6 Ways to Make Strategy Resonate with Skeptical Leaders
•February 20, 2026
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Why It Matters
Clarifying strategy accelerates consistent decision‑making across the organization, reducing escalation and improving agility during uncertainty. This shift turns a perceived overhead into a competitive advantage for fast‑moving firms.
Key Takeaways
- •Strategy deficit hampers decision clarity beyond senior team
- •Define strategy as limited, recurring choices
- •Live decisions reveal real trade‑offs quickly
- •New‑leader briefs expose alignment gaps
- •AI can synthesize hidden strategic artifacts
Pulse Analysis
In many high‑growth tech firms, CEOs proudly claim they operate without a formal strategy, viewing it as a slow, political exercise that distracts from execution. This mindset, reinforced by overconfidence, often leads to hidden decision‑making silos and blind spots as the organization scales. By reframing strategy as a minimal set of recurring choices—such as which customers to prioritize or how to balance margin versus growth—leaders can embed strategic thinking into the daily workflow, turning a perceived burden into a practical tool for faster, more consistent decisions.
The article’s six‑step framework provides a hands‑on roadmap for skeptical leaders. It starts with grounding strategy in the decisions that surface repeatedly, then uses a live, high‑stakes choice to surface trade‑offs and align the team. Simple diagnostics like a one‑page new‑leader brief or a rapid trade‑off matrix surface misalignments that often remain invisible in informal discussions. Leveraging AI to aggregate board decks, product roadmaps, and customer feedback further surfaces the organization’s implicit strategic logic, allowing executives to refine a shared narrative without reinventing existing work.
Finally, shock‑testing the distilled strategy ensures it holds up under pressure. By simulating plausible crises—cyber incidents, regulatory changes, or competitor moves—teams identify critical decisions, ownership, and non‑negotiable constraints. This exercise not only validates the decision rules but also builds a culture where strategic clarity becomes a defensive asset. Companies that embed these practices can convert strategy from a ceremonial artifact into a real‑time advantage, enabling faster response, reduced escalation, and sustained competitive edge.
6 Ways to Make Strategy Resonate with Skeptical Leaders
“We don’t have a strategy,” boasted a tech company CEO in our first conversation. He was justifiably proud of what he and his team had built. “We’ve done well without one, and we’re doing fine now. Strategy feels like a good way to take our eye off the ball.” To him, strategy was a slow, political exercise that invited too much debate, increased bureaucracy, and distracted the organization from what made it successful.
He’s not alone in this view. As a strategic advisor to CEOs and C‑suite executives for 30 years in 30 countries, I hear it from founders who have scaled their businesses through entrepreneurial spirit and instinct, from business‑unit leaders who deliver their numbers, and from functional heads who keep things moving through relationships and know‑how. This skepticism also shows up during uncertain periods, when attention focuses on immediate delivery and anything labelled “strategy” comes across as a detour from making progress.
Research on executive confidence helps explain why this “we’re fine” story persists for so long. CEO overconfidence is often associated with bold moves and strong performance. But it can also lead to misjudgments and make it harder to change course, as leaders remain committed to familiar trajectories even as the context changes.
Whether the driver is growth or uncertainty, the leadership challenge is the same: More good decisions need to be made, faster, and by people well beyond the senior team. Senior leaders’ judgment still matters—it just needs to be clear enough for others to learn from and apply so that the organization can act consistently without escalating everything to the top.
If you’re a chief of staff, head of strategy, or functional or business‑unit leader looking to convince a reluctant CEO or other C‑suite leader of the merits of adopting a strategic approach, you need to position it as an advantage, not a distraction.
In many successful organizations, strategy is often diluted into a vague sense of direction, replaced by instinct and a shared history in the leadership team. The organization still makes strategic choices, but they’re concentrated among a small circle, and those on the outside learn about them through inference or guesswork rather than clear communication.
Three myths that keep this pattern in place
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Strategy as a ceremony – Many senior teams have watched strategy turn into an off‑site, a deck, a long list of initiatives, and a warm sense of alignment that fades as soon as hard decisions come up. Leaders who care about delivery think of strategy as time away from delivering results.
