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7 Key Steps to Digital Transformation Success: A Common Sense Guide

Navigating Digital Initiatives with Common Sense


Have you been assigned to lead a digital transformation project, and you do not know where to start? 

It might be a modest endeavor or a significant one, possibly for a major client—or even for your own company or startup. 

Success is non-negotiable; there’s too much at stake.

You’re likely aware that digital projects have a notoriously poor success rate. 

Forbes reports that 7 out of 8 digital transformations fall short. Even more daunting, studies by McKinseyBCGKPMG and Bain & Company, place the failure rate between 70% and 95%.

More often than not, they fail, leaving behind a trail of missed revenue, damaged brand reputations – and derailed careers.

Yet, here you are, determined to beat the odds and achieve success. 

And you can—with the right approach.

This short article offers straightforward guidance for anyone equipped with common sense and a drive to excel in their next digital venture. 

You don’t need to be a digital wizard or hold an MBA to benefit from this advice. 

Just give this brief read your attention and reap the rewards.

Best of luck.

7 Simple Steps to Digital Transformation Success

Step 1: Transform with Purpose, Not Just for the Sake of It

You might be surprised, but most of my clients miss this point. 

Maybe yours too.

In business, change for change’s sake brings, at best, marginal results.

While I was working for a client in Frankfurt, Germany, an email from a partner company popped up in my Outlook inbox. The email proclaimed that this company had ‘digitally transformed’ its email. 

My first thought? This must be a joke!

With more than a decade of experience in ‘agile’ digital transformations, the concept of “transforming email” was a first.




[countable, uncountable] a complete change in somebody/something

– Oxford Dictionary

Yet, this was no joke. The only change was that the partner company had instructed us to use a new email address – that was all.

This example reveals the company’s pressure to showcase ‘digital transformation,’ even if superficial. So, by embarking on an operational Email Exchange Migration and branding it a digital transformation – without adding real value to the end customer – our colleagues at this company could claim that they had a digital transformation under their belts. And they did!

Senior management now should be happy – and they were!

The end result? Marginal gains to the business.

Yes, from an operational point of view, this initiative was likely necessary, I am sure. But transformative? Doubtful. 

The essential message here is that not all technological updates qualify as ‘Digital Transformation.’ Mislabeling minor enhancements as transformative can mislead everyone, including ourselves, creating a false sense of progress on the path to digital innovation. This misunderstanding is a key reason why many digital initiatives don’t meet expectations.

In the context of Digital Transformation—or any digital shift in business—it’s essential to aim for business outcomes based on value, not just to embark on digital projects just because ‘everybody else is doing it’ and branding them ‘transformational’. 

As illustrated in this example, they are not.

The business landscape pressures us into believing we must adopt the latest trend in business to survive, driven by unrealistic expectations from employees, bosses and clients alike. 

Resist this call. When someone asks you to ‘transform’, or ‘become more agile’ and so on, ask what the expected value is – and for whom. 

Ask whether these efforts are truly transformative – or just ‘same old but with a new app or process’. Make sure that you – and the requestors – understand how the project will add value to the end customer and if it should be called ‘transformation’ or instead, something else.

Before diving into digital transformation, ask 'Why?' 🤔 Scrutinize the use case until its value shines through. Don't just follow the trend; transform with purpose! #DigitalTransformation

Step 2: Make your Customer your North Star

We often believe we understand our customers and keep their best interests at heart. 

But, do we really?

Let’s say there’s a business case for change, like updating an email system to cut costs. It might seem logical. After all, who wouldn’t want that? 

However, optimizing operations and cutting costs, while necessary, is not necessarily transformative. 

True digital transformation never loses focus on the customer—your North Star. 

Practice the following: Visualize your customer, that human being worried about being late to your meeting and who is considering your products or services over their morning coffee. This idea is powerful. 

In some of my projects, we even had life-sized cardboard figures, depicting our target personas,  standing around us in the offices. This visual and tactile reminder helped our teams stay focused on our efforts by keeping the customers at heart.

See, without keeping this real person at the center of your digital initiatives, success will remain elusive. Even if you streamline operations and boost margins, and all that good stuff. If the customer sees no value added from your efforts, the project falls short.

Remember, a pat on the back for operational efficiency gains or other marginal improvements means little if it doesn’t translate to real benefits for the customer.

When asked to 'become more agile' or 'use the cloud,' always ask: What will the end customer gain? How will they notice the difference?

Step 3: Conduct a Candid Assessment of Where You Stand

Honesty is crucial.

