5 Big Bet Leadership Strategies at Amazon: Insights from John Rossman
Throughout my tech career, I’ve realised that most leaders are not lacking in ideas. What they often struggle with is providing clarity in a world full of ambiguity.
I had the pleasure of interviewing John Rossman, an ex-Amazon executive and author, where we discussed his new book Big Bet Leadership. The book focuses on successful strategies for navigating leadership challenges in this hyper-digital world we currently find ourselves. In this post, we’ll explore five key strategies from Big Bet Leadership that leaders can apply to succeed in complex digital transformation.
💡 1. Transform Ambiguity Into Clarity
Leaders often struggle to provide clarity on the problem that is being resolved and jump too quickly into solution mode.
Rossman advocates the Clear Path strategy which requires us to start with the customer problem and work backwards, rather than the other way around. In Big Bet Leadership, he elaborates on how Amazon hones this process through practices like the "What Sucks” memo. It insists that teams focus on the pain points that need solving, and later develop a single "solution." Once that big, hairy problem is crystal clear, work can begin to solve it.
But how can we as leaders put this into practice?
We can begin by writing out our ideas. It requires deep thought upfront, but it saves endless hours of back-and-forth debates later on. While it sounds simple, putting decisions into words builds momentum and clear direction for the team.
"Clarity is the most important strategic advantage." — John Rossman
For more episodes on leadership, take a look at The Captain's Playbook.
🔥 2. Make Big Bets Smaller Through Hypothesis Testing
When we hear the phrase "big bet," I think of a scene at the casino where the gambler stakes all of their money on red or black at the roulette wheel.
Rossman flips this on its head: the key to successful Big Bet Leadership isn’t gambling everything on one idea, but instead, rigorously testing key hypotheses before fully committing resources.
Start small. Test out that high-impact idea at a lower scale first. Most organisations can afford an MVP (minimum viable product) stage to validate assumptions or prototype crucial parts of a larger system. If you don't have a clear MVP, you're already in dangerous territory. The goal is to reduce the big bet’s risk into manageable, scalable chunks that can be tested quickly and iterated upon.
Start asking your team: What can I test early without going all-in? Then, stick to it without skipping validation steps. Not all ideas can or should be given the green light just because they seem promising upfront.
If you’re interested in building an experimentation mindset then I recommend Agile - Cultivating Transformations.
🚀 3. Maintain Velocity Through Clear Leadership Principles
It's one thing for a tech organisation to innovate; it’s another to sustain that velocity over the long term. Take Amazon, for example. During Rossman’s time at Amazon, it achieved its first billion-dollar quarter while still a sub-four-billion company. How did they maintain the velocity required to grow into a $600 billion business?
One secret is sticking to leadership principles that work across all levels, from entry-level engineers to executives. These principles become the guiding light that drive every action across the organisation. Everyone has clarity of what matters when those principles are clear.
One of Amazon’s methods that I've been curious about is the famous single-threaded leader concept. It champions having a single individual committed to a project's success. That person is the Directly Responsible Individual (DRI), and in Amazon’s case, they had the power to make decisions, rally stakeholders, and unblock bottlenecks.
When velocity breaks down, it's often because no one feels true ownership.
⚡ 4. Anticipate Disruption and Act Fast
As Rossman reminds us:
The last 25 years of digital disruption will pale in comparison to the next 25 years. Today’s Fortune 500 companies have a life expectancy of just 20 years, compared to 60 years in the mid-20th century.
Disruption is inevitable—but only the businesses with strategies aligned for rapid adaptation will survive.
But how do you anticipate disruption and act fast? The answer lies in deferring large investments until your team has de-risked as many assumptions as possible. Start small, focus on the challenges of today, and be agile with those medium-sized bets. This approach ensures that rather than inflating scope prematurely, you're validating every single pound/euro/dollar by ensuring the solution is sound at all levels. It’s an efficient way to stay on top of innovation while keeping the company structure lean.
Companies that are slow to react to AI and digitalisation will quickly find themselves turned into commodities—just look at the likes of Nokia.
If you are looking for more inspiration on how large organisations successfully implement agile ways of working, then check out this episode How I Led An Agile Transformation.
✅ 5. Meticulous Preparation Triumphs Over Endless Meetings
Finally, one of Rossman’s most impactful insights is around poorly executed meetings. If you’ve worked in tech for some time, you'll be familiar with how frustrating and wasteful meetings can be.
Rossman shares the Continue, Kill, Pivot, or Confusion approach. High-stakes meetings need three outcomes: keep it going (continue), change direction (pivot), or drop it (kill). Unfortunately, many poorly prepared meetings land in the fourth, unproductive option: confusion.
Bottom line? You can't avoid meetings, but you can prepare for them properly.
Memos sit at the heart of Amazon’s meeting prep process. These memos provide every detail of what needs to be done, alternatives that have been considered, and the challenges ahead. Instead of wasting valuable time arguing, memos help teams focus on what is important.
Conclusion: Become a Big Bet Leader
It's clear from John Rossman’s framework that real leadership isn’t about making decisions on the fly or hedging everything on a gut feeling. Impactful decision-making in complex situations comes down to clarity, sustained velocity, and disciplined testing.
Want more inspiration on how to develop your leadership approach? Then check out this episode Greatest Leader in History: What Can Agile Leaders Learn.
For more reading, I suggest checking out these books:
The Amazon Way by John Rossman
Think Like Amazon: 50 1/2 Ideas to Become a Digital Leader by John Rossman
The Lean Startup by Eric Ries
Guest: John Rossman
John Rossman is the author of four books on leadership and business innovation including the best seller The Amazon Way and Big Bet Leadership. He is an early Amazon executive who played a key role in launching the Amazon marketplace business in 2002. Today he is a leading keynote speaker on leadership for innovation and transformation. John is an operator and builder whose love is diving into business problems and customer needs designing innovative solutions and business models and creating durable enterprise value. He has served as the senior technology advisor at the Gates Foundation and senior innovation advisor at T-Mobile.
His new book, Big Bet Leadership: Your Transformation Playbook for Winning in the Hyper-Digital Era, is an actionable playbook for senior leaders to succeed at complex transformations.
John is the founder of Rossman Partners, a strategy & leadership solutions firm.
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