The Finance Gem 💎 #112: Your CEOs 100 Financial Blind Spots

Hi there, 

Most CEOs think success comes from having all the answers.

But if you can’t first ask the 100 questions that define your business’s financial health, strategy, and risk, you’re not running the company.

It’s running you.

You can’t optimize what you don’t measure.
You can’t scale what you don’t understand.
You can’t lead what you haven’t stress-tested.

Every board meeting, investor pitch, and leadership retreat ultimately asks the same thing:

Can you answer those key questions that determine your company’s future?

In today’s issue, I’ll show you how to identify the blindspots that keep CEOs reactive—and the financial systems that make leaders unshakably prepared.

Here’s what we’re covering:

1. Why you should sign up for Finance Connect at SAP Connect 2025 (Free Virtual Sessions)

2. My Free Cash Flow Masterclass on October 9

3. The 100 Questions CEOs shoud be asking 

🔴 On October 9 you’re invited to a brand new masterclass that I have never presented before.

The 5 Cash‑Flow Planning Mistakes That Derail Strategy & Crush Valuation

📅 Thursday, Oct 9
🕐 12 PM EST / 5 PM GMT

This masterclass is only happening on October 9. It’s scheduled before 2026 planning kicks off. If you don’t address these cash flow blind spots now, you may lock in a plan that’s already at risk. So make sure you join and attend live for the opportunity to have your questions answered in the Q&A at the end of the session.

This will be an exclusive session with limited spots which I am only having on October 9.

 Secure your seat now.

The 100 Questions That Define a CEOs Financial Leadership

1. Leadership and Strategy

A company doesn’t fail from lack of vision. It fails because strategy is divorced from financial reality.

CEOs who are in control anchor their leadership in measurable milestones, rolling reviews, and competitor awareness. They don’t “set a strategy” once a year and hope execution follows—they stress-test it quarterly against real outcomes.

The key questions here:

• Are strategic priorities linked directly to resource allocation?

• Do we have a Plan B if initiatives stall?

• Is innovation disciplined, not just aspirational?

When boards see leaders who can connect strategy to capital, they trust those leaders to execute. Without that connection, strategy becomes a slide deck, not a system.

2. Financial and Operational Discipline

Most CEOs know their P&L. Far fewer can describe the cash conversion cycle, capital intensity, or risk exposures that underpin it.

Operational discipline isn’t about reporting—it’s about foresight. Leaders who win don’t wait for quarterly results. They track rolling forecasts, model liquidity under stress, and know exactly how financial risks (FX, credit, tax, leverage) could impact execution.

The key questions here:

• What KPIs tell us if efficiency is improving—or eroding?

• Are we freeing or trapping cash in working capital?

• Can we flex cost structure without cutting into growth capacity?

This category determines whether finance is a control tower or a record-keeper. And at scale, discipline is what keeps strategy funded when conditions change.

3. People Management and Culture

Capital doesn’t move itself. People deploy it. And culture determines whether that deployment creates value—or burns it.

The most effective CEOs measure not only financial outcomes but the systems that sustain leadership bench strength, employee resilience, and execution accountability. They don’t hope people perform—they engineer conditions for performance.

The key questions here:

• Are we retaining high performers—or losing them to competitors?

• Are leadership pipelines ready for succession?

• Is burnout being measured and mitigated—or ignored until it costs us?

A company can only scale at the speed of its leadership capacity. CEOs who ignore this trade market capital for talent attrition—and valuations always reflect it.

4. Market and Customer Focus

Revenue without profitability destroys valuation. Customers who grow volume but erode margin destroy value.

Strategic CEOs treat customers as assets with cash yields, not just logos on a slide. They know contribution margins by segment, lifetime value vs. acquisition cost, and the velocity of customer cash inflows relative to strategy.

The key questions here:

• Are we pricing for margin, or chasing share?

• Are sales projections built on reliable data—or wishful thinking?

• Is marketing spend generating a measurable and favorable return?

Market and customer discipline ensures growth translates into enterprise value. Without it, revenue is noise and capital gets misallocated.

5. Technology and Global Considerations

In today’s environment, resilience requires more than domestic execution. CEOs must manage cybersecurity, regulatory shifts, and digital transformation while still protecting liquidity and returns.

Top-performing leaders don’t view technology as IT spend—they view it as capital strategy.

They set two-to-three-year digital roadmaps tied to revenue and efficiency outcomes. They stress-test global operations for FX volatility, compliance risk, and geopolitical exposure.

The key questions here:

• Are we ready for a cyber event tomorrow morning?

• Are our compliance frameworks current across all jurisdictions?

• Do we have contingency plans for key personnel, suppliers, and partners?

Technology and global readiness no longer sit in the background—they shape investor confidence, capital access, and valuation multiples.

Upgrade to paid access for the print-ready full resolution PDF along with access to the entire Gem archive.

Inside the CEO Financial Intelligence Program

In the CEO Financial Intelligence Program, I help CEOs and CFOs master asking the most strategic questions, and using answers to align strategy, capital, and cash.

In six weeks, you’ll transform your financial leadership with:

• A clear path from your strategy to your results and your financial reports

• A strategic cash flow planning system to fund what you need when you need to

• The ability to challenge assumptions, support execution and

If you want to lead with foresight and confidence—not fear and uncertainty—this is your foundation.

That’s exactly what this fall’s cohort of the CEO Financial Intelligence Program is built to deliver—capability, foresight, and the infrastructure to lead before the market or your board forces your hand.

Enrollment for The CEO Program closes soon, and this is the final cohort of the year. If you want to lead with foresight—not reaction—this is your opportunity. Secure one of the limited spots today.

The worst that can happen? You finally connect your P&L to your cash flow, your strategy to your results, and your communication to measurable impact.  

Warm regards,
Oana

P.S. Don’t forget—the free masterclass is on October 9. Seats are limited and they will go fast. Secure yours here.