Earlier in my career, I learned a concept that changed how I approached interactions with my team members and with my CEO. By creating a structure for “Working IN the Business” vs. “Working ON the Business,” we enhanced our productivity and strategic alignment.
The initial concept, introduced to me by my executive coach at the time, originally focused on team engagement during group meetings.
She emphasized the importance of management teams creating distinct opportunities to discuss operational aspects vs. strategic aspects of leadership. However, I found that this concept is equally applicable to how executives can engage one-to-one with the leaders on their teams.
In this article, I’ll explain the difference between “Working IN the Business” vs. “Working ON the Business”; I’ll share why this approach can be so powerful; and I’ll provide suggestions for how to put this structure in place.
Most leaders have regular meetings with their direct reports every week or two, which typically focus on communicating tactical or operational aspects of the business (status updates, questions, approvals, etc.) and basic problem-solving. The goal is to ensure that progress is being made and obstacles are addressed. This kind of touch-base meeting is what I would call "Working IN the Business" and it's what comes fairly naturally in most manager relationships.
Unlike your weekly touch-base meetings, the time spent when “Working ON the Business” is focused on the big picture aspects of leadership. This is where you’re examining whether the team’s work is strategically aligned, where you reflect on data, where you make adjustments if priorities have changed, and where you discuss trade-offs if you need to change course. It’s also an opportunity to reflect on strategies for managing across and collaborating with other teams.
Dedicating time to “Working ON the Business” creates the opportunity to pull yourself out of the weeds and ensure you’re heading in the right direction. I find that many organizations become overly focused on simply getting things done. However, balancing an execution-focused mindset with a broader strategic vision is crucial. Dedicating time to "Working ON the Business" ensures that you're not just making progress, but you're making progress in the areas that significantly impact the business.
Another benefit is that it provides an important opportunity for mentoring. Only 28% of high-potential ed-tech employees receive the necessary mentoring to grow as leaders. Having an hour of time to collaborate and think strategically with one’s manager can create a powerful setting for fostering the analytical and managerial skills necessary for higher leadership roles.
Continue to conduct your touch-base meetings as usual. They should typically happen on a weekly or bi-weekly basis and take between 30 and 60 minutes. This cadence is effective for most managerial relationships to ensure ongoing communication occurs, progress is being made and basic roadblocks are being addressed. This serves as your “Working IN the Business” meeting.
Schedule a second block of time that's dedicated specifically to “Working ON the Business.” This meeting might be every two or three weeks for 60 minutes. This should be a recurring meeting that is locked into your schedule–not an ad hoc session. This is where you’ll delve more deeply into strategic aspects of the work that often get squeezed out of your regular touch-base meetings.
The key to working "IN vs. ON" the business is to be extremely protective of that time. Ensure you don't schedule over or cancel these time blocks. Hold one another accountable for coming to that meeting prepared to think deeply about the business to be more forward looking strategically.
Be disciplined about preventing the topics or concepts from one meeting to seep into the other. When that happens, it’s OK to call that out, table the topic for the appropriate meeting, and be very purposeful with how you approach using your time!
Admittedly, implementing this IN vs. ON strategy with several of your direct reports can be challenging, especially if you’re already dealing with “meeting overload.” If you simply can’t squeeze in the time for another meeting, consider alternating between IN and ON focuses in your weekly meetings.
It’s still critically important, however, that you approach these as two distinct meetings with different purposes, which requires you to be disciplined about NOT blending these into a hybrid agenda of “Working IN + ON the Business”. Having a singular focus during those meetings enables you to drive your line of thinking and make sure you’re immersing yourself in either the tactical or strategic mindset.
Ultimately, you may find that the time spent digging into the business strategically actually saves you time in other ways. You’ll likely end up spending less time doing course correction and re-communicating priorities.
As leaders, it’s important that we continue to examine the business through various lenses. Implementing a cadence of “Working IN the Business” and “Working ON the Business” creates a setting where leaders can immerse themselves in that mindset and conduct the deep thinking—together—that will lead to success. The act of doing this work together with one’s manager creates a powerful mentoring relationship, fosters a culture invested in leadership growth, and creates a rigorous approach to managing business performance.