The Executives' Club The Executive 9

The Executive 9

9 questions. One round of reflection. Insights straight from the top.

Executives, take a moment for yourself.

This isn’t a typical interview—it’s a chance to step back, think critically, and reflect on your career, your business, and the rules you live by. Each of these 9 questions is designed to prompt real insight, encourage honest self-reflection, and reveal the lessons that only experience can teach.

By sharing your perspective, you’re not just reflecting on your own journey—you’re mentoring others. The insight you provide may help another leader navigate challenges, avoid pitfalls, or see opportunities they might have missed.

Answer at your own pace, share what resonates, and contribute to a collection of perspectives that other leaders can learn from—straight from the top.

Name

First

Last

Company

Title

1. Looking back at your career, what decision truly changed the course of your business—or your life as a leader?

Example: Choosing a new market, hiring a key person, or walking away from a deal.

2. If your business disappeared tomorrow, what problem in your industry or community would go unsolved?

Think about the unique value you provide that no one else fills.

3. What’s one "business rule" you follow religiously, no matter what?

Example: Always meet payroll first, never compromise on quality, or maintain transparency with your team.

4. What’s one "business rule" you tend to ignore—or break—because it just doesn’t fit reality for you?

Be honest—sometimes the textbook rule isn’t what works in practice.

5. What’s something your business had to stop doing in order to actually move forward?

Example: Ending a product line, dropping a client, or cutting an internal process that slowed growth.

6. Think about your blind spots. Which one challenged you the most, or are you still working on today?

Example: Delegating responsibility, managing conflict, or recognizing emerging trends.

7. What’s a lesson you learned the hard way—something no book or mentor could have prepared you for?

Example: Facing an unexpected market shift or a leadership failure.

8. Which early belief about leadership or business turned out to be completely wrong, in your experience?

Example: Thinking growth always equals success, or assuming employees don’t want transparency.

of your Looking

9. What’s one boring, unglamorous habit your business does consistently that you credit with long-term success?

Example: Weekly financial reviews, daily team check-ins, or rigorous customer follow-up.

Thank you!

Your answers to The Executive 9 will be shared selectively to create learning opportunities for other leaders.

Some insights may appear on our social media channels, while others will be discussed in private Executives Club meetings.

The goal is not publicity—it’s to capture real-world experience and unfiltered perspective, helping peers learn from successes, challenges, and the rules that guide or shape your leadership.