Your Strategy Isn't Failing. Your Discipline Is.
There is often a discipline crisis hiding inside what gets labeled a strategy problem.
Ask any CEO to describe their company's strategy, and you'll get a confident, well-constructed answer. Then ask their executive team, separately and without the boss in the room, to describe the same strategy. What you get is rarely the same answer twice. Call it the strategy confusion index: the gap between what leadership believes the organization understands and what it actually understands. That gap is almost always wider than anyone wants to admit. And closing it isn't primarily an analytical challenge. It's a discipline challenge.
The greatest leadership challenge today is not misreading the future – it is avoiding the often discomforting implications of clarity. Clear strategy demands trade-offs. Accountability demands consequences. Both require conviction. In a world of AI disruption and macro turbulence, what ultimately differentiates organizations is not the forces they face, but whether their leaders are willing to make hard choices, stand behind them, and insist that commitments translate into results.
Strategy Is Subtraction, Not Addition
A great strategy is defined as much by what you won't do as by what you will. Every approved initiative draws attention from focus, execution velocity, and organizational resources. The problem is that approving things is easy and feels productive. Killing things, especially the pet projects of politically powerful people, is hard and feels like conflict. When that calculus takes over, the pile keeps growing. The result is an organization where everything is a priority, meaning nothing is. Resources thin out. Accountability blurs. High performers, who understand better than anyone when the strategy is incoherent, quietly update their LinkedIn profiles.
When a leadership team can’t kill a mediocre project, it’s not an analytical failure. It’s typically a political one. No one wants to tell the SVP who championed the initiative that it’s no longer in the plan. That’s conflict avoidance dressed up as pragmatism, and it carries a real cost to organizational focus and execution momentum.
The Accountability Illusion
It's worth asking whether your company has accountability theater, lots of progress-tracking controls, and status reports rather than accountability consequences. When a critical initiative falls behind, the temptation is to quietly adjust the timeline, diffuse ownership, or deprioritize the goal without saying so out loud. The harder questions go unasked: Did we resource this adequately? Was the goal realistic to begin with? And most importantly, what does it say about our execution culture that we keep ending up here?
Real accountability requires leaders to be honest in public, when it’s not easy to do so. It means addressing a team member in a public setting and stating clearly: "This isn't acceptable, and here's what needs to change if we are to make expected progress." Leaders who are genuinely direct in one-on-one settings but soften into vagueness when others are present aren't practicing accountability. They're practicing the appearance of it.
When accountability lives only in private conversations, it tends to stay there, and the execution gaps widen quietly until they can no longer be ignored.
When the Leader Becomes the Execution Risk
One of the more underappreciated risks in strategy execution is the leader themselves. Not because of bad intentions, but because the feedback loops that once kept behavior calibrated tend to weaken at the top. What gets said in the room and what gets thought outside of it are often very different things, and over time, that gap shows up directly in execution.
Consider a few patterns that surface repeatedly. The leader who believes she has built a culture of candor, but whose team has quietly learned not to surface problems until they become crises – a dynamic that systematically delays the course corrections a strategy requires. The founder, whose conviction drives the business forward, but whose constant strategic pivots exhaust the organization’s capacity to execute anything to completion. The executive who is genuinely strong at strategic thinking but disengaged from follow-through creates an invisible gap between what gets decided and what actually gets done.
None of these is a permanent condition. They’re patterns, and patterns can be identified and changed. But not without honest feedback, and not without the willingness to connect one’s own behavior to the execution results the organization is or isn’t producing.
The leaders who invest in coaching aren’t the ones who are struggling; they’re the ones who understand that execution is a leadership variable, not just an organizational one. Even modest improvements in self-awareness, consistency, and follow-through compound meaningfully over time. The greatest athletes maintain coaches not because they lack ability, but because sustained high performance requires an external perspective that self-assessment alone cannot provide.
The Uncomfortable Conclusion
Every generation of leaders has faced conditions that felt uniquely difficult. What separates those who build enduring organizations from those who merely survive their tenure isn't smarter strategy or better market timing. It's the willingness to make hard choices, speak candidly about what's working and what isn't, and hold themselves and those around them to a standard that doesn't quietly lower itself under pressure.
At its core, this is a test of leadership character, discipline, and courage – a matter worth sitting with.
Angelo Santinelli is the founder of Entrepreneurial Edge Executive Coaching and Advising and a strategic advisor to PE-backed and founder-led companies. He works with CEOs and executive teams on strategic execution, leadership development, and organizational performance.
