aren't—became our differentiator. I see similar thinking in how DeepSeek just developed their AI model for (reportedly) $6 million while others spend billions. Sometimes the most powerful move is choosing a different game entirely.

2️⃣ Think Beyond Annual Plans

Most organizations get stuck in 12-month planning cycles. But real strategy needs a longer runway. I've consistently used an 18-month framework—what I call the "six quarter walk"—throughout my career. Where do we need to be in 18 months? What steps must we take today to get there?

This timeline works because it's long enough to drive real change but concrete enough to plan actionable steps. Five-year plans sound impressive, but 18 months forces you to get specific about the building blocks of transformation.

3️⃣ Make Meetings Matter

Remember that office with no chairs? In that fishbowl space, when someone came to talk, we'd both stand. These weren't "stand-up meetings" from agile development—they were genuine conversations that stayed focused because no one could settle in.

The results surprised me. Instead of scheduling 30-minute slots for five-minute conversations, we could resolve issues immediately. The physical act of standing kept us engaged and active. Even now with remote work, I encourage quick calls over scheduled meetings whenever possible.

4️⃣ Start With the End in Mind

One of my most powerful practices is discussing someone's last day during their first interview. This approach built trust through radical honesty. At Altimeter, we hired amazing people knowing we might not be able to support their entire career journey.

Being upfront created extraordinary trust. Instead of dancing around career growth or having people sneak off to interviews, we could have open conversations about development. When someone did leave, it became a celebration of their next step rather than a betrayal of loyalty.

5️⃣ Build a Feedback Culture

At Altimeter, we had a problem. Our brilliant team was also incredibly nice—too nice to give direct feedback. Meanwhile, the one person who was direct came across like a bull in a china shop. Neither approach served us well.

The solution came from the Center for Creative Leadership's Situation-Behavior-Impact framework. We started small, practicing with positive feedback: "When you opened that meeting with a joke, it put everyone at ease." Eventually, we could say, "Can I give you an SBI?" and create instant psychological safety for honest conversations.

6️⃣ Skip the Third Shift

Early in my career, someone gave me vital advice: Don't work the third shift. The first shift is your workday. The second is family and community time. The third shift is when you feel guilty about not doing enough in the first two.

This guilt serves no one. You can't do more than your best. When I catch myself working that third shift—anxious about what I haven't done—I remind myself to put that energy into being present in the first two shifts instead.

7️⃣ Know Your Superpower

"What's the one thing you do better than anyone else?" This question has guided my entire career. For me, it's making complex, scary, disruptive things simple enough for people to take action. 

Don't confuse this with unfair advantages like networks or credentials. I'm talking about that core capability you bring to everything you do. When I discovered my superpower was simplifying complexity for transformation, it shaped every role I took on, every book I wrote, every company I built.

The Path Forward

Leadership isn't about having all the answers. It's about creating environments where people can take risks, have honest conversations, and bring their strengths to work. Sometimes that means having no chairs in your office. Sometimes it means talking about someone's last day during their first interview.

But always, it means knowing that if they won't chop off your fingers, why worry about mistakes?

What I Can’t Stop Talking About: 

  • This year, I wish you failure. I mean it: The most innovative leaders embrace failure as evidence of taking real risks. If you're never failing, you're simply not pushing hard enough to create meaningful disruption. Bookmark this—and then go fail beautifully.

  • We formed pods in the pandemic. But Covid is over—and we're still hiring in pods. When facing uncertainty, we naturally gravitate toward the familiar. This similarity bias silently shapes our organizations as we default to people who think, look, and act like us. But what we need most during uncertainty is precisely what's hardest to embrace: diverse perspectives. 

  • Everybody needs somebody to remind them to speak up. My first manager transformed my career with one simple sentence: "You're in the room for a reason." That’s what leaders do, after all. They see and develop the potential in each member of their team. Here’s what I learned—and how I pay it forward.  

My Latest: 

  • Catch up on my webinars! You can still review the slides and recordings of my two new webinars. In “Unlocking The Power of Generative AI,” I explain how to set up a generative AI “playground,” three ways to elevate your leadership with step-by-step instructions, and the broad outlines of creating a strategy. In “Developing a Winning Generative AI Strategy for Competitive Advantage,” I walk through the steps needed to create a cohesive AI strategy. 

  • Five AI predictions that actually matter—and what to do about them. Most predictions just tell you what's coming, leaving you wondering "So what?" That’s why in Leading Disruption, I'm sharing five transformative AI trends for 2025 with clear actions to prepare—from implementing AI amnesty programs to developing your own "AI accountability ledger." Before spring has sprung, consider how your organization is preparing for what’s next. 

My Upcoming Appearances:

If you want me to speak at an upcoming event or conduct a workshop with your executive team, please drop me a note at [email protected]. 

If this information was helpful, there’s plenty more!

📌 Sign up for updates and early access to my upcoming book, co-authored by Katia Walsh, which is all about creating a winning generative AI strategy.

Thank you for subscribing to The Big Gulp Newsletter, which goes out to thousands of disruptors every other week to help you on your disruption journey—plus a curated recommendation list of the things I can’t stop talking about. 

Charlene Li

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