I don’t know how, but my daughters turned out to be really good with creative stuff. I’m talking about the paint and paper stuff, specifically. Although I’m pretty sure they are biologically mine, I am not very good nor do I love drawing, painting, sculpturing, etc. so I’m not entirely sure how they came to both like it and be good at it. 

They really create beautiful things. Even my younger daughter, who is currently 3.5 years old, already paints very nicely within the lines of printed characters and starts to draw things herself that actually resemble the original object – at least to a point that we can identify what she meant.

Now that I come to think about it, they probably got it from my sister who is extremely talented in all sorts of creative stuff. A few years ago she took a silver crafting class and created beautiful jewelry. She actually created them for every woman in our family except me. Sis, if you are reading this – I’m still waiting for mine!

Watching closely how my younger daughter’s creative process evolves, I noticed a few different skills that she develops over time. First, she needed to know how to hold a pen. Then, she needed to learn to paint within the lines. Nowadays she is learning how to draw stuff herself (and then paint them), while my older daughters operate at a completely different creative level: A lot of the thought goes into what to draw rather than how to draw it.

These levels resemble the different creative processes and thinking that I went through throughout my career. I guess many of you went through the same process. Each such level requires a different skill level and different frameworks, and moving from one to another (at least to doing it well) might take time and practice.

But understanding these levels and knowing what to expect can help you identify where you are at and which skills you need to develop to operate effectively at the next level.

Level 1: Painting Within the Lines

In my first official product role I joined Imperva, then still a relatively young company with ~100 employees, as the product manager of their database security product. The product was still young but already well-defined and deployed on customers’ networks. 

I did a lot of work there on improving the product and making it more suitable for the market, easier to sell and deploy, and contributed directly to the product’s success and business growth throughout my time there. I even remember that after the successful IPO in 2011, I told my husband that this was the first time that I felt my stock options and their value were truly related to the work I did. But as important as my work was, its boundaries were predefined. Even when I created a strategic roadmap, it refined the already existing product and extended it, but it didn’t create a whole new thing.

Most product people start at this level. In your first product role, you are most likely to work on an existing product and on relatively small changes. With seniority you will be working on more significant changes and even leading the strategic direction, but when the lines are already defined this is still a different work than the other levels listed below.

Level 2: Drawing the Lines

After Imperva I joined eBay as Head of Product for Catalog and Classification within the Structured Data group. One of the first things I needed to do was to define the next-generation catalog system. I got very detailed explanations about the deficiencies of the existing system, and why eBay needed a whole new approach for the creation of its product catalog. 

I loved this work so much. Over the course of a few weeks, we created a masterpiece document outlining the principles of the new catalog machine we wanted to create. These principles had to work seamlessly together to create a machine that can operate well under multiple scenarios. We knew the design was good when we saw that it can support in a reasonable way even edge cases that we didn’t think of in advance.

Defining the system (and then implementing it) wasn’t easy. It was a complex task, and since eBay was already 20 years old at the time, there were many existing constraints that we needed to take into account. Together with my R&D counterpart, we debated each and every such constraint, alongside the desired functionality to serve eBay’s future, and found answers to all of them.

But here, too, although I was the one to draw the lines, someone else told me what I should be drawing, at least at a high level. I was super proud of my drawing and thought this is as challenging as it goes until I landed at Twiggle.

Level 3: Deciding What to Draw

When I joined Twiggle – a seed stage startup – as the VP of Product, I thought I was extremely ready. Their domain was tightly related to eBay’s one, and their enterprise B2B model resembled what I did at Imperva. I already led a large product group at eBay and knew I would manage a much smaller one at Twiggle so this was also a no-brainer.

But the first thing Twiggle’s founders asked me to do was to decide which product we are going to create with the amazing technology that they have built so far. This required a whole new level of thinking and a deep understanding of product-market fit. I mean, the options are almost endless. 

And they go far beyond the product itself. I remember that at some point, one of the founders said in a meeting something like “we are a search company”. I stopped him and said that I’m not sure I agree. Our first product is indeed a search product, but is that the core of the company? I claimed we were an “eCommerce understanding” company (Twiggle had a language model that was able to understand eCommerce-related text and break it down to a structured form on which multiple algorithms could run). With that perspective, I claimed that search just happened to be our first product.

Deciding what to draw left me paralyzed for a while. Creating on a blank paper without guidance is much harder than creating when someone else gives you some boundaries and constraints, or at least a desired outcome like the one I had at eBay. It might be counterintuitive, because you would think that not having any constraint is a good thing, but with so much freedom it could be much harder to create.

Your responsibility at that level grows dramatically and with it the impact of making mistakes. That’s why making sure we define the right product is one of the things we spend the most time on during our programs – in the CPO Bootcamp or when consulting, for example. 

This level requires a whole new thought process with dedicated frameworks. It also requires an understanding of a much broader perspective than just the product itself. You would need to be involved in the work of every other leader in the company in order to define the product that serves everyone well and could become a business success.

This is a non-trivial leap from previous levels. It is always challenging, since even if you succeeded once, and new product is a whole new journey. But this is the level that will make you a real product leader. Are you up for the challenge?