It's Not About the Time Sheet

The Situation

This past week, two coaching clients brought me nearly identical conflicts. Both were frustrated with employees who repeatedly failed to submit their time sheets and expense reports on time. One CEO told me he had finally terminated a project manager after months of reminders, conversations, warnings, and second chances.

As I listened, I found myself asking a question that has followed me throughout my career: Why would someone risk their job over a simple administrative task?

The reason the question stayed with me is that I've lived on both sides of the conflict.

Early in my career, I hated filling out time sheets and expense reports. Every reminder felt like an interruption. My job was to solve problems, serve customers, and deliver results. That's where I wanted to spend my time and energy.

Part of me felt that my work should speak for itself. Part of me felt that my freedom to decide how I spent my day was being constrained. If I'm being completely honest, I sometimes felt the request was beneath me.

I had earned a Ph.D. I was being paid to solve complex problems and create value for the organization. A small part of me wondered why anyone cared whether I had completed a form by Friday afternoon. And if I'm being even more honest, there was another question lurking underneath it all.

Didn't the company trust me?

Looking back, I can see exactly what was happening. My esteem was getting involved. My autonomy felt threatened. Somewhere underneath it all was a question about trust.

Years later, I found myself sitting on the other side of the desk. Now I was the CEO waiting for missing reports. I was listening to finance teams explain why they couldn't close the books and trying to understand project profitability without complete information.

The irony wasn't lost on me. The very reports I had resented as an employee had become essential tools for running a healthy business.

As an employee, I saw paperwork. As a CEO, I saw information.

Information that helped people get paid accurately, allowed customers to be billed correctly, and helped me understand whether projects were making or losing money. It informed decisions about hiring, staffing, pricing, and growth.

The longer I sat with the issue, the more I realized that neither side was wrong. Employees wanted their work to be valued. They wanted autonomy and trust. Organizations needed visibility, accountability, and financial discipline.

Both sides had legitimate interests.

The Turn

Then another realization hit me.

Most of us aren't particularly good at filling out time sheets anyway.

Our days rarely unfold in neat, predictable blocks of time. Priorities shift. Meetings run long. Emergencies appear. Yet somehow, when Friday afternoon arrives, our time sheets often suggest that Tuesday looked remarkably similar to Wednesday, which looked surprisingly similar to Thursday.

We laugh about it because most of us have done it. Very few people track every minute and every dollar perfectly. Most of us are reconstructing the week from incomplete notes and fading memories while juggling competing priorities. Perhaps the exception is lawyers, who have spent entire careers turning six-minute increments into an art form.

The challenge becomes even greater when we consider how modern work actually happens. You're placing an order for materials to be delivered to a job site when a colleague calls with a project question. While you're talking, a text arrives from your spouse. An email notification pops up from a customer.

Ten minutes later, how do you log that time?

My fascination with the problem actually goes back to 1999. The internet was just beginning to transform how people interacted with computers, and I became convinced that technology could solve the time-sheet problem. I launched a browser-based front end for SAP that made entering time dramatically easier than the traditional interface.

The software worked. People liked it. But the problem never completely disappeared.

Looking back, that should have been my first clue. Better technology reduced friction, but it didn't eliminate the human side of the challenge. People still had to decide that recording their time was important enough to do.

The experience taught me an important leadership lesson. When behavior isn't happening, the first question shouldn't always be, "What's wrong with the people?" Sometimes a better question is, "What about the system is making success difficult?"

Which raises an interesting question: if employees see the exercise as an administrative burden and employers understand that the data is often an approximation, what is the real conflict?

The answer, I suspect, has very little to do with forms.

The Shift

Years after I retired, I encountered an even more puzzling example.

An employee left her job with thousands of dollars in unfiled expense reports sitting on her desk. The company owed her the money. The receipts were there. The reimbursement was waiting.

I've thought about that story for the last couple of years because, at first, I couldn't understand it. Why would someone walk away from money they had already earned?

