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How AI Helps Executive Leaders Visualize And Communicate Strategy

Jason Diamond Arnold

May 26, 2026

How AI Helps Executive Leaders Visualize and Communicate Strategy

Why visualization is the most under-leveraged executive skill of the AI era — and how leaders can leverage it to help develop and execute a winning strategy.

By Jason Diamond Arnold, Director of Leadership Solutions, Inspire Software | Featuring Chris Wollerman, CEO, Inspire Software

Executive Thought Leadership Series | Part 2 of 6

Last Updated Date: May 26, 2026

Most strategies fail not because the thinking is wrong, but because the strategy fails to connect to the everyday workflows of the people tasked with executing it. Only 5% of employees can describe their company’s strategy or how their work connects to it. AI now enables executives to compress the strategy-visualization cycle from 30–40 hours to just a fraction of the time, helping your organization visualize how everyone will align and execute what matters most to the company. Executive leaders who create a compelling visualization of the annual strategy greatly increase their chances of successfully executing it.

About the Interviewee: Chris Wollerman is a Strategy Executive Coach, CEO of Inspire Software, and a recognized authority on AI-enhanced strategy execution with over 25 years of experience helping organizations develop and operationalize corporate strategy.

About the Author: Jason Diamond Arnold is a leadership strategist, executive coach, and Director of Leadership Solutions at Inspire Software. He specializes in helping organizations connect strategy, OKRs, performance management, and leadership development into a unified execution system.

 

Why must executive leaders visualize strategy before executing it?

A strategy that cannot be seen cannot be executed. Most leadership teams know how to develop a strategy. Far fewer know how to show it to the people executing it. The gap between those two skills is where most strategic value is lost before it is even operationalized.

McKinsey’s research on AI in strategy development identifies communication of corporate strategy as one of the most critical areas where AI is reshaping executive work. Leaders who leverage AI can find an immediate, practical way to better communicate a well-developed strategy.

In other words, before AI changes how you make strategic decisions, it can change how visibly you communicate them. “A clear narrative of the strategic path and objective and their implications for the organization and its stakeholders is essential to mobilizing action.”[1] Leveraging AI to visualize strategy is an immediate, lowest-risk, highest-leverage move available to most executive teams in 2026.

And the urgency to adapt to AI is significant. Inspire Software’s State of Strategy Execution in 2025 research found that only 32% of organizations feel confident executing strategy at scale, and fewer than 25% trust their AI tools or dashboards to guide real-time decisions (p. 1)[21]. That is not a minor adoption gap. It is a strategic vulnerability that compounds each quarter when leaders delay finding effective ways to make strategy visible to the organization.

“You’ve got to be able to tell a story. And visual images speak more than words alone. A visual representation of the intent of the strategy is what people can relate to.”
— Chris Wollerman, CEO, Inspire Software

Visualizing strategy is no longer a quarterly design exercise to be outsourced to a graphic designer. It is a continuous executive discipline, and one that AI now makes accessible to every leadership team. Built on the foundational research of Robert Kaplan and David Norton, refined in practice by Inspire Software partner Paul Niven, and informed by over 25 years of executive leadership insights from Inspire Software CEO Chris Wollerman, the framework presented here gives leaders a structured way to make strategy visible, accessible, and continuously aligned across every level of the organization.

 

What happens when strategy is developed well but communicated poorly?

When employees don’t know what the strategy is or how it relates to their work, they often disengage from executing it, usually without anyone at the top realizing how much drag it has on the strategy before it’s too late.

The communication gap between executive strategy and frontline work is one of the most documented and most persistent findings in modern leadership research. This gap has been visible across three eras of study:

The Historical Baseline (2001)

Robert Kaplan and David Norton’s research on strategy-focused organizations famously found that only 5% of employees understand their company’s strategy[4]. That number became one of the most cited statistics in strategic management for a reason: it captured, in a single figure, the chasm between executive intent and organizational reality.

The Modern View (2008–2022)

More recent Harvard Business Review research has only confirmed that the gap between strategy and execution still exists well into the 21st Century. Cannon and Zook found that strategy communication remains one of the least developed executive disciplines for leaders. Most leaders assume their strategy has been communicated clearly long before employees understand it [6]. Earlier work by Neilson, Martin, and Powers traced execution failure to four specific breakdowns: decision rights, information flow, motivators, and structure[7]. None of those failures is about the quality of the strategy itself. All of them are about how the strategy is, or is not, translated into shared organizational understanding.

Inspire’s 2025 proprietary evidence

Two decades after Kaplan and Norton’s original finding, the gap remains. Inspire Software’s 2025 research makes its persistence concrete: 61% of employees do not understand how they contribute to the company’s strategy, and only 29% believe their day-to-day work aligns with it[22]. Most tellingly, only 16% of employees believe their performance reviews accurately reflect their alignment with their company’s strategy [22]. This data demonstrates that even the formal mechanism designed to connect individual work to strategy is failing in the eyes of the people it is meant to align.

