Don’t Bankrupt Your Team’s Culture

I was sitting in a legal update session when the presenter expressed the notion: “Penny wise and pound foolish.” Although leaders may want to avoid racking up legal bills, he cautioned us not to “go cheap” on matters that could lead to even more costly and contentious legal implications. Over the weekend, I caught myself sharing this same axiom with my son, who recently got engaged and was looking to “go cheap” on the wedding. As I continued to marinate on this concept, I couldn’t help but think about how this adage applies to a leader. While we may not have conversations directly about legalities or finances, leaders can fall into this trap with a currency far more valuable than cash: our time and energy.

When the pressure is on and the inbox is overflowing, it is incredibly easy to hoard our minutes. We skip the things that don’t have an immediate, tangible deliverable attached to them because we feel “too busy.” But hoarding minutes on foundational leadership habits is the ultimate way to bankrupt your team’s culture.

If you want to stop firefighting and start leading with high-yield impact, you have to stop saving pennies and start investing in the big wins. Here are three critical areas where you need to spend time up front to secure the ultimate long-term rewards and avoid being foolish.

1. Team Building: It’s the Infrastructure, Not an Afterthought

When schedules get tight, the first thing leaders usually slash is team building. We think, “We don’t have time for a workshop or a team lunch; we have real work to do.” That is classic penny-wise, pound-foolish thinking. Team building isn’t a luxury item or a secondary reward you hand out only when the calendar is clear. It is the very infrastructure that keeps your operation running.

• The Penny Saved: You gain an hour or two of immediate task execution.
• The Pound Lost: You risk misalignment, silos, communication breakdowns, and low morale which take months and massive energy to repair.

Investing time in team building builds trust, and trust is the ultimate lubricant for speed. Last week, we invested time in our District Leadership Team Retreat to build our team and work on the fundamentals of trust, communication, and fun. When people know and respect each other, projects move faster, friction disappears, and execution skyrockets. Don’t skip it because you’re busy. You’re busy because you aren’t doing it.

2. The 30-Minute Check-In: Small Investments, Massive Dividends

Upon joining the Oakwood Schools District, I was informed that the previous superintendent held 30-minute monthly check-ins with the people who reported to him. Since my calendar was open at the start of the year, I booked the meetings, unsure of what we would do during this time. After three years in the district, I would point to those times as a fundamental reason we are a top district. As a leader, it’s easy to look at a calendar packed with 1-on-1s and think, “Look at all this time I’m losing.” It might look on paper like these meetings don’t yield immediate, explosive results.

But true leadership is about the long game. For example, setting aside just 30 minutes a month for a dedicated check-in with each administrator is one of the highest-yield investments you can make.

These check-ins aren’t just about scanning a status report; they are about:

• Culture Building: Showing your colleagues that they matter more than just the tasks they complete.
• Real-Time Calibration: Catching small misunderstandings before they snowball into full-blown crises.
• Mid-Course Corrections: Helping each other pivot gracefully before they waste weeks driving down the wrong road.

Think of it like maintaining a high-performance vehicle. You can save 30 minutes by skipping the oil change, but you’ll lose weeks when the engine blows up. Protect that check-in time fiercely.

3. The Empowerment Long-Game: Slowing Down to Speed Up

This third area took me years to understand, and I still find myself falling into a trap of thinking, “it’s just faster if I do it myself.”

When you are moving at warp speed, taking the time to teach, train, and handover ownership to someone else feels like a massive time-drain. So, you hold onto the task. You save an hour today. But you just committed yourself to doing that task every week for the next year.

True leaders understand the importance of empowering others and leveraging the team’s talents and insights. A mentor modeled the upfront investment of sharing his expectations and core values, which helped me anticipate his future thoughts and mindset.

• Stop Micromanaging: Trust your team to execute.
• Build Autonomy: When you invest the time to empower your people and share a consistent set of expectations and values, you build a self-sustaining team that thrives even when you aren’t in the room.

By spending the energy to coach your team through new challenges rather than just taking over, you aren’t just offloading work; you are building future leaders.

Flip the Script

The next time you find yourself saying, “I don’t have time for that,” pause and ask yourself: Are you saving a leadership penny or losing a leadership pound?

Let’s stop trading our long-term culture and organizational health for short-term checkboxes. Invest the time in others, protect your check-ins, and build for the future. The ROI will speak for itself.