Collapsing Sliding Windows: A Strategic Planning Framework for Uncertain Events

Introduction

Effective agile planning processes strive to balance the forecasting and planning of future events with ensuring organizations can deal with uncertainties as new information comes to light. For many people, the responses to these events are well established. When they are imminent but responding to them only requires a modest investment, leaders capture them in roadmaps and handle them through everyday development practices. When they are imminent and responding to them requires a more significant investment, leaders handle them through a combination of development- and portfolio-management practices. 

These strategies are usually adequate under normal circumstances. But they have serious drawbacks when it comes to reliably anticipating, planning for, and managing events that are likely to occur outside of conventional planning-time horizons. Nor are these strategies sufficient for managing events whose timing is difficult to pin down because many of events are subjective and likely to be associated with complex factors, and/or whose outcomes can be dramatically improved through a consistent set of low-cost prior actions.  

Fortunately, there are planning techniques that can help organizations position themselves to reduce unnecessary downside costs and improve their chances of realizing any potential upside during uncertain event time horizons. These techniques give leaders the tools they need to be more planful about how they allocate their efforts and resources, helping them set up their organizations to best benefit from events, regardless of how fluid their timing is.

This paper introduces a new planning construct, Collapsing Sliding Windows (or CSW), that fills a critical gap in how organizations can prepare for events that may occur beyond one to three years, the time horizon that organizations that want to embrace agility and/or Lean development practices typically plan for.

CSW is a probabilistic planning construct that represents a bounded time range during which an uncertain future event is likely to occur, along with a probability density over that range. The “collapsing” refers to a contraction in opportunity space—an area where proactive options diminish as time progresses without action. The “sliding” refers to shifts in the window’s position in time. 

By better understanding the characteristics of these events and the dynamic nature of Collapsing Sliding Windows, business leaders can improve their strategic planning, prioritization capabilities, and emergency response preparedness while more prudently managing resources to achieve better, more predictable outcomes. Conversely, failing to leverage Collapsing Sliding Windows may precipitate overly reactive and potentially costly interventions, as organizations and individuals lose valuable options and find themselves scrambling to respond to events with diminished confidence and increased costs.

Throughout this paper we provide numerous examples of Collapsing Sliding Windows in action, and show how developing Proactive Action Strategies (PAS) and Proactive Action Plans (PAP) gives leaders more control over their future. 

Dissecting “Future Events”

Before we continue, let’s briefly review what we mean by future events.

An event is typically associated with a date, and the date of many future events is known with absolute certainty. Examples include birthdays, anniversaries, weddings, quarterly or end-of-year financial reporting, the closing date of a material financial transaction, or a new regulation impacting a business. These dates, whether recurring or non-recurring, form the basis of our planning. 

Of course, the events we care about may not be associated with the date. We may care more about the act of celebrating a birthday or anniversary rather than the date each occurred on, and when these dates fall on a weekday, we may schedule a party for the weekend before or after. This decoupled and adjusted date is, therefore, more meaningful than the actual date of the event. 

While the dates events may be set, the occurrence of the events is probabilistic. You may be entirely confident that you will attend your next birthday or anniversary. However, if we forecast far enough into the future, your confidence will start to wane: will you be alive at age 80? 90? 100? 

Our point is that even seemingly certain events like birthdays, or the publication of new regulations impacting your business, have embedded probabilistic components when reframed from an actor’s perspective (actor meaning individual person). 

We can illustrate this with a simple diagram. In Figure 1, for instance, dates known with certainty have been placed on a generic timeline indicating now and a later date.

Figure 1: Known Future Events

However, the date of many if not most future events are not known with such precision or certainty. Indeed, we may not even be entirely certain the event will occur at all, which makes planning for it challenging (to say the least). We need a way, then, to capture the potential occurrence of the event in such a way that we can plan for it. 

This is all pretty abstract, so let’s explore it through a real-life example: retirement. Most of us think of retirement as a positive future event and, therefore, something that we want to do. 

Let’s assume, then, that we want to retire at age 62. We can draw this on a timeline with a dark diamond to indicate it is a desired future event. 

Because we don’t know if we’ll retire exactly at age 62, let’s add a few more diamonds. These capture the range of when we might retire.

Of course, the realization of our retirement is not absolute. Instead, it is a probability based on several attributes, such as our desired lifestyle and the amount of money we believe is required to maintain this lifestyle (“a 401K with $1M in investments and a fully paid-off house”). We can capture this spectrum of possible dates in a probability density function, a curve that shows our expected retirement date (Figure 2). We refer to the timeframe we’re most likely to retire as the Window.

