Common Pitfalls of Digital Transformation - Part 1

Common Pitfalls of Digital Transformation - Part 1

When you’re standing outside of a transformation, watching project teams beavering away, you think, “Is it really that hard?” When you’re part of one of these teams, you’re often thinking, “Why is this so hard?”

I once had a colleague say, in an effort to give us hope, if it were easy, everyone would be doing it.

I thought to myself, during a transformation, everyone SHOULD be doing it and while I’m not expecting easy, it should be easier than this.

Below I'm sharing what I’ve seen and experienced as the common pitfalls of Digital Transformation. This week, I'm covering pitfalls 1 to 5.


Image: Common Pitfalls of Digital Transformation

Pitfall 1: Unclear Vision and/or Strategy

We’ve all seen the wordy vision statement on a slide. The kind of statement that leaves everyone staring with a furrowed brow thinking, “What are we doing?” Or in my case, “Those are words…”

For those who have a clear vision statement and strategy, I often see a gap between the statement and the work happening on the ground. Senior execs are left thinking, “How do they not get it?” As for the people on the ground, they’re left wondering “What does all the work amount to? What’s the common thread that stiches it all together? What does it mean for my program?”

What causes this? Let’s talk about Pitfall #2.

Pitfall 2: Leadership Gap

We put out a vision statement and activate project teams. Before you know it, there’s a plethora of slideware with all the trendy terminology. You’re being told this is going to change how your division conducts business. You look at the slideware and think “… but how exactly?” Of course, you don’t say it out loud. You’re middle management and everyone expects you to know what you’re doing. So you keep going assuming you’ll eventually figure it out.

Multiply this experience in each business vertical.

Modernizations are cross-functional by nature. The degree of complexity and number of variables make it such that the traditional top-down leadership model isn’t sufficient.

We need a distributed leadership model. Or said differently, we need middle management playing an active leadership role, starting by unpacking the vision statement to a greater level of granularity. Once each vertical understands how it impacts their program, they can work together to stitch the narrative and lead their teams.

Pitfall 3: Tech First Approach

Tell me if this sound familiar. Someone gets excited about a piece of tech. They spin up a project to jam it in. Months if not years later, when it’s finally implemented, we wonder what that entire project was for. More often than not, it was a solution looking for a problem.

Tech implementations are all consuming. They’re too often heavy and bureaucratic. They’ll consume the bandwidth of the most talented executive. It’s easy to lose sight of the business problem you’re trying to solve.

But the business problem must not only be the start point but the only point.

Pitfall 4: Unclear metrics of success?

Amazon launches a project by releasing a press release internally through their governance. They imagine being in the future when the proposed idea is fully developed and implemented.

And they write the press release. They start with the answer to the question “What does success look like for the customer?” Only if the story is compelling, do they get the green light to proceed.

More often than not, projects launch either without clear metrics of success or alignment amongst leadership on what success looks like.

Pitfall 5: Barriers to Adoption

“You’re expecting resistance. Why?”

“That’s just how they are.”

When I press, I get responses like, they’re unionized so we can’t touch them. They’re unmotivated. They’re too comfortable.

But why? Say more. There’s a tendency to take the first answer at face value rather than digging into the root of resistance.

For example, teams are unmotivated. Ok. How many layers of bureaucracy do you have? Do you have a culture of belonging? When was the last time they were asked their opinion? Have you created a situation where they feel like a cog in the wheel? If so, we need to solve for the cog.

Get to the root. Everything else is just symptomatic to the problem.


I’m a History major. I believe in learning from the past to avoid the same mistakes in the future. If I’m sharing this, it’s because there needs to be greater transparency and discussions around failed transformations. We need to collectively learn from these failures so we can better position ourselves if not in the present, at least in the future.

Come back next week. I'll cover pitfalls #6-10. Until then, please reach out if you want to talk about any or all of these.


Excellent post! It seems projects - whether physical or digital - play out in similar fashion. That's why the Building Industry is (starting) to employ the Lean Project Delivery system.

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