Digital Transformation Leadership: Practice Before Platforms

By Andrea Bednar | #ConsciousDoing #MasterExecutiveCoach

⸻

The Myth of the Digital “Rollout”

Everywhere I go, senior teams are talking about digital transformation.

The language is strikingly similar: “We’re rolling out the new system.” “We’re upgrading our tools.” “We’re training people on the platform.” “We’ve got 3 hour a week webinars to train us.”

Here’s the uncomfortable truth: most digital transformations fail — not because the tech doesn’t work, but because people never learn to work differently.

They learn the system. They complete the training. They tick the boxes.

But when the pressure hits, they revert to old ways — decision by email, siloed thinking, managing through willpower instead of strategy.

That’s not transformation. That’s habituation.

In the age of AI, new platforms and systems arrive faster than ever. The danger isn’t falling behind on the tech — it’s falling behind on the capacity to adapt.

⸻

Why Digital Transformations Fail

Leaders don’t fail at digital transformation because the technology is bad. They fail because their people haven’t practiced new behaviors — and because the organization hasn’t built structures that make practice possible.

Most rollouts are designed like deployments: launch it, train them, move on. There’s no rhythm for learning, no feedback loop, no time to experiment and integrate.

So what happens?

People perform digital competence while clinging to analog habits. The organization looks “modern” on the outside but runs on the same invisible wiring underneath.

The metrics might improve for a quarter or two, but the culture doesn’t shift.

And when the next tool arrives, the cycle repeats.

Transformation without practice leaves people pretending they know what they’re doing.

It breeds imposter syndrome, not innovation.

And transformation without structure?

That’s like trying to build a four-story building by stacking cardboard boxes. There’s no scaffolding. No container sturdy enough to hold the learning.

Practice gives people a way to experience change — to see what happens when they take the first step, try a new behavior, or run a different pattern. It turns intention into something tangible.

Structure gives that effort guardrails — a way to stay steady while things are still uncertain. It creates a safe container for experimenting, learning, and adjusting before the new way becomes second nature.

When both are in place, transformation isn’t theory anymore. It’s lived.

That’s what we build inside Team Alchemy — together, we create structures where teams can safely experiment, reflect honestly, and turn what works into shared practice.

No one learns to work differently just because they were told to or read the email announcement.

Digital fluency doesn’t come from a memo or a training deck — it comes from people trying, adjusting, and learning together until the new way becomes natural.

⸻

What This Requires of Leaders

Leaders who succeed at digital transformation don’t push harder for adoption — they design better conditions for learning.

They know that people don’t resist change because they’re stubborn; they resist it because they don’t feel safe failing in public. So those leaders build in the time, permission, and practice to learn in real time.

They reward curiosity over compliance.

They ask better questions instead of giving faster answers.

They measure not just how fast people adopt a tool, but how differently they think and work once they do — they measure the impact of the adoption attempts. 

This is the quiet work of leadership — hosting evolution instead of driving execution.

It asks something new from leaders:

 • The humility to not know everything about the tools.

 • The courage to let others experiment first.

 • The patience to stay steady through the messy middle.

In essence, digital transformation leadership is less about managing technology and more about curating the environment where new ways of working can take root.

Leaders must become both architects and gardeners — building the scaffolding that supports growth, and tending to the human side that keeps it alive.

That’s not a metaphor. It’s a skill set.

⸻

A Case from the Field: Building the Scaffolding

A firm we worked with had all the right pieces in place — a modern tech stack, and a visionary CEO.

Still, progress stalled. Deadlines slipped. Departments started working around the new system instead of through it.

The CEO brought us in, convinced they had a “people problem.”

They didn’t. They had a practice problem.

Here’s what we found:

Their people were smart, committed, and capable. But they had no structure for experimentation. There was no place in the calendar — or the culture — to test, learn, or reflect.

We helped them install three things:

 1. Weekly 20-minute “practice reviews.” Each team reported what small experiment they’d run with the new system and what they learned and any impacts produced (effective or not).

 2. A visible, shared digital “learning scoreboard”. Wins and missteps were tracked side by side. The goal was real-time data, not perfection.

 3. A leadership checkpoint. Every 60 days, the exec team reviewed what practices had stuck — and which needed to be redesigned or discontinued.

Within two quarters, adoption rates doubled — not because the system changed, but because the structure for learning did.

That’s digital transformation leadership in action. Not pushing harder. Not doing more training. Creating the scaffolding where new behaviors can take root.

⸻

What Leadership as a Living Lab Looks Like

Here’s the part we rarely acknowledge: real teams almost never operate like this. Humans are creatures of habit. We think, feel, and work in familiar grooves.

So when a team truly experiments — consistently, over time — it’s unusual.

