Strategy is the Work of Leaders: Give Up Strategic Theater and Embrace the Reality that Strategy is the Work of Leaders
An overview of my Strategy for the Win presentation from Computers in Libraries 2026.
Strategy is not a document, a retreat, or a five-year artifact that gets dusted off when governance requires a refresh. Strategy is a living story about how an organization intends to become something other than what it is. Strategy states how organizations intend to overcome the obstacles they face. That story only becomes real when it shapes budgets, policies, space, technology choices, metrics, and daily work.
The most dangerous failure in strategy is not poor formatting or weak facilitation. It is the refusal to name the real problem. Scenario planning matters because it forces organizations to confront uncertainty honestly, test assumptions against multiple plausible futures, and build resilience rather than betting everything on a single forecast. AI belongs inside that larger strategic story as a tool in service of mission, not as a separate strategy unto itself.
Strategy needs less ceremony and more consequence
Too many organizations still confuse motion with strategy. They gather people in rooms, produce posters, circulate polished PDFs, and emerge with aspirations dressed up as choices. The language sounds serious. The work often does not. What passes for strategy is too often a mix of initiatives, targets, values statements, and consensus language that offends no one and directs nothing. In those moments, the organization has not clarified its future. It has merely documented its discomfort with making trade-offs.
Real strategy is harder. It starts by diagnosing the challenge honestly. Not the public version. Not the board-safe version. The real version. What is the obstacle that keeps the organization from becoming what it needs to become? Sometimes, the first obstacle is that people cannot even talk openly about the problem. That silence is not a side issue. It is itself strategic data. If the pain remains unnamed, the strategy will remain ornamental.
This is why strategy cannot be reduced to slogans, growth targets, or an everything-stays-on-the-plate mentality. Strategy requires subtraction. It requires saying no. It requires telling good people with good ideas that their ideas are not the priority now. That is not cruelty. That is governance. Without those choices, there is no strategy, only accumulation.
A strategy is only real when it shows up in the work
Organizations reveal their actual strategy in quieter ways than they often admit. The budget tells the truth. The technology stack tells the truth. Space tells the truth. Training priorities tell the truth. Performance measures tell the truth. Job descriptions tell the truth. If the stated strategy does not appear in those places, then the organization is not executing a strategy. It is narrating one.
That is where many strategic planning efforts break down. Leaders may know the intended direction, but staff encounter little evidence that anything has changed. The work continues as before. The routines remain intact. Resource allocation stays tied to legacy assumptions. The organization says one thing and funds another. In that gap, cynicism grows. People learn quickly that the strategy matters less than the inherited workflow.
The practical test is simple. Can someone in the organization explain the strategy without opening a PDF? Can they see how their work contributes to it? Can they infer priorities from what gets funded, redesigned, measured, and stopped? If not, the problem is not communication. The problem is that the strategy is not embedded in execution.
AI does not need its own strategy
One of the most persistent strategic errors in 2026 is the urge to build a separate AI strategy as though AI were a department, a destination, or a self-justifying mission. It is none of those things. AI should be treated as a tool in the service of organizational purpose. The strategic question is not, “What is our AI strategy?” The better question is, “How does AI help us deliver on the strategy we already have?”
That framing matters because AI remains volatile, fast-moving, and poorly bounded. The real obstacle is not a lack of enthusiasm. It is uncertainty. Organizations are facing a technology that is already reshaping work, expectations, and interfaces, even as no one can say with confidence what its stable form will be. Trying to write a durable stand-alone AI strategy under those conditions is an invitation to institutionalize assumptions that will age badly.
A stronger move is to define the mission clearly enough that AI can be evaluated against it. During the presentation, I provided a hypothetical strategy for a library: helping people turn information into practical progress through learning, access, and trusted human support. Once that is the strategy, AI becomes easier to place. It can support navigation, discovery, translation, personalization, explanation, and service design. It does not become the point. It becomes another way to advance the point.
Leverage scenario planning to challenge assumptions
Traditional strategic planning often smuggles in a single assumed future and then treats that assumption as discipline. It is not discipline. It is wishful thinking. Scenario planning offers a better alternative because it forces organizations to explicitly identify uncertainties, develop multiple plausible futures, and test current assumptions against them. That work does not eliminate uncertainty. It makes uncertainty discussable, monitorable, and strategically useful.
This distinction matters. Forecasts collapse uncertainty into a story too early. Scenario planning resists that collapse. It keeps organizations from mistaking their preferred future for the most plausible one. It also surfaces fragile assumptions before those assumptions are embedded in capital plans, staffing models, service design, or technology investments. That is where resilience comes from. Not from being right about the future, but from being less surprised by it.
The value is not abstract. Scenario work creates room for innovations that linear planning rarely generates. I offered libraries as resilience infrastructure from recent scenario work, including the possibility of microgrids and expanded roles during climate disruptions. That kind of thinking rarely emerges from a conventional five-year plan because the plan is too busy defending the present. Scenarios, by contrast, force institutions into uncomfortable, hypothetical, but plausible situations that allow them to rehearse possibilities before actual circumstances force them to improvise.
Metrics should measure value, not just activity
Most organizations are drawn to metrics that are easy to gather and easy to compare. Those metrics are often the least revealing. Benchmarks can be useful, but they can also standardize mediocrity by pushing organizations toward generic measures untethered from their actual strategic intent. If the strategy is distinctive, the metrics must become more distinctive too.
A strategy centered on helping people move from confusion to capability cannot be measured only through circulation, attendance, or satisfaction scores. Those may still matter, but they are not sufficient on their own. The question becomes whether people are actually making progress. Are they gaining competence? Resolving friction? Navigating systems more successfully? Achieving better outcomes over time? Those are harder measures. They are also closer to the truth.
That harder truth extends to the long tail of value. Many strategic benefits do not appear in a clean reporting cycle. They accumulate through changed decisions, greater confidence, improved judgment, or delayed but meaningful action. The discipline is not to avoid measurement because it is difficult. The discipline is to measure what matters even when it resists easy dashboards.
Strategy when organizations act
The most useful lesson from my strategic planning presentation is the simplest one: every action edits the story. A strategy is not finished because a milestone was completed. Completion should trigger the next strategic conversation. Now what? What changed because that choice was made? What did the organization learn? Which assumptions still hold? Which priorities should now be reconsidered?
That is how strategy becomes a living system rather than a planning artifact. It evolves through choices, learning, and reallocation. It remains anchored by purpose, but never trapped by paperwork. It is not static because the environment is not static. An organization that wants resilience cannot afford a strategy that only updates when the calendar says it is time. Leaders facilitate―they don’t empower, encourage or dictate―an organization’s strategic dialogue
Key takeaways
- Name the obstacle. If the real problem cannot be spoken, the strategy is already compromised.
- Treat strategy as a living story shaped by daily choices, not as a five-year document.
- Make trade-offs visible. A strategy that never says no is not a strategy.
- Embed the strategy in budgets, policies, space, technology, metrics, and routines. Those are the organization’s real communications channels.
- Stop separating AI from mission. Use AI to advance the core strategy rather than inventing a parallel one.
- Use scenario planning to test assumptions against multiple plausible futures rather than betting on one forecast.
- Build metrics around the value the organization is trying to create, not just the activity it can easily count.
For more serious insights on AI, click here.
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All images via ChatGPT from a prompt by the author unless otherwise noted.
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