Working on the Business vs In It (Wrong Work). How Better Questions Lead to Better Leadership Decisions

You will learn:

• Why being busy does not mean you are making progress
• The hidden trust issues behind micromanagement
• How to stop firefighting and start thinking strategically
• Why asking better questions matters more than having answers
• How peer accountability accelerates clarity

Many business owners feel stuck even when their company is growing. In this episode of Close The Deal, Ewell Smith sits down with Sam Caruso, a Vistage Chair based in New Orleans, to unpack why leaders get trapped in the weeds and how to regain clarity, confidence, and control.

Sam Caruso's Top 15 Close The Deal Mindset Success Quotes:

Trust Quotes

1. "Most leaders struggle because they do not trust their team as much as they think they do."

   2. "Control often shows up when trust is missing."

   3. "Leadership improves when you stop trying to do everything yourself."

   4. "Trust is built by letting others own outcomes."

   5. "You cannot grow if everything depends on you."

Sales Process Quotes

  6.  "Closing the deal means solving the right problem."

  7."If you are selling before listening, you are already off track."

  8. "Real progress happens when clarity replaces urgency."

  9. "Better questions create better outcomes."

  10."Sales is about alignment, not pressure."

Mindset or Marketing Quotes

  11. "Busy work feels productive but rarely moves the needle."

  12. "Most leaders are asking the wrong question."

  13. "You cannot see blind spots without a mirror."

  14. "High performance does not automatically make you a great leader."

  15. "Growth starts when you slow down enough to think."

Working on the Business vs In It

How Better Questions Lead to Better Leadership Decisions

Running a business often feels like a constant balancing act. You are responsible for vision, growth, culture, people, and results, yet most days are consumed by urgent issues, interruptions, and decisions that demand immediate attention. Over time, many business owners and leaders begin to feel stuck. Not because they lack ability, but because they are too deeply embedded in the day to day operations to step back and think clearly.

In this episode of Close The Deal, I sat down with Sam Caruso, Vistage Chair and executive advisor, to unpack one of the most common and dangerous traps leaders fall into today. Working in the business instead of on it. What followed was a powerful conversation about leadership isolation, asking the wrong questions, and how clarity often comes not from working harder, but from slowing down long enough to see the real issue.

This blog breaks down the key insights from our discussion and shows how asking better questions can fundamentally change how you lead, decide, and grow.

The Hidden Cost of Being in the Weeds

Most business owners do not intend to micromanage. It usually starts as involvement. Then concern. Then control. Before long, leaders find themselves deeply embedded in decisions that should not require their attention.

Sam sees this pattern constantly.

Leaders convince themselves they are being diligent when in reality they are avoiding something harder. Letting go. Trusting others. Creating systems that allow the business to operate without their constant presence.

When leaders stay in the weeds, the business may continue to function, but it does not scale. Growth stalls. Energy drains. The leader becomes the bottleneck without realizing it.

Isolation at the Top Is Real

One of the most overlooked challenges of leadership is isolation. The higher you go, the fewer people you can speak with honestly. Employees filter information. Advisors have agendas. Even boards often respond with what they think the leader wants to hear.

Sam describes this as one of the primary reasons leaders remain stuck. Not because they lack intelligence or experience, but because they lack a true mirror.

Without honest feedback, blind spots grow. Patterns repeat. Problems feel harder than they should. This is why peer based advisory environments work. They remove hierarchy. They remove competition. They create space for truth.

Why Leaders Ask the Wrong Question

A powerful moment in our conversation centered on a real example from one of Sam’s Vistage group sessions. A business owner came in asking how to deal with a team member who was not aligned with company culture.

On the surface, it sounded like a personnel issue.

Through careful questioning, the group uncovered something deeper. The leader had never clearly defined what the company culture actually was. Expectations lived in her head but were never documented, communicated, or reinforced.

The question shifted from how do I fix this person to how do I define the culture of my business.

That single shift changed everything. Better questions lead to better decisions. And most leadership problems are really clarity problems in disguise.

Working On the Business Requires Space

Many leaders claim they do not have time to think strategically. Sam challenges this belief directly.

The issue is not time. It is protection.

Leaders often know exactly when they are most focused and energetic. Early mornings. Quiet windows. Uninterrupted blocks. Yet those are rarely defended. Instead, strategic work is postponed until everything else is done. Which means it never gets done.

Sam shared a simple but powerful exercise. Schedule fifteen minutes a day during your highest energy window and protect it. Use it only for thinking, planning, or reflection.

Small, consistent space creates momentum. Momentum creates clarity.

Control Often Masks Trust Issues

One of the most honest insights from the episode was this. When leaders struggle to step back, it is often not about competence. It is about trust.

Trust in systems. Trust in people. Trust that things will not fall apart without constant oversight.

Sam sees leaders who are already paying people to do the work, yet they still feel compelled to redo, review, and redecide everything.

This behavior exhausts everyone involved.

Strong leaders shift from doing to guiding. From controlling to coaching. From reacting to designing.

The Power of Peer Accountability

What separates insight from action is accountability.

In Sam’s groups, leaders do not just talk through problems. They commit to specific actions. They assign accountability. They revisit progress.

This structure removes isolation and replaces it with momentum.

When leaders know they will be asked what they did, clarity turns into execution.

Leadership Is About Solving the Right Problem

One of the most important moments in the episode came when Sam defined what closing the deal means to him. It is not about selling. It is about solving the right problem.

This philosophy applies far beyond sales. Leadership decisions improve when leaders stop reacting to symptoms and start diagnosing causes.

When you solve the right problem, progress feels lighter. Decisions feel clearer. Results follow naturally.

Final Thoughts: Better Thinking Creates Better Leadership

The difference between leaders who feel stuck and those who scale is not intelligence or effort. It is perspective.

Working on the business requires space, trust, and better questions. It requires stepping back long enough to see patterns instead of fighting fires.

This conversation with Sam Caruso is a reminder that leadership is not about doing more. It is about thinking better.



If you are feeling stretched, isolated, or buried in day to day decisions, this episode will resonate deeply. It will challenge how you think about your role and help you see where clarity begins.