90% of Your Digital Transformation Initiatives Are Going to Fail (Here's Why)
90% of Your Digital Transformation Initiatives Are Going to Fail (Here's Why)
Let me guess: Your company is in the middle of some big transformation.
Digital transformation. Cloud migration. AI implementation. Reorganization. Whatever buzzword you're using this quarter to describe "we need to change or we'll die."
And deep down, you know it's not going well.
I sat down with Rob Crabtree—CEO of Meta Ops Inc., author of five books on process improvement, and someone who's personally mentored thousands of people generating hundreds of millions in results—and he confirmed what you already suspect:
90% or more of digital transformation initiatives fail to deliver the results they should.
Not "struggle." Not "face challenges." Fail.
And before you tell me "our company is different" or "we're doing it right"—you're probably not. The math doesn't lie.
Rob shared a formula that will either wake you up or confirm you're screwed. Ready?
Discomfort × Vision × Skills = Your Likelihood of Success
Let's do the math on your transformation initiative right now.
The Burning Platform Nobody Actually Feels
First question: What's the level of discomfort in your organization with the current state?
0% discomfort = Everyone loves how we do things today. Change is scary. Nobody wants it.
100% discomfort = Everyone's freaking out. It's an existential threat. Jobs are at stake. People are demanding change.
Be honest. Where does your organization actually sit?
Most of you will say something like 50%. Half the company gets that change is needed. The other half is fine with the status quo.
50% discomfort. That's your first number.
But here's what's really happening:
Your C-suite feels 100% discomfort. They see the competitive threats, the market shifts, the burning platform.
Your middle management? Maybe 60% discomfort. They see some problems but they're managing.
Your frontline employees? 20% discomfort. They're doing their jobs fine. Change just means more work and disruption for them.
So your actual organizational average? Probably closer to 30%.
And you're already screwed. But let's keep going.
The Vision Nobody Understands
Second question: Does everyone who needs to do something different actually understand the vision?
Can they articulate their part in it? Do they understand HOW you're going to get there? Not just what the end state looks like, but what behaviors need to change?
Be brutally honest.
Half your organization understands the vision. The other half is nodding in meetings while internally thinking "What the hell are we even doing?"
50% vision clarity. That's your second number.
But again, here's reality:
Your executives crafted the vision. They get it.
Your mid-level managers sat through the presentations. They kind of get it.
Your employees got a company-wide email and a slide deck. They have no farcking clue what this means for their day-to-day work.
Real number? Probably 30% actually understand and can articulate the vision.
Keep that calculator handy. We're not done.
The Skills You Don't Have
Third question: What's the level of skills within the organization to actually execute on this?
If it's digital transformation—something new that requires people to learn and do things completely differently—this number is LOW.
Let's be generous and say 50%. Half your people have the skills. The other half will need significant training.
50% skills. That's your third number.
Now let's do the math:
50% × 50% × 50% = 12.5%
Your likelihood of success? 12.5%.
And that's if you were being optimistic about all three factors.
If you were actually honest?
30% × 30% × 30% = 2.7%
Congratulations. You have a 2.7% chance of success.
Welcome to why 90% of transformations fail.
The Union-Management War That Actually Got Fixed
Here's where Rob's story gets really good.
He worked with a healthcare benefits organization. Unionized. Six different unions. 600 employees. Long history of union-management conflict.
And they were facing an existential threat.
Private competitors were eating their lunch. If they didn't transform, they'd be out of business in a few years.
This is the part where most companies would:
Leadership crafts a transformation plan
Announces it to the organization
Expects everyone to fall in line
Wonders why there's resistance and failure
Rob did something different.
He sat down with the CEO, CFO, and Chief HR Officer and said: "Let's form a guiding coalition made up of union stewards and management."
They looked at him like he was insane.
"The union will never agree to that."
So Rob went and asked the union.
He gathered 60 union stewards and said: "You guys understand we have an existential threat here, right?"
They did.
"The invitation is to form a guiding coalition—union AND management—to define the future of this organization together."
They agreed.
Six management leaders. Six union stewards. One HR officer as a non-voting tiebreaker (which they never needed).
And they created something beautiful.
The Vision Statement That Actually Mattered
Most vision statements are corporate word salad:
"We strive to leverage synergistic solutions to maximize stakeholder value through innovative paradigms."
Nobody knows what that means. Nobody cares.
This union-management coalition created this:
"A unified team committed to providing exceptional service for our participants, employers, and maintaining a family-oriented organization. Every day, each of us must recognize the responsibility we have to provide benefits and strive to positively impact the quality of life of our participants and their families with dedication and integrity."
Read that again.
It's simple. Clear. Human. Something people can actually rally around.
Then they defined 12 specific behaviors. Things like:
Pay benefits timely, accurately, and do it right the first time
Answer all correspondence accurately, quickly, in an understandable manner
Treat all callers—even angry ones—as an opportunity to make a positive impression
Empower all employees to make changes that improve our services
This is what stakeholder engagement looks like when you actually mean it.
Not a poster in the break room. Not corporate buzzwords.
A coalition of union and management—historically adversaries—coming together to define shared goals because the alternative is everyone loses their jobs.
The Goals That Actually Drove Change
They didn't try to measure everything. They picked three KPIs:
Increase membership by 10,000 new members in the next year
Improve measured quality by 50% in the next year (customer satisfaction surveys, toll-free calls, escalations)
Improve measured customer satisfaction by 50%
Notice something?
