Lessons from the Digital strategy roundtable

This morning we hosted a roundtable on Digital strategy, bringing together senior leaders from diverse industries - each with years of experience in digital transformation. The goal was simple: share real-world challenges, successes, and lessons learned. What emerged was a candid discussion about the human, strategic, and cultural factors that make or break digital initiatives.

This isn’t just another theoretical take on digital strategy. It’s a practical breakdown of what actually works - and what doesn’t - based on the collective wisdom of leaders who’ve been in the trenches

Too many opinions will get your nowhere

One participant shared how their organisation’s digital strategy effort stalled before it even began. Why? Too many stakeholders, each pushing their own short-term departmental goals. The result? A fragmented approach with no clear direction.

The lesson:

• Align on outcomes, not opinions. Start with a shared vision of what success looks like for the organisation, not just individual departments.

• Limit the core strategy team. Involve key decision-makers, but avoid “design by committee.” Too many voices dilute focus.

• Use frameworks to structure discussions. A digital maturity assessment or strategy canvas can help ground conversations in data, not just opinions.

  
  

Practical takeaway: Before diving into strategy, ask: “What are the 3-5 non-negotiable outcomes we must achieve as a company?” Use these as guardrails to filter ideas.

Strong leadership is non-negotiable

The problem: Another leader described a familiar challenge: The company owner wasn’t invested in digital, the board had little influence, and the strategy shifted frequently. Without clear leadership, digital transformation became an uphill battle.

The lesson:

• Leadership must visibly champion digital. If the CEO or owner isn’t bought in, progress will be slow. Digital transformation isn’t an IT project—it’s a business imperative.

• Consistency matters. Frequent strategy pivots confuse teams and erode momentum. Leaders must commit to a direction and stick with it long enough to see results.

• Lead by example. Leaders who embrace digital tools, data-driven decision-making, and agile ways of working set the tone for the entire organisation.

  
  

Practical takeaway: If leadership isn’t engaged, start small: Find a high-impact pilot project that demonstrates quick wins. Use its success to build buy-in.

It's all about people

The Problem: Multiple participants emphasised that digital transformation isn’t about technology, it’s about people. Resistance to change, siloed cultures, and lack of shared purpose can derail even the best-laid plans.

The lesson:

• Culture eats strategy for breakfast. You can have a brilliant digital strategy, but if the culture doesn’t support collaboration, experimentation, and learning, it won’t stick.

• Communicate the ‘why’ relentlessly. People need to understand why digital matters—not just what they’re being asked to do. Connect the dots between digital initiatives and their daily work.

• Invest in change management. Train teams, celebrate small wins, and create feedback loops to keep everyone aligned.

Practical takeaway: Map your stakeholders. Identify who will be most impacted by change, and involve them early. Use workshops, storytelling, and quick wins to build momentum.

Digital is an enabler, not the end goal

The problem: Several leaders noted that organisations often treat “going digital” as the goal itself—leading to shiny tools with no real impact.

The lesson:

• Start with the business problem. Digital tools are means to an end. Ask: “What are we trying to achieve for our customers, employees, or operations?”

• Measure what matters. Track outcomes (e.g., customer satisfaction, operational efficiency), not just outputs (e.g., “we launched an app”).

• Iterate and adapt. Digital transformation is a journey, not a one-time project. Use data to refine your approach continuously.

Practical takeaway: Use the “So What?” test. For every digital initiative, ask: “So what? How does this move the needle for our business or customers?” If you can’t answer, rethink the initiative.

Data kills digital transformation for breakfast

One participant challenged us: "What really kills digital transformation?" His answer: Not culture, but data. Not the lack of it, but the low quality, fragmentation, and misuse of it.

The problem: Without clean, accessible data, you can’t track progress, prove impact, or even identify the right problems to solve. Bad data doesn’t just slow you down. It leads to wasted effort, misaligned priorities, and distrust in digital initiatives. When critical information is scattered across systems, teams end up working from different versions of the truth, if they use data at all. The result? Decisions based on guesswork, not evidence.

The lesson:

1. Start with what matters. Focus on the 20% of data that drives 80% of your key decisions (e.g., customer insights, operational metrics).

2. Assign ownership. Appoint data stewards in each department to ensure accuracy and accountability.

3. Embed data in daily work. Integrate it into tools teams already use, and train them to trust and act on it.

Practical takeaway: Fix your data before scaling digital. Without clean, trusted data, you can’t measure progress, make informed decisions, or align teams. Start small: audit your critical data, assign owners, and embed quality checks into workflows. Messy data = messy transformation.

Next roundtable: DLF 2025 in Vienna

Interested in joining a roundtable and learn from your peers? come join us for the Digital Leadership Forum 2025 in Vienna. Are you ready to bridge the gap between strategy and execution? I look forward to seeing you in Vienna!

Practical information

• Date and time: Monday, 3 and 4 November 2025.

• Location: Haus der Ingenieure, Vienna

• Who should attend: Professionals in digital transformation, strategy, communication, and leadership.

• Want to know more? View the full programme at Digital Leadership Forum 2025.

Discount code

Use the code ‘MODERATOR’ to receive a 35% discount on the entire event. That means two days of learning a great deal from other professionals, enjoying beautiful Vienna with a group museum visit, and delicious food.