“If organizations don’t have a clean, simple way to communicate the strategy to everybody, they run the risk of publishing documents that most won’t read; even less will understand.”
— Chris Wollerman, CEO, Inspire Software

 

Having trouble with your strategy?

The human eye can understand a one-page picture in seconds, while a 30-page strategy document takes hours and rarely survives the first week of distribution.

The question above is not new. It belongs to Robert Kaplan and David Norton, who posed it in their 2000 Harvard Business Review article of the same name[3]. Eight years after introducing the Balanced Scorecard[2], they returned to HBR with a sharper diagnosis: even organizations using the right measures still struggled to execute, because employees could not see how the pieces connected. Their answer was the strategy map — a one-page visual showing how learning and growth drive internal processes, drive customer outcomes, and achieve financial results[5].

Paul Niven, a long-standing Inspire contributor and the practitioner who translated Kaplan and Norton’s academic framework into a working, balanced strategy, methodology[9], has spent his career helping organizations build these maps in practice. Daniel Montgomery, managing director of Agile Strategies, also an Inspire contributor, extends this thinking with what he calls Minimum Viable Strategy™ — a short, high-level statement of strategic intent that is set, reviewed, and reset far more frequently than a traditional three- to five-year plan[13]. Together, these two methodologies form the philosophical backbone of how Inspire approaches strategy visualization: rigorous enough to honor the academic origin, agile enough to survive a market that no longer rewards five-year forecasts.

Chris Wollerman points to a useful, scaled-up example of what good strategy visualization looks like in practice:

“The National Security Strategy comes out every few years. When they publish it, they do a really good job of visualizing what they’re trying to communicate. They keep it high-level. And then they have levels below it that drill down on specific initiatives.”
— Chris Wollerman, CEO, Inspire Software

There is a common executive assumption that strategy visualization is something only consumer brands or startups need to bother with. But in fact, the largest, most consequential organizations in the world have been doing this for decades. They have learned that a strategy too complex to understand becomes invisible to the people tasked with executing it and is not executed.

 

What is the MAP framework for visualizing strategy?

MAP is Inspire’s three-part discipline for turning executive intent into a one-page picture every employee can act on.

Model, Anchor, Publish.

Where Part 1 of this series introduced the SCALE framework for developing a winning strategy, MAP picks up where SCALE leaves off — now that the strategy is built and approved, it's ready to launch into the organization.

Part 1’s SCALE asked:

  • How do executive leaders develop a strategy that AI can compound?

Part 2’s MAP asks:

  • How do executive leaders make that strategy visible, accessible, and persistent?

Chris Wollerman describes the way Paul Niven teaches this in workshops, using the ground floor of a house as the foundational level and building upward through each perspective until the top floor represents financial achievement.

M — Model the strategy visually

Inspire recommends a Balanced Scorecard–style structure. For example:

  • Learning and Growth as the Foundation
  • Process and Product on the ground level
  • Customer Focus on the top floor
  • Financial Outcome is the roof that covers the building.

The metaphor matters because it applies to any business — employees recognize what a house is and intuitively understand that you cannot put up the second floor before you lay the foundation and build out the structure. The model gives every level of the organization a shared visual understanding of the strategy, floor by floor.

A — Anchor the strategy in your industry’s language

Once the structural model is in place, anchor the visual in imagery that your industry recognizes. A defense contractor will resonate with a different visual vocabulary than a healthcare network or a fintech startup.

Wollerman describes Inspire’s own 2026 strategy visual: with several strategic objectives focused on AI adoption, the team felt the right metaphor was a rocket heading into space. They fed an AI tool images of NASA’s recent Artemis mission and the Orion spacecraft and asked the model to build on those reference images with a space background. The point is not the rocket. The point is that the chosen imagery was specific to where Inspire is going as a company and, therefore, meaningful to every employee asked to help get it there.

P — Publish the strategy where work happens

A strategy map that lives only in an all-hands deck decays. The third discipline of MAP is to publish the visual where work actually happens — embedded in the platform employees use to set goals, track key results, and have their weekly check-ins.

Wollerman describes the process of placing the strategy map in the top-left corner of the strategy view in their software, so people can refer back to it as they align. This is the difference between treating visualization as a one-time art project and treating it as an ongoing operational anchor.

 

How does AI accelerate the design of a strategy map?

AI compresses the strategy MAP design cycle from 30–40 hours of graphic designer time to a fraction of that and, when used well, raises the quality of the visuals rather than lowering it.

