— CIO Alice Wang’s Adventures in Tech Wonderland

“Why, sometimes I've believed as many as six impossible things before breakfast”
— Lewis Carroll, Alice's Adventures in Wonderland."

As a proud father of two daughters, over the years, I have become — initially reluctantly — somewhat of an encyclopedia of fairy tales, particularly those featuring girls as protagonists. Time flies too quickly, my two girls are now all grown up, but it feels like only yesterday that I tucked them into bed on many nights, immersing them in a world of magic and wonder as I told them bedtime stories, timeless tales from the East to the West, even making up a few along the way. 

A decade later, at Golden Section, I spearheaded an initiative to develop an AI tool designed to assist tech company CIOs in navigating the intricate process of software creation. Our team graciously allowed me to name the product, and I decided on "Looking Glass". The inspiration for the product likely stemmed from the epiphany I had years ago while telling Abby a bedtime story, "Alice's Adventures in Wonderland."

Many years ago, after a long, tiring day at work in my then-role as a CIO for a tech company, I tucked Abby into bed and fought my heavy eyelids while recounting Lewis Carroll's timeless classic to her. As I listened to her repeated pleas for "one more story, please," the nonsensical challenges I faced during the day and the weight of my CIO responsibilities lingered heavily on my shoulders.

With the book still clutched in my hand and Abby by my side, the protagonist of Lewis Carroll’s story seemed to transform into Alice Wang, a newly minted CIO…

Alice Wang found herself struggling to navigate the myriad of challenges of building the MVP for her company after receiving the initial seed round. As the tech company's co-founder, it was her responsibility to create a solid product to launch the business.

But Alice had too many issues on her hands, all of these weighing heavily on her shoulders, she murmured to herself —

* Two tech stacks seem similar, but which one is better?

* I'm not myself; am I the right tech leader?

* The team debates the product's direction, I don’t know which way to go.

* Development chaos feels like a never-ending mad party...

* Last-minute requirement changes from the customer, like altering all the icons' colors from white to red, made the customer clearly upset with me. Perhaps I didn't accurately understand the customer's requirements in the first place. I guess I assumed too much.

* How can I obtain accurate metrics and intelligence in our development process? This is the battle I must fight!

With no answers to these questions, Alice felt overwhelmed by helplessness and chaos…

Alice Wang Followed the White Rabbit, Fell into the Rabbit Hole

As Alice pondered the unanswered questions and felt burdened by the immense challenges, she consumed one too many Red Bulls and cups of green tea. Exhausted, she eventually fell asleep in front of her MacBook, a scene reminiscent of Neo's slumber in front of his computer in The Matrix…

"Oh dear! Oh dear! I shall be late!… The hurrier I go, the behinder I get," exclaimed the White Rabbit, his voice filled with urgency.

Alice Wang caught sight of the peculiar white rabbit, dressed in a waistcoat and desperately racing against time. The frantic hopping and constant movement resonated with her own busy self as a CIO. Intrigued by the odd scene, she followed the white rabbit and suddenly, tumbled down the rabbit hole…

She found herself in a strange and disorienting scene. The walls of the tunnel were filled with software code snippets, unfixed bugs, and unnormalized data schemas. She passed by clocks, indicating that the project was long overdue. As she continued her descent, the sight of the Wicked Witch of the East on her broomstick sent a chill down her spine. She also glimpsed a magic Looking Glass on the horizon, giving her a sense of strange power and comfort, but it was guarded by a fearsome beast.

Curiouser and Curiouser!

Somehow, when Alice caught sight of the Looking Glass during her fall, her fear vanished, and she felt the enchanting power of the Glass. At last, Alice landed in a strange, mesmerizing land – a Tech Wonderland.

"Shen Mo Qing Kuang? Curiouser and curiouser!" marveled Alice Wang, she was so much surprised, that for the moment she quite forgot how to speak good English. "Oh wait, maybe it's because my parents are from China. I must have learned some bad English from them," she mused. The land she had fallen into was undoubtedly strange and otherworldly, yet the characters she encountered were somewhat familiar, resembling the "awake" world of her office…Alice Wang now is now journeying in Tech Wonderland.

Tweedledum and Tweedledee: Choosing the Right Tech Stack

During her journey, Alice first came across the whimsical duo, Tweedledum and Tweedledee, who introduced themselves as competing "Tech Stacks" while animatedly urging her, "Pick me!" Alice felt perplexed, uncertain about which tech stack to choose for her product. They appeared so similar at first glance, but upon closer examination, the distinctions became more noticeable - one boasted greater speed while the other possessed superior strength.

A sudden epiphany struck Alice: the decision of which tech stack to select shouldn't be based on how flashy the technologies are. Instead, it should hinge on the functionality and performance objectives she aimed to achieve with her product. Leaving the dancing twins behind, Alice strode forward on her journey, her mind invigorated by the fresh insight and newfound clarity.

Caterpillar’s Transformation

Alice Wang noticed an old Caterpillar perched on a luminescent mushroom, surrounded by an ethereal glow. As he puffed away at his hookah pipe, his gaze seemed to pierce through Alice with great interest.

"Who are you?" inquired the Caterpillar.

Alice replied, "Because I'm not myself, you see."

Plagued by self-doubt, Alice questioned her ability to lead the tech team. With trepidation, she asked the Caterpillar, "Am I the right person to be a tech leader?"

The Caterpillar pondered before responding, "You can choose who you want to be while always remaining who you are. Choose your path with your heart, and you will transform..."

As he spoke, Alice watched in awe as he transformed into a breathtaking butterfly with iridescent wings, casting a kaleidoscope of colors around them. Inspired, Alice realized she too could embrace her own transformation and growth, just like the Caterpillar-turned-butterfly.

