Streamline Digital Transformation Discovery with Olive


Digital Transformation Discovery: Lessons Learned from a Fortune 50 Journey

Lessons Learned from a Fortune 50 Journey

Many companies still struggle to navigate the complex digital transformation journey effectively. The key to successful digital transformation lies in a well-executed discovery phase, which enables organizations to identify and evaluate the right technology solutions that drive meaningful change.

In this blog post, we will explore the significance of the digital transformation discovery phase and how Olive, a groundbreaking technology evaluation platform, can revolutionize this crucial stage for IT leaders and consultants. 

Understanding the Digital Transformation Discovery Phase

The Pitfalls of Rushing into Transformation, and Skipping Discovery

Embarking on a digital transformation journey without a structured discovery phase can lead to significant setbacks and wasted resources. It is crucial for organizations to avoid hasty decisions and instead embrace a more incremental and informed approach.

The discovery phase serves as the foundation for a successful digital transformation journey. It involves a comprehensive exploration and evaluation of the organization’s existing processes, challenges, and goals. By conducting thorough discovery, organizations can identify key pain points, opportunities, and potential technology solutions that align with their strategic objectives.

Even before digital transformation became a priority, skimping on the discovery process resulted in picking the wrong solutions and failed implementations. The discovery phase can be lengthy and time-consuming and (if done incorrectly) a waste of time, leading many organizations to think they can bypass or half-ass it. Whatever time or money they save by doing this creates exponential costs later on down the road. A poor discovery process is better than no discovery process. 

The Traditional Digital Transformation Discovery Phase

The discovery phase in traditional digital transformation endeavors has typically followed a predictable path, with the same pitfalls, time, and money-suck, and still, many organizations fail. Some may hire outside consultants to do this because it has historically been an incredibly manual process. Everyone has been so quick to digitally transform all of the processes EXCEPT for digital transformation discovery

Often, consultants and business analysts will spend months analyzing current processes, interviewing the people who perform these processes, documenting those processes, and then trying to build requirements based on those processes, all the while not really thinking about how to best evolve the processes themselves as they facilitate them with technology. This often turns into automating bad processes. 

Eliciting requirements from stakeholders is difficult enough in and of itself because often they know what they do in their day-to-day, but they don’t always know why

Lost in Translation: Stakeholder Interviews

Almost exactly 20 years ago, I spent my summer interviewing stakeholders at a Fortune 50 tech company, trying to figure out how to implement my solution so that it would best streamline their import/export process for their manufactured goods while also integrating with their current ERP and other critical systems. 

There were a dozen people involved in various steps of this process. We interviewed them together. We interviewed them separately. My team probably performed 200 interviews that summer, and it’s no exaggeration to say that each interview either negated other interviews or came up with something new and completely different. On top of that, none of the stakeholders knew what the person before or after them in their process did, nor why, though some were good at guessing (usually incorrectly).  

Like a scene from Office Space, one stakeholder gave us all the requirements to generate this huge green-bar report that he had to pick up at the “report window” every week (this was back when they used to send large reports to a central location to be printed on dot matrix printers on huge reams of paper so they didn’t tie up other shared laser printers). 

When we asked him what he did with it, he said he put it in his desk drawer with the other reports. 

“That’s it?” we asked.

“That’s it,” he said.

To add insult to injury, this company refused to use MS Office because they built competing products, so everything we sent them was unformatted in their applications. They finally purchased a few Office licenses, but it didn’t really matter. None of the stakeholders read what we wrote. They just blindly signed off on everything. 

You can’t blame them, though. Who wants to read through pages and pages of information documenting their process? And so, to cover all our bases, we’d interview each stakeholder again and again and again and read through their process with them in the room. 

At the end of one of these interviews, one stakeholder (we called him the “grouchy Louie Anderson”) unfolded his arms, leaned forward, and said, “That’s not what I do.”

“This is exactly what you said.”

“No, I didn’t.”

“OK, well, tell it to us again… “

And we wrote down his new process, scheduled another meeting, read it to him again, and, just like Groundhog Day, he told us that’s not what he did, and that’s not what he said. 