Research from Boston Consulting Group, in collaboration with academic researchers at Harvard Business School, MIT, Wharton, and Warwick, has documented substantial gains in both speed and quality when executives use generative AI for knowledge work within the AI’s capability frontier[19] — a description that fits strategy visualization precisely. The same study cautions leaders that when AI is applied to tasks outside its areas of expertise, users are 19 percent less likely to produce correct solutions than those working without AI as experts. The lesson for executive leaders is not "use AI more." It is "use AI where it compounds your judgment and productivity, not where it replaces or complicates it." Using AI for the strategy visualization process is one of the many ways AI can help executive leaders develop, communicate, and execute a corporate strategy more effectively, not complicate it.

The opportunities to leverage AI for company strategy are wide open. Inspire’s 2025 research found that nearly 74% of leaders lack confidence in using AI to help them set and execute strategy [21]. Most organizations are not behind on AI adoption overall; they are behind on AI adoption for the specific executive work that matters most: developing, visualizing, communicating, and executing strategy.

Wollerman’s firsthand experience using AI to craft strategy maps for Inspire makes the productivity case concrete. Before AI, Inspire’s annual strategy visualization followed a familiar rhythm:

“We’ve done this every year with a graphic designer. It usually takes us at least a good week to go over my initial concept, then have the graphic designer go off and give me the first three samples. Then we go back and forth through a few more iterations over the next week or two. It’s a good 30 to 40 hours of the graphic designer’s time. That’s a lot of time for the CEO to get the strategy to a visual state to communicate to the organization.”
— Chris Wollerman, CEO, Inspire Software

With AI image-generation tools that produce editable output, that cycle now happens in hours rather than weeks. The executive team provides strategic intent and a few reference images. The AI produces three or four candidate visuals. The executive team focuses on one clean concept and refines it through conversation with AI:

  • Make it more readable
  • Adjust the perspective
  • Change the color palette
  • Simplify the composition.

The result is a finished, on-brand strategy visual ready for the all-hands meeting—and, more importantly, ready to be embedded in the systems where work happens.

This is the practical, immediate compounding opportunity executive leaders have available right now. It does not require an organizational AI transformation. It does not require a contract for an enterprise AI platform. It requires a CEO and a strategy team willing to spend a few hours with the right tools, and the discipline to treat the resulting visual as a permanent operational anchor, not a one-time slide.

 

How should executive leaders roll out the strategy to the organization?

Executive leaders need to focus on connecting departments, teams, and individuals to the strategy, rather than just cascading them and hoping for the best. Strategy rollout is a structured series of conversations that transform a Strategy Map into shared organizational meaning and focus.

The language leaders use when rolling out a strategy matters more than most organizations realize. Decades of research by Edward Deci and Richard Ryan on Self-Determination Theory (STD) identifies autonomy, competence, and relatedness as the three psychological needs that drive sustained engagement in life and work[14]. Simply cascading goals down through the organization may unintentionally erode the psychological needs of the people you're asking to execute the strategy.

Susan Fowler, a motivation theory expert and valued Inspire Software partner, has translated Self-Determination Theory research into leadership applications. In a recent article for Fast Company, Fowler champions optimal motivation as a skill that leaders can actively build[16]. Fowler says, “People do not need to be told what to do so much as they need to understand how their work connects to something meaningful[15].” McKinsey’s research on modern performance management reinforces the same principle: the systems that drive strategy forward are those that focus on people, not forms.[17].

This is why the Inspire goal-setting language favors 'connecting' goals over 'cascading' them. A cascade implies a “waterfall” effect downward on passive recipients; a connection implies a living relationship in both directions. John Doerr’s Measure What Matters reinforces the same idea operationally. OKRs work best on a quarterly rhythm with bidirectional alignment, where teams both receive direction from above and propose the objectives that will deliver on it [12].

Doerr frames it cleanly[12], “a quarterly cadence is the backbone, and the connection between strategy and execution is the spinal cord.”

The rollout cadence

Chris Wollerman recommends adopting a structured rhythm. The first two weeks before the new quarter, focus on announcing the strategy map and the high-level corporate objectives and key results (OKRs). Shortly afterward, executive owners of each strategic objective and key result enter workshop mode with the teams responsible for delivering them. These workshops are not mandates; they serve as alignment conversations where teams clarify and collaborate on what their part of the strategy means in the context of their actual work.

“Most companies that we see that struggle with strategy don’t make the time to go into a workshop phase. There’s a critical gap — they’re not thoroughly communicating and getting everybody rallying around and connecting to the strategy.”
— Chris Wollerman, CEO, Inspire Software

This is the gap where strategy disappears into the abyss of everyday work. Companies that announce the strategy and skip the workshop phase end up exactly where the research says they will: in the 5% range of employees who understand it.

