Crafting a digital transformation vision is of paramount importance if you want your organisation to embrace digital change. Too many digital transformations start with a tool, a vendor, or a budget line — but no real vision. The result? Programmes that burn money, frustrate teams, and deliver little more than “digital busywork.”
A clear digital transformation vision is the compass that keeps transformation programmes on course. To inspire, it must answer the only question every stakeholder is really asking: “What’s in it for me?” – WIIFM
- For internal users: does this make my job easier, faster, or more rewarding?
- For customers (and their end-users): does this give me a smoother experience, faster service, or a better product?
When both groups can see their WIIFM, adoption accelerates and trust builds. Without it, even the best tech or the biggest budget won’t save you.
Why Most Digital Visions Fail
Despite good intentions, many “digital visions” fall flat. Here’s why:
Too vague — no clear WIIFM for anyone
Phrases like “be more digital,” “cloud-first,” or “AI-ready” sound impressive, but they don’t help a sales team understand how their daily work will change — or reassure customers what they’ll get out of it.
Too focused on technology, not outcomes
When visions revolve around platforms, integrations, or features, they miss the WIIFM. Internal users care about reduced admin or faster collaboration. Customers care about convenience and quality — not the software name.
Too narrow — owned by IT, not the business
If the vision only answers WIIFM for IT, the rest of the organisation won’t engage. Commercial, operational, and customer-facing teams need their WIIFM made explicit.
Too static — WIIFM fades over time
Markets evolve, expectations rise. If the vision doesn’t adapt, the WIIFM for both employees and customers evaporates. A living vision keeps answering “what’s in it for me?” as contexts change.
What a Strong Vision Looks Like
A strong digital transformation vision isn’t a slogan on a slide. It’s a unifying story that answers the one question every stakeholder is quietly asking: “What’s in it for me?”
When leaders fail to address that question, the vision never takes hold. People nod along in meetings, but in practice they resist, divert, or quietly disengage. When the WIIFM is clear for each audience, adoption accelerates — because everyone sees their place in the journey.
Customer-Centred
A compelling vision starts with the customer — and that means two groups.
For external customers and end-users, the WIIFM is about faster service, smoother experiences, and products that feel modern and intuitive. If they can’t see or feel the benefit, the investment quickly looks like internal navel-gazing.
For internal users, the WIIFM is just as important. They need to believe the transformation will make their work easier, not harder. Fewer spreadsheets, fewer workarounds, less duplication. If they can’t connect the change to something tangible in their daily role, they’ll revert to old habits the first chance they get.
Commercially Grounded
A strong vision also makes commercial sense. For a CEO or Board, the WIIFM is confidence that transformation links directly to growth, resilience, or differentiation in the market.
For a CFO, it’s transparent ROI — not vague promises of “efficiency,” but benefits measured in real financial terms. For a COO, it’s the assurance that day-to-day operations won’t collapse under the weight of change.
When these groups see their WIIFM, they move from polite support to active sponsorship.
Outcome-Driven, Not Tech-Driven
Many visions fail because they obsess over platforms, integrations, or features. But for most stakeholders, that’s not the WIIFM.
For sales and marketing leaders, it’s about gaining richer customer insight and shortening time-to-market. For product leaders, it’s about platforms that support faster innovation. For CIOs and CTOs, it’s about finally turning technology into an enabler of business outcomes — rather than a blocker or a cost centre.
Strong visions make the outcomes the headline, and the technology the supporting act.
Shared and Simple
Complex visions don’t stick. A strong vision can be explained in one clear line — and repeated consistently from the boardroom to the frontline.
That simplicity is the WIIFM for middle managers, who are often stuck translating lofty strategy into day-to-day direction. It’s also the WIIFM for HR and People leaders, who need confidence they can support adoption without overwhelming the workforce.
When the story is clear, every layer of the organisation can retell it without distortion.
Flexible and Evolving
Finally, a strong vision adapts. WIIFM isn’t fixed: customer expectations rise, markets shift, and tech moves fast. A vision that stays static soon feels irrelevant.
The strongest visions balance a consistent core purpose with the flexibility to evolve. That means the WIIFM for employees and customers stays alive — not just at launch, but long into the transformation journey.
Building Buy-In Around the Vision
Even the best-crafted vision won’t go far if it lives in a board pack or a strategy deck. To make it real, leaders need to build active buy-in across every layer of the organisation — and that means tailoring the WIIFM.
