The art of starting

I recently wrote The art of change and The art of forgiving about my transformation from a working at Google for 10 years to deciding to take more risks. I realized that I had to leave and start a new chapter. This is the next part of the story. It's about my first few months at a start up and some of the things I learned. Like before, I've told this story through my artwork/paintings.

For context, I joined PlanGrid in November. It's a series B-company in San Fransisco that has a game changing product-market fit in the area of construction productivity. The industry is rapidly transforming and construction companies are looking for technical advantages to differentiate. PlanGrid allows teams to create and share markups, issues, progress reports, and to communicate in real-time. Levi Stadium, for instance was built with PlanGrid.

Lesson 1: Be open minded and have a vision

I've been painting for a long time, but I don't enjoy it unless I'm really in the mood. It's an obsession more than a relaxation for me. I usually don't start painting unless I'm ready to work, and I'm not doing it so it can be finished quickly. I'm trying to get an idea on the canvas. Sometimes that idea isn't fully formed when I start and the act of painting shapes and refines the original thought further.

Obviously, I'm no Michelangelo but he had a great quote about this, "I saw the angel in the marble and carved until I set him free." He didn't set out to simply carve an angle. The artwork was a process, and not an end result. There's a big difference in this mindset. You can see this obsession in Rondanini Pietà that he was carving when he was 89 years old, and stopped just days before he died.

How this relates to work: My role as a leader is to build great teams, and not just creating bits. Creating bits is the byproduct of having great people and teams. And like art, building a great team takes a lot of improvisation and obsession. You need to go through the process of learning and adapting. It's important to be open minded and to understand before acting, but it's also important have a vision and values.

Lesson 2: Understand the subject

We have a cat in our family named "Trouble" and he's a lot like his name. A few months ago I wanted to do a drawing that captured his personality. I find portraits particularly challenging, since they need to communicate a deeper feeling about the subject.

There is a saying, that the eyes are the window to a person's soul. It is important to know how to handle eyes in portraits. The way eyes are represented can make or break the composition. For example, Steve McCurry's Afghan Girl photo, which appeared on the cover of the June 1984 National Geographic, was named "the most recognized photograph" in the history of the magazine. This was primarily due to her piercing sea-green eyes, staring straight at the camera, resulting in a very striking and appealing portrait. 

When I start a portrait, I try to capture the soul of the subject. The eyes tell us how they are feeling, what they are about, and how much to trust them. Focusing on the eyes, also means ignoring everything else for a bit. If you can find honesty in the eyes, everything else will fall into place.

How this relates to work: Like a portrait, the first few weeks I needed to temporarily ignore all of the excitement and whirlwind of starting a new role, and concentrate on why I was hired and making sure I deeply understood the role. Listening is the key. Be curious. Find out who the people on the team are and what they want to do.

Lesson 3: Create a solid foundation

The next phase of a drawing is building up the "under painting". It means switching gears from being very focused, to being very loose. It's a rough sketch that is typically done impressionistically. The intention is to get the right colors and strokes in the right places. If you don't stay loose in this phase, you end up with a drawing that feels tight and controlled. An art professor in college called this, "bombing the canvas."

An underpainting can take on many forms. Most commonly though, the goal of the underpainting should be to establish the values in the image. The values are the darks and lights. It’s how we see and perceive light. Without accurate values, you have no defined light. With no defined light in your work, and you will have a painting that feels flat.

How this relates to work: Like an under painting, my first weeks at PlanGrid were about getting a broad view from many perspectives of the company. I met with everyone - literally. Each person I met with added a bit of color. Within a few days, I had a basic sketch of their values. I was still forming opinions, but with a broad view from many perspectives, I was able to start understanding. I was also still listening more than talking.

Lesson 4: Fight the impulse to fix things

I love the Dutch impressionists like Vermeer. When I saw The Little Street in person, it blew my mind. What he was able to do with light was astonishing. After Vermeer had defined his composition and the basic lighting scheme through the underpainting, he proceeded to the next stage called "working-up." Working-up in Dutch was called "opmaken" which means to edit. During the working-up he gave everything its correct coloring, to render materials appropriately, and to fix the final shape of the forms.

In my drawing of Trouble, I started to work on the foreground and stayed away from the background. The background of a drawing is important and can hold the composition together, but if you spend too much time on it, you can get confused. The background and the foreground can become flattened together. One of the benefits of digital drawing is using layers and creating the illusion of depth in the drawing.

How this relates to work: After a month or two at PlanGrid, I started trying to combine my impressions with the goals I'd seen initially. I tried testing out a few ideas on people. I was listening, getting to know people, and trying to understand how everything fit together. The "big picture" was still a work in progress. I needed to be patient with myself and let it form at its own pace. As I showed trust, my new team did the same and we started building new ideas together. It was critical at this stage to not get too directive or assertive. In general, I love to jump in and try to help, but I needed to fight these impulses. I realized that I didn't know enough to have an opinion on most things.

At this stage, the drawing can look unreal. It's the messiest stage and the most confusing, but the character is starting to become alive. The potential of the subject is showing up. The composition is roughly defined. We're gaining confidence and feeling that the sketch is headed in the right direction.

Lesson 5: Dive deeply into the complexity

It's time to dive into the details. Details are extremely important and can make or break a drawing. The trick is to not "overwork" the subject. The greatest killer of freshness is to try to repeatedly correct things and you loose all those "happy accidents" and spontaneous strokes. Too much detail is as bad as too much fuzziness. It's give and take. We need to simultaneously be able to zoom-in on details and then zoom-out on the larger composition. We need to stay balanced. Adding details can increase the contrast and helps give the drawing a pop.

How this relates to work: At this stage of ramping up, like a drawing, you will either start to show up or fall apart. My approach is to step back, get out of the way, let the team emerge. Let things be messy if necessary, at a minimum it will expose the capability of the group. Let "happy accidents" occur and be ok with making some mistakes -- own them and show you are a real person.

Lesson 6: Publish your initial plan and move on

I consciously do not finish my paintings. Instead I just find a good place to stop. Resist the temptation to fix everything. Now is a good time to put on a few finishing touches and drop your brush. Lots of artists have a hard time at this stage. Some famous artists have taken months and even years to finish a painting. The 19th-century French artist Ernest Meissonier took 13 years to finish his painting Napoleon's victory at Friedland which is 53 1/2 x 95 1/2 in (136 x 242.5 cm) in size. Ingres took a decade to paint his Madame Moitessier, though he did put it aside for a while, he didn't spend all that time working on it!

How this relates to work: Like a team or a plan, if you fuss with a painting for too long, you run the risk of overworking it. Inversely, if you declare your learning phase on a team finished too soon, you run the risk of not building up enough credibility. Starting in a new team is like art - many things to balance and get right.

In summary, I believe that my role as a leader is to build great teams. Creating bits is the byproduct of having great people and teams. And like art, building a great team takes patients and time, and a lot of improvisation. You need to go through the process of learning and adapting. It's important to be open minded and to understand before acting. It's also important have a vision and values, and to have a sense for when to talk about them.

Summary

Lesson 1: Have a mindset of improvisation

Lesson 2: Know why you were hired

Lesson 3: Create a solid foundation

Lesson 4: Fight the impulse to fix things

Lesson 5: Dive deeply into the full complexity

Lesson 6: Publish your initial plan and move on