Why so many projects miss the mark, and what transformation leaders can do differently. 

The Real Gap in Transformation

If you've led a digital transformation project in the past five years, you might have picked up on a familiar pattern: 

Strategy is set. Vendors are chosen. Implementation begins according to plan. And then, somewhere between kickoff and go-live, the outcomes get fuzzy.

Was the goal to upgrade infrastructure or to improve decision-making speed? Was the new system supposed to reduce churn, increase forecast accuracy, or just "modernize" the tech stack? Has anyone written down what “modernize” is supposed to mean here?

Too often, "on-time, on-budget" is treated as the only true metric of success. But CIOs and executive teams know better: you don't get business value from a completed implementation. You get it from what happens next.

The Quiet Failure of "On-Time, On-Budget"

When we do post-mortems with CIOs, we often see this same pattern emerge. The system launched. The vendor delivered. On-time, on-budget. Yet the business impact is unclear. 

Sales teams don't use the new forecasting tool. Data quality is still an issue. Teams have returned to their silos. The reports aren't driving better decisions.

Why? I think it’s because many implementation plans are so focused on delivering tools (the new software, the reorganized team, the fancy AI tool) that they’re not grounding everyone in outcomes. They stop at go-live instead of designing for the REAL messy middle: the period where adoption either takes hold or fizzles out.

What Success Actually Looks Like

When we’re talking about digital transformations, success needs to be about hitting a business milestone, not just a project plan milestone. That means defining what "done" looks like before the kickoff—and “done” has to go beyond features and functionality.

Instead of getting stuck here: 

• "System is live" 

• "Training is complete"

• "Users have access."

We need to include business impact in our success metrics:

• "Sales managers can identify pipeline risk two weeks earlier."

• "Customer onboarding time drops by 30%."

• "Support tickets are resolved 25% faster."

These are measurable, actionable outcomes. When you define (and benchmark) them up front, everything downstream has a clear purpose.

What Adoption Really Looks Like

All that to say, adoption cannot be a one-time launch event. It needs to be a sustained behavioral shift across teams. In midsize companies, where bandwidth is tight and people wear multiple hats, adoption has to be designed into the workflow, not bolted on after go-live. In larger enterprises, we often see a false sense of completion once system access is granted, with no visibility into whether frontline teams are actually using the tools to drive the business outcomes they were promised.

If you want to know whether you’ve really driven a successful transformation, look for these signs:

• People stop relying on piecemeal spreadsheets and actually use the system

• Managers reference system data in meetings and decisions (without being prompted)

• The helpdesk isn't flooded with workaround requests

To get there, you need to build adoption into every phase: user context in discovery, relevance in training, and feedback loops after launch.

Four Change Management Myths That Keep CIOs Stuck

There are a lot of places that people get stuck in projects like this–even leaders with a lot of experience. Here are some I hear a lot:

1. "We just need a comms plan."
   Announcements aren't adoption. People need context, not just messaging.
   
   

2. "Our leaders will model the change."
   Most leaders are spread thin. If it's not built into their workflow, it won't scale.
   
   

3. "If we build it, they'll use it."
   New tech adds friction at first. People won't switch unless there's visible value.
   
   

4. "Change is the people team's job."
   Tech adoption is cross-functional. If business, IT, and ops aren't aligned, it all stalls.

The answer to all of these is to get our hands a bit dirty and work together to drive real transformation. That starts with knowing what the end goal looks like.

Aligning Execution with Outcomes

One of our favorite parts of being SaaS Business Advisors is helping clients think beyond the implementation checklist. I advise clients to build metrics into discovery, to align outcomes with use cases, and to stay engaged post-launch to make sure adoption is tracking toward business goals.

This isn't about doing more work. It's about doing the right work in the right order, so that transformation actually transforms something.

Ready to Close the Gap?

If you're in the thick of a project and wondering whether it'll deliver what it promised, I’m happy to talk. We can offer some tools from our toolkit that will keep your project on track.

Don't just go live. Get results.