Digital Transformation Chaos
Why digital transformation needs more than motion — it needs meaning.
“The absence of an accident does not mean the presence of safety.” It’s a statement I learned in industrial safety. And it applies perfectly to digital transformation. We like to assume that if nothing is going wrong, then everything must be going right.
No major failures? No resistance? No red flags?
Then the strategy must be working… right?
Not quite.
Most digital transformations don’t explode. They fizzle. Not with a bang — but with a shrug. Teams “do stuff with data,” initiatives “move forward,” and dashboards light up… but no one really knows why. Or if it’s even helping.
The Illusion of Progress
You know the signs:
✅ There are pilots running
✅ People say they’re “on the journey”
✅ Some automation has gone in
✅ The lights are on, and things are moving
But scratch below the surface and you’ll often find:
❌ No one can articulate the strategy in their own words
❌ Departments are solving problems in isolation
❌ Leadership is measuring activity, not impact
❌ And employees are quietly unsure what success even looks like
That’s not alignment. That’s ambiguity with momentum.
Strategy Isn’t a Schedule — It’s a Compass
Too many organizations treat strategy like a checklist. A sequence of steps to follow. A fixed schedule of technologies to deploy. But digital transformation doesn’t work that way — it’s not a straight road, and it’s certainly not linear.
A good strategy doesn’t tell every team exactly what to do. Instead, it provides them with the context to make better decisions. It gives people across functions and levels a way to think about problems, evaluate tradeoffs, and move in the same direction — even if the terrain shifts beneath them.
Think of it like a compass, not a calendar. A compass doesn’t dictate the exact path. It gives you a sense of direction, so when the map changes, you still know how to move forward with purpose. That’s the difference between chasing milestones and building momentum.
The goal of a strategy
It’s not about dictating every move your decision-makers should make; it’s about providing them with the guidance they need to make decisions that align with a unified goal. The strategy map isn’t a set of instructions but a compass - it shows the way, focusing on how to decide rather than what to decide.
From Strategic Silence to Strategic Clarity
Here’s the reality: most digital transformations struggle not because people resist change, but because they’re unclear what the change is for. Silence breeds confusion. And confusion leads to hesitation, inconsistency, and disengagement.
The antidote? Clarity. Repetition. Familiarity.
You don’t need a more detailed project plan.
You need to create an environment where everyone knows what direction they’re heading, why it matters, and how their daily work connects to it.
That’s how you turn strategy from a one-time presentation into a company-wide mindset.
Map It
If people can’t see the strategy, they can’t follow it.
You wouldn't start a cross-country road trip with only a vague idea of where you're going — and yet, that’s how many companies treat digital transformation. A few ambitious goals, some technology pilots, and a loosely defined “north star”… but no map.
To fix that, you need to visually codify your strategy — not just write it down, but design it in a way that people can understand and navigate.
A proven approach here is the Strategy Map from the Balanced Scorecard framework by Kaplan & Norton. It forces organizations to define the cause-and-effect relationships between initiatives and business outcomes — across financial, customer, internal process, and learning/growth perspectives. Think of it as a visual logic tree that connects every initiative back to enterprise value. It's powerful because it doesn’t just show what you’re doing — it shows why you're doing it and how everything fits together.
Another best practice is to integrate your map with the Playing to Win strategy cascade — clarify your winning aspiration, define where you’ll play and how you’ll win, identify capabilities, and manage systems. These aren't just slides; they become a strategic narrative that informs decisions from C-suite to shop floor.
And don’t stop at one version. Tailor your strategy map for different audiences: one high-level version for executives, a use-case-driven version for operations and IT teams, and a customer-facing version for alignment with external partners.
The goal? Make the strategy impossible to misinterpret.
Explain It
A map is useless if people don’t know how to read it.
It’s not enough to share the strategy — you have to teach it.
Every person in your organization should understand not just what the strategy says, but what it means to them. That’s where communication meets context.
One of the best models here is McKinsey’s 7S Framework — which shows that strategy must align with seven interdependent elements: Strategy, Structure, Systems, Shared Values, Skills, Style, and Staff. Most organizations announce the strategy and assume the rest will fall into place. But if you don’t tailor your message to each of the other S’s — especially systems, skills, and shared values — then the strategy will remain theoretical.
This is also where Wardley Mapping can play a role for tech-heavy transformations. It’s a way to visually represent how capabilities evolve over time, helping teams understand what’s being built, what’s being bought, and where the organization is heading. Use it in engineering and IT teams to explain which technologies are differentiators vs. commodities — and why your transformation is prioritizing them accordingly.
Above all, apply the principle of contextual translation: the process of adapting your strategy explanation based on department, role, and even individual responsibility. Operations leaders care about throughput, finance leaders care about margin impact, and IT teams care about architecture and scalability. Speak their language.
Because if they don’t understand how their work fits the strategy — they’ll fill in the blanks with their own.
Repeat It
If you only say it once, you never really said it.
Even the clearest strategies fade without reinforcement. That’s why repetition isn't redundant — it's required. The challenge isn’t creating alignment once. It’s sustaining it as priorities shift, teams grow, and market dynamics evolve.
One gold-standard approach is OKRs (Objectives and Key Results), popularized by Intel and Google. OKRs help translate high-level strategic goals into actionable objectives at every level of the organization. And more importantly, they’re updated frequently (usually quarterly), which forces teams to revisit, realign, and re-engage with the strategy on a regular cadence.
You can also borrow from Agile methodologies, especially the cadence of ceremonies: daily standups, sprint reviews, retrospectives, etc. These touchpoints aren't just for project tracking, they’re a perfect chance to embed strategic reminders, celebrate aligned wins, and realign when needed. When done right, your strategy becomes not a slide, but a rhythm.
And don’t just rely on meetings — use internal comms systems like Viva Engage, Teams, or Slack to push out micro-reinforcements. Share wins, spotlight aligned decisions, and show progress toward the map you created. You’re not just reminding people of the strategy — you’re reinforcing that it’s real, it’s active, and it’s theirs.
When people hear a message enough times, from enough angles, in enough contexts, it becomes cultural. That’s when the strategy sticks.
Video inspired by: https://www.instagram.com/p/CwNmci9K5KK/
