The Enterprise Execution Crisis: What 200+ Senior Leaders Actually Told Me
Over the past 15 months, I’ve had coffee, lunch, and countless video calls with more than 200 senior leaders—CTOs, COOs, CROs, and CHROs—at some of the world’s largest companies.
Different industries. Different challenges. Different org structures.
But in nearly every conversation, the same painful reality keeps surfacing:
The strategy is crystal clear. The execution is fundamentally broken.
“We’ve spent a fortune on transformation… and nothing’s changed.”
That quote? From a visibly frustrated CTO at a global financial services firm.
But honestly, I’ve heard some version of it in almost every conversation. Companies are pouring hundreds of millions into digital transformation. New platforms. New tools. New org charts.
And yet… the day-to-day friction—the slowdowns, the misfires, the missed targets—hasn’t gone away. In many cases, leaders tell me it’s getting worse.
Why?
Because execution isn’t just a tech problem. It’s fundamentally human.
Four Execution Roadblocks I Keep Hearing About
When you talk to enough leaders, patterns emerge. These four issues come up over and over. If you’re nodding along as you read, trust me—you’re in good company.
1. The Data Flows, But the Story Gets Lost
A VP of Sales at a tech company put it this way:
“Marketing hands us leads, but we get zero context. No clue what content they’ve seen, what they actually care about, or what problem they’re trying to solve. So every call starts from scratch.”
Most companies have technically connected their systems, but what’s missing is context—the stuff that actually makes data meaningful. Without that, your teams are just passing empty boxes down the line.
2. Everyone’s Responsible = No One’s Accountable
One CRO nailed the dysfunction:
“When a deal stalls, Marketing blames Sales. Sales blames Product. Product says they weren’t given proper requirements. And meanwhile, the customer walks.”
When workflows cross teams, accountability often disappears into the cracks. With no clear owner, execution suffers—whether it’s a sales cycle, product rollout, or internal initiative.
3. Decisions Are Made in the Dark
A Chief Product Officer shared this painful example:
“We delayed a launch by six months because Engineering was building to the wrong specs. The Sales team had updated customer feedback, but it never made it to the dev team.”
The information exists somewhere in the organization. But it’s trapped in silos. So teams make critical decisions based on partial information—and that leads to costly mistakes.
4. Change Doesn’t Stick
This might be the most frustrating issue of all.
“We rolled out this elaborate new process. Full executive support. Everyone said all the right things in the meetings. Two months later? Back to business as usual.”
Behavior change is hard. New dashboards and workflows won’t matter if no one actually uses them consistently.
The Real Problem: We’ve Overlooked the Human Element
This quote from a CHRO really stuck with me:
“We treated execution like a technology problem for years. But at its core, it’s a people problem. You can’t drive sustainable change just by handing someone a new dashboard.”
Exactly. The companies that are finally making progress are the ones investing in engagement, ownership, and visibility—not just new software.
Some are even borrowing principles from game design to make execution feel less like a chore and more like a challenge people actually want to participate in.
A retail CEO told me:
“We made the process transparent and genuinely rewarding. People wanted to participate because they could see their impact—and how they stacked up against their peers.”
So What Now?
We’re at a turning point.
The winners won’t be the ones with the most sophisticated tools. They’ll be the ones who create work environments where:
- Everyone can see how their work connects to real outcomes
- Cross-functional handoffs are clear, visible, and accountable
- People are motivated to show up, contribute, and follow through
So here’s the question I’ll leave you with:
What would fundamentally change in your organization if everyone had clear ownership, full visibility, and was genuinely engaged in making results happen?
I’d love to hear your take. What’s broken—or working—on the execution front in your world?