Let’s face it: Not every process in your company (or your client’s) is as good as it could be. It’s vital to confront this reality with sincere self-reflection.

Often, consultants shy away from discussing observed issues in their client’s processes, ideas, or values openly and constructively. Avoiding this conversation is a mistake that can lead to a domino effect of failures. 

Neglecting this critical evaluation is akin to ignoring that our metaphorical ship is too slow, undermanned or simply not seaworthy enough to reach the desired destination. We often wishfully think that we or our customers are well prepared for a digital initiative,  but in most cases, this is not necessarily true.

From the start, be forthright about what’s working and what isn’t. 

This honesty with your clients and with yourself is foundational. It enables all stakeholders to correctly gauge readiness – and it is a reliable predictor of success.

Being candid helps your client identify areas needing more preparation, increased management attention, or additional research. It helps to identify topics that may be too complex or costly –  or just of marginal value.

Yes, this approach might initially meet resistance or skepticism, but it’s essential. 

Contrary to what some may expect in a business culture at times wary to losing customers or that big contract, this type of honesty often garners respect and trust in how others perceive you.

Furthermore, it may help your customer identify blind spots that hinder success. After all, you have been trusted with this initiative and people have expectations of your professionalism. Here is when you can make it count.

And make no mistake: If honesty isn’t welcomed, it signals a need to consider other paths.

Initiatives built on a foundation where candid discussions and hard truths delivered in a constructive manner are disregarded are on shaky ground from the start.

Evaluate what works, refine or let go of what doesn't. Honesty with yourself and your client is key. If honesty is not welcomed then you are working at an already failed project.

Step 4: Prioritise Customer Value Above All Else

While in business school, we were drilled in the art of analyzing and improving case studies for businesses – large, small and startups. 

Our teams would huddle, brainstorm, and emerge with proposals for efficiency gains and cost reductions for companies of all sizes and industries. Being “lean and mean” was applauded. Convincing rhetoric made the professors nod approvingly.

Yet, often, these well-intentioned efforts missed the mark. The reason? A common oversight of the ultimate goal: delivering value to the customer. Unfortunately, this oversight is not limited to academia. It is an everyday occurrence in today’s business world.

For instance, the email “transformation” we read about earlier was prioritizing Corporate Value, thus providing solid, but marginal gains. True transformations are value transformations that prioritize Customer Value, and the expected gains are orders of magnitude greater.

Incorporate customer value at every stage of your digital initiative to ensure alignment with your customers’ needs.

For starters, it is important to highlight that we might believe we’re already focused on customer value when we are not.

Ask yourself – or even better, ask your client, team and stakeholders if the initiative is truly aligning with the customer’s needs, and if so, how is this alignment being implemented in everyday processes? 

Try it in your next project meeting. Watch the client and his team pause and reflect.

Talking about customer value, is one thing; genuinely “baking it” into our actions that end up shaping our products and services via a digital initiative is another.

Here’s an actionable step for you: Download the Value Canvas from Strategizer. It’s a deceptively simple yet powerful tool that can revolutionize how you approach the everyday work you do for your customer. It ensures that customer value is at the heart of everything you do. 

Let customer value be your guiding principle—not just in words, but through sincere implementation.

Shift your mindset to what truly matters: Customer Value. Bake it into your process. Dive into tools like the Value Canvas from Strategizer to embed this priority into every project phase.

Step 5: Embrace (Customer) Value Streams Over Silos

If there is one secret sauce to joining the upper echelon of 1 of 8 digital transformation projects that deliver, it’s this: Think in terms of customer Value Streams rather than efficient but isolated Silos.

A value stream is the set of actions that take place to add value for customers from the initial request through realization of value by the customers.

– Project Management Institute

This approach acts as the essential binding agent for any transformation. It will elevate your digital initiative from ordinary to extraordinary. 

Great! But… what exactly does this mean? We already have our specialists talking to each other in meetings, many meeting indeed, and even working together in ‘war rooms’. Shouldn’t that be enough?

Well, no.

It is a mind shift.



si·lo ˈsī-(ˌ)lō 

 an isolated grouping, department, etc., that functions apart from others especially in a way seen as hindering communication and cooperation

– merriam-webster dictionary

Your specialists can be all in the same meeting, talking serious stuff and also making jokes, and yet, they likely are focusing on making their area of expertise shine. Well, why not, they are the experts!

And here lies the problem: In everyday businesses contexts, everyone regularly operates in Silos, working diligently and expertly on a series of tasks but forgetting to connect the dots, so to speak.

While working for a premium brand manufacturer based in Munich, I noticed that the client and a key vendor had been discussing how to implement automated cloud solutions for more than a year to quality control the periodic launches of their digital products.

