From Pentimenti to Cultural Change

A Step-by-Step Guide to Painting A New Future for Your Organization 

There’s a lot more to a painting than what you can see on the surface.

Most paintings have layers — and no, I don’t mean the metaphorical layers of the art’s meaning. Actually, most traditional paintings have physical layers, such as previous drafts now painted over and the underdrawing and underpainting of the process itself. These leftover images are referred to as the “pentimenti,” and they are an essential part of painting something beautiful. That said, without the help of X-rays or infrared lights, a painting’s pentimenti is practically invisible to everyone.

This filtered perspective is exactly why it is so difficult to understand how working culture can change. Most people only see a snapshot of a company’s culture — a specific moment in time designed to look and feel as good as possible. Simply put, we see the final painting and absolutely none of the pentimenti. Consequently, most leaders fail to grasp just how much trial-and-error is necessary to institute cultural changes that last.

Many leaders want the product — the uplifting and efficient culture — but they have no respect for the process. They want to create cultural initiatives, but they have little understanding of where the company has been or where it needs to go. They just want to paint over the pentimenti and move on to something new. Unfortunately, this isn’t how you paint a masterpiece.

I’ve spent decades coaching widely diverse and highly successful C-suite professionals. In that time, I’ve witnessed the entire spectrum of success when it comes to cultural transformations. Some cultural movements lose steam before they even get started, while others inspire significant and sustainable shifts in the company. The difference is almost always in understanding and respecting the process, and this step-by-step guide can serve as your reminder.

This is the pentimenti that sits behind the masterpiece you’re trying to paint.

Step 1: Paint the “perfect” picture. 

Start with an ideal vision of success. What should this masterpiece look like? What themes should it portray? What emotions should it invoke? What is your idea of a “perfect” working culture?

This step has very few restraints. It isn’t about what’s practical, so much as it’s about what’s possible. An ideal viewpoint is the perfect first addition to our painting’s pentimenti, and that idealism is going to act as a framework for the entire process. Simply put, this is the skeleton of an eventual masterpiece.

Not surprisingly, idealistic leaders excel at this stage of the process. Their strong sense of vision and convicted values means the foundation of the painting is always pushing against future compromise. In fact, some studies show idealistic leadership is even an effective buffer against greed-driven fraudulent activities.

Step 2: Listen closely to first impressions. 

Now, the steps start to get tougher. Why? Because feedback has officially entered the conversation. Creations and concepts can feel very precious, especially when those ideas are deeply connected to how we imagine the future of our organization. That said, it’s not uncommon for even the most seasoned professionals to recoil at criticism toward something they hold so dear.

Unfortunately, this would be a missed opportunity — not only due to the fact that 41% of employees have left a job because they felt no one was listening, but also because it’s the only way to create the culture you need. Otherwise, the painting would stop at its first layer. No evolution. No adjustments. No masterpiece.

Did you know advanced imaging techniques have revealed Mona Lisa’s original left hand was a jumbled mess? It looked more like something from a cursed AI compilation than an Italian master. It was only after several layers of pentimenti that the painting reached its final form. This is why the successes of learning leadership and feedback-seeking behavior go hand in hand.

Step 3: Turn those impressions into actionable insight. 

Of course, those first impressions amount to very little unless they are recorded and categorized in service of action. I’m always surprised when I come across organizations who have gone to all the trouble of creating elaborate employee feedback programs without a focus on actionable resolutions. In many cases, these programs do an excellent job of collecting feedback and highlighting meaningful data.

However, they often fail to ask the most basic question: “Which of these data points demands action?”

Step 4: Sketch out an outline of what should change. 

Remember the original framework for your masterpiece? The skeleton of idealism? Well, it’s time to make some serious adjustments. If you’ve already identified the data that demands action, then this is simply about getting a rough idea of what that action needs to be. Remember, even though you do paint a masterpiece one section at a time, you always need to know where you’re going.

This framework should look like your first childhood attempts at those “How to Draw” books. Lots of erased markings. Lots of redrawn lines. Lots of pentimenti. Then, a final skeleton sketch that inspires pride because of what it took to get there.

Step 5: From there, fill in the details. 

If I wanted to keep things brief, this step would simply read, “Repeat steps one through four until you’re done.”

Of course, that advice doesn’t paint the whole picture for you, but it does give you a good idea of what it takes to create the culture your organization wants and needs. It takes a lot of iteration and a lot of back-and-forth. After all, the pentimenti of a painting isn’t there because the artist just really likes doing the same thing again and again. It’s there because that’s what was necessary to realize their vision.

Unlike art, your vision is a shared vision. It isn’t a singular concept by one person with every revision in service of that vision. Instead, it is willful collaboration where every layer of the pentimenti is added in an attempt to create a masterpiece that wows everyone.

Start respecting the pentimenti. 

Painting a masterpiece and creating sustainable cultural change are both daunting tasks, and they aren’t normally things you get right on the first attempt. That’s why pentimenti is an expected and respected part of the process. Try and fail. Conceive and reconceive. Ideate and revise. Release and receive feedback. This is the give-and-take that makes these daunting tasks possible over time. This is the sort of iteration that puts your uplifting and efficient culture within reach.

Written by Dr. Sam Adeyemi.
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