Creating a Digital Strategy That Actually Works

Introduction: Why Strategy Fails (and How Yours Won’t)Let’s face it—most digital strategies fail not because people don’t care, but because they get lost in translation. They sit in folders, not in workflows. They’re written by committees, not for people.

Whether I’m working with a college senior leadership team or the board of a growing startup, my advice is the same: a digital strategy should be practical, people-centred, and relentlessly focused on outcomes. This post breaks down how to build one that works in the real world—for education, for business, and for your team.

Step 1: Start with Purpose, Not Platforms

Before you touch technology, get clear on your “why.”

• What problems are you solving?

• Who benefits from digital improvement?

• What does success actually look like?

If the purpose is “everyone else is doing it,” stop. You need a stronger reason.

“The best digital strategies I’ve supported started with a single sentence: ‘We want to make learning and working easier, faster, and smarter for our people.’ That’s the clarity that fuels progress.” — Billy Smith

Ask your team and stakeholders: What would a good day look like if digital was working better here? The answers will surprise you—and guide you.

Step 2: Audit What You Have (Honestly)

You can’t chart a course if you don’t know where you’re starting from.

Conduct a digital audit by looking at:

• Systems & Tools – What platforms are used regularly? Which are underutilised?

• Skills & Confidence – Where are staff thriving, and where are they just surviving?

• Culture & Practice – Are people innovating or just coping with tech?

For education settings, tools like the Jisc Digital Experience Insights Survey can provide great benchmarking data. In businesses, use pulse surveys or facilitated workshops to assess digital maturity.

Don’t overcomplicate this step. Focus on usability, value, and gaps—not just licenses and logins.

Step 3: Define Measurable, Achievable Goals

Here’s where most strategies go wrong: they talk big, but track little.

A goal like “improve digital engagement” is too vague to guide action.

Instead, use SMART goals:

Poor Goal	SMART Goal Example
“Improve digital systems”	“Reduce average onboarding time by 20% by July”
“Train staff on technology”	“Deliver 3 digital CPD sessions per term”
“Adopt a new VLE”	“Launch Moodle to 100% of learners by September”

Every goal should have an owner, a timeline, and a way to measure progress.

Step 4: Prioritise People Over Platforms

Fancy platforms don’t change lives—engaged people do.

This is where digital strategies must focus on:

• Training and CPD – Not one-offs, but ongoing learning that builds confidence.

• Support Structures – Create digital champions or peer mentors within departments.

• Culture Shift – Make it safe to try, test, and even fail. Digital fluency grows in low-stakes spaces.

A school I worked with launched a “15-minute tech Thursday” where staff shared one tool weekly. Over time, it transformed their approach to digital adoption. No external systems required—just time, trust, and tea.

Step 5: Align Your Tools to Your Goals

Once your purpose, people, and priorities are clear, then it’s time to look at tech.

Ask:

• Does this tool support our goals?

• Is it interoperable with our current systems?

• Will our staff actually use it?

Choose fewer tools, used well. Integration and adoption matter more than novelty.

Avoid shiny-tool syndrome. I’ve seen organisations chase “the next big thing” while underusing 80% of what they already pay for.

Step 6: Build the Strategy Into Your Rhythm

The best digital strategy is one that people can recall and use without opening a PDF.

Make it visible:

• A one-page dashboard or visual

• Monthly updates in team meetings

• A living Trello board or shared Notion page

Embed it into performance reviews, team targets, and annual CPD.

“If your strategy isn’t part of the Monday morning conversation, it won’t be part of the Friday outcome.” — Billy Smith

Also: review it. Quarterly check-ins allow you to celebrate wins and fix what’s not working—without waiting for the next academic year or fiscal cycle.

Common Pitfalls (And How to Avoid Them)

• Too Many Tools: Keep your tech stack lean and purposeful.

• Top-Down Delivery: Involve staff from the start—co-creation leads to commitment.

• Neglecting Training: Every tool needs a rollout plan and skill development.

• Chasing Trends: Align with long-term value, not short-term hype.

Conclusion: Your Next 3 Steps

1. Gather your digital audit – What’s the real picture right now?

2. Draft 3 clear goals – Use SMART thinking and align to your core mission.

3. Book 30 minutes – Share your draft with a trusted colleague and refine it together.

A great digital strategy doesn’t live in documents—it lives in actions, confidence, and conversations.

And when that happens? You’ll feel it in your culture, not just your systems.