Expectations are interesting things.

They can be as utilitarian as making the bed each morning.

Or as majestic as climbing a mountain, literally or figuratively.

They have power to shape us in many ways.

Our expectations of the work that is Digital Transformation are no exception.

When it comes to my experience leading digital transformation, I have found that managing my own expectations is a finely choreographed ballet between managing the frustration that comes from the reality of where an organisation is right now, and ensuring the ambition for transformation remains bold.

Here’s a story of how I learned to harness the power of expectations to help me stay the distance when transformation is hard (which is basically all the time).

I was watching the (Nylex) clock one day…

Several years ago, I was driving along the M1 in Melbourne thinking about the day ahead of me. I was approaching the Nylex clock at Cremorne. It distracted me from my thoughts, leading me down the path of the challenges that seemed to mean this iconic clock might never again light the Melbourne sky, and abstracting that problem onto the challenges I was experiencing in my role.

I was in the early stages of a major digital transformation program and everywhere I turned there seemed to be road blocks. My frustration levels seemed to be growing by the minute as there were so many things that seemed much more difficult than I believed they needed to be.

As I looked at the clock (I was still watching the road, so don’t stress) I started thinking about my expectations of the degree of difficulty of this transformation.

I asked myself, just how difficult did I think the challenges of this role would be when I took it on?

Reflecting on this, I realised I had been captive to the “shoulds”.

If I was honest with myself, I had to admit that I hadn’t given sufficient thought to either the degree of difficulty, or the degree of change required.

Instead, I had focused my energy on the gap between how I thought things should be operating, and how they were operating. And the gap between the two states was causing me considerable frustration.

Two things came to mind through this reflection.

  1. A fair degree of my frustration stemmed from what I realised was an unrealistic view of how the transition “should” progress, and
  2. The gap between reality and my view on the “should” state depended on changes to both culture and ways of working; aka the work of transformation.

My subconscious brain was wanting to skip the hard work of transformation and just get there already!

The reality was that closing that gap between today’s challenges and the future vision was the transformation project.

I was the source of my own frustration.

When we want things to change before we’ve done the work to change them, we’re like my friend’s toddler son.

Beginning to be independent, he didn’t want anyone else to fill up his sippy cup with water. He’d obviously observed the cup filling process and thought he could easily do it on his own. He took it to the fridge himself, opened the fridge door, put his empty cup on the shelf, and closed the door. He waited a few seconds, opened the door and took his cup out. He tried to take a sip, shook the cup, and growled with frustration to find it still empty. Repeating the process several times, his frustrated growls increased with each failure on the part of the cup.

I would love to tell you that the insight from that morning drive led to breakthrough change. But that would be magical thinking and that didn’t happen.

The fridge didn’t magically fill up the sippy cup. And my transformation didn’t get any easier either.

But my insight into my own expectations became a powerful tool to calm my frustrations and help me better understand the cultural and other barriers that were making transformation difficult.

It helped me take a more nuanced approach to the barriers I encountered, helping me be both patient and tenacious depending on the challenge at hand. It also provided clarity on the ways in which cultural and work practices needed to shift to support and drive the transformation work, and my role as a leader in influencing the pace of change.

This story reminds me of the many times that I have found that the core of digital transformation is about people, much more than it’s about technology. Here’s what I have written about this earlier.


Sidenote: I can’t claim any credit at all here, high expectations or otherwise, but in other news, the Nylex Clock will soon be lighting up the Melbourne skyline once again …