How to Make Digital & IT Transformation Stick — Big or Small

If you’ve been in digital or IT long enough, you’ve seen your share of transformations.

Some are driven by commercial goals. Others start with compliance or risk. Some are rushed in by a burning platform or customer dissatisfaction. And many begin with good intentions — a bold vision, a big bang announcement, an external consultancy, and a few million dollars earmarked to ‘make it happen’.

Yet, so many transformations fail — or at best, deliver only a fraction of the value promised.

I’ve had the privilege (and at times the scars) of being on both sides of the table — as a consultant delivering high-pressure change, and later, as a transformation leader inside the belly of the beast. I’ve led changes involving:

• Mission-critical infrastructure with Six Sigma requirements

• Commercially driven digital rebuilds and e-commerce transformation

• Agile and SAFe operating model changes

• Platform shifts involving Salesforce, MarTech, and personalization at scale

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And across these diverse contexts, I’ve asked the same question again and again:

Why do some transformations stick, while others don’t?

I’ve come to believe that three factors — above all — determine whether a transformation becomes a turning point or a cautionary tale.

🔑 1. Skin in the Game: Sponsors Who Show Up and Stay

You can smell a doomed transformation from the start — when the executive sponsor signs off, launches the change with a town hall or press release, and then disappears.

The most successful transformations I’ve seen had one key ingredient: a sponsor who showed up — consistently and authentically.

That doesn’t mean micromanaging Jira boards. It means:

• Making time to communicate the “why” at every level of the org

• Walking the floor (or joining standups virtually) and thanking teams

• Being vulnerable when things go off track — and resetting calmly

  
  

I still remember a mission-critical digital migration where our sponsor — a very senior executive — joined weekly showcases and stayed back to chat with junior testers. The energy in the room shifted. People started owning the outcomes. No spreadsheet or playbook could create that.

This reflects what Stephen Covey teaches in The 7 Habits of Highly Effective People: "Be Proactive." Great sponsors don’t wait for a weekly update or quarterly review. They lean in and lead visibly. And when they do, teams follow with purpose.

Leadership takeaway: Culture is shaped by who shows up. If the sponsor cares, everyone cares more.

🧠 2. Empower Translators, Not Bureaucrats

One of the biggest traps in transformation is building process for process’s sake. PMOs balloon. Reporting becomes an industry. And the people who actually get things done get buried under admin.

Here’s what works better: find the translators — those rare individuals who:

• Understand business context

• Speak technology fluently

• Know how to manage budgets and outcomes

• Can lead people with empathy and urgency

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When you cut the red tape and put these leaders at the helm, magic happens. They know how to:

• Navigate ambiguity

• Say “no” to gold-plating

• Spot when something’s not adding up (before it’s too late)

  
  

During one e-commerce transformation I led, we empowered a small team of cross-functional leaders — each with hybrid skills in product, tech, and finance. They ran weekly “huddles,” made calls without waiting for three layers of approval, and co-created with stakeholders. We shipped faster, learned more, and recovered quicker from setbacks.

The philosophy behind this came from Agile from the Trenches, a book I first read during my IBM days. Back then, Agile was still debated in meeting rooms. That book grounded me in real-life Agile thinking, not ceremony-driven implementations. It taught me that transformation happens on the ground — not in decks.

Execution takeaway: If the people running your transformation don’t understand both tech and business, and can’t lead with trust — you’re building on sand.

📊 3. Measure What Matters (and Talk About It Often)

We’ve all seen vanity dashboards. Charts that go green before go-live — and red after. Metrics that tell us everything’s “on track” — until the customer tells us otherwise.

Real transformation requires real measurement. I’ve found OKRs (Objectives and Key Results) to be the most powerful tool — but only when they’re:

• Owned by teams, not imposed from above

• Aligned top-down and bottom-up

• Regularly reviewed, with a mindset of learning, not blame

OKRs help connect daily work to strategic intent. When set well, they:

• Make trade-offs visible

• Give people a sense of progress (even during tough phases)

• Provide early signals when things are drifting

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But measurement alone isn’t enough. The feedback loop matters just as much. Teams need psychological safety to say, “This isn’t working,” and pivot. Customers should be involved early. Data should inform action — not justify sunk costs.

I’ve seen one-page OKRs change the direction of a $10M program — because they helped us realise we were solving the wrong problem. We adjusted early and delivered something smaller but far more valuable.

Measurement takeaway: If you’re not measuring impact regularly, you’re just managing activity. And if teams don’t feel safe to call things out, your OKRs are just theatre.

Why It All Comes Down to Culture

The technology will change. The delivery methods will evolve. The tools will get smarter. But in the end, transformation sticks when culture supports it.

That culture needs:

• Leaders who care and communicate

• Teams who are empowered, not controlled

• Systems that reward learning over perfection

  
  

I’ve seen transformations that failed despite perfect plans — and ones that succeeded despite chaos — simply because the people trusted each other and stayed committed.

So the next time you kick off a big program or a small improvement, ask yourself:

Do we have skin in the game?Are we letting the right people lead?Are we learning from what we measure?

If the answer to all three is yes — you're not just doing transformation. You're building a foundation that lasts.

📌 TL;DR – What Makes Transformation Stick?

🔑 Principle	🚀 What It Looks Like in Practice
1. Sponsor Skin + Humility	Visible leadership, real communication, presence
2. Empower Translators	Hybrid leaders who cut red tape and lead cross-functionally
3. Measure + Learn	Clear OKRs, real feedback loops, course correction mindset

📚 Influences That Shaped My Thinking:

• The 7 Habits of Highly Effective People by Stephen Covey — especially “Be Proactive”

• Agile from the Trenches — for grounding Agile in real delivery, not theory

• Teams with transformations inside high-growth, high-aspirations environments