Digital Transformation Lessons from the Coffee Cup

For nearly a decade, I’ve navigated digital transformation as a consultant, business owner, and CEO. The other day, a realisation hit me. My most profound lesson in digital transformation didn’t come from any high-tech seminar or workshop. Instead, it came from a coffee cup.

Well, not a literal coffee cup. The coffee cup was the only icon available for a custom button on software called “Tracker” — a Sales Force Automation system from the days before we called it CRM.

It’s taken me nearly 20 years to recognise that the tale of this coffee cup, or more accurately, the Visual Basic macro activated by it, resonates with every digital transformation project I’ve participated in. It astounds me that I’ve only grasped its true lesson after all this time.

The Coffee Cup Story

In my early professional journey, I stumbled into an events industry job selling stand space for a technology event — it seems this is how most people get into the industry by complete accident.

Times were tough, and as a fresh graduate, I was just grateful to have a job. Little did I know this role would start a 25-year relationship with the events world, where I would continuously challenge technology integration and adopt and drive new digital practices.

Every Friday, as part of the sales team, we would reconcile our sales against the accounts department’s records. We were a small company, but this task consumed our entire afternoon. Despite our Sales Automation system, discrepancies between our records and the accounts’ were frequent, primarily due to our paper-based processes.

I’ve always had an aversion to wasted time. As salespeople, we would’ve rather been at the pub, either consoling each other after a rough week or celebrating our successes. So, I dived into the Tracker software and crafted a Visual Basic macro that streamlined the reconciliation process. My Friday afternoons were suddenly free, but my colleagues weren’t so fortunate.

Seeing my newfound freedom, my team wanted in. I shared my macro with them, and that’s when the challenges began. Everyone had their unique way of recording sales, making it difficult to maintain and standardise the macro.

But it was challenging. I was swamped for the next three weeks, supporting the team as they grappled with the new tool. And just as I thought we were getting the hang of it, a stark realisation dawned on us. Each of us had our unique approach to sales recording, which the macro hadn’t accounted for — because I wrote it for me. This epiphany alone took another month of discussions, tweaks, and trials.

And just when we thought we’d ironed out the kinks, another hurdle appeared. Our accounts department needed help to sync their data with our new system. This integration challenge added another month to our timeline. But the dependencies didn’t stop there. Every tweak and every change meant adjustments to the macro — which I was doing in my own time, binding us in a cycle of dependencies that lasted another 4 to 6 weeks.

The entire saga spanned four months from inception to a somewhat stable system.

This phase taught me two vital lessons about digital transformation:

1. Prototypes Aren’t Always User-Friendly. Something functional for one person might not be for another.
2. Standardisation is Essential. While processes should always be adaptive, having a standardised baseline ensures effective digital implementation.

The Ripple Effect

As we began collaborating, we realised that we needed consistent reporting methods to benefit from this tool. We held meetings (yes, at the pub) and streamlined our processes for the sales team and the accounts department.

I realised that the actual coding of the macro took only a few hours. However, ensuring it was helpful for everyone, standardising processes, and aligning departments took months.

These reflections brought two more insights:

1. Digital Transformation is More Than Just Tech. It’s more complex than buying software and assuming the task is complete.
2. People and Process Adaptation Takes Time. And sometimes, the journey is so prolonged that momentum wanes.

But that is not why I am sharing this story. The biggest lesson I derive from the Coffee Cup comes next, and it is what we should bring to any transformation project, whether it’s as challenging as Digitising Events or something else.

The BIG Lesson from the Coffee Cup — Make It Human

We changed processes, argued with management, and collaborated freely in our own time and willingly. No team member gave up throughout our quest to make the coffee cup system efficient. Our spirit remained strong, and we persisted.

Why? No one had told us to do this.

Because we shared a profound, unspoken goal: to reclaim our Friday afternoons, this camaraderie, these moments of collaboration and connection, became our driving force. And this gets me to the most powerful lesson from the Coffee Cup.

Digital transformation initiatives thrive with a clear, human-centric “why” at their core. Our “why” were those cherished Friday afternoons. While we stumbled upon it by luck, many transformation programs are less fortunate. I invest significant time, sometimes frustratingly, for my clients, identifying this human-centric reason — I have experienced its power.

When you have this shared value, digital transformation ceases to be a daunting, cumbersome task. Instead, it transforms into an exhilarating, engaging journey for everyone involved. Regrettably, many frameworks prioritise a cold, depersonalised value — leaning heavily towards corporate benefits over individual ones.

Talk about AI bias :-) Midjourny thinks this is Friday afternoon in a pub :-)

Our Friday afternoons, enabled by the coffee cup system, encapsulated this perfectly. Beyond the evident corporate advantages — like improved cash flow due to fewer non-invoiced sales and enhanced business visibility — the real value lay in the intangibles. Those Friday afternoons became platforms for collaboration, problem-solving, and fostering an invaluable team spirit.

Had we approached this as a typical digital transformation project, the sole focus would’ve been automation, cash flow, and reporting. Such an approach never resonates with a team. You have to make tangible what each individual can win back.

In any digital transformation endeavour, articulating value that resonates with everyone involved is paramount. Vital when Digitising Events and it drove my creation of the CVI + CVO Framework™ because digitising anything is tough, but if we can tap into that Coffe Cup reason you do it as a team, you move faster and remove the roadblocks with much less friction.