Hackernoon logoDigital Transformation Strategy: Dinosaurs, Harpoons, Greek Myths and YOU! by@artshectman

Digital Transformation Strategy: Dinosaurs, Harpoons, Greek Myths and YOU!

Art Shectman Hacker Noon profile picture

@artshectmanArt Shectman

Art Shectman is the Founder and President of Elephant Ventures and co-founder and President of Ultranauts

"Digital transformation is not one single thing to implement, it is a core alignment with continuous investment in innovation and excellence", writes Arthur Shectman, President and Founder of Elephant Ventures. In this article, we'll talk about some tips for setting up your Digital Transformation strategy.

Ask for Help

So you’ve finally come to a place where Digital Transformation is a ‘thing’. Somewhere in the executive food chain, someone up high enough has gotten the message that you need to leverage modern technology and practices to remain a competitive business.

That executive is diving into learning about lean thinking and failing fast and..well..wait, hang on, ok, so that executive has decided to ask for help (please dear Zeus tell us that they asked for help from people that understand technology and process change and aren’t just putting buzzwords into PowerPoint slides!).

Build a Team

Are you that lucky person in charge of creating a Digital Transformation Strategy?

Let’s assume somewhere along the way, you are involved in setting an organizational strategy. That’s the first great point.

Build a team. Involve a cross-functional set of stakeholders, so that your planning can properly incorporate your business needs from as diverse a set of stakeholders as you can.

Then also let’s remember that stakeholders come in many sizes and many levels of job function and experience, and quite frequently the folks on the front lines (not the executives responsible for them) have the largest trove of information about what needs to be transformed first.

So super, you’ve now got a team, all you need to do is sit back and wait for the transformation to start happening right? Oh yah you betcha, no problem that’s what DOES NOT HAPPEN.

The first step at setting up a Digital Transformation strategy is to make some decisions about what you want to accomplish, what you need to accomplish, and what is in your sphere of influence to actually make happen (more on that later). 

Grandpa Mike - Decide what you want to do

Miles Kafka, who leads our Engineering team, grew up in rural Minnesota and had very prescient instruction as a child about success in all things. For you our reader, we are bestowing upon you, Grandpa Mike’s rules for success in all things: 

  • STEP 1: Figure out what you want to do. 
  • STEP 2: Do it.

The hardest part of setting up a Digital Transformation Strategy is that it has the long ‘transformation’ word in the middle. That means, loosely speaking, that the thing you had before is not the thing you have afterward.

You are going to change something. It’s going to take a bunch of time and cost a bunch of money. You are going to have to make a slide deck about it, ‘convene’ people around the idea, get ‘consensus’ that it’s a good idea, then you’ll need to do the actual changing, you’ll mess it up a bunch, course correct, and several months or years later, you’ll emerge the triumphant Digital Transformation hero, cape and all.

Or, in this universe, this project you are about to embark on that is fraught with land mines, risks of failure, and possible dead ends, is going to be hard, and at some point will try your patience and commitment.

It really pays to know what you are setting out to Transform and why.

If you know all that going in, why bother? Remember all that mumbo jumbo about needing to stay competitive that the executives put in their slide deck when they told you to lead this project? Well, it’s actually true.

You need to set a careful strategy for some portion of continual innovation and transformation or your business will succumb to competitors and you will be eating ramen while you break captchas 14 hours a day at $0.0001/each so that you can pay your rent.

Jurassic Park is the best teacher

If you haven’t seen Jurassic Park or read the book, beware spoilers ahead (maybe just stop here and go read it or watch the movie, and then come back and thank me and before you read the rest of the article?).

At the point in the movie where they are confronting the designers of the dinosaur island where all hell breaks loose, there is a quote after the cuddly old man tells the protagonist about his beautiful vision for the dinosaur theme park, where the guy stops and says something like “What did you think would happen?”. This is immeasurably true.

There is no doubt in my mind that there are folks in your organization that if you asked them (and some, who you don’t even ask, but they feel compelled to tell you) on their opinion of your budget allocations, decision making. and your choice to forestall technology investments and upgrades. Or even rebuilds, or at least retrofits of your old systems in favor of chasing shiny new things that maybe don’t really impact the core operations of your business, these folks in as loving a way as possible would tell you ‘What did you think would happen?’. Let’s just call these folks Cassandras.

If you don’t have a Greek Mythology reference at the top of your head, Cassandra is my spirit character from Mythology. In short, she was gifted the power of prophecy but also cursed with never being believed.

If you can imagine always knowing what would happen and telling people about it and having them not believe you, then having to watch what you predicted actually unfold, you’d be a bit irritable right? So let’s just say that the Cassandras in your organization have a bone to pick, and a right to be a bit testy. (for the curious, don’t look up the full Cassandra myth, it’s horrible, and once read, cannot be unread, the ancient Greeks were some twisted hombres).