What we usually see are strong starts followed by fade-outs, quick relapses, or moving on to the next shiny thing.

Part of the problem is that experimentation feels like chaos to people who don’t have regular practice habits. But it doesn’t have to.

A true laboratory is designed — it runs safe-to-fail tests and turns what works into practice.

We encourage teams to experiment in their Goldilocks Zone — not too easy, not too disruptive, but just right. That means picking one or two things to try that stretch the system without breaking it.

Case in the Field: When “Digital Transformation” Meets Real Life

A regional financial services company we worked with had invested millions in its digital transformation — new CRM, AI-powered analytics, sleek client dashboards. On paper, it was flawless.

In reality? Leaders were still running reports by hand before meetings. Decisions were based on instinct, not data. When I asked why, one VP admitted, “We don’t know for sure these new reports work. They’re supposed to, but when I’m in a hurry, I don’t want to mess around fixing something that isn’t right yet. And let’s be honest — we all know AI makes mistakes. I’m not betting my client relationships on that.”

They didn’t need more tech. They needed practice with trust.

So instead of another rollout meeting, we built a different kind of experiment: shadow decisions.

For one quarter, every manager recorded two sets of decisions each week — the usual “instinct call,” and then a parallel decision based solely on the AI data. Both went into a shared log. The team compared outcomes at the end of each week.

The first month was rocky — lots of defensiveness, eye-rolling, and “see, I told you so.” But patterns began to emerge. The AI calls weren’t always right, but they were measurably faster. And when managers combined their judgment with the system’s data, and they reduced client follow-up corrections by 18% — fewer “we need to update your report” calls, and more right-first-time results.

That led to a second experiment: a cross-department “data circle” where analysts, client reps, and branch leaders reviewed cases together — not to assign blame, but to learn what the AI data missed and why.

By the end of six months, the company didn’t just “use the new tools.” They trusted them — because they’d practiced seeing where the tools were strong, where they failed, and how human discernment fit back into the loop.

No dashboards. No 15-minute reviews. Just structured learning embedded inside real work.

That’s Conscious Doing: not practicing in theory, but learning in the field, inside the system that’s already running.

And once what works becomes habit, that’s Conscious Doing in action.

⸻

Engage With This Now

Inquiry

What would if your leadership team operated as a laboratory instead of a hierarchy?

Ask your team — what rhythms, permissions, and boundaries would make it safe to practice new ways of working? You aren’t committed to doing anything out of an inquiry. You’re having the conversation to explore something. You may need several inquiries before you take action on any of them. 

Action

For one week, ask your team to note every moment they bypass a digital tool (“I’ll just do this by hand,” “It’s faster if I email them”). Gather those examples and look for patterns. Which ones point to lack of skill, lack of trust, or poor system design? Pick one to address next week.

Practice

For the next 30 days, build learning in public into your digital transformation.

Every time a team member encounters a new tool, feature, or workflow, have them pause for three minutes at the end of that session and note:

 • What worked the way I expected?

 • What confused me or slowed me down?

 • What do I need to learn next?

Capture the answers where everyone can see them — in the comments of the shared workspace, a project channel, or even on your dashboard. Don’t polish them. Leave the mess visible.

By the end of the month, you’ll have built a living record of adaptation — not a “review,” but a living document of learning, course adjusting, and impacts.

⸻

The Last Word

Most digital transformations don’t fail because people are lazy or resistant. They fail because leaders don’t give them the time or space to learn while doing.

We keep mistaking communication for change.

We send the email, run the training, check the box — and then expect fluency. But learning doesn’t work that way, and neither does transformation.

People need repetition. They need guardrails. They need permission to be clumsy for a while. That’s how confidence is built — not through talk, but through trying.

When we work with teams inside Team Alchemy, this is what we help them build: the scaffolding that holds real learning. It’s the difference between knowing the steps and being able to dance.

Digital transformation isn’t about mastering the tools. It’s about creating an environment where practice can happen long enough for new habits to take hold.

And that takes leadership. Not the kind that commands or announces, but the kind that stays steady through the awkward middle — the kind that knows growth doesn’t look like progress at first.

If you want your digital transformation to work, build the space where people can practice being new at something. Let them learn in public. Let the mess be visible.

That’s where real transformation starts — not with the software, but with the humans using it.

⸻

Andrea Bednar’s latest book, Doing: How Leaders Harness the Transformative Power of Conscious Action, is for leaders ready to stop admiring activity and start creating impact that lasts.

A master executive coach and founder of AndreaBednar.com, Andrea has spent three decades in boardrooms and offsites telling leaders the truths they don’t always want to hear — and giving them the practices to change anyway.

Explore more at www.AndreaBednar.com.