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Analyzing Individual Investments

Lesson 6: Management Team Evaluation

Introduction: The Importance of Leadership

Behind every strong business is a team making decisions on strategy, spending, growth, and communication. 

And that team often determines whether a company succeeds or slips.


A great business with poor management can still fail. But a decent business with great management can thrive. 


In this lesson, you’ll learn how to: 


  • Evaluate a company’s key executives and their track record
  • Understand how leadership impacts execution and growth
  • Spot signs of alignment (or misalignment) with shareholders. 


In this lesson, you’ll learn how to: 


  • Size up a company’s market opportunity using TAM, SAM, and SOM
  • Analyze the competitive landscape and spot a company’s edge
  • Track industry trends and external forces like regulation or macro shifts

Meet the Key Executives

When you invest in a company, you’re trusting its leadership to make smart decisions and grow shareholder value.

So it's worth asking: Who’s running the show?


CEO (Chief Executive Officer)

  • Sets the company’s vision and long-term strategy
  • Often the public face of the business
  • Responsible for overall performance and culture

Look for: A clear communicator with a proven track record of results, innovation, or transformation


CFO (Chief Financial Officer)

  • Manages financial health, reporting, and risk
  • In charge of budgets, forecasting, and capital allocation
  • Often speaks on earnings calls and investor days

Look for: Strong financial discipline and the ability to fund growth sustainably


COO and Others

  • COO (operations), CTO (technology), CMO (marketing), etc.
  • Focus on executing day-to-day business and delivering on strategic initiatives

Tip: Smaller companies might have fewer execs, so leadership style and multitasking capacity matter even more.

How to Research Leaders

  • Company website → “Leadership” or “Investor Relations” pages
  • LinkedIn for professional history
  • Press releases and earnings transcripts
  • Financial media and past interviews

A great product is powerful. But in the hands of a weak leadership, it can still fail.

company leadership

Leadership's Ability to Execute

Having a bold vision is great. 

But delivering on it is what separates strong leadership from empty promises.


Here is what you need to look for: 


Track Record of Results

Ask: 

  • Has the company hit its financial targets?
  • Did they follow through on big promises (e.g., launching a new product, expanding into new markets)?
  • How has the business evolved under current leadership?

Tip: Look at revenue growth, profitability, and strategic shifts over the last 3–5 years.


What to Listen For

Earnings calls and shareholder letters often reveal a lot:

  • Do leaders take responsibility, or just blame ‘macro headwinds’? 
  • Are they transparent about setbacks and plans?
  • Are they focused on the long-term, not just the next quarter?


Strategic Execution

  • Have past M&As created value or backfired?
  • Are they reinvesting wisely (R&D, talent, innovation)?
  • Do they adjust when markets shift, or keep pushing the same playbook? 


Execution is where strategy meets reality. Look for leaders who follow through and adapt - not just talk big.

Shareholder Alignment: Are They On Your Side

The best leaders not only talk about creating shareholder value, but also have their own money on the line. 

When leadership wins only when you win, that’s alignment.

Insider Ownership

  • Do executives own meaningful amounts of stock?
  • Are they buying shares, or just selling them? 

Why this is important:

Owners think long-term. Hired hands might think quarter-to-quarter.


Compensation Packages

  • Are bonuses tied to performance, or just for showing up?
  • Look for incentives based on ROIC, revenue growth, or shareholder return.

Warning sign: 

Large compensation with no clear performance metrics. 


Capital Allocation History

  • Did leadership make smart use of profits? 
  • Investing in growth
  • Paying dividends
  • Repurchasing shares wisely
  • Or did they chase hype, overpay for acquisitions, or dilute shareholders?


You want leaders who act like owners, and build wealth alongside you - not at your expense.


Red Flags to Watch For

  • Even the most promising company can stumble under poor leadership.


    Here are the signs that should make you pause (or even dig deeper): 


    High Executive Turnover

    • Frequent CEO/CFO changes can signal instability, internal conflict, or poor board oversight
    • Ask: Why are key leaders leaving? Who’s replacing them?


    Excessive or Misaligned Compensation

    • Huge bonuses despite poor performance
    • Stock awards not tied to results
    • Perks and payouts that suggest a “cash grab” mindset


    Questionable Capital Decisions

    • Overpaying for acquisitions with no clear synergy
    • Diluting shareholders with unnecessary stock issuance
    • Cutting R&D or innovation to hit short-term numbers


    Weak Governance or Transparency

    • Poor communication with investors
    • Avoiding questions or downplaying setbacks
    • Internal drama, lawsuits, or regulatory issues


    Alongside growing revenue, strong leaders also build trust.


Quiz

  1. What’s a good sign of shareholder alignment?

    a) Executives with no stock ownership

    b) Large bonuses unrelated to performance

    c) Leaders who own significant shares and buy more over time

  2. Which of the following is a red flag?

    a) A CEO who’s been in place for 10+ years

    b) A CFO leaving after two years, with no reason provided

    c) A company tying executive bonuses to long-term ROIC

    3.What’s one way to evaluate a leader’s track record?

    a) Count their social media followers

    b) Look at recent press releases

    c) Review financial performance and execution of past goals


See the answers at the bottom

Exercise: Evaluate a Company's Leadership

  1. Pick a public company and find the following: 


    1. Who are the CEO and CFO? What’s their background?
    2. What’s their compensation package like? Do they own stock? 
    3. Have they delivered on major goals in the last 2–3 years?
    4. Do you see any red flags? 


    This helps you think like a long-term investor. 


Summary and Key Takeaways

    • Great leadership can elevate a company. Poor leadership can sink it.
    • Know who’s running the business. Look at the CEO, CFO, and their past performance.
    • Focus on execution, not just big talk. Did they hit goals? Adapt to change?
    • Strong leaders are aligned with shareholders through stock ownership and performance-based pay.
    • Watch for red flags like executive churn, poor capital decisions, or lack of transparency.


    Final thought: When you invest, you're backing people as much as products. Choose leaders you’d trust with your money - because you literally are.


Answers to the Quiz and Exercise Questions

Quiz Answers:

1) What’s a good sign of shareholder alignment?

Answer: c) Leaders who own significant shares and buy more over time

2) Which of the following is a red flag?

Answer: b) A CFO leaving after two years, with no reason provided

3) What’s one way to evaluate a leader’s track record?

Answer: c) Review financial performance and execution of past goals

Additional resources

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