By Jean Foster
For over a decade, “digital transformation” has dominated boardroom agendas. Companies have poured billions into AI tools, CRM systems, and automation platforms, often with little to show for it.
The hard truth? Most organizations don’t have a digital transformation problem.
They have a leadership transformation problem.
“We see this every day,” said Shayne De la Force, Founding Partner at The CMO Syndicate. “Too many transformations fail not because of flawed technology, but because executive teams aren’t aligned on the business purpose behind it.”
According to Deloitte, McKinsey, and others, up to 70% of transformation initiatives fail. The technology isn’t the problem; leadership is.
So how can leaders turn transformation fatigue into sustainable progress? The CMO Syndicate team explored this question during their latest webinar, sharing real-world examples and proven principles that separate success from failure.
The Real Issue Isn’t Tech — It’s Alignment
Transformation starts with why, not what.
“The most successful organizations like John Deere, Walmart, Siemens, and L’Oréal didn’t start by asking what technology they should implement,” explained Jean Foster, Associate Partner at The CMO Syndicate.
“They began by asking: How do we stay relevant for the next hundred years? Then they used technology to serve that vision.”
John Deere, for instance, now operates as an AI-driven company; its self-operating tractors use real-time data to optimize resource use. Walmart has redefined retail through a data-driven customer experience, while Siemens digitally simulates (“twins”) factories before they’re even built.
Each case underscores a single truth: technology follows strategy, not the other way around.
“Too often, companies start with the tool and then try to retrofit the strategy,” added Foster. “That’s where the cracks begin.”
Why 70% of Transformations Fail
The research and The CMO Syndicate’s experience points to a familiar pattern:
“Technology doesn’t create resistance; people do,” said De la Force. “If your leadership team isn’t aligned from the start, no amount of technology can fix that.”
The Six Principles of Leadership-First Transformation
After guiding hundreds of CMOs and C-suite leaders through transformation, The CMO Syndicate has distilled the process into six leadership principles that drive success:
Don’t begin with the platform; begin with the purpose.
“Ask what you’re trying to achieve for the business and the customer,” said Foster. “Then assess whether your team and culture are ready to support it.”
Transformation is an enterprise-wide responsibility, not an IT project.
At Siemens, each business unit owns a portion of the outcome, ensuring accountability across the organization.
“Culture can either accelerate or kill transformation,” said De la Force.
“You can’t ask people to innovate if they’re punished for failure.”
Incentives, governance, and rewards must all align with innovation goals.
Technology is not the hero, your people are.
Focus less on tech stacks and more on how technology improves customer experience, agility, or productivity.
“Even innovation leaders like Walmart revisit their AI investments constantly,” said Foster. “Agility isn’t just a buzzword, it’s how transformation stays alive.”
Run pilots, learn fast, and iterate often.
System uptime and app downloads aren’t success metrics.
Tie transformation KPIs to revenue growth, margin expansion, and customer satisfaction, and make leaders accountable through compensation.
Transformation Is a Leadership Imperative
At its core, digital transformation is human transformation.
Technology amplifies leadership; it doesn’t replace it.
“When CEOs and executive teams align behind a shared vision, culture, and accountability, transformation becomes sustainable,” said Foster.
“When they don’t, even the most advanced technology fails.”
Or as De la Force put it:
“Don’t become a statistic. Technology won’t save you, leadership will.”
Final Thoughts
The next time your organization plans a “digital transformation,” start by transforming your leadership mindset. Ask:
If the answer isn’t a confident yes, pause the technology rollout and start with the people at the top.
At The CMO Syndicate, we help CEOs and leadership teams realign their marketing and transformation strategies to drive measurable growth.
📩 Contact us here to learn more about how The CMO Syndicate can help you with your digital transformation problem.
🎥 Missed the webinar? Watch it here!