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Imagination: a strategic tool
May 02, 2025

With all the change of late, imagination has been on my mind. Silly, one would think that what I should do with my stocks would be more front of mind or what new business building strategies will be effective in this economic environment, but here I am writing about imagination!

I’m granting it this mental space, because I think it’s important in this moment: the quality of imagination impacts what’s possible and what’s ultimately achieved.

Up until the recent past, I’ve received the conversation around imagination with mixed feelings. I often hear imagination referenced in strategic design and innovation circles, and some of the studios I most respect explicitly center it in their work. Imagination certainly is in question in the decisions around technology and our resulting relationship with it. And, in this time of uncertainty and change we can all feel something new is emerging, but what is that something new?

While I’ve been open to how centering imagination as a driver for strategy and to better outcomes, I have a confession to make that feels scandalous as a strategic designer: a part of me has felt it frivolous. A bit disconnected, say, from the on the ground modernization in an organization like the VA where practical, pragmatic improvements mean life changing outcomes for the beneficiaries of VA services.

Certainly, big blue sky thinking alone without being grounded in real needs or at some point connected back to real outcomes can be frivolous and disconnected. But as I’ve personally looked deeper into it, prompted by a personal conversation that made me realize how important it is to manage our limiting assumptions for ourselves, the people we care about, and the world we’re building or contributing to, it’s evolved. As with anything, it’s not either or. Value comes in finding the mix or the substance in the contradiction.

Most of us know or have heard about anchoring bias at some point or another, likely in an economic or negotiation context. For example, in salary or contract negotiations, studies show that the first number mentioned strongly influences the final outcome, even if it’s extreme or obviously biased. In another study, participants given a random but high anchor price in car negotiations paid much more than participants given a random low number, even when participants had been informed the number would be random.

Let’s take that concept and apply it to strategy, innovation and transformation work. What is the starting point of a new idea, a new offering, or a new business if not the imagination? Our imagination (or lack of) is similar to an anchoring bias. The limits of our imagination are also the limits of our ability to innovate. We can’t strive for an outcome that we cant imagine – no matter how big blue sky or pragmatic.

When we’re talking about innovation and transformation, we are creating new possibilities and opportunities, beyond what has already been made or thought of or thought possible. For the sake of this post, I’ve oversimplified it into a linear process with four steps that work towards new ways of thinking or seeing:

  1. Define the desired outcomes of the transformation. Here’s where we sometimes think outcomes are solutions (they’re not), or sell ourselves short when trying to think big.
  2. Understand the context in which this creative and transformative effort will take place. We all know data is important. But data and transformative insights are two different things.
  3. Brainstorm with ideas that reframe the context and the outcomes in new ways. Get out of your shell here and think differently. There are entire fields and careers built on facilitating a mental, emotional and physical space that helps people come up with ideas.
  4. Make explicit the drivers and containers that shape or limit those new possibilities. Here’s where the rubber starts to hit the road, and you have to bridge big blue sky and on the ground context.

(In reality, it’s rarely linear, nor is it this clearly defined, nor is true divergence from the norm easily done on-demand. It requires time, space, exposure and the right context.)

You know what impacts our ability to do the above? Anchoring biases / our imagination (or lack of). It is a strong determinant for how transformative or innovative your work can be, exactly because of the assumptions and values that define or drive an effort without necessarily having ever been made explicit. They can be informed by:

  • Past experiences and legacy thinking
    • For example, a city planning team imagines the future of public transport, but all their ideas assume private car ownership is still the norm. The past anchors their imagination, and they risk seeing the shifts in preferences and technology that create other, more impactful possibilities.
  • Current trends (and, no, innovation is not doing the new thing everyone else is doing)
    • “AI is the future, so let’s build everything around AI.” A company anchors its strategy on a popular technology trend without examining whether it aligns with their customers, environmental impact, or deeper societal trends. Innovation becomes reactive, not grounded in real possibilities, and not visionary.
  • Dominant narratives
    • In early stages of ideation, the first decent-sounding concept becomes the anchor, and everyone converges too soon, missing other voices or more novel directions. The result is defaulting to the person who speaks first most of the time, or not flushing out an idea sufficiently and increasing risk in the project.

