How to be the Hero in Your Company’s Digital Transformation

TLDR: Find two more heroes and have them find two more heroes. Then have those people find two more heroes. Then have them find two more… You get it.

(That’s basically the gist of this post, so you can leave now if you’re busy. I won’t be offended.)

You’re still here? Ok cool. Let’s imagine a scenario. You’ve discovered a revolutionary new technology that could transform your business. So what do you do next?

Most of us (myself included [until recently]) imagine the following:

  • Create a detailed presentation or memo about the technology, its potential uses, and the impact it could have for the company. (Bonus points if your name is nice and big on the cover slide.)
  • Create functional demos or proofs-of-concept that show some potential uses of the technology. (Bonus points if the POC is in a repo or branch with your name on it, or in a system that you control.)
  • Draft a press release (either digitally or mentally) announcing the company’s novel application of the technology and with some smart pithy quotes from yourself, the hero, who helped spearhead this new and valuable initiative, and how lucky the company is to have someone as bright and innovative as yourself.
  • Browse the Design Within Reach website to imagine some slick furniture for your new corner office.

If that wasn’t clear enough, let me hit you over the head with it: Along with innovative technologies comes the allure of personal power and success. New tech is no different than Frodo’s ring, and we should resist the temptation to hoard it for personal gain. We all know where that leads.

“GPT3 is the one true AI!”

But anyone that’s read a business book knows that it’s a team sport, and you should value the success of the company over your own individual aspirations.

So that’s why to maximize the potential of a new technology you need to get it in the hands of as many people as possible. Some guidelines:

  • Default to open: Larger public conversations provide more value than smaller private ones. If you find yourself hoarding information or expertise, find ways to get it into the hands of others so you’re not the bottleneck.
  • Look around: Find people in your organization (whether they’re below you, above you, or parallel to you) who can benefit from this new technology and get it into their hands today. Resist the urge to build something yourself if there’s someone else who can be equally inspired and build it themselves. They will, in turn, inspire others who will keep the momentum going.
  • Find the fear: New technologies often come with fear of the unknown, which manifests in swirling conversations around job replacement and the downfall of society. Find the fear and address it with clear examples of what the technology can (and can’t!) do, and your company’s unique (and hopefully humane!) approach to leveraging the technology. And remind folks that technology doesn’t replace jobs; people that use technology replace jobs from people who don’t.

Speaking of fear, I went down a bit of a rabbithole around fear and technology and want to share some thoughts. (Unless you want to leave, which is cool too. Seriously, nobody’s keeping you here.)

Is “Digital Transformation” Cringe?

The term “digital transformation” makes me cringe a little bit, and I wanted to understand why. I mean, shouldn’t the idea of “digital transformation” sound exciting and inspiring to a nerd like me?

Let’s dive a little deeper.

What happened in 2016??

It looks like the term started to get popular around 2016. But why? Let’s ask our trusty frenemy GPT-3:

Why did "digital transformation" get more popular around 2016 according to google trends?

The term “digital transformation” became more popular around 2016 due to a number of factors. The increasing prevalence of technology and digital services in everyday life has made it necessary for companies to become digitally savvy. This has been further compounded by the rise of the Internet of Things (IoT) and the increased accessibility of cloud computing, which have created an increasingly interconnected digital economy. Additionally, the rise of big data and analytics has made it easier for companies to gain insights from their data and make more informed decisions. These factors, combined with increased competition and the need to stay ahead of the curve, have all contributed to the increased popularity of the term “digital transformation” around 2016.

Interesting. But you’ve gotta fact check those GPTs. (Remember, they’re language models not real intelligence.)

Ok, that’s something. It looks like “cloud computing” pre-dates the rise of “iot”, “digital transformation”, and “big data” and seems to be growing in popularity while the others stagnate.

So my working assumption is that cloud computing seems like a real trend compared with “iot”, “digital transformation”, and “big data.”. I guess that makes sense to me, and can maybe explain why I’m a little skeptical of the term “digital transformation”. It feels like a buzzwordy fad which is confirmed by my super intense and exhaustive research above.

Finding the Fear

But speaking of the above, let’s return (“circle back”) to the GPT-3 response because it touched on an interesting topic. (Emphasis mine)

"These factors, combined with increased competition and the need to stay ahead of the curve, have all contributed to the increased popularity of the term “digital transformation” around 2016."

If you read between the lines you can smell something else besides the business talk: fear.

With the increased competition brought about by new technologies, people are scared. Any why wouldn’t they be? Moats are shrinking and your next competitor could be a teenager living in their parent’s basement. Your company could fail at any moment and your life and livelihood are at stake.

It’s a scary world. And fear makes smart people do some pretty silly things. (For example, hiring 3rd parties to handle your company’s “AI Strategy” because they make it sound so exotic and appealing, meanwhile you’ve just willingly outsourced what could be a key differentiator for your company to a parasitic vendor.)

It’s people’s fear that clouds their judgement and makes them hastily hire companies like these, which are basically just startups that make API calls to GPT-3.

This meeting could have been an email? These startups could have been an API call to GPT-3.

A wise person once said “Every human decision is either made from fear or from love” and it’s stuck with me.

Because if you’re looking for answers to your problems out of fear, you might not be clear-headed enough to make the right decisions. But if you’re making decisions based on love – love of your company’s mission, love of your co-workers, love of your hope for this technology to improve the human condition – then you’re on the right path to achieving real change and not just personal ambition.

Technology is Like Soylent Green

It’s people! And if you leverage your love of people, not just technology, you’ll have a better chance of helping your company embrace new technologies in an increasingly competitive and scary world.

So get people involved and find ways to encourage their sparks of enthusiasm. Then you’ll finally be able to sit back, pour yourself your beverage of choice, and watch the transformation happen from your slick corner office.

AI Disclosure This article was influenced by a generative language model in the ideation phase. For details please expand the sections below.
Human Computer

A generative text language model (GPT-3) was used in the ideation phase of this article to help clarify the author’s thinking.

Prompts used were:
“Why does the term “digital transformation” make me cringe?”
“What is digital transformation”
“What are some barriers to digital transformation in a company?”
“How is digital transformation like the ring in lotr?”


The outline for this article was created without the assistance of any generative AI.


This article was written from its outline without the assistance of any generative AI.


This article was edited without the assistance of any generative AI.