Most executive leadership teams agree they should spend more time working on the business rather than in it. Far fewer have a practical system for doing so.
The concept has become something of a leadership cliché — invoked at off-sites, referenced in operating reviews, and promptly forgotten once the week’s fires resume. That’s not because leaders lack commitment to the idea. It’s because the idea, as usually presented, offers a diagnosis without a prescription.
Summary
Most executive teams know they should spend more time working on the business but revert to operational mode anyway, because urgency always wins without the right structures in place.
The core problem isn’t intent. It’s that “working on the business” is rarely defined precisely enough to act on, and most leadership teams have no operating infrastructure to sustain enterprise-level thinking once day-to-day pressure resumes.
This article covers four practical shifts:
- Understand the pull — Operational gravity is real. Leaders reach executive roles by being great operators, and those instincts don’t switch off. A hidden amplifier
;: when leaders don’t have the right people in the right seats, they have no choice but to stay in the operations. Countering the pull requires structure, not just willpower.
- Apply the 80/20 principle concretely — The target ratio is 80% of leadership attention on the business, 20% in it. Audit where time goes (most teams find it’s closer to inverted), protect enterprise work on the calendar, and filter leadership team agendas to weight toward enterprise questions over operational ones.
- Build enterprise leadership habits — Speak for the organization before your function, name tradeoffs explicitly rather than deferring them, and practice thinking collectively under pressure — not just at offsites.
- Stop leading in reaction mode — Create regular time for enterprise-level decisions, make it clear who owns cross-functional issues, and consistently connect leadership behaviors to business results.
The starting point is simpler than a redesign: ask honestly where your collective leadership attention went over the last 90 days — and what that ratio tells you.
The Real Distinction
Before building those structures, it helps to be precise about what “working on the business” means because ask five executives and you’ll get five different answers.
For some leaders, working on the business means delegating more. For others, it means focusing on long-term planning. Some associate it with innovation, while others see it as creating more space to think. None of these views are exactly wrong, but they are too vague to be useful.
Here’s a more operational definition:
Working in the business means your attention is concentrated on execution within the current structure — resolving problems, managing functional performance, and responding to immediate pressure.
Working on the business means your attention is concentrated on the conditions that determine whether the organization can execute effectively over time. The questions look different:
- Are our stated priorities competing with each other across functions?
- Where is execution slowing down — and is it a people issue, a structure issue, or a decision-rights issue?
- Are we making enterprise-level tradeoffs, or deferring them?
- Does the organization have the capacity to execute what we’ve committed to?
- Are accountability structures clear enough that problems surface quickly, rather than accumulating?
These questions are less urgent than operational problem-solving in any given week. They are almost always more consequential over a quarter or a year.
Why the Default Is Always Operational
Understanding the pull toward operational work isn’t an academic exercise; it’s the first step to countering it.
Most executives reached senior roles by being exceptional operators: fast problem-solvers, accountable for outcomes, and decisive under pressure. Those instincts don’t switch off with a promotion. If anything, they get reinforced. The business keeps generating urgency — customer escalations, staffing gaps, competing departmental priorities — and capable leaders feel the pull to engage. Solving a real problem today is satisfying. Strengthening the organization’s capacity to solve problems next year is harder to see and harder to measure.
There is a less-discussed amplifier of this pattern: many executive leaders don’t have the right people in the right seats among their direct reports. When the team below you can’t be trusted to own operational execution independently, staying in the details doesn’t feel like habit, it feels like a necessity. Some leaders avoid the hard conversations required to address capability gaps. Others genuinely intend to invest in developing their people but find that “it’s easier to just do it myself” becomes the default under pressure. Neither path is sustainable. Both keep leaders anchored in the business rather than working on it. The team you build directly determines how much altitude you can afford to take.
This creates a pattern that’s common in growing organizations: the leadership team becomes highly effective at running the business as it currently exists, while systematically underinvesting in the organization’s ability to scale, adapt, and execute over time.
The issue isn’t effort or intent. It’s operating discipline — specifically, the absence of structures, rhythms, and the right people in place to consistently free executive leadership attention for enterprise-level work.
The 80/20 Principle (and How to Apply It)
With a clear definition in place, the next question is practical: how do you shift the ratio.
The most effective executive teams maintain a deliberate imbalance in where attention goes; roughly 80% on strengthening the business, 20% on operating within it.
The ratio isn’t sacred. The principle behind it is.
Executive teams that stay too operationally immersed lose the altitude needed to see systemic issues. Those who become too detached from operations lose the context required for sound judgment. The goal is a clear default — enterprise thinking is the primary mode — without becoming disconnected from the realities of the business.
In practice, calibrating toward 80/20 means three things:
1. Audit where your time goes — not where you believe it goes. Most executive leadership teams significantly overestimate how much time they spend on enterprise-level questions. A simple two-week time audit, categorizing meetings and decisions as either operational or enterprise-level, is often clarifying. Most teams find the ratio is closer to inverted: 20% on the business, 80% in it.
