A Leader’s Guide to Digital Transformation Failure (And Strategies for Success)

Note: This article is sponsored by the 365 Leadership Summit from C5 Insight.

Most digital transformation journeys begin with high hopes and ambitious goals.

But the data tells the real story: According to McKinsey, BCG, and KPMG, between 70% and 95% of digital transformation initiatives fail to deliver expected results.

Even as Microsoft continues to launch groundbreaking technologies like Microsoft 365 Copilot and advanced AI Agents, many organizations watch promising investments turn into costly missteps.

• Projects routinely run over budget and miss deadlines
• Employees resist new tools, clinging to familiar ones
• New software becomes shelfware—licensed, but rarely used
• Overlapping apps confuse users, fragment data, and waste resources
• ROI is unclear—or nonexistent

Sound familiar? Believe it or not, the technology is rarely to blame. 

Let’s look at how companies fail fast when investing in digital transformation solutions.

5 Ways to Fail Fast at Digital Transformation

AI and modern workplace solutions like Copilot Studio and Microsoft 365 have the potential to revolutionize how your business operates, driving efficiency, innovation, and growth at scale.

Despite this potential, many organizations rush into implementation with the mindset of “if you build it, they will come.” The reality? They won’t.

There’s a misconception that technology alone guarantees success, which overlooks the intricate web of human behavior, organizational culture, and strategic planning that underpins any successful transformation. 

Here are five tried and true ways companies set themselves up for digital transformation failure:

1. Chase shiny new objects: Investing in the latest tools and technologies without assessing their alignment with business goals.

2. Implement solutions reactively: Deploying tools rapidly to address immediate needs without a strategic long-term vision and phased rollout.

3. Disengaged leadership: Mandating changes without owning the change themselves—or considering its realistic impact on the workforce.

4. Skip change management: Expecting employees to just “figure it out” without investing in training, upskilling, or ongoing support.

5. View transformation as a one-time project: Treating the go-live date as the finish line instead of the starting point to ensure long-term success. 

Maybe you’ve read impressive case studies on digital transformation powered by Microsoft solutions, but those are summaries of success that don’t often highlight the strategic preparation, roadblocks, and missteps along the way. 

Experts in Failure, Partners in Success

Without deliberate effort to foster business and technology alignment, employee adoption, and skill agility, even the most promising Microsoft solutions fall short. 

At C5 Insight, we’ve spent more than 20 years rescuing failing digital transformation projects, helping organizations recover from past failures, and charting a course toward sustained success.

And we’re bringing that experience to the 365 Leadership Summit.

365 Leadership Summit: The Premier Microsoft AI and Digital Transformation Event for Business Leaders & Change Influencers

The 365 Leadership Summit isn’t about technology, it’s about transformation. Unlike most Microsoft conferences, it’s a non-technical summit centered on leading and influencing successful digital transformation in the AI age.

Here’s how it compares to other Microsoft-focused events.

Microsoft Community Conferences: Where Technology Leads and Strategy Get Left Behind

The primary focus of Microsoft community conferences is often on technology and training, which serve an important purpose, but leave leaders out of the conversation. Business strategy gets put on the back burner while technology takes center stage.

Key highlights of these Microsoft community events include:

• Product roadmaps and visionary demos
• Hands-on training and certifications
• Large-scale networking opportunities 
• Expo floors and partner booths

But knowing about the newest technology, or even training teams to use the latest features, won’t automatically drive business results. “Shiny object syndrome” can quickly lead businesses astray at these conferences, resulting in more shelfware. 

365 Leadership Summit: Where Strategy Leads and Digital Transformation Success Follows

C5 Insight created the 365 Leadership Summit to bridge the gap between Microsoft technology and business strategy. The summit is specifically designed for organizational leaders and change influencers, not power users.

• Strategic Content: Sessions address business-level topics and share key strategies for increasing employee adoption, embracing AI, and leading change.
• Results-Driven: Every session connects relatable business challenges with Microsoft solutions that drive ROI—no technical deep dives.
• Real-World Success: Hear from other business leaders and influencers who share their experience navigating Microsoft-powered digital transformations.
• Limited Attendance: With only 100 seats available, attendees will have high-touch experiences alongside peers, Microsoft, Dynamic Communities, and others.

In less than two days, leaders and influencers will create a vision for the future of work in their organization, develop an agile mindset that sees innovation as opportunity, and use proven strategies to lead digital transformations that drive business results.

Event Details

Join C5 Insight, Microsoft, Dynamic Communities, and other leaders and influencers like you at the 365 Leadership Summit.

• When: September 18–19, 2025
• Where: The Ritz-Carlton, Denver, CO
• Cost: $995 with discount code MSDW

[ Register Now ]