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Strategy vs. planning – Strategy supports delivery when it addresses recurring questions that slow work down, such as which customers come first, what quality means, how margin is traded against growth, which risks are worth taking, and which opportunities are declined even when they look attractive. A useful distinction helps here: Planning allocates actions within your control; strategy is a set of choices about how you will win.
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Blind spots from familiarity – Leadership groups can move quickly because they’ve learned each other’s instincts, developed a shorthand, and trust each other. They can anticipate where the CEO, founder, or business leader will land on a trade‑off. But that familiarity also creates blind spots as the organization grows. New leaders, partners, and teams don’t share the same history and context, so what feels obvious at the top can feel ambiguous elsewhere. People start guessing what matters, then make different calls while still believing they’re “aligned.”
Strong leaders often improvise well in a crisis, and many organizations have stories that prove it. The challenge is that responding to shocks requires different leaders to make immediate decisions in different places, sometimes before the senior team can convene. If they don’t have a common frame to work within—expressed through a strategy (what to stop, pause, protect, and communicate in the case of a crisis)—they make conflicting calls, which can cause confusion, delay, and avoidable escalation.
That’s the practical heart of what I call a “strategy deficit”: the gap between the strategy an organization is living and the strategy it can explain and apply consistently beyond the senior group. When business is going smoothly in a steady state, this gap lurks under the surface. It comes to the fore when the organization has to make strategic decisions in response to developments—e.g., a shift in customer sentiment, a competitor’s moves, the arrival of a new set of leaders, or a period of uncertainty—faster than the senior team can coordinate informally.
Those are also the moments when attempts to “sell strategy” can misfire. Leaders who feel they’re performing well tend to resist anything that sounds like an imported process or corporate theatre. Persuasion by envy—“look at what admired companies do”—can heighten that resistance because it frames strategy as imitation rather than as a source of advantage.
It’s more persuasive to frame strategy as a source of decision clarity for the situations the organization is already facing. Strategy becomes useful to doubters when it keeps focus intact and makes decisions easier to repeat across the organization. Six actions can help you position strategy in a way that resonates with skeptical leaders:
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Define strategy as a small set of choices – When I asked the CEO what he meant by “we don’t have a strategy,” he didn’t mean the organization lacked direction or focus. He meant the top team didn’t need more process. We used a definition that stayed close to his reality: strategy as a small set of choices and trade‑offs the leadership team can rely on so that the same debates don’t resurface in different disguises.
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Ground the definition in recurring decisions – Research supports this idea of strategy as an ongoing leadership capability rather than a calendar event: a way organizations sense change, align attention, and adjust choices over time. A quick way to make this definition concrete is to ask: Which decisions do we keep coming back to when the logic isn’t fully stated? For example, resource allocation, pricing exceptions, which customer to serve first when capacity is tight, and which risks get accepted by default. Those recurring decisions are the raw material for strategy.
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Use a live decision to surface trade‑offs – Together with the CEO’s team, we chose a decision already shaping behavior across functions: how to respond to a competitor’s move into an adjacent segment the CEO had always treated as “not our territory.” Around the table, the instinct was to copy the move, matching the competitor’s offer and message, hoping that customers would stick with them. It felt decisive, and it also raised a more demanding question: What would that response pull the organization away from doing?
We asked a small set of questions the team could answer without jargon:
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What decision do we have to make in the next 30 days? Position it as a choice between two options.
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What would we be saying no to if we choose Option A? And if we choose Option B?
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What must be true for this choice to be the right one?
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What precedent are we setting?
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What downstream decisions might this lead to?
Those questions surfaced the real choice: what the organization would defend and what it would stop chasing.
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Run a “new leader brief” test – A simple test brings the strategy deficit into view. We asked each senior leader to write a one‑page “new leader brief” that answered five questions:
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What are we trying to win at, and how will we recognize a win?
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Who are we built for—what “job” are we helping them do—and whom do we deprioritize to stay focused?
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When we say words like “premium/speed/reliability,” what do we mean?
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What are the three priorities that matter most right now, and what trade‑offs do they create?
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What three decision rules should leaders apply without escalating? (Write each as “When we X, we Y.”)
Comparing the briefs revealed whether the organization’s logic was shared or fragmented. In our case, leaders described different versions of the core challenge and the “win,” resulting in more priorities than were helpful. They also relied on familiar labels—“premium,” “speed,” “reliability”—as if those words had shared definitions. They didn’t. Each meant something different in practice, which sent mixed signals downstream, triggered more escalation, and made execution harder than it needed to be.
