Entrepreneur? StartUp? Product Manager? Why & How to Develop Your Sketching Skills

Six years ago I moved out to Silicon Valley.  Since that time, the number of startups and entrepreneurs and product managers that I have worked with, both professionally and personally, has been astonishing.  These people are bright, creative, and intensely motivated.  They are also oftentimes shy or apologetic when they try to sketch, or reluctant or fearful to sketch out their ideas.  It's obviously something they would like to be better at, but for most of them it simply feels like something that's out of reach.  Maybe the reason is lack of time.  Or lack of interest.  Or fear.     

So, if you're a startup founder, or working at a startup, or a product manager, or even someone just tinkering with an idea, why take the time to learn how to sketch more effectively?    

A Thousand Words

A sketch has the unique power to bridge language, time and cultures.  Images can be strategic communication tools for those that find themselves working in the emerging global economy.  Think about the small miscommunications that can happen in your company, with your co-workers.  Many of whom may sit right next to you and speak the same native language.  Or how people with different academic and disciplinary backgrounds have their own interpretation of the meaning of a word.  Words are slippery.  You need to provide the professional pine tar. 

Exhibit A: Let's say that you and three startup colleagues spend every night for 1 week hammering out your brand pillars over some fashionable microbrew IPAs.  You've decided that "sophisticated" is a pillar of your brand personality.  And then I ask each of you, individually, to name a product you feel most embodies "sophisticated".  Unless you've practiced your stories together, chances are we're going to have four different answers.  Why?  Because languages and words have histories.  They have baggage.  (See: "product design" when used in the Bay Area, USA.  I can't even.  It's a linguistical hot mess.)  Words have multiple meanings, and every individual has their own memories that have formed unique perceptions of the meanings of those words.  

So we need to wipe the slate clean.

Reboot

Picture yourself in the ubiquitous accelerator/incubator/consultancy meeting room.  Free (slow) WiFi.  Oversized table.  Sporadic moments of searching for a way to adjust your chair like you're a MIG pilot in Top Gun.  After some terse discussion, someone finally gets up and approaches what was intended to be an erasable white wall.  They begin to start a sketch.  The first marker doesn't work.  Someone more familiar with the lay of the land finds the aspiring artist a working marker.  Le artiste begins anew.  

What are they sketching?  Where is that line going?  Where is the next line?  What is it!?  Maybe this isn't exactly what you are thinking, but the key is you have no freaking clue what they might sketch.  Your understanding of what they are trying to communicate started at ground zero when they began sketching.  Your understanding only developed as the image developed.  The idea is born within your dome piece with no memory, no history, no preconceived notions, no skeletons in the closet.  Cognitive freedom.  

Revolution starts with stick figures. 

Google SketchUp Doesn't Count

The potential of "3D Lite" software as a way to visualize ideas is absolutely tremendous.  However - and some of you know where this is going - software has constraints, and these constraints taint and dilute ideas.  Maybe you think the idea is simple, but a vision is a complex, nuanced thought.  Using 3D software to accurately communicate the subtleties of an idea is like trying to blow "Bohemian Rhapsody" on a kazoo.  And yes, there are some people out there that can do this.  The 3D thing.  But this requires deep, innate talent, and all you require is skill.  Which leads us to....

Skill vs. Talent

For the purposes of this discussion, skills are abilities that can be taught to a certain degree of proficiency.  Talent is an innate ability that cannot be simply taught by one human being to another.

So what is sketching?  Skill?  Talent?  It's both.  It's a skill than can be taught to the limit of someone's talent.  Some people may tell you that it's an innate talent that you can't learn or teach. I don't really buy into that. I cannot honestly say whether my talent for sketching was the result of something I was born with, or whether it's something that developed because I started so young. I began drawing things from my imagination at an extremely early age, and did a lot of it.  Most of the designers I have worked with in my career that are really talented at sketching began at a very early age.  

So what came first?  The skill or the talent? 

My personal feeling is that sketching from your imagination - and being good at it - is partly the result of many hours of practice and partly the result of innate talent.  If you try something, and you like doing it, and you begin to get better at it, then the practice and the ability just feed each other.  There is a lot of recent information about the hours of practice it takes to become an "expert" at something.  The reason so many people will simply tell you to continue to practice is that sketching from your imagination requires you to build up specific hand-eye and muscle coordination skills.  Continuous practice helps build up your muscle memory and improve your ability to make what I call the "translation" accurate.

 As a startup CEO, or budding entrepreneur, or a motivated product manager, it will greatly benefit your ability to get exactly what you want if you can visually communicate what can't be seen, on command, to your audience.  As a product designer, I need to use sketching (or some other media) to accurately portray the visions and ideas that are being pulled strictly from my imagination every day.  Sketching from your imagination involves a combination of being able to imagine what you cannot see, visualize and hold complex images in your mind, and then have the hand-eye coordination to accurately portray what you are imagining.  More than likely, you will find the most difficult part is the "translation" from mind to paper.  Something falls apart.  The line work is there, but you find yourself thinking, "It doesn't look like what I see in my head".

