Working In vs Working On the Business: Why High-Performing Leadership Requires Both and Knowing When to Do Each

Many leaders are incredibly busy and still feel like progress is slower than it should be.

This usually is not a motivation problem.
It is not a capability problem.

More often, it is a focus and timing problem.

One of the most important distinctions a leadership team can make is understanding the difference between working in the business and working on the business and aligning each to the correct cadence.

What It Means to Work In the Business

Working in the business is execution-focused. This is the work that keeps the organization running week to week.

It includes:

• Reviewing scorecards and metrics
• Solving current issues
• Making short-term decisions
• Managing people and priorities
• Ensuring commitments are met

For most leadership teams, this work belongs in weekly leadership meetings.

Weekly meetings are designed to create traction. They keep the train moving, ensure accountability, and help teams respond to what is happening right now.

This work is essential. Without it, execution breaks down.

At the same time, weekly meetings are not designed for deep strategy, long-term planning, or structural redesign.

Trying to do that work in a weekly cadence often leads to frustration, rushed decisions, or conversations that never quite land.

What It Means to Work On the Business

Working on the business requires a different altitude.

This work focuses on improving how the business operates and where it is going, not just what is happening this week.

It includes:

• Clarifying vision and long-term direction
• Reflecting on what is and is not working
• Designing systems, processes, and structure
• Adjusting roles and accountability
• Setting quarterly and annual priorities
• Identifying root causes rather than symptoms

This work belongs in quarterly and annual planning sessions.

These sessions create the space required for thoughtful conversation, alignment, and forward-looking decisions. They are meant to slow leaders down enough to see patterns, not just problems.

Quarterly and annual planning is not about doing more work. It is about doing the right work at the right time.

Why Timing Matters More Than Most Leaders Realize

When leaders blur the line between working in and on the business, a few predictable things happen:

• Weekly meetings feel long and unfocused
• Strategic conversations get postponed indefinitely
• The same issues reappear quarter after quarter
• Leaders leave meetings unclear or overwhelmed

This is not a discipline issue. It is a cadence issue.

Weekly meetings exist to run the business.
Quarterly and annual sessions exist to build the business.

Both are necessary. They simply are not interchangeable.

A Simple Leadership Gut Check

When deciding where a conversation belongs, ask:

“Does this need traction this week, or does it need design for the future?”

• If it needs traction this week, it belongs in the business
• If it needs design for the future, it belongs on the business

This question alone can dramatically improve meeting effectiveness and leadership clarity.

HOW TO: Align Your Work With the Right Cadence

1. Honor weekly meetings for execution
   Use them to review metrics, solve current issues, and move priorities forward.
   
   
2. Protect quarterly and annual planning time
   Keep these sessions focused on reflection, strategy, and future direction.
   
   
3. Capture ideas that arise at the wrong time
   Do not force strategic conversations into weekly meetings. Park them intentionally for planning sessions.
   
   
4. Set expectations with your leadership team
   Help everyone understand that not every good idea belongs in every meeting.
   
   
5. Trust the rhythm
   The cadence exists to reduce friction, not create it.
   
   

Last words 

Working in the business keeps things running.
Working on the business makes things better.

Strong leaders do both and know where each belongs.

-Kristie Clayton
HERverse Founder
#HERthoughts