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Identify recurring trade‑offs – A short exercise can be done in 30 minutes. Ask each senior leader to answer privately, then compare their responses:
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What are the three trade‑offs we keep revisiting? (Write each as A vs. B—e.g., margin vs. growth.)
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For each trade‑off, what’s our default? (When it’s a close call, we choose X.)
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What’s the exception, and who can make the decision?
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What will we stop doing as a result? (Name one activity, offer, feature, client type, or promise.)
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How will we know we’re drifting? (One early‑warning metric or signal for each trade‑off.)
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What assumption makes this trade‑off sensible, and what’s the trigger to revisit it? (If X changes, we will Y.)
The value lies in the comparison, because it surfaces when leaders make different calls while believing they’re aligned. It also creates space for a useful kind of discovery; strategy work often reveals risks that success has kept hidden.
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Leverage AI to synthesize existing artifacts – By this point, most leadership teams already have the raw material for a strategy. Much of it sits in documents they don’t label as “strategy” at all: board presentations, investor updates, marketing narratives, product roadmaps, pricing papers, customer research, sales win/loss notes, operational KPIs, and even the CEO’s town‑hall messages. Taken together, these artifacts reveal what the organization is already choosing to prioritize, what it tends to protect, and where it’s holding back.
AI tools can help by synthesizing the material into a shared draft that the leadership team can react to, refine, and use. Before you use any tool, strip out confidential, proprietary, and personal data from the materials you provide, and use approved enterprise tools and settings rather than consumer defaults.
With the tech company, we started with a tight, relevant set of artifacts (sanitized as needed): recent board updates, investment cases, product roadmaps, quarterly business‑review notes, win/loss summaries, key customer feedback, and leadership communications. We asked the tool for three outputs in plain language:
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A draft description of the strategy, expressed as choices: where you concentrate resources, where you hold back, and what you tend to prioritize when priorities compete.
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A list of inconsistencies, showing where different parts of the organization seem to be operating with different logic or definitions.
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A short new‑leader briefing, capturing the priorities and decision rules someone would need in order to make good calls quickly.
We then shared the draft with the leadership team, positioning it as a contribution and an opportunity for improvement. Each executive highlighted what was accurate, what needed revision, and which trade‑off was missing. This kept the conversation focused on judgment and choice, grounded in the organization’s own evidence. Later, we turned the revised draft into a single‑slide visual of the strategy—a clear description showing the core choices and how they connect. The discipline of boiling strategy down into one visual forces precision, and it quickly shows where leaders’ mental models diverge.
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Shock testing the strategy
A shock test brings strategy into the conditions where leaders most need it: where time is short, information is incomplete, and decisions get made in several places at once.
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Choose a plausible scenario (e.g., a cyber incident, regulatory intervention, reputational issue, supply disruption, or a competitor undercutting you in a key segment). Keep the setup concrete: what has happened, what’s at risk, and what has to be decided in the next 48 hours.
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Run a focused session – I ran a 45‑minute session with the senior team and a small number of operational leaders who would have to act immediately, using four questions:
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In the first 48 hours, what are the three decisions we must make, and who owns each one?
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What do we push forward, and what do we put on hold for now?
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What is off‑limits in this scenario because it would weaken our long‑term position?
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What coordination failure is most likely—and what simple rule prevents it? (e.g., “One voice to customers,” “No bespoke deals.”)
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Use AI as a teammate – AI can play a useful “teammate” role in the room. We fed it the scenario and the current strategic choices, then asked for options, second‑order effects, and questions the team should address before committing. We treated it as an input and a disruptor to existing thinking, not the answer, so we used it with careful supervision and interpretation.
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Capture the outputs on one page – Where you play, how you win, the trade‑offs you accept, decision rules for uncertainty, and the assumption you want to watch most closely (with the signal that would trigger a revisit).
The pride in “we don’t have a strategy” often comes from a sense of achievement. But strategy becomes valuable when this success is supported by clarity that others can use. Leaders across the organization respond faster and more consistently when they share the same decision rules. That’s when strategy stops feeling like a distraction and starts feeling like an advantage.
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