This revelation instilled Alice with newfound confidence in her role as a CIO, understanding that she could shape her identity by embracing change and learning, just as the Caterpillar had.

Cheshire Cat: Embracing Change and Adaptation

In the dark forest, not sure which way to go, Alice saw the Cheshire Cat, its enigmatic grin lingering long after its body had vanished into thin air. The elusive feline's mischief reminded Alice of her own uncertainty about her product's future direction.

Unsure if she was dreaming or awake, but undeniably lost, Alice inquired, "Would you tell me, please, which way I ought to go from here?"

"If you don't know where you are going, any road will get you there," the cryptic cat responded.

Realizing the wisdom in its words, Alice retorted with a smile, "I must first determine my destination, and then create a product roadmap to guide me there." She watched the Cheshire Cat's toothy grin fade into the shadowy forest.

Mad Hatter's Tea Party: The Endless Development Cycle

As Alice Wang ventured further into Wonderland, she stumbled upon the Mad Hatter's frenzied tea party, where vibrant characters congregated around a table laden with teacups, saucers, and a medley of quirky refreshments.

The Mad Hatter, with hair as wild and unruly as her real-world developers, epitomized the never-ending cycle of development and the absence of an organized process.

The chaotic scene mirrored the disarray and stress that often burdened Alice in the realm of software development. Alice hastily bid farewell to the Mad Hatter, not even waiting for the completion of their boisterous "Happy Unbirthday" song.

Off with their heads!! Queen of Hearts: the Tough Customer

Alice walked into a beautiful rose garden, where she saw playing card soldiers hastily painting white roses red. Suddenly, the irate Queen of Hearts appeared and scolded them —

"I wanted red roses, and you planted white ones! Off with your heads!"

The Queen's outburst caused her playing card soldiers to tremble in fear, fully aware of the seriousness of their mistake. The unfortunate cards braced themselves for the wrath of the notoriously temperamental queen, who was infamous for ordering beheadings.

Alice found the Queen of Hearts reminiscent of those unreasonable clients or stakeholders who may have unrealistic expectations or demand abrupt changes to project requirements, posing challenges for CIOs to manage.

Alice was reminded of the importance of attentively listening to customers' needs and not relying on assumptions — red roses, not white roses.

Fighting the Jabberwock

As Alice ventured into the heart of Wonderland, she entered an open space, where there lay a massive and magnificent chessboard. At the opposite side of the chessboard, resting on an ornate pedestal, a shining object caught her eye - the Looking Glass, its surface shimmering with an otherworldly glow. Guarding the Looking Glass was the fearsome Jabberwock. Alice knew that to claim the magical tool, she would have to face the formidable creature.

The Jabberwock spotted Alice and lunged at her with its sharp claws. Alice swiftly dodged the attack, grabbed the sword lying on the chessboard, and fought back courageously. She successfully evaded several of the Jabberwock's assaults, discovered a weak spot beneath its neck, and in a split second, struck the beast's throat, ultimately vanquishing the monster.

Filled with a sense of awe, Alice approached the Looking Glass and carefully lifted it from its pedestal. As she held the magical mirror in her hands, a warmth spread through her body, instilling her with newfound wisdom and confidence.

Having conquered the Jabberwock and claimed the Looking Glass, Alice now possessed a legendary and powerful tool that would guide her through the many challenges of both Wonderland and the real world. With the Looking Glass in hand, she felt prepared to face whatever trials lay ahead, knowing that the magic mirror would always guide her forward.

There was this famous non-sense poem of Jabbawacky, recorded by this dramatic moment.

Jabberwocky (a Nonsense Poem)

'Twas brillig, and the slithy toves
Did gyre and gimble in the wabe;
As Alice fell through the rabbit hole,
She sought to conquer bugs and maze.

From Carroll's dreamy realm to GitHub's codes,
In Isaac's dream, with Abby close,
Looking Glass, a magic mirror for CIO
Development Intelligence arose.

The fabled Jabberwock, with eyes of flame,
Came whiffling through the VerySoft Azure Cloud,
And burbled as it came, its roar
Proclaimed its presence, fierce and loud.

With keyboard sword in hand, Alice stood,
Prepared to face the fearsome glitch,
And as the Jabberwock drew near,
Her courage swelled, her resolve enriched.

Yi, Er! Yi, Er! And click and drag,
The vorpal cursor went snicker-snack!
The Jabberwock, defeated now,
Collapsed with a thunderous thwack.

With the Jabberwocky slain, Alice claimed
The Looking Glass, now hers to wield,
A magic tool for tech insights,
A powerful ally by her side.

And hast thou tamed the Jabberwock?
Come to my arms, my beamish CIO!
O frabjous day! Callooh! Callay!
Her triumph echoed, high and low.

Awake x 2

Alice Wang awoke from her dream, drenched in sweat from her thrilling adventure. A sense of epiphany washed over her as wisdom from the dreamland seeped into her waking reality. Alice knew that the magic of Looking Glass would somehow manifest in her real life, helping her solve so many problems.

She brewed a fresh cup of coffee and walked to her computer, feeling recharged and liberated from her experience in the dream.

That's when Alice noticed an email from David Stagg in her inbox, with the subject line:

"Magic Looking Glass on the wall, who is the smartest CIO of them all..."

* * * * * *

… I woke up from my own dream, glancing over to see Abby sleeping peacefully beside me, her hair as black as ebony. The memory of Wonderland lingered in my mind, etched with vivid clarity. I felt a strong surge of inspiration, and I knew I had to create a tool for Alice, the Looking Glass she was looking for…

By Isaac Shi
April 7, 2023