During my leadership years, I encountered a team dynamic that taught me something crucial about functional excellence. I worked with a team of all-stars.
Each person excelled in their role – the sales director consistently met targets, the product head delivered features on schedule, and the operations lead maintained efficient systems. Individually, they excelled.
But collectively, they were dysfunctional. Sales promised features that Product couldn’t deliver. Operations built processes that Sales couldn’t follow. Product prioritized technical debt while Sales needed customer-facing improvements.
“I hired the best people,” the leader told me. “Why can’t they figure this out?”
The problem wasn’t individual competence – it was that they’d never learned to optimize for shared outcomes instead of individual success. Each person was winning their game while the team was losing theirs.
Most leaders assume that hiring great people will automatically create great team performance. As they say, your team is as strong as its weakest link, but what if the weakness doesn’t stem from employee competence, but from the interconnectedness of working towards a unified goal? In my career, I’ve learned that functional excellence often creates functional silos that work against enterprise effectiveness.
The companies that break through this understand that cross-functional alignment requires explicit design, not wishful thinking.
To address the challenge of siloed work, we began by establishing shared metrics. Instead of sales hitting revenue targets and products hitting delivery dates independently, we created combined metrics that they had to achieve together. Sales and product share responsibility for customer satisfaction scores. Operations and sales jointly owned pipeline conversion metrics.
Then, we changed how they planned; instead of each function setting goals and hoping they’d align, they started with customer outcomes and worked backward to functional requirements.
The transformation took three months, but the results were dramatic. Same talented people, but now their individual excellence served collective impact instead of competing with it.
Try this week: Identify two departments that should collaborate but often work at cross-purposes. Create a shared metric that both teams influence, making them accountable for it.
Process: The Strategic Initiative Graveyard
Throughout my years scaling companies, I kept seeing the same pattern with strategic initiatives.
Fifteen strategic initiatives from the past two years. Three completed, five “in progress,” and seven that had quietly disappeared without formal cancellation or explanation.
“We’re great at starting things,” I remember thinking. “We’re terrible at finishing them.”
This is what I call the Initiative Graveyard – the place where good ideas go to die slowly, through neglect rather than decisive abandonment.
Most growing companies suffer from this. They have more opportunities than capacity, more ideas than execution ability. But instead of making hard choices about what not to do, they keep adding initiatives while previous ones fade away.
I’ve learned that companies don’t fail because they pick wrong initiatives – they fail because they pick too many initiatives, and execute none of them well.
The breakthrough framework: treat strategic initiatives like investment portfolios. You can only hold a limited number of positions, and adding a new one means explicitly closing an old one.
For my team, we implemented a “5 initiative limit”. At any time, they could have a maximum of five active strategic initiatives. Starting a sixth required formally stopping one of the existing five, with clear communication about why and what they’d learned.
The discipline this created was transformative. Instead of accumulating half-finished projects, they started completing things before moving to the next priority. The psychological momentum of completion energized the team in ways that perpetual “progress” never could.
Try this week: List all your active strategic initiatives. If you have more than five, pick the two with the least momentum and formally decide: kill them or resource them properly. Stop the slow death spiral.
Data: When Silos Undermine Strategy
Early in my career, I saw a team excited to “harness data for strategy”; this excitement was swiftly followed by data overwhelm when we realized every department’s data sat in its own system, out of sync, out of reach. Sales tracked deals in one platform, marketing in another, and customer service in yet another. Quarterly strategy meetings led to endless reconciliations, duplicated effort, and critical gaps that went unnoticed until it was too late.
The problem wasn’t data volume, but data fragmentation.
How?
Well, siloed data limits visibility; Leaders make decisions on partial, outdated, or conflicting information. Collaboration suffers because teams pursue separate (sometimes competing) goals, lacking a unified picture. Data integrity erodes, inconsistent formats or duplicated records lead to reporting errors and wasted resources. Missed opportunities consistently arise; you can’t spot trends, risks, or efficiencies when key signals are trapped in disconnected systems.
Over time, I’ve learned that data silos aren’t just a technical issue; they’re a cultural and strategic one. Even the best analytics or AI are useless if they don’t have access to all the relevant data, with business context intact.
What changed everything? We launched a single, shared dashboard: one source of truth across functions. This required hard conversations about standardizing definitions and regular cross-functional reviews, not just new software. But for the first time, strategy was informed by holistic, real-time insight. Teams spent less time reconciling and more time acting. Innovation picked up. Trust grew.
Try this week: Map a key strategic project. Where does the data live? If it’s spread across disconnected systems, schedule a cross-functional session to identify gaps and start the work to build a shared view.
Tonio’s Corner: One phrase to unearth strategic clarity.
Keeping with the theme of alignment. In my experience, I have found it imperative to assess whether my leadership teams actually understand and are aligned with our strategies and where we are headed.
In private, I ask each leader how we win complete this phrase: “We win in the market by being the company that…“
Then compare their answers.
This straightforward question helps identify and rectify misalignment. Varied responses from leaders indicate strategic confusion, as each operates on a personal interpretation of success rather than a shared understanding.
The companies that execute effectively can pass this test. Every leader completes that sentence in a similar way, regardless of departmental differences, because they’ve done the hard work of making strategic choices explicit and memorable.
Most strategy problems aren’t about picking the wrong direction – they’re about not being clear enough about the direction you’ve picked.
Try this week: Test your own leadership team with this exercise. If the answers vary significantly, schedule a session to align on how you actually compete to win.
The Compounding Effect
Businesses experiencing these issues constantly find themselves in a vicious cycle that kills strategic execution.
All-star individuals who can’t work together struggle to complete strategic initiatives because they’re optimizing for different outcomes. Incomplete initiatives force teams to make decisions with fragmented data from disconnected systems. Data silos prevent teams from seeing the full picture, making strategic confusion inevitable. And strategic confusion prevents teams from knowing which shared outcomes to optimize for.
But when you fix one, the others become dramatically easier.
Teams aligned around shared outcomes naturally complete more initiatives, because they’re pulling in the same direction. Completed initiatives create the momentum needed to invest in unified data systems. Shared data visibility enables strategic clarity because everyone is working from the same information. And strategic clarity helps everyone understand which shared outcomes to optimize for.
What’s one insight from this week that you’ll try in the next seven days?
“A system is never the sum of its parts; it’s the product of their interactions.”
– Russell Ackoff