After about the fourth iteration of this, we discovered he had retired and was gone. Just like that. Gone. We asked everyone else if they could fill in for him, but nobody knew what he did, and nobody knew who would take over his job.  

10 Best Practices for a Successful Digital Transformation Discovery Phase

The Traditional Digital Transformation Discovery Process 

It would seem that this outdated, manual discovery process should be automated by now, but the root of the problem (as with many processes organizations are trying to digitally transform) isn’t the lack of automation. It’s the process itself. 

“Discovery” needs to start with identifying problems and determining why people do what they do, rather than what they do. What is the purpose of their job? Start there. If they don’t know, then you need to find someone who does. Only then can you tackle the “what” and then the “how” and then finally determine how technology can help with those processes. 

What that means is that “discovery” should have occurred before we even got there. It should have occurred before the company purchased my product. It should have occurred before the company decided to purchase any solution. It should have occurred before the company decided that this particular process was the one they needed to automate better. 

Fast forward 20 years, and you would think that all of us have learned from the past. You would think that there is a method to the madness of how decisions are made with regard to digital transformation. 

You would be wrong, and what’s more, is that the digital transformation process has been the last process people have thought to automate, and the discovery part of that process is often largely ignored. 

I talked to a friend recently who is a low-level IT executive at a large hospitality company and asked him how they prioritized their digital transformation initiatives. There was a long explanation, but the net of it seemed to indicate that there was no real rhyme or reason, but most decisions were made at the c-suite level, and nobody knew the reasons why those decisions were made. They did have high-level initiatives like “moving to the cloud,” but then how did they prioritize what got moved and when and how?

That’s when consultants got involved.

It should be noted here that the one system that facilitates what is arguably their most important process is several decades old (and possibly made by the company I discussed earlier). Granted, ripping and replacing a core system is not an easy endeavor and nobody wants to be saddled with having made that decision if it all goes sideways. 

On the other hand: Southwest Airlines. 

Evolving the Digital Transformation Discovery Process

Embrace Collaboration, Iteration, and AI 

The entire digital transformation process needs to be digitally transformed and, the root of this is implementing a solid digital transformation discovery process and automating it.

Companies must start with identifying problems and determining which ones need to be solved in what order before even considering possible solutions. Everyone in an organization is a stakeholder, so you need a process that makes it easy and fast to collaborate. 

More importantly, you need to iterate. Note that “iterating” isn’t just going around in circles. It’s making short, small (but meaningful)  incremental improvements. Rather than taking hours of stakeholder’s time for months on end, you need to create a process that takes a few minutes of their time each time they provide input. 

The traditional approach to digital transformation is failing at a rate of at least 70%. It leaves organizations vulnerable to biases, subjective opinions, and limited insights, leading to suboptimal software selection decisions. 

The rigid nature of the traditional discovery phase limits exploration stifles innovation, and hampers the potential for transformative digital solutions. To overcome these pitfalls, organizations must embrace a new paradigm that fuses collective knowledge and AI capabilities, revolutionizing the internal software selection process and paving the way for successful digital transformations.

Digital Transformation Discovery with Olive

Olive is an AI-powered platform that empowers IT leaders to drive digital transformation initiatives internally and save significantly on third-party services.

With Olive, organizations can seamlessly collaborate on the discovery and use AI to skip over manual processes. 

Using Olive’s in-platform user-friendly project discovery wizard and discovery process, users can explore their problems, potential solutions, and related pain points. This stimulates critical thinking and expands their understanding of the challenges at hand.

Olive’s AI generates recommendations and creates a project structure that can be shared with teams and vendors in real-time, accelerating the evaluation and qualification of solutions. By incorporating must-have requirements and user stories derived from identified pain points, Olive streamlines the process and enhances solution evaluation.

Don’t Skip Discovery

The discovery phase is a vital component of successful digital transformation initiatives. By adopting a structured and informed approach, organizations can identify the right technology solutions that drive meaningful change. Incorporating Olive into the discovery process enables organizations to optimize their initiatives, following best practices and unlocking the full potential of their digital transformation journey.


AI, Automation, Commentary, Digital Transformation, IT Decision Making
Agile Digital Transformation, Digital Transformation, Digital Transformation Tools

Streamline Digital Transformation Discovery with Olive

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