2. Design your calendar to reflect the ratio, not just aspire to it. If enterprise-level work isn’t protected on the calendar, operational urgency will fill the available space — every time. This means standing time for cross-functional alignment, strategic review, and organizational health isn’t a luxury reserved for offsites. It’s a recurring structural feature of how the leadership team operates.
3. Create a different decision filter for executive leadership team meetings. A useful test for any agenda item: Is this a question about running the current business, or about shaping the organization’s ability to run future business? Operational items belong to operational forums. Leadership team time should be weighted heavily toward the second category.
The Transition from Functional to Enterprise Leadership
Shifting the calendar is a necessary condition for 80/20 but it’s not sufficient. Sustaining that balance requires a different leadership orientation, one that doesn’t come naturally to most executives who built their careers as functional experts.
Functional leadership rewards depth: expertise within a domain, decisiveness, accountability for a clear set of outcomes. Enterprise leadership requires something broader: the ability to optimize across functions, to make tradeoffs that serve the whole organization rather than any single part of it, and to hold tension productively within the leadership team without that tension fragmenting into dysfunction below.
That last point is important. Strong enterprise leadership teams are often more willing to challenge each other, pressure-test assumptions, and surface competing priorities directly. What distinguishes them isn’t harmony — it’s the ability to disagree at the table without creating organizational fractures in the field.
Developing this capacity takes deliberate practice. A few specific habits accelerate it:
Speak for the enterprise, not just your function. In leadership team discussions, make a habit of asking what’s best for the organization before advocating for what’s best for your area. This isn’t selflessness; it’s recognizing that functional optimization at the expense of enterprise performance is a losing trade.
Name the tradeoffs explicitly. Many leadership teams avoid surfacing hard prioritization choices because it creates uncomfortable conversations. But unacknowledged tradeoffs don’t disappear; they show up as execution failures, misaligned teams, and lost momentum. Making them explicit is the job.
Build the habit of collective thinking under pressure. The test of enterprise leadership isn’t how a team operates during an offsite. It’s whether they can think together when the quarter is going sideways; the pressure is high, and the easy answer is to retreat into functional mode. That capacity is built through small, consistent practices — not breakthrough moments.
What Breaks the Reactive Cycle
Building new habits at the individual leader level matters, but it isn’t enough on its own. Without structural support, those habits erode under pressure.
Organizations commonly experience this pattern: leadership team leaves a planning session aligned and energized; within three to four weeks, everyone has reverted to reactive operating patterns. The strategy didn’t change. The intention didn’t change. The operating infrastructure wasn’t strong enough to hold the new orientation against day-to-day pressure.
Fixing this requires building three things:
Operating rhythms that reinforce enterprise thinking. Not just quarterly strategy reviews, but regular (weekly or biweekly) forums where the leadership team is specifically evaluating organizational health, cross-functional friction, and execution against priorities — separate from operational standup and functional performance reviews. Structure signals what matters.
Clear ownership for enterprise-level questions. Operational work usually has clear owners, and executive teams are used to that kind of accountability. Enterprise-level questions — how decisions are made, where accountability is unclear, and how priorities are sequenced across functions — need the same level of ownership. Too often, they sit in a gray area where everyone assumes someone else is handling them. When the executive team explicitly owns those questions, they get addressed with the same discipline as operational work.
A feedback loop between leadership behavior and organizational execution. The most effective leadership teams develop some mechanisms for understanding how their operating patterns affect the organization below them. This could be structured listening sessions, skip-level conversations, or clear data on where execution is slowing. Without it, leadership teams often operate on a significant lag; making structural decisions months after the problems they’re solving have already cascaded.
The Practical Starting Point
If this all feels like a significant shift from how your leadership team currently operates, it probably is. That’s normal. The move from functional to enterprise leadership is one of the harder transitions in organizational life, and most teams make it incrementally rather than all at once.
A reasonable starting point isn’t a wholesale operating redesign. It’s a single honest question the leadership team asks together:
When we look at where our collective attention has gone over the last 90 days — not where we intended it to go, but where it actually went — what ratio are we operating at?
That conversation, done honestly, tends to surface both the gap and the specific operating habits that are sustaining it. From there, the path forward becomes considerably more concrete.
Organizations that scale well don’t just have better strategies than their peers. They have leadership teams that are more disciplined about how they operate collectively — how decisions get made, how priorities are reinforced, how accountability is maintained, and how execution stays coordinated under pressure.
That is what working on the business requires: less time pulled into day-to-day operations, without losing touch with how the work gets done. It means leading at the enterprise level while staying tightly connected to execution — and building the structures to sustain that discipline when the week gets hard.
