The Discipline of Playing Offense in Leadership

In today’s unpredictable environment, leaders cannot afford to sit back and wait for circumstances to dictate their future. Playing offense is not about being loud or aggressive—it is about being deliberate, consistent, and prepared to act. The most successful organizations are those that have built financial flexibility, studied their markets, anticipated threats, and positioned themselves to seize opportunities before their competitors.

Financial Discipline as the Foundation

The story of educational endowments provides a cautionary lesson. In 2024, endowments on average held just 2% of their assets in cash, 6% in bonds, 8% in U.S. stocks, and 16% in international stocks. The remaining two-thirds were tied up in private funds and other illiquid assets. When crisis hit in 2009, 7% of these funds admitted to selling assets into a bear market, while 9% had to borrow money at punitive rates. More recently, political threats—such as U.S. President Donald Trump’s proposal to cut federal funding to some Ivy League universities—have forced institutions to scramble for liquidity. Brown borrowed $300 million, Northwestern $500 million, and Harvard $700 million in April 2025, simply to prepare for potential shortfalls.

These decisions reflect a lack of flexibility. As Lawrence Siegel of the Ford Foundation once warned, some institutions could run out of cash in as little as two years. Poor financial management forces leaders onto the defensive, reacting from a position of weakness. The leadership lesson is clear: financial discipline during prosperous times creates the reserves needed to go on offense during crises. A clean and orderly balance sheet provides the latitude to act decisively when conditions turn adverse.

Playing Offense Through Market Focus

Financial readiness is only part of the equation. Playing offense also means knowing your customers and serving them better than anyone else. OpenAI recognized that India had become one of its largest markets—its second-biggest by users, one of its top five developer bases, and home to the largest student population on ChatGPT worldwide. Instead of waiting for competitors to move in, OpenAI introduced an India-only subscription plan at $4.57 per month and opened an office in New Delhi.

This proactive approach illustrates the essence of offensive strategy. Market analysis is not a defensive exercise; it is about anticipating customer needs while sales are strong, not only when they start to decline. Leaders who continuously study what customers are buying, how preferences evolve, and where value is shifting position their organizations to dominate, not just survive.

Offense in Tough Markets

The restaurant industry shows how offense separates winners from losers. In 2025, U.S. restaurant traffic fell 1.8%, with fast-food chains down 2.8%. Yet Chili’s defied the trend, doubling its net income and increasing sales by 22%. It did so by introducing high-value promotions like a $10.99 burger special with bottomless chips and salsa, improving meal quality and portion sizes, and even going viral on TikTok.

Rather than resting on its success, Chili’s kept innovating, adding ribs and frozen margaritas to its menu. Meanwhile, competitors like Hooters fell into bankruptcy, and Applebee’s scrambled to imitate Chili’s strategy. McDonald’s also demonstrated offense by renegotiating franchise pricing and emphasizing customer value. The lesson is that downturns punish those who failed to prepare during the good times. Grit, especially when conditions are favorable, is the hallmark of an offensive mindset.

The Language of Leadership

One subtle but telling sign that a leader is playing defense is in how results are communicated. During BJ’s August 2025 analyst call, the focus fell on challenges rather than opportunities, even though customers were actively seeking value—a clear opening for growth. BJ’s posted $150.7 million in profits, up from $145 million, but revenues fell short of expectations.

When leaders emphasize external pressures more than internal strategies, they project resignation rather than resilience. Words shape culture. A winning attitude begins with the language leaders use to describe their work. Offense is not only about actions; it is about setting a tone of determination and readiness to fight for market share.

Offense with Governments and Regulators

Playing offense is not limited to markets; it extends to regulatory landscapes. Waymo, owned by Alphabet, has already logged over 10 million rides across five U.S. cities. As it pushes to expand to 10 more, including New York City, it faces extensive regulatory hurdles: human operators in autonomous vehicles, mandatory data-sharing, and recurring safety reviews.