Make sure your strategy has 2 key things:

So as you are setting your strategy you need to keep in mind 2 critical things. First, know that you are part of a business that operates and exists and has done so somewhat successfully for some time. Otherwise, this initiative would be called ‘build our new product’ or ‘go be an entrepreneur’.

The key here is that something exists that needs transformation. You need to have a really good understanding of what parts of that system or systems are critical to your business, and therefore cannot have them be in downtime or fail. You should also be aware of what is the prize for disrupting and improving them (a.k.a. “Digitally Transforming” them).

Next, the second thing your strategy needs is an incremental strategy to progressively transform those old but mission-critical systems.

Thar be Dragons!

On old maps, when they didn’t know what was in a place, they just labeled it ‘thar be dragons’ as a warning not to go there. Similarly, with our Digital Transformation strategy, you also need to know what you don’t know and figure out what you’ll do about that. Explore it or avoid it.

You need to plan steps, which when connected get to your end goal. Ideally, these steps also define the failure case that says ‘If this step fails our alternate plan is ???’.

If the steps in our Incremental Digital Transformation Strategy (IDTS) don't have a plan B, that there is known, professionally, as a ‘doozy’, or alternatively a ‘single point of failure’, or a ‘polish up the old resume, you just got fired, Ted’.

If you find anything that is a single point of failure, then you need to test it early, ASAP with some kind of proof of concept to validate that your broader strategy is viable.

If you don’t do this, then you have what we call an Incremental Digital Inspiring Obfuscation Transformation Strategy, or IDIOTS for short. When you are part of an IDIOTS strategy team, you can expect lots of obfuscation of the truth, of progress, and generally do not have any idea where exactly you are transforming your way to. I would strongly advise that if you are on an IDIOTS transformation project that you politely request a transfer before you are in the land of ramen and captcha.

Behold the White Whale!!

Where are the digital harpoons? What? You don’t have any digital harpoons around? How could you possibly be thinking about creating a Digital Transformation Strategy without any digital harpoons at your disposal?

When you go to tackle the Incremental Digital Transformation of a giant whale of a system, you need to have digital harpoons to attack that problem with. In my head, that old system is never going away in one fell swoop.

You need to make an incremental plan for how to start functioning bits of your workflow, analytics, and business processing with pieces of your business in the new world of new software, while still peacefully coexisting with ole Moby the whale.

It is likely that at this point the Cassandras in your organization will begin to fire up the nope cannon and gleefully remind you of the point they had expressed the ‘ship had sailed’ on all of the options for module by module upgrades or system replacements.

It will be very difficult for the existing operating team to focus as a result. You see that team will have been coaxed by the business immune system that tries to maximize stability, and minimize volatility.

It recruits people and begets processes that are aligned to stability and being super risk-averse. You’ve likely set up things like reviews and bonuses and promotions that reward stability, avoid risk-taking and stamp out failure. All of those things will also stamp out the chances of success of your Digital Transformation strategy.

Now for digital harpoons. If you can figure out what parts of the business operation are within your ‘sphere of influence’ to change, the things where you feel you have the time, budget, and political air support to change, you can isolate your Transformation needs to certain bits of data or certain events or notifications between systems that are single points of failure for your Transformation strategy.

If you can imagine from your tiny life raft of digitally transformed awesomeness, that you can point a digital harpoon, festooned with fiber optic brilliance and a laser guiding system, and fire that thing into ole Moby, at precisely the system and data junction that you need to interact with, then you can apply focus to your discussion with the Cassandras. With your newly acquired focus, you have the ability to transform your IDIOTS plan into a super successful IDTS plan and then you can keep eating organic kale carnitas bowls and doing Zumba. 

Teach your Culture to Celebrate your Failures

The last bit of your Digital Transformation strategy is to make sure that it includes deliberate and defined ceremonies, cadences, and rewards for public failures as well as incremental success.

The hardest and most crucial part of any successful Digital Transformation is helping your team to have the psychological and career safety to begin taking risks.

You need to engineer the cultural shift that empowers people to do so and you need to care for the humans in those moments of defeat, to make sure that organizational learning takes place and that those people get up and iterate again to try to make your team’s plan a success.

It’s a long journey and you'll need to acquire new habits that meter out and celebrate your successes as well as your failures to reinforce and sustain the focus and energy of your Transformation team along the way. Your job as the architect of the Digital Transformation strategy is to make sure this happens above all else.

Art Shectman Hacker Noon profile picture
by Art Shectman @artshectman. Art Shectman is the Founder and President of Elephant Ventures and co-founder and President of UltranautsRead my stories

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