What Game Are You Playing?
A Strategic Lens for Family Business Leaders and the Family Enterprise Game Plan
A Lesson from Geopolitics
In a recent article, David Marcus described U.S. Presidential leadership styles in a way that immediately resonates: as games.
He suggested that Barack Obama approached global affairs like a Jigsaw Puzzle—methodically fitting pieces together into a coherent whole. George W. Bush, by contrast, operated more like a game of Chess, focused on positioning, sequence, and decisive moves. And Donald Trump, in Marcus’s view, has treated geopolitics as a high-stakes Poker Game—centered on leverage, timing, reading opponents and winning.
Whether one agrees with those characterizations is not the point.
The point is that the “game” a leader is playing shapes everything—how decisions are made, how risk is evaluated, and ultimately, what outcomes are achieved.
Family Business Leaders operate the same way. But unlike political leaders, you are not just managing a single system. You are simultaneously navigating family dynamics, business operations, ownership structures, and long-term legacy objectives.
That makes the choice of “game” even more consequential.
The Games Family Business Leaders Are Playing
1. Chess — The Game of Structure and Foresight
Some Family Business Leaders approach their role like a Chess match. You think several moves ahead, you value structure, and you are deliberate about governance and succession.
This mindset is powerful when designing boards, ownership frameworks, and leadership transitions. It creates stability and predictability—two things every Family Enterprise needs.
But Chess assumes a relatively stable and knowable environment. When markets shift quickly or Family dynamics evolve unpredictably, a purely Chess-based approach can become too rigid to respond effectively.
2. Poker — The Game of Risk and Leverage
Other Family Business Leaders operate like Poker players. You are comfortable making decisions with incomplete information, you understand leverage, and you are often highly effective in negotiations and transactions.
These are the dealmakers—the ones who drive acquisitions, structure complex agreements, and capitalize on opportunities others hesitate to pursue.
But Poker introduces volatility. Over time, a strategy built too heavily on risk and instinct can produce uneven outcomes—particularly in a Family Enterprise that must endure across generations.
3. Monopoly — The Game of Asset Accumulation
Many Family Business Leaders are, in effect, playing the game of Monopoly. Your focus is on acquiring assets, building cash flow, and expanding the Family’s economic footprint.
This is often how real wealth is created—through disciplined ownership of businesses, real estate, and investments.
Yet Monopoly contains a hidden assumption: that all players are aligned. In a real Family, that alignment cannot be taken for granted. Without intentional governance and communication, financial success can coexist with fragmentation and conflict.
4. The Jigsaw Puzzle — The Game of Integration
At higher levels of complexity, the Family Enterprise begins to feel like a Jigsaw Puzzle. Family Business Leaders find themselves working to fit together legal structures, tax strategies, Family relationships, and business operations.
This integrative mindset is essential. It reflects a recognition that no single decision exists in isolation.
But there is a risk here as well. The Jigsaw Puzzle can become endless—constantly being refined, but never fully assembled. Execution can be delayed in the pursuit of completeness.
5. Survivor — The Game of Relationships and Influence
Not all dynamics in a Family Enterprise are structural. Many are relational.
In this sense, parts of the Family Enterprise often resemble the TV game of Survivor. Alliances form, influence shifts, and decisions are sometimes shaped as much by trust and perception as by objective performance.
This is particularly true in Family governance, Shareholder relationships, and Board interactions.
The risk is not that these dynamics exist—they always will. The risk is when they operate beneath the surface, unmanaged, quietly shaping outcomes in ways that formal structures never intended.
6. Risk — The Game of Expansion
During periods of growth, the Family Enterprise often shifts into a game more like Risk. Leaders are deciding where to expand, how to allocate resources, and how far to extend their reach.
Growth creates opportunity—but it also creates exposure. Expansion without sufficient infrastructure, leadership depth, or capital discipline can lead to overextension.
Many Family Businesses encounter their greatest challenges not during decline, but during rapid growth.
7. Tetris — The Game of Operational Efficiency
On a day-to-day basis, many Family Business Leaders are playing something closer to Tetris. Time, talent, and capital must be continuously arranged in ways that keep the organization functioning effectively.
This is the operational layer of the Family Business—where efficiency, responsiveness, and execution matter most.
But Tetris has no long-term direction. It rewards immediate optimization, not strategic clarity. A Family Business can become very good at operating without ever stepping back to ask where it is going.
8. The Relay Race — The Game of Succession
At critical moments, the defining game becomes succession—more like a Relay Race than anything else.
Success is not determined solely by the strength of one leader or the readiness of the next, but by the quality of the handoff between them.
Many Family Businesses perform well for decades, only to falter at this transition point. Roles are unclear, timing is off, or expectations are misaligned—and the baton is dropped.
9. The Auction — The Game of Value Discovery
There are also moments when the Family Enterprise enters an entirely different type of game—an Auction.
Whether through a sale, recapitalization, or internal buy-sell process, value is tested in real time. What the Family believes the Family Business is worth is compared against what others are willing to pay.
These moments can be clarifying—or unsettling.
Without a structured and competitive process, Families often leave value on the table or misunderstand the true market position of their Family Business.
The Bigger Insight: You Are Playing Multiple Games
When viewed together, a clear pattern emerges.
Most Family Business Leaders are not playing one game.
You are playing several—simultaneously.
- Strategy may look like Chess
- Deals may resemble Poker
- Wealth building may follow Monopoly
- Family dynamics may reflect Survivor
- Operations may feel like Tetris
- Succession becomes a Relay Race
The problem is not the existence of multiple games.
The problem is lack of alignment between them.
The Endgame: From Playing Games to Orchestrating Them
At the highest level, the most effective Family Enterprises move beyond any single game.
They begin to resemble something more like a Symphony.
Different players. Different roles. Different timing.
But all aligned around a shared direction.
This is where the Family Enterprise Game Plan becomes essential.
It provides:
- A framework for aligning Family, Business, and Ownership
- A structure for coordinating multiple forms of capital
- A process for ensuring continuity across generations
And it begins with a deceptively simple—but strategically profound—question:
What game are we playing today—and is it the right one for where we are going?
Because the goal is not simply to win a game.
It is to build a Family Enterprise that continues to win—during your time in action and from generation to generation.
Related Attorneys