Waymo’s willingness to navigate these requirements shows that offense is about persistence and compliance, not avoidance. In highly regulated industries, leaders must meet government expectations proactively to unlock opportunities. Patience and discipline in negotiation are critical—Nvidia provides another example.

Caught in U.S.–China trade disputes, Nvidia has been restricted in exporting advanced chips. Although the U.S. allowed sales of a weaker H20 model, Beijing itself stalled orders, citing security risks. Rather than retreat, Nvidia’s CEO continued working with both governments, stressing that AI innovation would advance globally with or without U.S. support. This persistence highlights that offensive strategy often requires long, painstaking engagement. Leaders must ask themselves: are we patient enough to endure negotiations that span years, involve multiple stakeholders, and face constant setbacks?

Innovation as a Weapon

Innovation remains one of the most powerful forms of offense. In the crowded energy drink market, Celsius has distinguished itself as a fitness-oriented alternative to Red Bull and Monster, offering diverse flavors and healthier positioning. Its sales grew 29% in a single quarter. But its real advantage lies in strategy: pricing itself between its bigger rivals, while also competing against indirect alternatives like ready-to-drink coffee and tea.

Offense in this context means never relaxing in a competitive market. Leaders must push their teams to find new ways to differentiate, using data and consumer insight to refine offerings.

Quiet, Consistent Offense

Offense does not always mean dramatic moves. Bank of America, an institution few associate with cutting-edge AI, has quietly built one of the sector’s strongest AI portfolios. Since 2018, it has pursued more than 1,400 patents, with about half approved. Its chatbot Erica has handled over 3 billion customer interactions, while an internal chatbot supports 90% of its 213,000 employees.

Its recent commercial banking AI tool, which generates prep documents for client meetings, illustrates disciplined innovation. Importantly, the bank has avoided unnecessary AI applications, recognizing cost realities and customer preferences—for instance, private banking clients do not want voice interactions. Offense here is consistency: building capability steadily over years without chasing flashy trends.

Discipline Secures the Future

Financial discipline also enables offensive opportunities in asset ownership. While most department stores have sold real estate to generate cash, Dillard’s took the opposite route, buying Longview Mall in Texas for $34 million. Unlike real estate firms that neglect maintenance, Dillard’s plans improvements to increase foot traffic and sales. This move was possible only because of its strong balance sheet—over $1 billion in cash—and a loyal customer base. Offensive strategy in this case is about long-term control: securing assets that ensure future growth.

The Limits of Offense

Yet leaders must recognize where not to play offense. Cracker Barrel learned this the hard way when it redesigned its decades-old logo in 2025. Intended to modernize the brand, the change triggered backlash, calls for boycotts, and a 9% stock drop, on top of traffic already 16% lower than in 2019. Customers accused the company of abandoning its distinctiveness.

This misstep underscores an important truth: the one place a company should never go on the offensive is against its customers. Offensive strategy must be cautious, like testing ice before walking across it. Leaders must introduce changes thoughtfully, test them with diverse groups, and avoid backlashes that undermine trust.

Conclusion

Playing offense is not about aggression or showmanship. It is about discipline in finances, persistence in negotiations, creativity in innovation, and attentiveness to customers and regulators alike. Whether through Dillard’s financial prudence, Chili’s customer-driven promotions, OpenAI’s market targeting, or Nvidia’s patient diplomacy, the common thread is that leaders who prepare in good times, stay focused on customers, and commit to long-term consistency are the ones who thrive.

In business, defensive leaders survive only as long as conditions remain stable. Offensive leaders, however, create their own stability by staying disciplined, innovative, and forward-looking—turning uncertainty into opportunity.

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I’m Nduati

I dissect the strategies, decisions, and personal philosophies of notable business leaders—examining not just what they do, but why they do it, and how their leadership style shapes the success or struggles of their organizations.

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