“In reactive problem solving we walk into the future facing the past — we move away from, rather than toward, something. This often results in unforseen consequences that are more distasteful than the deficiencies removed”  – Russell L. Ackoff

The value a good strategic designer and facilitator can provide is to support purposeful anchoring and grounded imagination that sparks prosocial, sustainable and truly transformative innovation. Some of the methods or practices we might use to help break out of habitual ways of thinking and framing and free the imagination / break free of limiting anchors are:

  • Work backwards from desired outcomes (also known as backcasting)
  • Use fiction or artifacts as prompts
  • Start brainstorms based in first principles, not solutions
  • Brainstorming for breadth by using futures cones – map preferred, plausible, and wild futures to see beyond dominant anchors.
  • Assumption storming – list and challenge current assumptions, e.g. “What if democracy weren’t based on voting?”
  • Ethical scaffolding – use moral or planetary boundaries as anchors to expand innovation within sustainable limits.
  • “Prebunking” Instead of just debunking false info after it spreads, prebunking introduces accurate context early, before misinformation takes root. This shifts the “anchor” to truth or nuance before the false narrative sets in. (Audrey Tang on Great Simplification)
  • Values storming – brainstorm each quadrant of the Values As Assets matrix to make your values and the assumptions they drive explicit. 

We are in a time of uncertainty and change. If we rush to fill gaps in the ways that are immediately available to us without pushing our imagination for what’s possible, we risk not making the most of this moment. Imagination at its most impactful can speak straight to the core of what matters. It can uncover limitations that had been taken at face value for too long, and it can bring to the forefront whats in people to thrive. We can and must use intentional imagination to replace limiting anchor biases as an important tool in the strategic design and innovation toolbox… and in our personal lives, too.

Decision making is a strategic capability. It’s also a good indicator for organizational health and predictor for success. It directly influences the ability to navigate complexity, drive innovation, and align actions with goals. Identifying the decisions that need to be made and how you go about making decisions are critical determinants of success. Here are a few reason why it’s so critical.

1. Navigate ambiguity and complexity

The one certainty we can rely on is change. From shifting customer needs to evolving regulations and emerging technologies to complex internal dynamics, strategic design and innovation always involve unknowns. Considered decision making helps leaders and teams make sense of incomplete information, connect dots, take calculated risks, and keep momentum going in complex environment.

2. Drive Focus and Prioritization

With change comes options, and sometimes there will be multiple paths or ideas that need to be prioritized. Using the right decision making approach for the context helps determine signal from noise, evaluate trade-offs between competing priorities, and align initiatives with strategic goals.

3. Accelerate Learning and Innovation

Modern strategic design and innovation processes require constant decisions (and feedback loops) about which ideas to develop, translating insights into next steps, and maintain momentum by knowing when to pivot or persevere.

4. Facilitates Collaboration and Alignment

 Strategic initiatives often require buy-in from diverse stakeholders. Bringing in multiple perspectives and transparently communicating the rationale behind choices with evidence-based and value-driven decisions ensures initiatives are strategically relevant and embedded into organizational strategy and processes.

5. Supports Long-Term Impact

Strategic initiatives and organizations are like large ships. To ensure focus and effectiveness, strategic decision making often involves anticipating future trends and needs, principles that guide work, and systemic changes that pave the way for outcomes.

Not all decision-making frameworks perform equally across contexts. For example, the decision making needs I have facilitated in the philanthropic programmatic context have diverged from decisions making needs in some Fortune 100s. That’s why the ‘how’ of decision-making must be as context-aware as the ‘what’.

This post intends to provide some structured considerations and examples of frameworks that can guide the next decision you need to make.

 

Key Considerations

At a high level, the framework the authors of Crucial Conversations use to identify four common ways of making decisions is helpful:

    1. Command – decisions are made with no involvement.
    2. Consult – invite input from others.
    3. Vote – discuss options and then call for a vote.
    4. Consensus – talk until everyone agrees to one decision.