Figure 2: When We Will Retire

How we determine the nature of this curve varies:

• We can start with a specific target (“I want to retire at 62”) and then establish a confidence interval (“I could retire at 60, but it might take me to 63 to save enough”).
• We can start with a range of likely dates and draw a curve that covers their span.

The important point is that unless a future event is known with absolute certainty, it’s more useful to capture it in a probability curve that illustrates the time range in which we are confident the event will occur. Fortunately, the precise shape of the curve isn’t that terribly important; just drawing an approximate shape is good enough to get started.

How Windows Slide

As time progresses, our actions, feelings, the macroeconomic environment, and other factors all contribute to whether we think we’re getting closer to or farther from our “retirement event.” 

As shown in Figure 3, receiving a financial windfall may slide our retirement to an earlier point in time, while suffering a financial hardship such as losing a job or persistent high inflation may slide it further into the future.

Figure 3: Retiring Sooner or Later

How Wide Is a Window?

As we get closer to retirement, our retirement “number” or date becomes more precise, and we may find ourselves adjusting our expectations for how we will live in retirement to align with our present and more tightly forecasted economic circumstances, thus changing the probability curve (Figure 4):

Figure 4: Changing the Probability Curve

Note that a probability curve does not guarantee that an event will actually occur. We might, for example, die in an untimely and improbable way before our retirement, God forbid.

Objective and Subjective Events

Some retirement events are objective: you reach the mandatory retirement age in your organization and are terminated. In this scenario, we can model the certainty of retirement as the furthest time in the future of the CSW, with the knowledge that you could retire sooner or may prefer, but are unable to, retire later.

Figure 5: An Objective Event

Other retirement events are subjective: you determine the attributes and the criteria that must be met for you to stop working at your current job, and once they are, you retire. Subjective retirement events can be simple, such as choosing to stop working when you are comfortable with the savings you have accumulated, or complex (you, your partner or spouse, and possibly others, such as your children, have different needs, interests, and goals and therefore collectively influence ‘when’ retirement occurs), all, by definition, with the broader CSW that captures the range of time associated with retirement.

Figure 6: A Subjective Event

If there are multiple actors, these attributes may or may not be shared, since each may believe the event has occurred for any number of different privately held or openly shared reasons. For example, a husband and wife may agree on the timing of the wife’s retirement event even if they differ in their motivations for their agreement.

When a Window Collapses

The Proactive Action Strategy (PAS) defines the actor’s approach to maximizing upside potential and minimizing downside risks associated with a CSW. The PAS is interdependent with the CSW, as actions taken can adjust the window, and the window’s adjustments may affect future plans, decisions, and actions.

A window that slides sooner/forward in time may motivate us to update our strategy and/or implement our action plan sooner in time. A window that slides later/backward may similarly motivate changes to our strategy or plan. In both cases, we assume that we are able to plan for and benefit from the event.

A window can be said to collapse when the only remaining actions an actor can take to prepare for an event focus on minimizing adverse outcomes should the event occur. A collapse can be due to a change in the probability curve. Typically, this happens when actors have failed to implement a Proactive Action Strategy and action plan, or they’ve simply chosen to ignore the negative consequences of the CSW. In either case, the actor ignored the potential gains and/or losses that were coupled to the CSW. Disregarding the opportunities and risks associated with a CSW leaves the actor with the best of the worst options rather than the best of the best ones that would have led to a better outcome. In extreme cases, all positive options can evaporate.

For example, suppose a company with a charismatic CEO nearing retirement fails to implement a robust succession plan. Eventually, the opportunity to prepare for the CEOs departure will eventually collapse. And, if the CEO were to announce an unexpectedly early retirement, the window would also collapse. In both of these cases, the most favorable options evaporate. The only remaining options are net-negative.

A window may also collapse due to unforeseen factors, such as a natural disaster or a disruptive technology that upends an industry. In these cases, identifying the CSW, developing a proactive action strategy, and implementing an action plan helps the organization prepare for and respond to the event. Instead of being completely unprepared, the organization may accelerate one or more aspects of a longer-running plan, creating a better long-term outcome.

Of course, not every sliding of a window or a change in probabilities results in collapse. If you’re lucky enough to win the lottery, go ahead and retire early!

