Running a business can sometimes feel like being a contestant on a game show. You’re under the lights, faced with three doors. Behind one is a grand prize, and behind the others, well, not much. Do you stick with your first choice, switch doors, or just walk away? Decisions are constant, outcomes uncertain, and stakes often high.

Now, throw culture into the mix. Imagine that the audience is yelling advice at you in ten different languages, each with its own unspoken rules. What some see as enthusiasm, might come across as chaos to another. Suddenly, the whole decision-making process feels a lot more complicated.

Two brilliant books can help you navigate this chaos: Thinking in Bets by Annie Duke and The Culture Map by Erin Meyer. Duke, a former professional poker player, teaches us how to make decisions under uncertainty. Meyer, a cultural expert, offers a roadmap for decoding cross-cultural communication. Together, they provide a powerful toolkit for anyone trying to lead, negotiate, or simply not lose their mind in today’s hyper-connected, unpredictable world.

And as someone who’s had to mediate cultural clashes during Merger and Acquisition negotiations and guide teams through tough pivots (as I shared here or here), I can tell you these insights are lifesavers. I was brought in to help navigate the challenges of merging a South Asian company with a European one. The task wasn’t just about figuring out product integration or aligning markets (though that alone could fill several sleepless nights). The real complexity lay in the cultural and decision-making differences between the two teams.

How do you align a top-down decision-making structure with one that thrives on collaboration? How do you communicate with one side that prefers clear, direct instructions, while the other values subtlety and context?

That experience taught me a lot about cultural dynamics. It also forced me to reflect on how we make decisions, especially under pressure. 

Annie Duke’s Thinking in Bets flips our understanding of decision-making. Most of us judge the quality of our decisions based on outcomes. If things turn out well, we assume we made the “right” call. If not, we beat ourselves up for being “wrong.” Duke’s central argument is that this mindset is fundamentally flawed. Decisions, she says, are bets. They’re guesses based on incomplete information and probabilities. Not certainties.

This distinction is critical because it shifts the focus from outcome to process. Duke encourages us to think like poker players, where success is about making consistently good bets over time, even if some hands don’t pan out. Here’s how it applies in real life:

1. Embrace Uncertainty, Don’t Fear It

Decisions are rarely black and white. There’s always some level of ambiguity, and that’s okay. Duke advises reframing decisions as experiments. Instead of asking, “Is this the right move?” ask, “What are the odds this move will work based on what I know now?” Consider Jeff Bezos and Amazon’s decision to launch AWS (Amazon Web Services). At the time, the idea of a retail company offering cloud computing seemed bizarre. But Bezos wasn’t betting on certainty. He calculated that the odds of businesses needing scalable infrastructure were high. AWS became one of Amazon’s most profitable ventures, not because Bezos had a crystal ball but because he was willing to experiment with uncertainty.

2. Avoid Resulting

Resulting is when you judge a decision solely by its outcome rather than its logic. Just because your last-minute pivot led to a big win doesn’t mean it was a smart move. It might’ve been sheer luck. Likewise, a failed marketing campaign doesn’t necessarily mean the strategy was flawed. Let’s say you decide to launch a new product and it flops because a global pandemic hits two weeks later. Was the decision bad? Probably not. The process might have been sound, the timing just stunk. Duke’s advice? Evaluate your decision-making framework, not just the results.

3. Create a Culture of Better Bets

Duke emphasizes the importance of team collaboration in decision-making. Encourage dissent, welcome diverse perspectives, and treat every meeting as a brainstorming session to improve your collective odds. Pixar is known for its “Braintrust” sessions, where directors present rough story ideas to a group of colleagues who critique and refine them. These meetings aren’t about tearing people down. They’re about making the best bet for the movie’s success by improving the decision-making process.

If Duke teaches us how to navigate uncertainty, Erin Meyer shows us how to decode cultural complexity. In The Culture Map, Meyer explains how cultural norms shape communication, feedback, decision-making, and leadership styles. Whether you’re leading a global team or expanding into a new market, understanding these differences can make or break your success.

1. High-Context vs. Low-Context Communication

In high-context cultures (e.g., Japan, India), communication is subtle, indirect, and full of unspoken nuances. In low-context cultures (e.g., the U.S., Germany), people value clarity, directness, and explicit instructions. Imagine you’re working with a Japanese client who nods during a meeting. In Japan, nodding doesn’t necessarily mean agreement. It often means, “I hear you.” A German client, on the other hand, might explicitly tell you they disagree with your proposal. Without understanding these nuances, you might assume approval where there isn’t any or be put off by direct criticism.

2. Giving and Receiving Feedback

Cultures differ wildly in how they deliver criticism. Americans often sandwich negative feedback between positive comments, while Dutch professionals might deliver it bluntly, without sugarcoating. Meyer recounts the story of a French manager who called his American employee’s report “not bad.” The American, accustomed to enthusiastic feedback, interpreted this as harsh criticism. The French manager, however, thought he was being generous.

3. Hierarchical vs. Egalitarian Leadership

In some cultures (e.g., South Korea, Mexico), hierarchy is deeply ingrained, and employees expect leaders to give clear, top-down directives. In others (e.g., Sweden, Denmark), decision-making is more collaborative, and leaders are expected to act as facilitators. If you’re leading a multinational team, assume nothing. A Danish employee might expect a brainstorming session where everyone contributes equally, while a Brazilian colleague might prefer clear guidance. Flexibility and cultural sensitivity are key.

The real magic happens when you combine Duke’s decision-making insights with Meyer’s cultural frameworks. Consider this scenario:

You’re expanding your business into Southeast Asia, negotiating a partnership with a local company. Duke’s lessons help you frame the negotiation as a bet: What’s the likelihood this partnership will succeed given the risks? Meyer’s framework reminds you to adapt your approach. Focusing on relationship-building (high-context culture) rather than diving straight into the numbers (a low-context tendency). By blending these perspectives, you’re not just making a bet. You’re increasing your odds of success.

At its core, leadership in today’s world is about navigating uncertainty while respecting diversity. Annie Duke’s Thinking in Bets gives you the tools to make smarter, more flexible decisions in unpredictable environments. Erin Meyer’s The Culture Map teaches you how to connect across cultural divides, ensuring your decisions resonate with everyone involved.

Together, these books remind us that success isn’t about having all the answers. It’s about asking better questions, staying open to new perspectives, and embracing the complexity that comes with working in a global, fast-changing world. Whether you’re pitching to investors, building a multicultural team, or simply arguing with yourself about whether to order takeout again tonight, these tools can help you navigate the chaos with confidence and maybe even a little humor.

Takeaways

1. Think in Bets: Treat decisions as experiments based on probabilities, not certainties. Evaluate the process, not just the outcome.
2. Understand Context: Cultural differences in communication and leadership matter. Adapt your style to your audience for better results.
3. Avoid Resulting: Don’t judge decisions solely by their outcomes—focus on the logic behind them.
4. Leverage Cultural Diversity: Build teams and strategies that draw on diverse cultural strengths, rather than assuming a one-size-fits-all approach.
5. Stay Curious: Better questions lead to better decisions. Keep an open mind and learn from every experience.