Over the years of experience in innovation and strategy, a number of key considerations have become apparent when choosing an appropriate approach that is more likely to set you up for success:

    1. Who should be involved? The “who” is perhaps the most critical factor, as it dictates the perspectives, expertise, and buy-in needed for a successful decision.
    2. How do identified stakeholders best collaborate and contribute? To get the maximum outcome of participation, it helps to do things in way that everyone can participate and be at their best.
    3. What are the scale(s) at which you need to be making decisions? Consider timelines, size / scope, and impact or risk levels.
    4. What’s the nature of the problem? Is it well defined? If so it lends itself to more concrete processes. If it’s a wicked problem, then ongoing
    5. What are the resources needed to lead to informed buyin and agreement? And are they available? Do you have the time, budget, expertise and knowledge/data needed? Or does this process provide you with any of those?

Frameworks

There are a number of frameworks to consider. Here I cover (*with inputs from AI):

    1. Design Thinking
    2. Decision Making Under Deep Uncertainty
    3. OODA Loops (Observe, Orient, Decide, Act)
    4. Real Options Analysis (ROA)
    5. Multi-Criteria Decision Analysis (MCDA)
    6. Cost-Benefit Analysis (CBA) and Cost-Effectiveness Analysis (CEA)
    7. Adaptive Management (and Adaptive Governance)
    8. Participatory Approaches & Deliberative Processes

You’ll see that some methods below naturally accommodate some considerations more than others. And some have overlap. More importantly, most can be borrowed from and adapted to bring in strengths and minimize weaknesses needed in context if done thoughtfully.

Design Thinking

Design Thinking is a human-centered, iterative process for creative problem-solving. It typically involves five (or more) stages: Empathize, Define, Ideate, Prototype, and Test. It focuses on understanding user needs, challenging assumptions, generating diverse solutions, and testing them rapidly.

Strengths:

    • Human-Centered: Ensures solutions are desirable and truly meet the needs of users.
    • Iterative & Experimental: Embraces learning through doing and allows for refinement of ideas.
    • Generates Novel Solutions: Encourages divergent thinking and challenging the status quo.
    • Reduces Risk: By prototyping and testing early, it helps avoid costly failures.
    • Collaborative: Fosters cross-functional teamwork and diverse perspectives.

Weaknesses:

    • Can Be Perceived as “Soft”: Its emphasis on qualitative insights and empathy might be seen as less rigorous by those accustomed to purely quantitative methods.
    • Scope Creep: Without clear problem definition and constraints, ideation can become unfocused.
    • Implementation Gap: While excellent for generating solutions, bridging the gap between a successful prototype and full-scale implementation can be challenging.
    • Time & Resource Commitment: Effective design thinking requires dedicated time for research, ideation, and iterative cycles.

Decision Making Under Deep Uncertainty

DMDU is a set of approaches designed for situations where experts disagree on appropriate models, probability distributions of key variables, or how to weigh alternative outcomes. Instead of predicting a single future, it explores a wide range of plausible futures and seeks “robust” strategies that perform well across many of them, rather than optimal strategies for a single “best estimate” future. It emphasizes iterative learning and adaptive pathways. This is commonly used in climate change, resource management, in healthcare systems managing quickly changing technologies, policies or health events (outbreaks).

Strengths:

    • Addresses True Ambiguity: Directly confronts situations where traditional forecasting fails. It acknowledges that uncertainty is not just about probabilities, but about the unknown unknowns.
    • Robustness over Optimality: Prioritizes strategies that are resilient across a spectrum of possible futures, making them less brittle to surprise.
    • Promotes Adaptability: Encourages the design of flexible and adaptive plans that can be adjusted as new information emerges.
    • Facilitates Stakeholder Alignment: By exploring multiple scenarios and identifying common robust actions, it can help diverse stakeholders find common ground and build consensus.
    • Reduces “Analysis Paralysis”: Shifts the focus from trying to perfectly predict the future to designing adaptable responses, which can free up decision-makers from gridlock.

Weaknesses:

    • Resource Intensive: Can require significant time and resources for scenario development, modeling, and stress-testing.
    • Complexity: The methods can be conceptually and technically challenging, requiring specialized expertise.
    • Requires Cultural Shift: Organizations accustomed to “predict-then-act” approaches may find it difficult to embrace the inherent ambiguity of DMDU.
    • Output Can Be Broad: While it identifies robust strategies, it might not always yield a single, clear “best” path, which can be unsettling for some decision-makers.

