Starting Your Digital Readiness Journey: A Practical Guide

I've written a lot over the past year about digital readiness — what it means, why it matters, where businesses get stuck. But I realize I haven't laid out a clear, practical guide for actually getting started. So that's what this is. No theory, no frameworks with fancy acronyms. Just the steps I've seen work for real businesses with real constraints.

If you're running a business with 50 to 200 people and you know things need to change but aren't sure where to begin, this is for you.

Step One: Talk to Your People First

This sounds obvious, but it gets skipped constantly. Leaders tend to jump straight into strategy sessions, vendor evaluations, or technology research. All of that has its place — later. First, talk to the people who do the work every day.

Not a survey. Not a town hall. Actual conversations, one-on-one or in small groups, with people across different teams and roles. Ask where they waste time. Ask what frustrates them about their tools. Ask what they wish worked differently. Ask what information they need but can't easily get.

You'll learn more in a week of those conversations than in a month of strategic planning. Your people know where the problems are — they live with them daily. They just haven't been asked.

When we do readiness assessments, this is always where we start. And the patterns that come out of these conversations almost always point to the real priorities — which are rarely what leadership assumed.

Step Two: Map What's Actually Happening

Once you've talked to your people, map your key processes as they actually work. Not how they're supposed to work, not how they're documented (if they even are), but how they truly operate day to day.

That means capturing the workarounds, the manual steps, the "oh, we also check this spreadsheet" moments, the information that lives in someone's head. It means documenting where data moves between systems, how it gets there, and where it gets stuck.

This is almost always eye-opening. I worked with a company that discovered their order fulfillment process had 23 manual handoff points — steps where information moved from one person or system to another through manual effort. They thought it was maybe eight or nine. That gap between the perceived process and the real one explained a lot about why things kept falling through the cracks.

You don't need fancy process mapping software for this. Whiteboard sessions with the right people work fine. The goal isn't a beautiful diagram — it's shared understanding of what's actually happening.

Step Three: Measure Where You Are

Before you can improve anything, you need a baseline. Doesn't have to be exhaustive, but you should know some basics about your current state.

How long do key processes actually take, end to end? Where are the bottlenecks? How much time does your team spend on manual data movement? What's the error rate on critical processes? How quickly can you pull the reports you need to run the business?

These measurements do two things. They help you prioritize — the biggest gaps are usually where to focus first. And they give you something to point to later. Six months from now, when someone asks "is this working?", you'll have numbers instead of gut feelings.

Step Four: Prioritize Ruthlessly

By now you'll have a list of problems that's probably longer than you'd like. The temptation is to tackle them all, or start with the most exciting one, or chase whatever a vendor pitched you last week.

Resist all of that. Prioritize on two dimensions: impact and feasibility. Which problems, if solved, would create the most value? And which of those can you realistically address given your current resources and your organization's capacity for change?

Where those two overlap is where you start. That usually means two or three things, not ten. It means saying no to good ideas so you can say yes to the best ones. It means accepting that the big, transformative changes come later — and that's fine.

I've watched businesses try to change everything at once. It almost never works. The ones that succeed pick their battles and build momentum through visible wins.

Step Five: Start Small and Show Results

Your first initiative should be something you can finish in weeks, not months. Something that makes a noticeable difference in people's daily work. Something that gives you a win to build on.

Maybe it's connecting two systems that currently require manual data transfer. Maybe it's automating a report someone spends hours compiling every week. Maybe it's putting a simple workflow tool on a process that currently runs on email and memory.

The specific project matters less than the approach: pick something contained, execute it well, measure the results, and make sure people feel the difference. That credibility fuels everything that comes after.

Step Six: Get an Outside Perspective

I'll be upfront — this one sounds self-serving coming from a consultant. But I genuinely believe it matters, so I'm saying it anyway.

When you're inside a business, it's hard to see the patterns. You're too close. Things an outsider would immediately flag as inefficient feel normal because they've always been that way. Internal politics make certain conversations difficult. And you can't easily benchmark yourself when you only see your own operation.

An external perspective — whether it's a consultant, an advisor, a peer group, whatever — can accelerate things significantly. The key is finding someone who'll be honest with you, who understands businesses like yours, and who isn't just trying to sell you something.

The Most Important Thing

If there's one takeaway here, it's this: don't wait for a perfect plan. The businesses that make the most progress on digital readiness are the ones that start with imperfect action rather than waiting for perfect strategy.

Talk to your people. Understand your current state. Pick one thing to improve. Do it well. Then pick the next thing.

Digital readiness isn't a project with a finish line. It's a way of operating — a commitment to continuously understanding how your business works and making it work better. The journey matters more than the destination, and the best time to start is now.

If you want help figuring out where to begin, reach out. We help businesses assess where they are, figure out where to focus, and build a practical path forward. No hundred-page strategy decks. Just honest assessment and practical next steps.