Inspired by Peter Drucker and Frances Hesselbein | Executive Coaching Insights from 6S Advisory Inc.

Author: Cole Dolny, Executive Coach & Founder of 6S Advisory Inc.

A Personal Note from Cole

I’ve been studying the work and thinking of Peter Drucker for decades. No other thinker has shaped my approach to business, leadership, and results more deeply. So when Drucker—widely regarded as the father of modern management—said that Frances Hesselbein was the best CEO in America, and that she “could run any company in the country,” I paid attention.

In fact, Drucker didn’t just admire her—he once called her “the greatest leader I have ever met.” Coming from a man who advised presidents, Fortune 100 CEOs, and global NGOs, those words carry weight. And for me, they were a signal: learn everything you can from Frances Hesselbein.

What I found were seven deceptively simple—but profoundly powerful—questions. These are questions I now integrate into my work with business owners, CEOs, and leadership teams of small and midsized businesses—whether in-person or remotely.

The Seven Questions Every Leader Should Ask

1. When I look around, what do I see that needs to be done?

  • Why it matters: This question helps you cut through the noise and focus on what truly matters. It asks you to observe, not react.
  • In coaching: Use this as your “situational scan.” Look at your team, your operations, your client experience. Where are the gaps?
  • Tip for Leaders: Identify one area each month that needs meaningful attention—before it becomes a problem.

2. What are two relationships I can build in order to pursue what needs to be done?

  • Why it matters: No leader operates solo. Growth depends on trust, alliances, and shared accountability.
  • In coaching: Relationships are strategic assets. Whether it’s a team lead, supplier, or peer, build a plan for meaningful connection.
  • Tip for Leaders: Choose one internal and one external relationship to intentionally strengthen this quarter.

3. How can we best define tomorrow, recognizing our history but not being bound by it?

  • Why it matters: Many SMBs stay stuck in old structures or stories. Legacy is important—but evolution is essential.
  • In coaching: This is your pivot question. It helps you lead change while respecting the culture and people who got you here.
  • Tip for Leaders: Don’t ask 'What worked before?' Ask 'What must work next?'

4. Where can we raise the bar?

  • Why it matters: Incremental improvement compounds over time. Raising the bar is how great companies distinguish themselves.
  • In coaching: Look at performance, communication, client service, or accountability. Find where “good enough” has crept in.
  • Tip for Leaders: Choose one key metric or habit to elevate over the next 30 days.

5. How can I elevate other people’s performance or ability to serve?

  • Why it matters: Your impact is multiplied when others around you grow. That’s how great teams are built.
  • In coaching: This is a direct reflection of servant leadership. Who are you helping become better? What are you delegating? What are you mentoring?
  • Tip for Leaders: Leadership isn’t about being the hero. It’s about creating more heroes.

6. Do others say that I really listen to them—and what is their evidence?

  • Why it matters: Listening is not measured by your intention. It’s measured by how others experience you.
  • In coaching: This is one of the most humbling and powerful questions a leader can ask. And the answers may surprise you.
  • Tip for Leaders: Ask three people this question—and be open to what you hear.

7. Am I being the leader I want to be?

  • Why it matters: All leadership growth starts with self-awareness. This question brings you back to center.
  • In coaching: Define the kind of leader you aspire to be. Then check in: where are you aligned, and where are you off-track?
  • Tip for Leaders: Journal this once a week. Then take one small action to close the gap.

Why These Questions Matter More Than Ever for SMB Leaders

Leading a privately held or family-run business is personal. These questions aren’t theoretical—they’re practical tools for self-correction and strategic focus.

At 6S Advisory, we integrate them into coaching sessions, strategic planning workshops, and leadership development programs for business owners and their teams.

What Makes This Different from Generic Leadership Advice?

Most leadership tips are abstract or disconnected from day-to-day execution. This framework works because:

  • It centres reflection without analysis paralysis
  • It encourages responsibility without ego
  • It prompts action without chaos

These questions also align with the 6S Framework: Strategy, Structure, Support, Systems, Scalability, and Sales—all powered by People.

Start With These Seven Questions

If you're leading a business and want to improve clarity, performance, or alignment—these questions are a powerful place to begin.

Want to take the next step?
We’ve created a free, downloadable worksheet you can use with your team or in your own self-reflection time. It’s yours—no email gate required.

Download the Leadership Questions Worksheet

Start leading with greater clarity, confidence, and connection.

About the Author

Cole Dolny is the founder of 6S Advisory Inc., a firm that supports business owners, CEOs, and executive teams of SMBs through executive & business coaching, mentoring, advisory services, strategic facilitation, and performance improvement. Drawing on over 25 years of CEO experience and a deep understanding of what drives results, Cole works with leaders to improve how they think, act, and lead.