These aren't internal process metrics. They're not "implement this technology by Q3."
They're outcomes that matter to customers and the business.
This is relationship-driven revenue growth in action. Not transformation for transformation's sake. Transformation that actually serves the people you're trying to help.
The HR Forms Turnstile That Cost 1,000 Hours
Here's my favorite part of Rob's story.
They did a "waste walk"—basically just observing processes to see where time and energy are being wasted.
They walked into the HR department. There's this turnstile with all the forms employees need. Dental forms, vacation requests, application forms, whatever.
The leadership team is standing there observing. They quickly agreed:
600 employees use this
3-4 times per year
Spending at least 15 minutes each time trying to find what they need
Then a woman named Lady—who manages the front desk—hopped out of her chair and interrupted them.
"No, no, no. Half the time they have to come over and interrupt ME, and I have to stop what I'm doing to help them find it."
Suddenly the math changed:
1,000 person-hours per year being burned just on HR forms.
Because nobody thought to ask the person who actually dealt with this process every day.
This led to complete digitization. Everything online, on-demand. Eventually, no turnstile at all.
But it started with listening to the employee who knew the problem better than leadership ever could.
What You're Getting Wrong About Transformation
Most transformation failures happen because you're missing one or more of these:
1. You don't have actual discomfort
Your executives feel urgency. Your employees don't. You can't manufacture a burning platform with PowerPoint presentations.
Solution: If the burning platform is real, make it visible to everyone. If it's not real, don't do the transformation.
2. Your vision is corporate gibberish
"Digital transformation" isn't a vision. "Cloud migration" isn't a vision.
"We're going to answer customer questions accurately and quickly in an understandable manner" is a vision.
Solution: Define what behaviors actually change. What does success look like in plain English?
3. You don't have the skills
You're asking people to do things they don't know how to do, without training, support, or time to learn.
Solution: Either build the skills first, or admit you need different people.
The Guiding Coalition You're Not Building
Rob's biggest insight: You can't transformation from the top down alone.
You need a guiding coalition. People from different levels, different departments, different perspectives.
Union and management. Sales and operations. Tech and business. Whoever's actually going to do the work.
Get them in a room. Give them real authority. Let them define what success looks like together.
Most of you won't do this because:
You're scared of losing control
You don't trust your people
You think leadership knows best
You're worried about slowing things down
And that's exactly why you're going to fail.
The companies that succeed at transformation are the ones that build broad coalitions, create shared vision, and empower people to make changes.
Not the ones that announce changes from on high and expect compliance.
The Math Doesn't Lie
Go back to Rob's formula:
Discomfort × Vision × Skills = Likelihood of Success
If any of those three factors is low, your chances plummet.
50% × 50% × 50% = 12.5%
30% × 30% × 30% = 2.7%
But here's the good news: You know what to work on.
If discomfort is low, you need to make the burning platform more visible (or question if you should do this at all).
If vision is unclear, you need to bring people together to define it in plain language.
If skills are lacking, you need training, hiring, or both.
You can fix this. But only if you're honest about the gaps.
The Human Connection Nobody's Prioritizing
Every transformation Rob described succeeded because of one thing:
They brought people together to solve problems collaboratively.
Not mandates from leadership. Not consultants telling them what to do. Not copying what worked at some other company.
Humans, working together, defining their future.
This is what building business relationships in your own organization looks like.
This is what authentic client connections start with—authentic internal connections.
This is how you create sustainable business expansion—by building it on a foundation of shared vision and real buy-in.
But most of you are too busy rolling out the next initiative to actually connect with the people who have to execute it.
Watch the Damn Episode
This conversation with Rob went even deeper into transformation frameworks, process improvement, and why listening to the people doing the work is more valuable than any consulting report.
If you're leading any kind of organizational change, struggling with transformation initiatives, or just want to understand why your last three "strategic priorities" went nowhere—this episode is essential.
Watch the full episode here because Rob's frameworks for company culture transformation and trusted advisor relationships (yes, even internally with your own people) are the difference between the 10% that succeed and the 90% that fail.
P.S. That formula—Discomfort × Vision × Skills—applies to literally every change you're trying to make.
New CRM implementation? Run the math.
Moving to remote work? Run the math.
Adopting AI tools? Run the math.
If you're not willing to honestly assess all three factors, you're setting yourself up to be in the 90% that fail.
And you'll blame "resistance to change" or "execution challenges" when the real problem is you never had the foundation for success in the first place.
P.P.S. That moment when the HR lady hopped out of her chair to correct the leadership team?
That's what happens when you actually include the people doing the work in the process.
She knew the problem better than anyone in leadership. She had ideas about how to fix it. But nobody had ever asked her.
How many solutions to your transformation challenges are sitting in your employees' heads right now, waiting for someone to actually ask them?
Go watch the episode. Learn from Rob. And for god's sake, stop announcing transformations and start building coalitions. The math doesn't lie—you need all three factors working together, and you can't do that from the C-suite alone.
Karl Pontau hosts The Human Connection Podcast, where we talk about the stuff that actually matters in business: the humans running it. Because whether you're B2B or B2C, it's really H2H—human to human. Subscribe so you don't miss the next episode where we probably say something that'll make your HR department uncomfortable.
