One of the most challenging aspects of vision and action is usually the bridging of the gap between the abstract digital possibility and concrete business reality in a way that makes stakeholders feel a sense of ownership and not uncertainty.

Here’s why this is so difficult:
The “everything is possible” paradox: Digital strategies often suffer from being simultaneously too vague and too ambitious. Leaders talk about “digital transformation” or “becoming data-driven,” but some stakeholders struggle to visualise what success actually looks like in their day-to-day reality.

Your vision needs to be inspiring yet tangible enough that people can see their role in it.

Competing mental models: Your CFO sees digital through a cost-efficiency lens, your CMO through a customer experience lens, your IT director through a technical debt lens, and your frontline managers through an operational disruption lens. Getting full alignment means you’re not really setting ONE vision, but you’re translating it into multiple languages that resonate with very different priorities and concerns.

The certainty trap: A familiar one, where stakeholders want a detailed roadmap with guaranteed ROI before committing, but digital initiatives inherently require experimentation and adaptation. A digital team is comfortable with testing and innovating, a different team may see that as a waste of time and unnecessary. The challenge is building those key relationships so that there is real confidence in a direction without promising false certainty. You need people to trust the process when the outcomes are still emergent.

What I’ve seen work best is building the vision with collaboration, rather than presenting it. Instead of unveiling a complete strategy, bring your stakeholders into the process of shaping it through structured workshops where they wrestle with real customer problems or competitive threats. When people help build the vision, they’re already on the journey with you, rather than being passengers you need to convince.

The hardest part isn’t setting the vision; it’s creating the conditions where stakeholders feel safe enough to commit to something that will inevitably evolve as you learn.

What’s your experience been? Are you finding resistance at a particular level or around specific aspects of digital strategy?