Great Leaders Take Risks: Optimize How You Lead with Daily Experiments

Cohort-based Course

Continuously improve your leadership by taking risks, learning from failure, and proving the impact of your unique leadership style.

Previously at

Adobe
Slack

Course overview

Master the tools to lead your team to greatness

Not satisfied with your team’s performance? Let’s change that. But if you want change, it's on you to make it happen—whether you're the CEO or an individual contributor. 


That's leadership. And often that's where we get stuck. We want to be sure we're making the right decisions, but there are no sure things—in life or leadership! Don't miss your opportunity to create change by waiting to be sure.


Great leaders take risks. That’s why I coach startup CEOs, founders, and executives to pursue their boldest ambitions by embracing risk instead of avoiding it. Instead of waiting to be sure, we experiment daily with how they lead and prove empirically how they can achieve their ambitions. By learning from their failures, envisioning a better future, and asking for help achieving it, over time they develop their own uniquely effective leadership style.


I want to offer everyone the same opportunity to maximize their team's performance by optimizing how they lead. In this course, I'll share the same tools I use with clients so you can apply them to your own leadership challenges—and discover your own uniquely effective leadership style.


Let me be your guide. I've helped 50+ startups upgrade their cultures and boost their performance by learning to embrace risk. I’ve spent 20+ years in the tech world: as a founder backed by top investors, an operator at companies like Slack and Adobe, and now a coach and trusted confidant to startup leaders.

Who is this course for

01

Leaders who are disappointed with their team's performance but aren't sure how to drive the change they desire.

02

Managers who are trying to lead their teams effectively but are fed up with their own leadership making it so hard.

03

Anyone who dreams of making a bigger impact at work but isn't sure where to start or how to make time in their already busy day.

What you’ll get out of this course

Prove empirically how you can cultivate high performance at your company by experimenting daily with how you lead and seeing what works.

You'll let go of "making sure" before you act and embrace experimentation to prove which leadership behaviors create the best results for you—and in your specific organization.

Build the confidence to embrace risk by reducing your stress—even when faced with big expectations and heavy uncertainty.

You'll let go of stressing about getting every decision right and embrace trusting yourself to handle any outcome—even failure. If you know you can handle any outcome there's not much left to stress about!

Transform your failures into inspiration by understanding what happened and changing how you lead—instead of denying it or blaming others.

You'll let go of explaining away your failures and embrace them—both as opportunities to learn what didn't work and inspiration for what you'll try next time around.

Set a high bar by envisioning and pursuing your boldest ambitions—instead of waiting for a sure thing or settling too soon.

You'll let go of playing it safe and give yourself full permission to chase your wildest dreams. Whether you succeed or fail, you'll always know you gave it your all.

Scale the impact of your leadership by asking for help proudly yet humbly—instead of trying to coerce others or do everything yourself.

You'll let go of ineffective methods of influence and embrace building genuine relationships with your leadership, peers, and reports—so they genuinely want to help you.

What’s included

Kenneth Berger, Executive Coach

Live sessions

Learn directly from Kenneth Berger, Executive Coach in a real-time, interactive format.

Lifetime access

Go back to course content and recordings whenever you need to.

Community of peers

Stay accountable and share insights with like-minded professionals.

Certificate of completion

Share your new skills with your employer or on LinkedIn.

Maven Guarantee

This course is backed by the Maven Guarantee. Students are eligible for a full refund up until the halfway point of the course.

Course syllabus

Week 1

Oct 7—Oct 12

    How Risk-Taking Drives Results

    • Oct

      7

      Session 1

      Tue 10/75:00 PM—7:00 PM (UTC)

Week 2

Oct 13—Oct 19

    Stress and Learning from Failure

    • Oct

      14

      Session 2

      Tue 10/145:00 PM—7:00 PM (UTC)

Week 3

Oct 20—Oct 26

    Envisioning a Better Future and Asking for Help

    • Oct

      21

      Session 3

      Tue 10/215:00 PM—7:00 PM (UTC)

Week 4

Oct 27—Oct 28

    Discovering Your Unique Leadership Style

    • Oct

      28

      Session 4

      Tue 10/285:00 PM—7:00 PM (UTC)

Course schedule

3 hours per week

  • Live sessions Tuesdays 10am – 12pm PT

    October 7th, 14th, 21st, and 28th 2025


  • Weekly projects

    ~1 hour per week


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Great Leaders Take Risks: Optimize How You Lead with Daily Experiments

What people are saying

        Getting coached by Kenneth changed my life. Kenneth taught me lifelong skills to use as my career transitions and progresses, which can often be scary. Kenneth helped be go from an individual contributor, writing code all day, to a full time engineering manager with many direct reports.
Ryan Warner

Ryan Warner

Engineering Manager at mmhmm
        Kenneth really puts you in the driver seat, challenges you, helps you remove personal barriers and tackle challenges with the skills you already have—you don't have to become someone else. He has a ton of tools to teach you. His process might be genius and will definitely help you redefine your future in the best way possible!
Deep Datta

Deep Datta

Product Director at JuliaHub
        When I initially sought a coach to work on my communication style and organizational skills, I had envisioned transforming into a more assertive and decisive manager, akin to "Workzilla." Kenneth provided a deeper perspective shift, helping me understand that true transformation lies in how we respond to life's challenges.
Fanette Jobard

Fanette Jobard

Demand Generation at Sentry
        I wholeheartedly recommend Kenneth. In our time together, he has significantly impacted both my professional career and personal life. His curiosity, ability to refine aspirations, and insight into what was always within me have unlocked a truer version of myself that I didn't believe existed.
Jaymes Downer

Jaymes Downer

VP of Product, FM
        Godsend. Rockstar. Total boss. As a coach, Kenneth is fantastic, and I couldn’t recommend him more highly.
Stephen Lamb

Stephen Lamb

Co-Founder & COO, ZBiotics
        Kenneth is an amazing coach that will not take you where you expect him to, but where you need to go. My journey with Kenneth has been one of going to the basics and growing from there, stopping to create good answers to foundational questions I didn't have clarity on. I would definitely recommend him and will probably engage again in the future.
Pau Minoves

Pau Minoves

Former CTO, Typeform

Meet your instructor

Kenneth Berger, Executive Coach

Kenneth Berger, Executive Coach

Pursue your boldest ambitions by embracing risk instead of avoiding it.

Kenneth Berger coaches startup CEOs, founders, and executives to pursue their boldest ambitions by embracing risk instead of avoiding it. Great leaders take risks. There are no sure things in life or leadership! Don’t miss your big opportunity by waiting to be sure. Instead, Kenneth helps leaders experiment daily with how they lead and prove empirically how they can achieve their ambitions. After 20+ years in the tech industry, he’s a trusted confidant to CEOs, a former founder backed by top investors, and an experienced operator from Slack and Adobe. These days, he's working on a book to share his techniques for embracing risk with the world. 

Get to know him on Lenny’s Podcast

Why not asking for what you want is holding you back | Kenneth Berger

Learning is better with cohorts

Learning is better with cohorts

Active hands-on learning

This course builds on live workshops and hands-on projects

Interactive and project-based

You’ll be interacting with other learners through breakout rooms and project teams

Learn with a cohort of peers

Join a community of like-minded people who want to learn and grow alongside you

Frequently Asked Questions

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Great Leaders Take Risks: Optimize How You Lead with Daily Experiments