OODA Loops (Observe, Orient, Decide, Act)

Developed by U.S. Air Force Colonel John Boyd, the OODA Loop is a continuous cycle for rapid decision-making and action, especially in dynamic, competitive, and uncertain environments. The goal is to cycle through the loop faster than your competitors, thereby “getting inside their OODA loop” and disrupting their ability to react effectively. I’ve mostly considered this on the scale of a single decision maker, for example, startups or in fast-moving clinical environments)

Strengths:

    • Speed & Agility: Optimized for quick, iterative decision-making and rapid adaptation.
    • Action-Oriented: Strongly emphasizes taking action and learning from the results.
    • Competitive Advantage: Designed to outmaneuver opponents by creating disequilibrium.
    • Continuous Learning: The “Act” phase generates new observations, feeding directly back into the loop for continuous improvement.
    • Applicable at Various Scales: Can be used for individual decisions, team dynamics, or organizational strategy.

Weaknesses:

    • Risk of Hasty Decisions: The emphasis on speed can sometimes lead to decisions made with incomplete information if not balanced with sufficient “Orient” time.
    • Requires Strong Orientation: The “Orient” phase, where sense-making and mental model updating occur, is critical but can be challenging to do effectively under pressure.
    • Can Overlook Deeper Issues: Its rapid, reactive nature might sometimes prioritize immediate action over deeper systemic understanding.
    • Cultural Fit: Requires a culture that tolerates rapid iteration, experimentation, and learning from failure.

Real Options Analysis (ROA)

Borrowed from financial markets, ROA views strategic investments as “real options:” opportunities, but not obligations, to take future actions (e.g., expand, defer, contract, abandon) based on how uncertainties unfold. It values the flexibility inherent in certain investments, especially in volatile environments.

Strengths:

    • Values Flexibility: Explicitly quantifies the value of strategic flexibility and adaptability, which traditional NPV (Net Present Value) methods often miss.
    • Manages Uncertainty: Provides a framework for making decisions when future outcomes are highly uncertain, allowing for staged commitments.
    • Reduces Downside Risk: By having the option to abandon or scale down, it can limit potential losses.
    • Encourages Staged Investment: Promotes breaking down large, uncertain projects into smaller, reversible stages.

Weaknesses:

    • Complexity & Data Requirements: Can be mathematically complex and requires estimates of volatility and other parameters.
    • Difficulty in Application: Identifying and valuing “real options” can be more challenging than valuing financial options due to their unique nature.
    • Assumes Rationality: Like many financial models, it assumes a degree of rational decision-making, which may not always hold in practice.
    • Not a Standalone Solution: Best used as a complement to other strategic planning tools, not a replacement.

Multi-Criteria Decision Analysis (MCDA)

MCDA (also known as Multi-Criteria Decision Making, MCDM) is a structured approach for evaluating and comparing alternative options when there are multiple, often conflicting, criteria and objectives. In sustainability, these criteria often span environmental (e.g., GHG emissions, biodiversity impact), economic (e.g., cost, ROI, job creation), and social (e.g., equity, community well-being, public health) dimensions. Various techniques exist within MCDA (e.g., AHP, ELECTRE, PROMETHEE) to weigh criteria and score alternatives.

Strengths:

  • Handles Complexity: Effectively manages decisions with numerous competing objectives and diverse data types (quantitative and qualitative).
  • Transparency: Makes the decision-making process explicit, showing how different criteria are weighted and how options perform.
  • Facilitates Trade-off Analysis: Helps decision-makers understand the compromises involved in choosing one option over another.
  • Supports Stakeholder Engagement: Can integrate diverse stakeholder preferences and values into the evaluation process.

Weaknesses:

  • Subjectivity in Weighting: The assignment of weights to criteria can be subjective and prone to bias.
  • Data Intensive: Requires significant data for each criterion and option.
  • “Garbage In, Garbage Out”: The quality of the output depends heavily on the quality of input data and the chosen criteria.
  • Can Be Complex to Implement: Some MCDA methods require specialized software and expertise.