I have spent time teaching drawing classes to people without a fine arts or design background.  Honestly, the "translation" was the one area where I struggled the most to help people increase their ability. I found that I could teach a brick to render (drawing what can be seen) but that teaching sketching (accurately communicating what exists only inside the your head) was a totally different animal.

My experience is that it's difficult, but significantly improving your ability to draw from your imagination can be achieved.  I'm not sure if there's any holistic, step-by-step proven method for helping with this translation, but for you aspiring product visionaries out there preparing to put your ideas on the line with millions of bones at stake, the following is a starter list of things you can do to help bring your ideas to life. 

Develop a Solid Foundation

One of the things I touched upon earlier is the ability of a sketch to more accurately communicate your vision than talking or writing about it.  This assumes that you can accurately translate what is in your head to a visual.  Of critical importance to making this happen is to develop a thorough understanding of the underlying principles of how humans see things.

Knowledge of things like orthographic views, one-point perspective, two-point perspective, etc. are an absolute must for developing a solid foundation so that you can accurately sketch from your imagination. Once you figure out what type of perspective you want to use for your sketch, there are step-by-step procedures to follow that will help you construct the perspective line work that will act as visual guidelines for your final line work. These guidelines act as the visual basis for your sketch, helping to ensure that what you sketch is an accurate portrayal of how humans see things.  The steps for drawing in perspective from your imagination are far too involved to completely cover here, but there are plenty of books and online resources for learning the basics of perspective.  The main thing is that you need to develop an understanding of how humans see their reality in order to make your imagination the reality.

Sketch It Like a Polaroid

One of the things that I was never consciously aware of as a child when sketching my ideas was that I was many times creating an imaginative "polaroid" in my head of what I wanted to sketch. And I was constantly comparing what I was drawing to what was in my head. Many artists and designers do this unconsciously or even incompletely - they only know the basic "feel" they are aiming for and they draw and redraw until the sketch appropriately reflects the ideas they want to communicate.

Take a few moments to close your eyes and really focus on the idea.  Picture the idea in 3D space, but don't rotate it.  Start with just one "view" of it and try to hold that image in your head.  Click.

Capture that moment like a photograph, and hold on to it. 

2D Sculpting

I know as a child that I would draw and redraw lines over and over and over until the sketch began to look like what I was imagining.  My hands would become coated with the extra pencil lead that matriculated to my face and hair.  I would look like someone just pulled me out of a dumpster fire.  I didn't bother erasing, I just kept going at it, almost like 2D sculpting.   

Reach into your mind and pull out that photograph.  When you are first beginning to translate your idea from your head to paper, it's OK to search with your lines.  Keep your foundational bearings, but don't be afraid to explore.  Keep searching.  Lay another piece of paper over the initial lifework.  Go at it again.  Copy the lines that feel right to start with and then build upon that foundation.  Over time that polaroid and what is on the paper will (hopefully) begin to align.   

Imagine the Line

When it comes time to begin to make your sketches more visually accurate, the process begins before actually putting that line down on the paper.  Put down two dots that represent where you want the line to start and end. Imagine that line on the paper - see it before you draw it. And then start the line before your first dot and finish it after your second dot. Drawing over your guidelines or through your perspective points is sometimes referred to as "drawing through" (Google: Scott Robertson). "Drawing through" gives your line work more accuracy and what designers refer to as "line confidence".

Line confidence is often the result of speed and consistency. The less your line wavers or shows hesitancy of thought, the more "confident" the line appears. This is one of the reasons "drawing through" is important - it helps you maintain a constant speed between your two points, and leaves the speeding up and slowing down for before and after your points or uses your perspective guidelines to help give you confidence in drawing your lines.

Miming

As you begin to tighten things up, one technique that will help you get the line work the way you want it to be is to "mime" the movement with your pen or pencil over the paper before actually putting it to paper. It's like a practice swing.  

When you mime, you are getting your muscles and your hand-eye coordination prepared to make the movement and building up a rhythm.   My ability to get the lines right the first time has increased to the point where I can draw things like complex S curves exactly as I want them on the first attempt. This obviously goes back to the "practice makes perfect" adage.  

Tell Your Story

If you have the ability to communicate your idea with a sketch, you have the ability to tell a visual story to others, whether they be investors, development partners, co-workers, et cetera.  Great storytelling is an extremely powerful medium because it reaches people on an individual level.  It captures people because there is a part of the story that they can personally relate to.  Visual storytelling can help you capture your audience more completely than any amount of typing or talking ever will.  It allows others to build upon an idea that is free of linguistic chains and make the idea even more meaningful.  The real power of sketching is that it will empower you with the ability to go beyond mere innovation and achieve invention.

So get to it.   

I have the distinct pleasure to work with an amazingly talented group of individuals at Whipsaw.  A creative by birth, a designer by trade, a business development strategist by profession.