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Is this the look of “fear of change” or “surprise at personal accomplishment”? You’ll see both throughout your digital transformation and the people at each end of that spectrum will surprise you.


Previous articles in this series explained how digital transformation requires an enterprise strategy that balances culture and technology. Under culture, we discussed change readiness and digital proficiency, along with change management. I’m always amazed at who struggles with transformation and who rises to the challenge. It’s rarely the people you expect in each category.

The Emotional Rollercoaster

Every digital transformation, like most change initiatives, has its ups and downs. There are predictable emotional cycles that always take place.

We promote a new endeavor across the company to generate excitement and buy-in. As the project starts, expectations are at a peak.

Then the reality of the workload sets in. Vendors don’t always bring their “A” players. Conflicting priorities put pressure on the team members. And some deadlines are invariably missed. The team starts to lose confidence in the vendors, in their own team, and in the project. Expectations move from a peak to a valley.

Then the breakthrough occurs, and we turn a corner. The project seems to be back on track. The less-satisfying up-front work, like current state documentation and requirements gathering, is behind us and we’re doing more exciting things, like actually building the solution. And our expectations level off to a reality that sits somewhere between that peak and the valley.

The emotional setback was temporary. The excitement returns. As solutions fall into place, personal satisfaction sets in. The team feels pride in their achievements and that fuels them to the finish line.

These challenges are real. They should be expected. Anticipate them and manage your communication accordingly.

When the CEO interrupts a project team meeting for just 15 seconds and says, “I know how tough this is and how hard you’re all working. I just wanted to let you know that it’s appreciated, and I have confidence in you. Thank you all,” and then walks out. That is such an amazing boost to the team. I’ve seen it time and again.

Anticipate the natural cycles of the project and help the team along the emotional rollercoaster. You’ll see amazing results.

Who Me?

My first true business transformation was in 1992 and 1993. It was before the term “digital transformation” was even discussed. We leveraged technology to create a differentiated customer experience and dramatically improve internal processes. I was the VP of IT and was credited with taking the company from its biggest loss in its 20+ year history to its greatest profit ever.

When we started the project, several executives discussed who among the staff would flourish in the new environment and who would struggle and resist.

We could not have been more wrong!

Sure, some people that we thought would find the transition easy did end up struggling a bit. But the bigger surprise was a long-time employee named Marilyn, who was just downright scared of the new technology. Guess who became one of the power users and the top salesperson? Yup. Marilyn.

Lesson Learned

That experience taught me, with absolutely indelible images in my head, to never doubt the doubters.

I took that lesson to my next company, and the next, and carry it with me to this day. And, with numerous digital transformations behind me, I can say that my colleagues are surprised every time by who struggles and who grasps the paradigm shift and succeeds.

Be wary of pre-judging your team based on past experiences and the current state. Apply change management techniques. Make sure every individual understands his or her role in achieving the company’s vision. Help them understand the personal growth opportunities. And be generous with training. You’ll be amazed at who steps up and shines.


The picture caption asked, “Is this the look of “fear of change” or “surprise at personal accomplishment”? It’s both. One happens early in your digital transformation and the other finds its way in later.

Projects have natural cycles, peaks and valleys, that we have to manage. And people have real fears that we also have to manage.

When you manage these effectively, you’ll be amazed at who the superstars turn out to be.

What’s Next

We will wrap up this series next week with an article about The New World After Digital Transformation.

If you’re embarking on a digital transformation, planning to do so, or just don’t want to wait for the last article, email Emily at Emily@WolffStrategy.com and she’ll be happy to schedule a call with me to discuss any or all of these topics in this series.


larry wolff

Larry Wolff is the founder & CEO of Wolff Strategy Partners, a boutique consulting firm specializing in Enterprise Strategy Management, Digital Transformation, IT Leadership, and Executive Coaching. Larry has served as CEO, COO, CIO, Chief Digital Officer, and management consultant for public, private, international, and emerging growth companies. His specialties include corporate and IT strategic planning, technology led business transformation, business and IT turnarounds, merger integration and large-scale project rescues. His methodologies span industries and scale to companies of all sizes.

LWolff@WolffStrategy.com                     https://WolffStrategy.com

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