Cost-Benefit Analysis (CBA) and Cost-Effectiveness Analysis (CEA)

Cost-Benefit Analysis quantifies all costs and benefits of a proposed action in monetary terms to determine if the benefits outweigh the costs. In sustainability, this often involves monetizing environmental and social impacts (e.g., value of avoided climate damages, health benefits from cleaner air). Cost-effectiveness analysis compares the costs of different interventions that achieve the same outcome (e.g., reducing carbon emissions) but focuses on which option achieves that outcome most efficiently (e.g., cost per ton of CO2 reduced). These have traditionally been leveraged in environments ranging from enterprise operations and strategy to climate and sustainability.

Strengths:

    • Economic Efficiency: Provides a clear economic rationale for decisions, appealing to economic stakeholders and policymakers.
    • Comparability: Allows for direct comparison of disparate projects or policies on a common economic metric.
    • Transparency (in theory): Forces explicit articulation of assumptions and valuations.

Weaknesses:

    • Difficulty in Monetization: Many environmental and social benefits (e.g., biodiversity, ecosystem services, aesthetic value) are hard to quantify and monetize, leading to underestimation.
    • Ethical Concerns: Critics argue that not all values should be reduced to monetary terms.
    • Distributional Impacts: CBA often focuses on aggregate net benefits, potentially overlooking who bears the costs and who receives the benefits (equity issues).
    • Discounting: Long-term impacts (common in climate change) are heavily discounted, potentially making future benefits seem insignificant.

Adaptive Management (and Adaptive Governance)

This is a systematic approach for improving management policies and practices by learning from the outcomes of implemented actions. It treats interventions as experiments, monitors their effects, and adjusts future decisions based on what is learned. It’s an iterative cycle of planning, acting, monitoring, evaluating, and adjusting. Adaptive governance extends this to multi-stakeholder and multi-level decision contexts.

Strengths:

    • Learning in Action: Particularly valuable for complex systems like ecological or climate systems where perfect prediction is impossible.
    • Flexibility & Resilience: Enables continuous adaptation to changing conditions and new information.
    • Reduces Risk: Allows for small-scale experiments before large-scale commitments.
    • Stakeholder Engagement: Often involves ongoing participation of stakeholders in monitoring and adjustment.

Weaknesses:

    • Requires Strong Monitoring: Demands robust and sustained monitoring programs.
    • Time & Resources: Can be slower than traditional “decide-then-implement” approaches and requires dedicated resources for learning loops.
    • Institutional Barriers: Can be challenging to implement in rigid bureaucratic structures that prefer fixed plans.
    • Complexity: Can be difficult to attribute specific outcomes to specific interventions in complex systems.

Participatory Approaches & Deliberative Processes

Given the diverse stakeholders and contested values in sustainability, these approaches prioritize inclusive engagement. They involve bringing together various groups (e.g., community members, Indigenous peoples, policymakers, industry representatives, scientists) to deliberate, share perspectives, build common ground, and co-create solutions. Examples include citizen assemblies, stakeholder forums, consensus conferences, and co-design workshops.

Strengths:

    • Legitimacy & Ownership: Decisions made through participatory processes are often seen as more legitimate and are more likely to be implemented successfully.
    • Addresses Power Imbalances: Can help ensure marginalized voices are heard.
    • Generates Diverse Solutions: Taps into a wider range of knowledge, experiences, and creativity.
    • Builds Social Capital: Fosters trust, understanding, and collaboration among diverse groups.
    • Addresses Ethical and Equity Concerns: Central to achieving “just transitions” and equitable climate action.

Weaknesses:

    • Time & Resource Intensive: Can be slow and require significant facilitation expertise.
    • Risk of “Tokenism”: If not genuinely inclusive, can lead to frustration and disengagement.
    • Managing Conflict: Requires skilled facilitation to navigate differing interests and potential conflicts.
    • Scaling Up: Challenging to implement effectively at very large scales.

– – –

There are endless decision making frameworks, and so this list is far from exhaustive. But it intends to provide a prompt for thinking strategically and intentionally about the how of decision making.

Which of these frameworks resonates most with the decisions you’re facing right now? Are there others you’ve found especially useful (or overrated)? I’d love to hear what’s working and not working in your context.

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