The one digital transformation question that changes everything

What’s the one leading digital transformation question you need to ask that can make the difference between a successful transformation program and one that fails to address your organization’s needs or drive success? 

Read on to find out. But first, let’s start with an analogy…

Why purpose drives performance

Ask ten people at the gym why they are there, and you’ll get different answers – lose weight, build muscle, mental health, social reasons… 

But imagine if they just turned up without knowing their reason. They might still lift weights or run on the treadmill, but with no clear purpose, motivation fades, progress stalls, and they are likely to quit.

Many things in life follow the same pattern:

• A product team can build the most technically impressive solution but if they never truly define why it matters to the customer, it risks becoming just another piece of software people tolerate rather than rely on.
• A project can hit every milestone on time. However, if the team does not understand why the work is important, engagement and momentum fade.
• Sales teams can pitch features all day long but without a clear “why” behind the value, it is just another product in an already crowded market.

The hidden cost of jumping straight to “what” and “how”

The problem? Too often, organisations focus first on what needs to be done and how it will be delivered – because those feel like the practical, tangible things that get results. But without first understanding why it matters, teams risk delivering something that ticks every box on paper but fails to make an impact where it counts.

Scope, budget, and timeline are important – but they are not what drives success. The real key to delivery, leadership, and product development is answering the digital transformation question too many teams forget to ask: why?

The ripple effect of a weak “why”

When the “why” is unclear, projects, products, and teams all suffer in ways that are frustratingly predictable:

• Misalignment – Teams, stakeholders, and leadership have different interpretations of success, leading to conflicting priorities, endless debates, and rework.
• Scope creep and churn – Without a clear why, decisions feel arbitrary. Priorities shift, new ideas get thrown in last-minute, and work drags on longer than planned.
• Poor adoption – A solution that makes sense on paper but does not resonate in reality will struggle to gain traction. If the end users do not understand the value, they will not engage with it.
• Demotivated teams – People need to know why their work matters. If the purpose is vague or constantly shifting, engagement and momentum drop fast.

Ever worked on something where these problems snowballed? It usually starts with a missing “why.”

Examples of when “what” without “why” fails

The CRM system that no one used

A business invests in a new CRM platform to “streamline customer interactions.” The system is built exactly to spec, with all the features requested. Yet when it goes live, adoption is far lower than expected. Sales teams find it more of an admin burden than a helpful tool. Leadership expects better data but did not define how success would be measured.

Delivered perfectly, barely used. Sound familiar?

The “successful” product launch that no one bought

A company launches a feature-rich new product with great internal excitement. On paper, it does everything expected – except drive customer demand. Despite the marketing push, sales numbers stay flat.

It turns out that, while the product was innovative, customers did not see how it solved their real challenges. But instead of revisiting the core problem, the response is often to add more features, more automation, or – lately – just slap “AI-powered” on the label and hope that fixes it.

Seen it happen?

The perfectly delivered project that solved the wrong problem

A company spends a year implementing a new operational system to improve efficiency. When launched, it functions exactly as planned – but it does not fix the real business issue. The team executed brilliantly on the request, but the underlying challenge – whether supply chain inefficiencies, team workflows, or outdated policies – was never properly addressed.

Right execution, wrong problem. Been there?

How defining “why” changes everything

When teams start with why, everything else – scope, priorities, execution – becomes sharper and more focused:

Leadership and stakeholder alignment

The best leaders do not just set goals; they clarify purpose so teams are not just delivering work, but solving the right problems. When stakeholders align on the “why,” decision-making speeds up, rework is reduced, and teams avoid the trap of constant last-minute direction changes.

Better decision-making at every level 

When everyone understands why something matters, they make smarter choices. A developer does not just code a feature – they prioritise the right functionality because they see how it impacts the customer. A project manager does not just track progress – they proactively remove blockers that threaten the real objective.

Customer-centric delivery 

A project delivered on time and on budget is useless if it does not solve the real problem. When the why is clear, teams are more likely to deliver solutions that drive measurable adoption, improve efficiency, or create real customer value – rather than just shipping a feature for the sake of it.

It sounds simple, but it is often the step that gets skipped in the rush to execution.

Getting the why right is not just a leadership exercise – it is the foundation of every great product, project, and strategy.

What’s next?

Understanding the why is just the first step. Actually defining, aligning, and embedding it into how teams work is where the real challenge begins. That is something I’ll be breaking down in an upcoming article – how to turn “why” from a vague idea into a practical framework that drives real impact.

But before we get to that, let’s take a step back. If defining “why” is critical, then who is responsible for doing it?Leadership? Delivery teams? Product managers? Or all of us?

That’s what I’ll explore in the next article in this series: “Why we are all leaders (even if we don’t realise it yet)”. Don’t miss it!

Time to start asking the most important digital transformation question in future

In the meantime, I hope reading this article means you won’t forget to ask that all-important digital transformation question during your next project, and keep its purpose and ultimate value firmly in mind. 

If you’re embarking on a technology project, such as a Salesforce implementation, VRP Consulting would love to help. Our experts will make sure all the important questions are asked and answered, so that your end results match up with your goals and your customers’ or employees’ needs. 

Get in touch with us today and let’s explore how we can help you make the most of the power of “why”. 

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About the Author

Mark Crutchfield

Regional Head of Delivery (UKI, US, Benelux), VRP Consulting

Mark is a Delivery leader and Agile specialist at VRP Consulting, where he drives informed leadership, digital transformation and excellence in delivery - bridging technology, strategy, and innovation for high-impact execution and smarter business decisions.