STRATEGIC THINKING
Strategic Thinking Can't Be Faked at the ELT Table
December 2025 · 7 min read
December 2025 · 7 min read
There is a moment that happens in nearly every executive leadership team meeting where a new member reveals whether they think strategically or operationally. It usually comes within the first month. Someone presents a market challenge or a competitive shift, and the new executive responds with a detailed plan of action — timelines, resource requirements, milestones. The plan is excellent. And it completely misses the point. The rest of the table was having a conversation about whether this is the right problem to be solving at all, and the new executive just demonstrated that they can't tell the difference. This is the same trap that catches leaders in the director-to-VP transition — engaging at the wrong altitude.
This is how tactical leaders get exposed at the ELT table. Not through any single failure, but through a pattern of engaging at the wrong altitude. They answer questions that weren't asked. They solve problems before the problem has been properly framed. They bring operational excellence to a conversation that requires strategic judgment. And the gap is painfully visible to everyone else in the room, even when the executive themselves doesn't see it.
Strategic thinking is not planning. This is the most common misconception, and it trips up even very senior leaders. Planning is the process of determining how to achieve a known objective. Strategy is the process of determining which objectives to pursue, what to deprioritize, and what the organization should explicitly choose not to do. A strategic thinker at the ELT table can sit with a complex, ambiguous situation and resist the urge to immediately solution it. They ask different questions: What are the second-order consequences? What does this mean for our position in eighteen months? Which of our current assumptions does this invalidate?
In my experience, the clearest signal of strategic thinking is the ability to articulate trade-offs. Any competent operator can build a plan to pursue an opportunity. A strategic thinker can explain what pursuing that opportunity costs in terms of other opportunities, organizational focus, and competitive positioning. When I sit in ELT meetings, the executives who command the most respect are not the ones with the most comprehensive plans. They are the ones who can frame a decision in terms of what the organization gains and what it gives up, and then make a clear recommendation about which trade-off to accept.
There is a simple test for whether someone is thinking strategically or tactically, and it shows up in how they respond to new information. A tactical thinker hears that a competitor has launched a new product and immediately starts talking about the response: feature parity, timeline to match, resources needed. A strategic thinker hears the same news and asks what it reveals about the competitor's direction, what customer segment they are targeting, and whether this changes the assumptions underlying our own roadmap. The first response is about action. The second response is about understanding. Both are necessary, but at the ELT table, the second must come first.
Second-order thinking is the practice of asking "and then what?" at least twice before forming a position. If we enter this market, what does the competitive response look like? If they respond that way, what does that do to our margins in the core business? If margins compress there, what does that mean for our hiring plan and our ability to invest in the platform? This chain of reasoning is what the CEO and the board expect from every member of the ELT. It is also exactly the muscle that operational excellence does not develop, because operational environments reward fast, first-order decision-making.
The leaders who get promoted to the ELT are almost always exceptional operators. They have track records of delivering results, managing complex programs, and scaling teams. These are real capabilities, and they matter. But as we explore in what got you promoted will get you fired, operational excellence creates a specific set of habits that actively work against strategic thinking. Operators are trained to reduce ambiguity, move fast, and execute. Strategic thinking requires you to sit in ambiguity, slow down, and question whether you are solving the right problem. These are opposing impulses, and the transition from one mode to the other is genuinely difficult.
I've seen this play out dozens of times. A brilliant SVP of Engineering joins the ELT and within weeks starts turning every strategic discussion into a technical architecture review. A VP of Sales who consistently crushed quota joins the leadership team and can't stop framing every conversation in terms of quarterly pipeline. They are not doing anything wrong by the standards of their previous role. But the ELT doesn't need another operator. It needs someone who can zoom out from their function and think about the business as a system — where the leverage points are, where the risks are accumulating, and where the organization is making implicit bets that should be explicit.
Strategic thinking is a skill, not a personality trait, and it can be developed with deliberate practice. The first step is creating space for it. Most executives at the VP and SVP level have calendars that are packed with operational reviews, one-on-ones, and cross-functional syncs — especially in the first 90 days of a new role. There is no space in a typical week to think strategically because every hour is consumed by tactical demands. The executives who develop strategic capability do so by ruthlessly protecting time for it — blocking two to three hours per week with no agenda other than thinking about the business at a systems level.
The second practice is learning to read across functions, not just within your own. Strategic thinking requires understanding how the pieces of the business fit together. If you are a product leader, you need to understand the unit economics of the sales motion. If you are a sales leader, you need to understand the technical constraints of the platform roadmap. Not at a deep level — you don't need to become an expert in finance or engineering — but at a sufficient level to understand the trade-offs that other functions are navigating. The executives who think most strategically at the ELT table are the ones who have invested in understanding the business beyond their own domain.
The ELT table doesn't reward the leader with the best plan. It rewards the leader who can frame the decision the rest of the room didn't know it needed to make.
The third and most difficult practice is learning to hold multiple scenarios simultaneously without committing prematurely to any of them. Operational leaders are conditioned to pick a path and execute. Strategic leaders need to maintain two or three plausible futures in their mind and make investments that create optionality across them. This feels inefficient to operators, and it is — in the short term. But organizations that commit too early to a single strategic path regularly get blindsided by shifts they should have seen coming. The ability to say "we don't have enough information to commit to a direction yet, but here are the three things we should be doing in the meantime to preserve our options" is one of the highest-value contributions an executive can make at the ELT table. It is also one of the rarest.
If you are a strong operator who recently joined or is about to join an executive leadership team, recognize that the game has changed. Your operational instincts are still valuable, but they are no longer sufficient. The organization didn't put you at the ELT table to run your function better. It put you there to help the leadership team make better decisions about the business as a whole. That requires a different mode of thinking — one that is slower, more ambiguous, and more consequential than anything your operational career prepared you for. Building that capability is not optional. It is the price of admission at executive altitude. Strategic thinking coaching is designed for exactly this shift.
Planning is the process of determining how to achieve a known objective. Strategy is the process of determining which objectives to pursue, what to deprioritize, and what the organization should explicitly choose not to do. A strategic thinker at the ELT table can sit with a complex, ambiguous situation and resist the urge to immediately solution it. They ask different questions: What are the second-order consequences? What does this mean for our position in eighteen months?
Operational excellence creates habits that actively work against strategic thinking. Operators are trained to reduce ambiguity, move fast, and execute. Strategic thinking requires you to sit in ambiguity, slow down, and question whether you are solving the right problem. These are opposing impulses, and the transition from one mode to the other is what makes the director-to-VP transition so difficult.
Second-order thinking is the practice of asking "and then what?" at least twice before forming a position. If we enter this market, what does the competitive response look like? If they respond that way, what does that do to our margins in the core business? This chain of reasoning is what the CEO and board expect from every ELT member.
Strategic thinking can be developed through deliberate practice. First, ruthlessly protect two to three hours per week for thinking about the business at a systems level. Second, learn to read across functions rather than just within your own domain. Third, practice holding multiple scenarios simultaneously without committing prematurely to any of them.
There is a simple test: how you respond to new information. A tactical thinker hears that a competitor has launched a new product and immediately starts talking about the response. A strategic thinker hears the same news and asks what it reveals about the competitor's direction and whether this changes underlying assumptions. At the ELT table, understanding must come before action. See our coaching packages for developing strategic leadership skills.
We coach the specific skills behind strategic leadership at enterprise scale.
