Working in & on the organization
Many teams, especially leadership teams, feel overwhelmed by daily challenges. Decisions pile up, issues demand immediate attention, and the operational drumbeat never stops. Under that pressure, time to think evaporates. Strategy, market awareness, and innovation rarely fail because teams don’t care. They fail because these topics require distance, focus, and continuity, exactly the things that disappear when urgency dominates.
Bill Hewlett (HP) once said that great companies don’t fail for lack of ideas, but for lack of execution. You miss your shot for greatness not because you were not busy enough, but because you did not spend enough time making the right choices.
The challenge is often described as working in the business versus working on the business. The distinction is familiar. The frustration is real. What’s missing is a clear, practical way to resolve it without pretending daily work can simply be ignored.
The distinction between working in and on the business is older than today’s technology cycles. It was articulated most clearly in the 1980s by Michael E. Gerber in The E‑Myth, as an explanation of why growing companies get trapped by the systems they build. Periods of rapid technological change tend to surface the same tension: execution speeds up, while reflection struggles to keep pace. In earlier decades this tension slowed organizations down. Today, with AI accelerating execution, it can push them off course faster than ever.
Why AI makes this tension impossible to ignore
Teams are adopting AI to move faster, producing more output, with fewer delays and lower costs. Tasks that once consumed hours now take minutes. Yet many organizations report a familiar feeling: speed without clarity. Execution improves, direction does not.
AI primarily amplifies whatever mode already dominates. In teams focused on execution, it accelerates working in the business: more tickets closed, more content shipped, more activity per week. Without deliberate reflection, this speed compounds yesterday’s decisions.
When the cost of doing work drops, the value of choosing the right work rises. AI does not remove the need to work on the business; it raises the penalty for neglecting it. Faster execution means faster drift when direction is unclear.
What working in and on the business really means
Working in the business means serving customers, answering messages, closing tickets, shipping features, and fixing bugs. It is visible, urgent, and socially rewarded. It feels productive because it is productive. Without it, nothing works.
Working on the business is the work of redesigning processes, questioning assumptions, and deciding what should exist at all. It asks why problems recur and which constraints are self‑inflicted. It is less visible, less urgent, and therefore easier to postpone.
Both modes are difficult, just in different ways. Working in the business is hard because urgency never ends. There is always another request, issue, or escalation. Working on the business is hard because it offers no immediate payoff and no external pressure. One exhausts attention, the other demands it.
The popular framing suggests that working on the business is somehow superior. That creates a false hierarchy. Execution without reflection leads to drift. Reflection without execution leads to theatre.
Teams rarely decide to ignore on‑the‑business work. It simply gets crowded out. Calendars fill with operational meetings. Incentives reward responsiveness. Over time, the organization forgets that a choice is being made at all.
How teams find (and lose) the balance
Understanding the distinction between working in and on the business does not change behavior. Insight without structure quickly collapses under pressure. The question is not whether teams agree in principle, but whether their daily operating system deliberately makes space for both modes in daily work.
When leaders examine their calendars objectively, a pattern becomes visible.
“Research from McKinsey & Company shows that senior leaders consistently underestimate how much of their time is consumed by operational coordination. Calendar analyses reveal that strategic reflection occupies a far smaller share of executive time than leaders assume.”
Three tips for working ON the business
Design the meeting rhythm to protect on‑work.
If every recurring meeting is operational, priorities are clear regardless of strategy decks. Teams that schedule regular reviews focused on systems, priorities, and trade‑offs make on‑the‑business work legitimate rather than extracurricular.Encode reflection into roles.
When roles are defined purely by function, people default to execution. When team members have a second set of responsibilities that include explicit ownership of processes, quality, or interfaces, working on the business has owners. Without this, improvement becomes nobody’s job, or equally problematic, one person’s job.Create deliberate distance from execution.
Teams immersed in day‑to‑day work normalize their constraints. Periodic distance, through retrospectives, peer exchange, or external perspectives, helps distinguish between genuinely hard problems and simply unexamined ones.
Three tips for working IN the business
Delegate outcomes, not just tasks.
Delegation that merely removes work increases coordination overhead. Delegation that transfers decision rights creates leverage. The question shifts from who can help me to who owns this going forward, and that shift keeps execution strong without pulling leaders into every decision.Use questions to signal the mode.
Operational questions focus on speed and resolution: What is blocked? What is late? Who needs help? Clear execution depends on leaders reinforcing focus, ownership, and flow through the questions they consistently ask.Make goals and performance visible.
Clear execution depends on shared visibility. Teams need transparency on organizational goals, team‑level objectives, and how operational performance maps to both. Without this line of sight, leaders hesitate to let go, step back, or reduce firefighting because they lack confidence that the system will hold.
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Working in and working on the business are not enemies. They are complementary modes that require deliberate design. Teams that understand this do not escape tension, but they stop being surprised by it. And leaders regain the ability to steer deliberately and shape the direction of their organization.