Working with Ambiguity (Step 1: The Three Bricklayers)

Over the last ten years or so, one of the most frequent topics on which mentees seek advice or guidance on is “pitching/socializing big idea projects”. Even as recently as a couple of months ago, I have encountered variants of this mostly in the form of “I have an idea. I don’t know how to convince my manager / skip to ‘fund’ it.”

There’s really no secret sauce approach to this. It is a function of an honest assessment and presentation of the time and resources to be expended and trade-offs / compromises involved weighed against the ultimate value delivered by a desirable outcome and the cost of failure as well as the opportunity cost of "not doing this".

The shape and content of socializing a big idea as worth doing also depends a lot on the personality of the originator as well as the “DNA” of the audience (and of course, the resources and constraints of the organization).

But at the core of it is a simple mechanic - inspiring confidence in the intended audience lies in resolving the ambiguity inherent in getting “from here to there” and then charting a clear path to a desirable outcome as well as contingency to deal with failures and sub-optimal outcomes along the way.

One of the big transitions from being a high performing Software Engineer to a Staff or Senior Staff level (on the path to a Principal Engineer level) is about creating a path forward rather than being handed a mostly fleshed out path. This resolution of ambiguity is one of the harder skills to learn and often decides one’s career trajectory. The first step of dealing with ambiguity is best illustrated by a well known story that one of my mentors once told me.

TL;DR -- Step 1: Know the "big picture" context that forms the outer bounds of the labyrinth of ambiguity one has to traverse.

The Story of the Three Bricklayers (aka "The Big Picture")

Once upon a time, a person rode by on a horse and saw three bricklayers hard at work on a hot summer day - laying bricks, of course!

The rider asked the first one, “What are you doing?”.?

The first bricklayer was irritated at the interruption. Without stopping what he was doing, he answered with an edge in his tone, “What do you think I’m doing? I’m laying bricks.”

The rider moved on and asked the second one the same question. The bricklayer stopped to wipe the sweat off his brow.?

“I’m building a wall”, he said.

The rider reached the third bricklayer and repeated his query.

The third stopped what he was doing and smiled at the rider. He stepped over to the side of the rider and with a wide sweeping gesture pointed out the empty expanse beyond the area of work.?

“We’re building a castle. This shall look over a great city and protect it.”

I love this story.

The first step in any attempt to socialize an idea is the concept of the “castle” -- the ultimate goal of the sequence of tasks. This "Big Picture" understanding provides the cost and objective functions to make any trade-offs or optimizations down the way. Making the transition from thinking about “just laying bricks” to “building a wall” to “building a castle” is the progression that an engineer has to ingrain into their mental framework in order to learn and grow.

Once we know the big picture of the context, we still have to traverse from “here to there” -- from our current ambiguous state to producing whatever we’ve embarked upon to deliver.

The first part of this involves a lot of exploration (One of my mentors Kent Beck has an excellent series of notes called “3X - Explore, Expand, Extract” that lays out a very well thought out path).

The hardest part about “selling” an exploration is that the very nature of an exploration makes it not fit any cadence of success/outcomes. This is the trickiest part of the investment one makes into charting a path through the unknown. A breakthrough might be just a few minutes away from the approach you either give up out of fatigue / frustration or are forced to.

TL;DR: Exploration is the most "subsidized" part of dealing with ambiguity, a place where most of your capital - be it personal, professional, or resources has to be spent without a concrete initial guarantee of success.

In the next part of this series, we’ll use Kent’s 3X framework as well as anecdotes from my own personal experience to chart out some of the best practices to explore the initial ambiguity and capture some insights into inspiring investments into the prototypes/explorations (e.g. "Fail Fast", "Know what not to do", "The Promised Land" etc.)

Or simply put, how do we inspire confidence in our intended audience to back our proposal as well as figure out how to accomplish the unenviable task of making the square peg of measurable metrics and a steady cadence fit the round hole of exploring an ambiguous domain, while giving us enough "runway" to explore and find a viable path forward.