When Someone Says “Use Your Initiative,” What Are They Actually Asking?

Most organizations tell people to show initiative. Very few explain what they actually mean by it.

My teams and I called this the $20 pizza problem, or sometimes just management 101 around here. The company needs you to order a large pizza with everything on it and deliver it to the Senior Management conference room. The company gives you $10 and says, “Yeah, I know it isn’t enough, so you are going to have to find the other $10 on your own.” The pizza needs to be delivered in two hours, and before you can object they say: “Just make it happen.”

That is initiative in a nutshell. The question is what kind of gap you are being asked to close. In my experience there are two completely different versions of it, and they require completely different things from the person being asked to show it.

Think of it this way. Someone tells you to get from St. Louis to Chicago in five hours. You can take any combination of roads, planes, or trains. You just have to be at a specific spot in Chicago in five hours. Nobody tells you how. The objective is yours to achieve and the method is yours to find.

Now you try to book a plane and they say it is too expensive. You try to book a train and they say it is against company policy. Every method you find runs into an internal wall. A rule, a policy, an approval process. That is initiative against internal constraints. The organization’s own system is what is blocking you.

Now imagine the same trip but no internal restrictions. You just do not know which combination of roads, planes, and trains gets you there in five hours. That is initiative against uncertainty. The organization is not in your way. You just have not figured out how yet.

The first is initiative against internal constraints.

• The objective is clear and the method is yours to find. When you find a method, the organization’s own rules block it.

The second is initiative against uncertainty.

• The objective is clear and the method is yours to find. The organization is not blocking you. You just do not know how yet.

In both cases nobody tells you how. What changes is what you run into when you start figuring it out.

My first job out of college was a management trainee in a national food company. It was so long ago that everyone used to smoke in the office. Man, I do not miss those days.

After about three months on the job, I was invited to the annual corporate meet and greet with all the other management trainees in the company hired along with the directors over those facilities. Everyone who traveled to the event stayed at the same hotel, so we all met that evening in the hotel bar. Bill, my director, approached me and said, “I am going to order drinks for everyone, but you need to put it on your room bill, so you are going to pick up the tab.” I was shocked and said, “I couldn’t afford to pay for that.” He laughed and said, “You wouldn’t have to. I can approve your expense report but not my own, so there would be no questions. Don’t worry about it.”

The next week, after we got back from the trip, the office controller came to see me and said, “Andy, the company will not pay for a two hundred dollar bar bill at the hotel, and this is against company rules, so you will have to pay for this yourself.” At this point, I got very nervous and said, “Bill told me to do it and that he would take care of it.” The controller sighed and said, “Ok, I understand. I will get with Bill and see what had happened.” I never heard anything about it. When I contacted my director, and he just said it was handled and not to worry about it.

What that experience taught me was simple: sometimes the gap between what you are expected to deliver and what the system allows you to do is just handed to you. Closing that gap is your job. So is the risk that comes with it.

Later in that same program, the VP of HR was visiting our location and was hosting a community event. He walked up to me and said, “I need you to get a pallet of our products, enough for 30 people, delivered to the meeting by 6:30 pm so we can give these out to the people there before they leave,” and then he walked away. I was actually so surprised that I did not even ask any questions, not that he was offering any either.

I had no idea how to do it. The meeting was on the other end of town. I went to Shipping and asked. They pointed me to someone who knew a driver willing to help. We got the pallet loaded and transported. When we arrived, I discovered the pallet needed to be broken down and restacked before it could get where it needed to go. We did that ourselves. Time was running short, so I made a judgment call about where to leave it so people could access it when they arrived. I stayed and helped distribute the product as the meeting started.

The next day, the VP gave me a pat on the back and a wink. He said, “You pulled that off just barely,” and walked away.

He was not impressed that I knew how to ship a pallet. What he was watching was whether I could figure it out under pressure and still deliver. The just barely was the point. I did not execute a polished plan. I hit obstacle after obstacle and kept solving the next problem until the objective was accomplished.

What that experience taught me was simple: I don’t have to know how to do something, but it is still my job to execute it and get it done.

Both experiences taught me something true about how corporations actually operate. Organizations have rules that don’t always make sense, obsolete procedures, and contradictory requirements. Sometimes getting useful work done really does require pushing or bending something.

The danger is when rule-bending becomes the expected operating model while the formal rules remain in place. When that happens, initiative becomes a euphemism for: you carry the risk of circumventing our own system.

Initiative against uncertainty is a leadership capability worth building. It is how people learn to operate in ambiguous situations, find resources they do not already have, and adapt when plans meet reality.

When initiative against internal constraints becomes routine, it is a sign that the organization’s formal rules and actual expectations are no longer aligned.

Not all initiative against internal constraints is the same.

In many factories, finished goods are counted the day they are produced. At the end of the month, production teams often hold back a small buffer. They make ticket, stop counting, and carry the remainder into the next period as a cushion. It is technically against the rules. Most operations managers know it happens. It is a way of managing the fact that the month resets and the pressure starts over.

That is initiative against internal constraints. It is working around a rule to manage a legitimate operational reality.

What it is not is putting 1,000 units into the system when you only produced 500. That is falsifying records. That is fraud. That is the dark side of constraint navigation and it is not what we are talking about here.

The difference matters. Working around a rule that does not fit the reality of your operation is uncomfortable but sometimes necessary. Misrepresenting what actually happened crosses a line that the organization’s own controls exist to prevent.

When someone says use your initiative, there is usually a simple question underneath.

What obstacle are they asking you to overcome?

I failed many times in my career when I could only see the internal constraint and not the whole problem.

Let me go back to the $20 pizza problem. Based on the directions I was given, I do not have enough money to buy the pizza. So I can beg, borrow, or finesse the extra $10. Or I can go to the store quickly, buy a large frozen pizza, and cook it in the time it takes to get there.

Sometimes I could not see that second option. My creativity was blocked because I was so focused on what was wrong with the system that I stopped working the problem.

Using initiative is a learned skill and it is necessary in corporate life. You will be most successful when you stay focused on solving the problem rather than on what is standing in your way.