Resources & Solutions

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.

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.

Big Bet Leadership Story

Introducing the Big Bet Leadership Storyboard Carousel – your summary overview to master transformative leadership and strategic innovation. This carousel distills the essence of “Big Bet Leadership” into a compelling visual journey designed to inspire and equip leaders with the tools and insights to successfully navigate high-stakes transformations.

The Hyper-Digital Era Demands Bold Leadership

Some say we have entered the “age of AI”, but the forces at play are much bigger than AI, or even technology, and the impact is going to create a new era of business winners and losers. Here’s the critical context for why we wrote Big Bet Leadership now.

Big Bet GPT

Unlock Your Leadership Potential: Big Bet GPT Revolutionizes Strategic Decision-Making!

10x your ideas and speed? Use our Big Bet Leadership GPT

Author Q&A Video — with Kevin McCaffrey & John Rossman

Start with the “Why” Behind Big Bet Leadership: Get to know John & Kevin, our motivations and influences in our Author Q&A video. Discover firsthand insights, behind-the-scenes stories, and the powerful strategies that can transform you into a Big Bet legend. This video is a must-watch for anyone ready to make bold moves and lead their organization to groundbreaking success.

Big Bet AI Strategy Playbook

The Big Bet Leadership AI Playbook is a step-by-step guide designed to empower business leaders in crafting and executing a cutting-edge AI strategy through the lens of the acclaimed Big Bet Leadership framework. Tailored for visionary leaders aiming to navigate the complexities of AI implementation, this playbook provides a step-by-step methodology from conceptualization to testing, ensuring your AI initiatives align with strategic objectives, drive innovation, and secure competitive advantage. With actionable insights, real-world case studies, and expert guidance, the playbook is your essential resource for turning AI ambitions into impactful realities, fostering clarity, velocity, and prioritization of risk and value in your organization’s journey towards AI-driven transformation. Includes three hours of expert consultation from Rossman Partners