Resources & Solutions

The Chief Repeating Officer PDF

“The single biggest problem in communication is the illusion that it has taken place.”
— George Bernard Shaw

Big Bets fail when leaders don’t repeat the right messages. The Chief Repeating Officer ensures clarity through repetition until it’s second nature to the team.

#Leadership #BigBetSuccess

Free “Why Memos?” Appendix for Big Bet Leadership

The research and benefits for using memos to think through hard problems and to work as a team is extensive. Here’s the appendix to Big Bet Leadership titled “Why Memos?”.

Click the “download” button at the bottom of this page.

Three Chapters from Think Like Amazon: 50 1/2 Ideas to Become a Digital Leader

Amazon’s famous “working backwards” approach to writing narratives, a future-press release and a set of FAQs is outlined in this set of chapters.

Big Bet Leadership GenAI Prompt Worksheet

Supercharge your thinking and writing using these GenAI prompts. Engineered to deliver the Big Bet Leadership memos. Get ready to 10x your ideas and writing with these prompts!

Big Bet Leadership Workshops

You are planning a bold move, a major transformation, an annual plan, or a significant initiative. You are not sure you have the right concept, clarity for success, or a worthy business case. We offer a fixed-fee workshop to accelerate your progress and set you up to become a Big Bet Legend!

Let’s talk about your situation and craft the high-impact BIg Bet Leadership workshop.

Executive Coaching and Advisory — Become a Big Bet Legend

Our CxO coaching and advisory approach is like no other. We focus on a business problem, measure up front, and meet typically on an every-other week basis, and measure progress after a quarter. There is homework between our meetings and adhoc discussions. You have access to our experts for specific needs. We develop your leadership expertise on being the transformational leader you aspire to be by solving a wicked problem and developing a big bet.

The outcomes are that we help your business succeed at a Big Bet, and your leadership skills are adjusted for major transformations, putting you on the path of becoming a Big Bet Legend.

Big Bet Turn-Around and Pressure Tests

Big Bets often go sideways, or you want to find out where the weakness and unsurfaced risks are for your Big Bet. You are not alone. Using proprietary techniques, we deliver an independent opinion and concrete plan for turning your transformation or situation around. Remember, Big Bet Legends do three things to succeed at Big Bets —  they create clarity, maintain velocity, and accelerate risk and value. Let’s put these habits to work for you.

We aspire for a radically different “power-to-weight” ratio — 10x insights at a fraction of the effort or expense of traditional management consulting.

Author signed copy of Big Bet Leadership

Get a copy of Big Bet Leadership signed by the author, John Rossman. This includes a limited edition Big Bet Leadership holographic sticker!

Available to US addresses only.

Big Bet Playbook Advisory Session

Embark on a transformative journey with Big Bet Leadership One-on-One Coaching a premium, personalized coaching session designed to supercharge your strategic initiatives. Directly engage with the authors of Big Bet Leadership for an hour of in-depth advice and tailored guidance. This exclusive session offers you a unique opportunity to explore the nuances of your specific challenges, gain insights into applying the Big Bet Leadership framework effectively, and develop actionable strategies for your ambitious projects. Whether you’re navigating complex transformations, spearheading innovative ventures, or seeking to drive significant growth, this coaching experience equips you with the wisdom and clarity needed to lead with confidence and achieve groundbreaking success.

Big Bet Leadership Journal

Big Bet Leadership is a playbook, meant to be put to work in developing your Big Bet Thinking, Environment and Management. This journal bridges the book into action and serves as an essential guide to become a Big Bet Legend.

The Digital Leader Newsletter

Strategy and Techniques for Change Agents, Strategists and Innovators. A newsletter from the author of “Big Bet Leadership”, “The Amazon Way” and “Think Like Amazon” John Rossman. A substack newsletter with thousands of subscribers.

Big Bet Preflight Scorecard

Embark on Your Big Bet Journey with Confidence: Introducing the Big Bet Leadership Pre-Flight Scorecard

Ready to elevate your strategic initiatives but unsure where to start? Or do you have an in-progress significant transformation and are unsure if it will be successful? The Big Bet Leadership Pre-Flight Scorecard is the perfect framework to give a holistic and fast score to indicate the strengths and areas of concern.

Big Bet Introduction Video

How’s your digital transformation, growth strategy, operating model transition or AI strategy going? Over 80% are considered failures, with only 0.5% of major initiatives deliver on time, on budget and deliver expected benefits. Big Bet Leadership is a playbook for you to become a transformational leader — a Big Bet Legend. Listen to this short video to get started.

Designing Your Leadership Principles

The Amazon Way is a durable best seller — but it’s not about Amazon! It’s about you and what you can learn from a company like Amazon to innovate, improve customer centricity, creating a data driven and accountable high-performance team. The third edition had a new appendix — how to build your leadership principle. Don’t forget to “etch the in Jell-O”!