But as long as a window has not collapsed, there is still opportunity to maximize the potential for more positive outcomes and neutralize or at least reduce the risks associated with an untimely collapse. 

In a Nutshell: Collapsing Sliding Windows

In summary, Collapsing Sliding Windows have the following characteristics:

• The event’s occurrence is not known precisely in advance and is captured through a probability curve that defines its likely occurrence.
• The probability curve that describes the likely occurrence of the event might “slide”— that is, shift earlier or further in time from the curve’s original estimate. These shifts may be based on changes in the environment and by the actions taken by (or inactions of) actors within and outside the organization.
• Objective events occur independently of the actors they impact. Subjective events are typically characterized by multiple attributes or factors considered after the fact to assert that the event has, in fact, happened.
• The event itself is not intrinsically positive or negative—it is factual. It is our relationship to the event and their implications that determine the event’s effect on us and our organizations.

The value of embracing the CSW planning construct is its ability to help leaders identify, plan for, and ultimately respond to events that are likely to have undesirable outcomes if not intentionally and proactively managed. That is, unless a leader develops a strategy and takes planful action to put into practice, their opportunities to manage the event (i.e., solve the problem or capitalize on the opportunity) will typically become more challenging, complex, and costly as time progresses.

While a given event might not occur, implementing an action plan typically has both a positive effect and a low opportunity cost, making the identification and evaluation of CSWs a useful planning construct.

Moreover, depending on the nature of the event, some action plans may actually alter the probability of the event’s occurrence, giving actors more agency over their future. And these characteristics can be leveraged to create competitive advantage through the techniques we describe below. 

Collapsing Sliding Windows Surround Us

Collapsing Sliding Windows are everywhere in both our personal and professional lives. Since we explored how CSWs work in our personal lives (the retirement examples), we will now concentrate on examples from business. Note that each of these events begin as opportunities…until they aren’t. 

• Leadership succession. We know that senior leaders will eventually leave our organization. Accordingly, succession planning should be captured as a Collapsing Sliding Window.
• Pending or anticipated legislation. Most regulatory bodies provide notice of pending or anticipated legislation that can be captured as a Collapsing Sliding Window.
• Changing suppliers. While many organizations strive to establish long-term relationships with key suppliers, there are often reasons to change them. This desire can be captured as a Collapsing Sliding Window, providing the organization with the planning opportunities needed to implement a smooth and successful transition. In this scenario in particular, the organization probably has some control over sliding the window into a timeframe that’s advantageous to the organization.
• Launching a novel product. The launch of a novel product, especially one that’s physical, can be captured through a Collapsing Sliding Window. Note that if the launch window slides, so should marketing, sales, and any other dependency.
• A competitor beating you to an opportunity. This is out of your control, but how you respond to it isn’t. Consider Apple smart watches vs. Samsung watches, a situation when being first seemed to really matter. Samsung got the watch to market first, but Apple had a better overall strategy for engaging consumers, so they ultimately launched a more successful product. Apple’s window didn’t collapse.
• Mergers, acquisitions, and divestitures. M&A activities can also be captured as a collapsing sliding window, since during the process there are a significant number of events that can materially change the likelihood of a transaction and its near and long-term value to the buyer and seller.

The examples listed above rarely occur in isolation. In real life, CWSs tend to show up in clusters and overlap. So, to determine which windows deserve our attention and in what order, we must be clear about the relative impact of each window and the likelihood of the event’s occurrence. It’s all about priorities.

Collapsing Sliding Windows in business are not only associated with large companies. Two of the most common CSWs in startups include raising capital/funding, and exits (such as being acquired or going public); in both cases, the specific timing of the event is uncertain.

Collapsing Sliding Windows provides a new way to assess future events. Once you become comfortable using them, you will undoubtedly find more examples of them in your personal and professional lives. 

How to Plan for and Monitor CSWs:A Temporal Readiness System

“No one can anticipate everything that might happen. Sensing possibilities, though, is better than having no sense at all of what to expect.”

— John Lewis Gaddis, On Grand Strategy

To help individuals and organizations visualize the CSW process, we created a graphic showing each of its steps:

Let’s go over them one by one.

Conclusion

The Collapsing Sliding Windows framework is a powerful tool to help leaders prepare for future events, not by pretending to eliminate uncertainty, but by engaging with it thoughtfully. It allows leaders to navigate the terrain between near-term agility and long-range strategy by integrating probability, timing, and impact into their planning conversations.

