I’ve led, coached and advised dozens of transformation efforts — some worked and some didn’t. You’d think the right tools or plans would guarantee success, but they rarely do. Companies invest in technology, hire consultants, and create detailed roadmaps, but still struggle to see results. Why?
From my experience, the difference between a transformation that fizzles and one that succeeds comes down to leadership, behavior, and human-centered culture not the technology itself. And what I’ve experienced confirms the research: technology isn’t what determines success.
Successful transformation starts with a purpose people can feel and relate to, not just metrics executives’ track. When people understand the purpose, they engage — not just comply.
Answer:
Example:
Adobe shifted from boxed software to a subscription, cloud‑based model. The “why” wasn’t tech, it was survival and renewed relevance in a changing market. This clarity helped win employee buy‑in during a risky business model shift.
Takeaway: A compelling purpose clarifies choices and shapes decisions. It keeps people moving forward and gives meaning to their work when the going gets hard.
In a complex transformation I led, we made conscious tradeoffs at the start (standardization vs. customization, decision rights) that cut friction and rework later.
From the beginning it is helpful to:
What I’ve seen land well:
Walmart invested heavily in cross‑functional alignment as it moved to a cloud‑centric model aligning supply chain, stores, digital products, and data teams to a shared view of how the tech would surface value.
Takeaway: MIT research shows that cross-functional alignment upfront is a strong predictor of transformation success. When leadership is coherent, teams move faster.
We often audit infrastructure, platforms, and data readiness but skip the critical question: Are people ready?
This includes:
Real shifts look like this:
Capital One didn’t just adopt cloud; it rethought roles, built digital talent, and created psychological safety so teams could experiment with AI and DevOps practices.
Takeaway: When people feel equipped and safe, adoption becomes ownership rather than compliance.
There’s no clean journey from start to finish. Transformations get hard in the middle. Progress slows, enthusiasm dips and setbacks are inevitable.
To succeed:
· Rewarding effort, not just output
· Re-energizing people by acknowledging struggles and showing compassion
· Regarding setbacks as learning opportunities for growth
Take Domino’s, for example:
When they first launched online ordering and digital platforms, adoption was slow, and early systems had glitches. Instead of giving up or rushing, the team iterated rapidly. Each “failure” became insight, and each iteration brought improvement. Today, digital channels account for the majority of Domino’s sales, and the company is recognized as a technology-enabled business, not just a pizza chain.
Takeaway: Progress during the messy middle comes from learning fast, rewarding effort, and using setbacks as fuel for improvement.
Sustainable change requires habits:
What this looks like in action:When Satya Nadella became CEO of Microsoft, he shifted the company’s culture from one of internal competitions to one grounded in empathy, active listening, and growth mindset. By encouraging leaders to listen to employees and customers, fostering psychological safety, and breaking down silos, Microsoft increased collaboration and innovation driving measurable ROI
Takeaway: Routines are the scaffolding that turns new behaviors into norms that make change stick.
Leaders who treat transformation as human and strategic work not just technical work get outcomes that last.
Technology enables change, but whether it lasts depends on how leaders think, act, and engage with their teams. I’ve learned that when purpose is clear, assumptions are challenged, people are ready, setbacks are managed with empathy, and routines anchor new behaviors, transformation stops being a buzzword and becomes real.
When you lead with those things first, the rest follows.
Small improvements add up to remarkable results. When you focus on the process, not just the outcome, you can truly find success.
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