Today I Choose to be Shrewd – How to be Shrewd

When I first started helping my current CEO with a marketing project and was in his offices in Utah for that, I shrewdly noted the lack of harmony between the accounting team—especially the CFO—and the rest of the C-Suite. I also overheard that taxes were three years behind, despite a huge accounting staff.

When a brouhaha erupted between the CFO and the CEO and COO, I waited for the dust to settle and calmly asked how I could help. I jumped into the situation with confidence and both feet. I was able to catch up their books and their taxes in six months.

That strategic move led to my position as CFO for the past ten years.

Looking back, that moment taught me everything about strategic thinking: observe carefully, read the room, position yourself as the solution rather than part of the problem, and act decisively when opportunity presents itself.

Today, I choose to be strategically astute—not manipulative, but intelligently aware of dynamics and opportunities that others might miss.

The Art of Strategic Observation

True business acumen begins with the ability to read situations that others either ignore or misinterpret. While most people focus on surface-level interactions—the formal presentations, official org charts, and stated policies—strategic thinkers notice the subtle dynamics that actually drive organizational behavior.

In that Utah office, the official story was that they had a robust accounting department handling all financial matters. But my trained eye picked up on tension, inefficiencies, and the kind of dysfunction that often signals deeper systemic problems. The body language, overheard conversations, and general atmosphere told a different story than the one being presented in meetings.

This kind of observational skill isn’t about being nosy or gossipy—it’s about developing the ability to see patterns and connections that reveal underlying realities affecting business operations.

Reading Between the Lines

Strategic intelligence involves interpreting information that isn’t explicitly stated. When I heard that taxes were three years behind despite having a large accounting staff, that wasn’t just an interesting fact—it was a red flag indicating serious management or competency issues that would inevitably create crisis and opportunity.

Most people hear such information and file it away as “not my problem.” Strategic thinkers hear it and immediately begin calculating implications: What does this suggest about leadership oversight? How long can this situation continue before exploding? What capabilities would be needed to resolve it? Who would have the authority to hire someone to fix it?

This kind of analytical thinking allows you to position yourself advantageously before crises fully emerge, rather than scrambling to respond after problems become obvious to everyone.

Timing and Positioning

Perhaps the most crucial aspect of strategic thinking is understanding when and how to act on your observations. I didn’t immediately offer to help with the tax situation—that would have seemed presumptuous and might have been perceived as criticism of existing staff.

Instead, I waited for the inevitable crisis to create an opening where help would be welcomed rather than resented. When the dysfunction finally erupted publicly, I was ready with a calm, confident offer of assistance that positioned me as a solution-bringer rather than another problem to manage.

This patience and timing turned what could have been seen as opportunism into genuine value creation for the organization and career advancement for me.

The Confidence to Act Decisively

Strategic thinking is worthless without the courage to act on your insights. When the opportunity presented itself, I didn’t hesitate or second-guess my assessment. I jumped in with both feet, confident in my ability to deliver on what I was promising.

This confidence came from accurate assessment of both the situation and my own capabilities. I knew I could clean up their books and taxes because I had done similar work before. I knew the organization needed this help because I had observed the dysfunction firsthand. The strategic move was connecting my capabilities to their needs at the optimal moment.

Practical Applications of Strategic Thinking

Developing shrewd business instincts requires consistent practice in observation, analysis, and strategic positioning across various situations.

Study organizational dynamics. Pay attention to who actually makes decisions, where conflicts exist, and what problems are being avoided rather than addressed. These observations often reveal opportunities.

Listen for what’s not being said. In meetings, conversations, and presentations, notice gaps, inconsistencies, or topics that seem to make people uncomfortable. These often point toward significant underlying issues.

Assess your unique value. Identify capabilities you possess that could address problems you’re observing. Strategic positioning requires matching your strengths to organizational needs.

Time your moves carefully. Wait for moments when your assistance will be welcomed and valued rather than forcing help on situations that aren’t ready for intervention.

Follow through completely. When you commit to solving a problem, deliver comprehensively. Your reputation for reliable execution creates future opportunities for strategic positioning.

Strategic Thinking vs. Manipulation

There’s an important distinction between strategic thinking and manipulative behavior. Strategic thinking involves accurately reading situations and positioning yourself to create mutual value. Manipulation involves deceiving others or creating artificial advantages at their expense.

My Utah situation created genuine value for the organization—they got their books cleaned up and taxes filed, which solved real problems and likely saved them significant money and legal complications. I benefited by demonstrating valuable capabilities that led to career advancement. This was strategic positioning that served everyone’s interests.

Healthy strategic thinking looks for win-win opportunities where your success contributes to others’ success rather than competing with it.

Building Strategic Relationships

Long-term strategic success depends on building relationships based on genuine value creation rather than just personal advancement. The reason I’ve maintained my CFO position for ten years isn’t just because I solved their initial crisis—it’s because I’ve continued to provide valuable service that justifies their investment in me.

Strategic thinkers understand that short-term tactical victories are less valuable than long-term relationship building based on mutual benefit and genuine competence.

The Long View

Perhaps the most important aspect of strategic thinking is maintaining perspective on long-term goals while navigating short-term opportunities. My decision to help with the Utah crisis wasn’t just about solving an immediate problem—it was about positioning myself for the kind of career opportunity I wanted.

This requires clarity about your own objectives, honest assessment of your capabilities, and patience to wait for situations where your strategic moves serve both your interests and those of others.

Today, I choose to be strategically astute not to gain unfair advantages over others, but to recognize and create opportunities for mutual success through intelligent observation, careful positioning, and decisive action.

Because the shrewdest move of all is building a reputation for creating value wherever you go.