As I learned more about her circumstances, I began to understand that the expense reports were connected to a broader struggle she was having with her finances. What looked like a simple administrative task from the outside felt much heavier to her.

What appeared irrational from the outside began to make more sense once I understood a little more about what she was carrying.

That realization reinforced something I had already learned during my years as both an employee and a CEO. When people consistently avoid something that is clearly in their own best interest, there's usually more going on beneath the surface than we can see.

The coaching clients I worked with initially viewed the situation as a people problem. Their instinct was to focus on who was failing to comply and how to increase consequences. Instead, I encouraged them to become curious.

Rather than asking, "Why are you late again?" I suggested they ask, "Help me understand what's making this difficult to complete consistently."

That small shift changed the conversation.

One employee admitted he was reconstructing hours from memory every Friday because his schedule was packed with client meetings. Another described how travel receipts accumulated until the task became overwhelming. A third pointed out that client work was praised and rewarded while administrative work felt invisible.

None of those explanations excused the behavior, but they did explain it.

Something else became clear during those conversations. The managers and employees had been focused on their positions rather than their shared objective.

The employees didn't want to spend valuable time filling out paperwork. The managers needed accurate information to run the business. As long as the conversation stayed at that level, the best outcome was likely a compromise where neither side was particularly happy.

Progress began when both sides recognized a common goal. They all wanted a healthy company that served customers well, paid people accurately, and continued creating opportunities for everyone involved.

Once that shared objective became visible, the conversation changed. They were no longer arguing about time sheets. They were working together to solve a common problem.

One employee agreed to spend two minutes entering time at the end of each day rather than trying to reconstruct an entire week on Friday afternoon. Another began using a mobile app to photograph receipts as expenses occurred. A third blocked fifteen minutes on Friday afternoon for administrative work and treated it with the same importance as a client meeting.

One manager even considered recognizing teams that achieved 100% on-time submissions for an entire quarter. The idea wasn't really about the reward. It reflected a different leadership question: How can we make the desired behavior easier, more rewarding, and more visible?

That mindset often produces more creative solutions than another warning email.

AGENT in Action

What Made the Difference

The breakthrough came when everyone stopped arguing about the paperwork and started talking about the interests underneath it. Once they recognized a common objective, they could begin designing solutions that served both the organization and the employees.

That's the difference between compromise and collaboration. Compromise asks each side to give something up. Collaboration begins with a shared goal and then searches for ways everyone can win.

AGENT, Briefly Mapped

AWARE: The managers recognized that repeated frustration was turning a performance issue into a relationship issue.

GROUND: They clarified what truly mattered: accurate payroll, client billing, forecasting, compliance, and operational visibility.

EMPATHIZE: They became curious about what was getting in the way instead of assuming employees simply didn't care.

NEGOTIATE: They stopped debating positions and focused on their shared objective, creating solutions that addressed both organizational needs and employee realities.

TIE: They established clear expectations, accountability, and support moving forward.

The lesson is simple. Win-win solutions become possible when people stop asking, "How do I get what I want?" and start asking, "What are we trying to accomplish together?"

Practice This Week 🛠

Try This Before Your Next Conflict

• What common objective might exist beneath our competing positions?

• What legitimate interests exist on both sides of this disagreement?

• How could we make the desired behavior easier, more rewarding, or more visible?

You don't have to lower accountability. You simply have to understand the conflict before you try to solve it.

Reflection

I've been the employee who rolled his eyes at time sheets, and I've been the CEO who chased them. Both perspectives were real, and both were incomplete.

What finally changed my thinking was realizing that the conflict was never really about the paperwork. It was about finding a shared purpose that could support both accountability and autonomy.

The moment people discover a common objective, they stop being adversaries and start becoming partners in solving a problem.

Conflict doesn't define us. How we show up in it does.

See you in the win-win moments this week!

Sam