To my surprise, such a great initiative had remained just a circular discussion of an idea for more than a year.

I talked to the business, and to IT, noticing that each siloed function could expertly provide sensible solutions in its own right, but not in a manner that would make sense to the end customer. For instance, IT could provide lightning-fast queries that marketing did not know how to use, while marketing understood exactly how to present the information to the board for maximum impact, but lacked the means to collect it.

Two worlds of expertise talking to each other without the other side listening.

What to do?

Leveraging my business and technical backgrounds, I decided to give it a shot and bridge the gap between these highly qualified professionals.

The result? In 3 months we had delivered a working prototype of an automated cloud solution. Was it as fast as IT would have wanted? No. IT’s solutions ran in 5 seconds in the backend systems, my in 1 hour using cloud technologies in the front end. Was it as good as Marketing wanted it. No. The Dashboard needed to be manually initiated every time by me in order for the results to be refreshed and visible online.

But what about the value to the end customer? Any defects of the client’s products were automatically detected in about an hour of launch as a last live quality control check, so the chances that the customers found an error on the product was reduced to an hour window, not days (or even weeks). Just about an hour. This agility was truly transformative and translated directly to a superior brand experience for the end customer.

My client loved it.

Focus on the end-to-end Stream, not on each individual area (Silo).

How many times have you called customer service to ask for help with a specific problem, only to be told that the issue relates to a different department, or worse, to a different organisation? In Germany, where I am based, this is all too common. It reflects a mind-set of siloed thinking.

And yet, you might think these occurrences are slowly but surely becoming a thing of the past. Nowadays, after decades of initiatives and management advice, everybody is ‘transforming’ to a better way of conducting business. it can’t be that so many years of investment in digital transformation initiatives are not working, right?

As a customer yourself, you be the judge.

On the other hand, when we experience a true comprehensive (customer) value-oriented approach, when the call center resolves your issue during your first contact and the organisation provided integrated answers on the spot (thanks to their digital initiatives), you marvel and of course, you come back to purchase more. That is the type of digital initiative you want to deliver.

The good news is that this is exactly the digital initiative your client wants you to deliver!

In my experience however, even highly regarded corporations still focus today on optimising the specialized areas instead of the whole.

Why? Because it is easier. It is safer. You do what you know how to do best. Your boss or client does. Normally, nobody would lose their job for doing a good job in their area.

Thus, there is no innate motivation to move beyond the specialist’s vision towards a more vast approach in your digital initiative. Your customer, teams, and peers tend to gravitate towards their areas of comfort, hamstringing your digital initiative.

And by doing this, teams only make-believe they are transforming something, they make believe their bosses, peers and stakeholders that ‘something was done’.

Exactly as in the case of our email “transformation” mentioned above.

Raise above the crowd and start thinking – and delivering – in terms of Value Streams.

Ready to unify your ideas and concepts? There is a tried and true method to do this: Value Streams. Even the best professionals can get lost in the details. Keep an eye on the big picture - which is the delivery of customer value.

Step 6: Show your Progress early, even if it is Faulty

You’ve mastered the right approach and mindset—well done! 

But there’s no time to rest on your laurels. Immediate action is crucial; otherwise, all your efforts could be wasted, especially if the competition is doing the same.

It’s okay if your idea isn’t fully polished or if you can only roll out a portion of your app’s core functionality initially. Really.

What’s important is making progress.  Now. 

Yes. today.

By showing your work to your client early, you stand to learn invaluable lessons—some might be tough, but all will be enlightening. Each iteration brings improvement, making you more adept at your work.

If you have followed the steps outlined in this article, and are doing the right project for the right reasons, if you have been honest to yourself and to your customer, if you have searched for real value for your client, if you know the type of project you are doing, and are unifying your efforts in streams, then your customer will trust you and your approach. 

That means, concretely, you have a chance to show an imperfect – even faulty – result to your client – and the client will know that you are doing this while keeping her at the centre of your well intentioned efforts. Your client will appreciate what you are doing. 

This means you will present work that may not be perfect, with the understanding that these efforts are part of a well-intentioned process centered around your client’s needs. This transparency fosters appreciation and trust from your client towards you.

You will gain invaluable learnings from the ultimate teaching source: Your customer. And fast.  

Launch fast, learn faster! Don't wait for perfection; act now to gain invaluable insights and improve with each iteration. If you explain your approach, most customers will positively welcome incremental value.