The strength of the CSW framework is not in predicting the future, but in preparing for it. By acknowledging that windows slide, narrow, or collapse, we reclaim agency over events that might otherwise take us by surprise. We shift from reactive firefighting to proactive, intentional action.

When adopted with discipline, curiosity, and humility, CSWs enable smarter investments, better timeline control, and greater alignment—within teams, across portfolios, and throughout an entire enterprise. In a business environment increasingly shaped by volatility, uncertainty, complexity, and ambiguity, that may be the most strategic advantage of all.

References

1. Michael D. Watkins, The First 90 Days: Critical Success Strategies for New Leaders at All Levels (Harvard Business School Press, 2003).
2. Harry Max, Managing Priorities: How to Create Better Plans and Make Smarter Decisions (Two Waves Books, 2024).

Appendix: Related Frameworks and Planning Constructs

While a novel approach, Collapsing Sliding Windows has natural relationships with several existing planning constructs. Understanding how CSW overlaps with these frameworks will help you apply it with greater nuance and better integrate it into your existing strategy practices.

• Real options provides a structured approach to investing designed to create future flexibility. It recognizes that some strategic decisions are best framed as options, not commitments. CSWs and real options are symbiotic: CSW helps surface when and where real options should be created, while real options offer a financial or operational model for managing uncertainty within the window. For example, securing the right to develop a novel hardware solution through investments in patents can be viewed as a real option within a CSW related to forecasted customer needs.
• Scenario planning explores multiple possible futures to test the robustness of strategies. CSW complements this by framing when these scenarios may become real and what actions to take in the lead-up. The probability curve in a CSW helps prioritize which scenarios warrant active monitoring and proactive engagement.
• Rolling wave planning embraces uncertainty by planning in greater detail for near-term work while leaving future work at a higher level. CSW enriches this approach by explicitly identifying windows where uncertainty is highest and where early, light-touch planning can create outsized leverage later. They offer a rationale for when and how to refine future waves.
• Assumptive goal setting recognizes that many strategic objectives are built on underlying assumptions. CSW provides a framework for stress-testing these assumptions over time. When the probability curve of a CSW starts to shift, it often signals that one or more of our assumptions are no longer holding—prompting us to reassess our goals and strategies.
• Decision trees model choices, uncertainties, and payoffs. CSW adds a temporal dimension often absent in decision trees, helping decision makers consider how the value of their choices changes over time, and what they must do before a branch becomes viable or foreclosed.

Taken together, these constructs form a powerful toolkit. CSW isn’t meant to replace them; rather, it provides scaffolding for integrating them into real-time strategic thinking. 

The future isn’t just out there—it’s actively approaching. CSW helps us meet it well prepared.

Appendix: Collapsing Sliding Windows and SAFe 

The Scaled Agile Framework (SAFe) includes multiple constructs that can be naturally extended to incorporate CSWs. Here are a few:

• PI Roadmaps capture foreseeable events within a 1–3 Planning Interval time horizon. CSWs that manifest within this range are best modeled in the roadmap, where teams can align around short-term execution.
• Solution Roadmaps extend planning further into the future. They are well-suited for CSWs that have a longer but still tangible timeframe (e.g., a compliance mandate expected within 36 months). Adding CSWs to Solution Roadmaps is particularly useful for organizations experiencing high rates of growth or operating in extremely volatile environments, since they help leaders deal with frequently changing probability curves.
• Epics, particularly those that require significant investment, are ideal vehicles to fund exploration or mitigation strategies for CSWs. Extending the Lean Business Case to include CSW-specific elements (notably, probability curves and proactive action strategies) supports members of the LPM team in making portfolio investments.
• Solutions by Horizon can be correlated with CSWs to help organizations prepare for the transition of solutions between horizons.
• Architectural Runway is involved when the Proactive Action Strategy involves technical enablers. For instance, beginning a gradual migration to cloud infrastructure in anticipation of significant growth in usage leaves the organization prepared if the usage materializes faster than expected. 

The unique planning feature of CSWs is that they allow organizations using SAFe to plan for events beyond the canonical time horizons defined in SAFe. For example, CSWs are well-suited to time horizons of 5, 10, 20, or even 40 years. 

The point is not to bolt CSWs onto SAFe, but to let CSWs inform and enrich the strategic and budgeting mechanisms already present in SAFe. In a world of increasing uncertainty, CSWs give SAFe practitioners a way to lean into the unknown while retaining organizational agility.

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