Secure the Board and C-Suite
At board level, the vision must be anchored in outcomes that matter commercially. For the CEO, it’s about competitive edge and strategic delivery. For the CFO, it’s about predictable spend and measurable ROI. For the COO, it’s about operational stability.
When those WIIFMs are spelled out explicitly, you don’t just get signatures on a budget — you get leaders who will defend and champion the transformation when pressure builds.
Engage Stakeholders Beyond IT
One of the fastest ways to kill momentum is to position transformation as “an IT project.” The WIIFM for commercial leaders, product teams, marketing, and HR has to be front and centre.
- For sales and marketing, frame the vision as better customer insight and faster growth.
- For product, it’s freedom to innovate.
- For HR, it’s improved employee experience and capability uplift.
By translating the vision into each group’s WIIFM, you create alignment where otherwise you’d get polite head-nods — and quiet sabotage later.
Make It Tangible for Internal Users
For frontline teams, WIIFM is everything. They’ll decide whether the transformation takes root or fades. If they believe it means more admin, new hoops to jump through, or systems that don’t talk to each other, they’ll resist — overtly or subtly.
That’s why you need to show, in concrete terms, how the transformation makes their working day better: fewer duplications, fewer errors, more time to focus on value-added work. Small, relatable examples land better than grand strategy slides.
Communicate Simply and Repeatedly
A strong vision isn’t something you announce once. It’s a story that needs to be told — and retold — in different forums, using language people understand.
The key is consistency. Leaders at every level should be able to give the same one-line explanation of what the transformation is really about. That repetition builds trust and reduces space for confusion, misinterpretation, or sabotage.
How to Communicate the Vision in Practice
- Layer the message: adapt frequency and content for board, managers, and frontline teams.
- Make it visual: use simple diagrams, one-page infographics, or props that stick.
- Open two-way channels: town halls, Q&A forums, feedback loops — not just broadcast emails.
- Repeat relentlessly: use consistent language everywhere, until it becomes part of the culture.
- Adapt the tone: talk numbers with the CFO, simplicity with the frontline, outcomes with customers.
When communication is clear, layered, and consistent, the WIIFM stays front of mind — and the vision becomes something people not only understand, but repeat and defend.
Co-Create, Don’t Dictate
Finally, buy-in is strongest when people feel they’ve shaped the vision. Involving key stakeholders in workshops, discovery sessions, or design sprints helps them see their fingerprints on the outcome. Their WIIFM becomes not just about what they’ll gain, but about the ownership they’ve earned.
This also flushes out potential blockers early. If someone’s WIIFM is missing or misaligned, better to surface it and adapt the vision than to discover resistance in the middle of delivery.
Oak Consult’s Role in Vision-Setting
At Oak Consult, we’re often brought in when the ambition is clear but the vision hasn’t yet crystallised — or when the existing vision isn’t landing with the people who need to believe in it.
Our role isn’t to drop in a generic framework or a glossy slide deck. It’s to help leadership teams translate ambition into a vision that inspires and sticks.
That usually means:
- Facilitating alignment between commercial and technical leaders, so the vision makes sense to both.
- Turning ambition into clarity — shaping bold intent into outcome-led statements that everyone can understand.
- Mapping WIIFM across stakeholders, ensuring the vision resonates with the board, with internal users, and with customers.
- Building a foundation for delivery, so the vision doesn’t stay abstract but becomes the anchor for practical roadmaps and execution.
Because we’ve led transformations ourselves, we know the traps: visions that are too vague, too tech-heavy, or too divorced from the day-to-day. Our job is to help you avoid them — and create a vision that both inspires and survives first contact with reality.
Vision Is Only the Beginning
A clear, inspiring vision is the foundation of every successful digital transformation. It aligns leaders, engages teams, and reassures customers that change is worth the effort. Most importantly, it answers the question every stakeholder is asking: “What’s in it for me?”
But vision alone doesn’t deliver outcomes. The hard work begins when strategy meets reality — when milestones start to drift, stakeholders pull in different directions, and delivery risks losing momentum.
That’s the focus of the next part in this series: Leading Digital Transformation: From Vision to Reality. We’ll explore why so many programmes stumble in the gap between intent and execution — and what strong leadership needs to look like to bridge it.
In the meantime, if you need some help crafting your digital transformation vision, please get in touch!