Step 7: Adjust, Repeat, and Cultivate Grit

Who hasn’t provided some honest, constructive advice just to watch it being rejected – even ridiculed, by the client, stakeholders or peers?

During an Agile Transformation at a Frankfurt-based international corporation, I recommended integrating Slack or similar for better team communication. This was before the corona time, so video conferences and chats were not necessary as we were all 5 days a week at the client. Nevertheless, a chat app like Slack seemed a logical and obvious improvement over traditional email – and a sensible complement to our Jira based workflow. 

Despite the simplicity and potential efficiency gains of my suggestion, it was harshly dismissed in favor of continuing with email and WhatsApp (!) for official communications. 

My reaction of this minor incident? Well, I felt not only disappointed, but even slighted. 

Was my reaction wrong? Probably. But it was real – and I was angry.

I am sure you can relate with an example of your own.

It doesn’t matter how small these negative experiences can be. Sometimes little and some times large situations trigger negative emotions in us. When this happens, sometimes we want to stop providing our good advice, for starters. Or, if the slight is major, we think of calling our favourite head hunter later in the day.

My advice: If you indeed plan to succeed in your chosen digital initiative: Instead of dwelling on situations like this, one has to move on emotionally and mentally. In this case, I chose to focus instead on the larger goal: succeeding in the complex and frankly exciting Salesforce implementation ahead. 

This decision to move past initial rejection and continue striving for project success underscored the importance of resilience and adaptability in achieving long-term objectives.

This can be tough.

How exactly can we achieve this? How can we choose to bury the thousand cuts that we might experience in our projects and transform them into effective action guided by a disciplined ethos?

The answer is grit.

Develop grit. It is key for you to succeed in your digital initiative – and in many other endeavours in life. 

When going through neglect or disregard of your advice, it is necessary to embrace a mindset of toughness, focus and drive. This package is best described as grit.

In our example, months later the corona pandemic forced itself onto companies of all sizes and industries, including the one mentioned in this example. What it meant for me? I felt vindicated. The company finally switched to Microsoft Teams as senior management frowned upon having to share the personal with the professional. Besides, other teams not directly under the direction of a particular manager balked at the idea. 

But the outcome was small fare and total secondary to the real prize: Our project succeeded. The professional experience gained was invaluable. The friendship with new colleagues worth it. And personally, at the end, I felt good and successful. 

Echoing the insights of Dr. Angela Duckworth from McKinsey, success hinges significantly on “grit”—the perseverance and passion for long-term goals. 

She elaborates on this pivotal attribute in her seminal TED Talk (here), underscoring it as a key driver of success across various endeavors.

Embody this principle by continuously adjusting and iterating on your projects. With each cycle, apply the lessons learned, make the necessary tweaks, and launch again. 

You may feel down at times, but remember to always look up.

This relentless pursuit of improvement, driven by unwavering commitment, is what ultimately leads to achieving and surpassing the goal of reaching that elusive success in digital transformation. 

This is what will truly make you part of that 1 out of 8 successful projects.

Remember to keep an eye on the ultimate prize. 

Remember to clearly and honestly communicate your professional opinion to the client. 

If your advice is not heeded, remain calm, emotionally centred and mentally tough. Always focus on the big picture. 

Persevere with grit.

"Grit is the one and most coveted skill for success"


As we’ve navigated the complexities of digital transformation together, our exploration of seven key steps reveals an essential truth: digital initiative change devoid of purpose is akin to wandering without a map—a sure path to failure rather than success.

True success in digital transformation does not happen by chance; it’s meticulously and deliberately created through a deep understanding and prioritization of your end customers’ genuine needs and values.

Embedding customer value at the heart of all your efforts is critical, but also do not overlook the comprehensive strategy outlined in this short guide, from conducting honest self-assessments and presenting candid, hard truths constructively, to integrating customer-centric practices like Design Thinking into your everyday routines. 

These steps collectively forge a robust, sensible and consistent ethos for making your digital initiative a part of that coveted class of 1 of 8 digital initiatives that succeed, transforming your efforts from the conventional to the extraordinary.

Picture of Jonathan Lugo, MBA PMP

Jonathan Lugo, MBA PMP

Jonathan, a KPMG alum turned Germany-based expat, has led digital initiatives for notable names like Canadian Petroleum, Simon & Schuster, BMW, Revlon, United Technologies Corporation, and Kia Motors, among others. He's adept at distilling complex digital concepts into clear, user-friendly insights and is currently focused on incorporating Generative AI into client projects in the south of Germany. Living in Frankfurt, he often commutes to Toronto and Montreal, where he enjoys long walks on the beaches of Lake Ontario.

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