Bidirectional alignment, not top-down imposition

The mechanics of rollout matter as much as the message. Wollerman is passionate about this: “teams must be allowed to align with the strategy as well as receive cascaded objectives from above. Goals that feel imposed produce compliance; goals that emerge from a genuine collaboration between corporate key result owners and the teams below them produce engagement.” Inspire’s own research reinforces the cost of getting this wrong. Only 16% of employees believe their performance reviews accurately reflect alignment with strategy (p. 12)[22]. The performance system is where the bidirectional principle either lives or dies.

 

AI WARNING: What are the data protection risks of using AI for strategy work?

Wollerman warns about the risks of using Open AI, versus protected AI tools on platforms like Inspire. “Consumer-grade AI tools — including paid Pro and Premier subscriptions — typically do not protect the data you feed them. Strategic work belongs in enterprise-grade environments with explicit data isolation guarantees.”

No serious conversation about AI in executive leadership roles is complete without a discussion of data protection. Strategic plans, financial models, customer concentration data, organizational restructuring scenarios are precisely the kinds of inputs leaders are tempted to paste into whichever AI tool is open in the browser. They are also precisely the kinds of inputs that should never leave a controlled environment.

“You do not want any employees, including the CEO and executive team, using off-the-shelf AI to develop your strategy if you don’t want it out in the open.”
— Chris Wollerman, CEO, Inspire Software

Wollerman’s caution is more specific than most readers expect, or are being exposed to. The common assumption is that paying for a Pro or Premier subscription includes data protection. It often does not. Individual paid plans on most consumer AI products still permit some training use of inputs, often by default. Real data isolation requires an enterprise account with explicit contractual guarantees that prevent prompts and outputs from being used to train future models. The cost difference is usually small. The protection difference is significant.

For executive leaders seeking a structured framework for data governance in AI-enabled work, Gartner’s A Practical Guide to Data Governance for AI-Ready Data[20] outlines the controls organizations need in place before strategy and other sensitive work move into AI-enabled environments. The principles translate cleanly to executive practice:

  • Classify your data
  • Choose tools that match the classification
  • Train every employee — including the CEO — on what belongs where.

If the strategic information would damage the company if a competitor saw it tomorrow, it does not belong in a consumer AI subscription today.

 

Why does visualizing strategy generate a competitive advantage?

Visualizing strategy genearates a competitive advantage because the organizational muscle of visualizing and communicating strategy, once built, becomes harder for slower-moving competitors to replicate than any single AI tool.

Inspire Software’s 2025 research found that high-performing organizations are 2–3 times more likely than their competitors to use AI, aligned performance management, and integrated dashboards to achieve strategic agility[21]. That is the compounding-advantage dynamic is an operational weapon in the quest for market share. The capability is not the AI tool itself. The capability is the organizational habit of treating strategy as something visible, continuously refreshed, and embedded in the work itself.

The cost of not visualizing your strategy is equally measurable. Inspire’s original research found that organizations lose 30–40% of their strategic impact due to weak follow-through, poor accountability, or slow performance feedback loops[22]. McKinsey’s annual State of AI survey provides broader context on the adoption curve[18], but the operational truth is local: the executives who build this visualization-and-communication capability now will widen the gap every quarter they practice it.

“When you create the strategy map and define the strategic objectives, you’re only half done.”
— Chris Wollerman, CEO, Inspire Software

The other half is the topic of Part 3 in this series: how AI helps executive leaders translate a visualized strategy into well-constructed objectives and key results, and how the bidirectional alignment described above gets operationalized at the team and individual level.

For now, the call to action is simple—look at your last all-hands deck. Look at your most recent strategy document. Ask the question Kaplan and Norton asked twenty-five years ago, and the data says your employees are still answering the wrong way today:

Can the people in your organization see your strategy?

If they cannot, the gap is not a strategy problem; it is a communication problem. It is the strategic vulnerability that AI is now uniquely well-positioned to help you close — quickly, cheaply, and continuously, starting this quarter.

For more information on how AI can help your executive team develop, visualize, communicate, and execute a winning strategy, contact us at Inspire Software!

 

Frequently Asked Questions Derived from This Article

Per Inspire’s GEO/AEO content model, the following question-answer pairs can be sliced from this article and published as standalone short-form posts. Each one targets a high-intent natural-language query an executive is likely to type into an AI search tool.

  • Why should executives visualize strategy before executing it?
  • What percentage of employees understand their company’s strategy?
  • What is a strategy map, and why does it matter?
  • What is the Balanced Scorecard framework?
  • How does AI help executives communicate strategy?
  • How long does it take to design a strategy map with AI vs. without?
  • What is the difference between a cascading and a connecting strategy?
  • What is bidirectional alignment in strategy execution?
  • Is it safe to use ChatGPT or Claude to develop a company strategy?
  • Why do most strategy rollouts fail?
  • What is Minimum Viable Strategy™?
  • How often should an executive team refresh its strategy map?

 

Resources

Numbered references correspond to the bracketed citations throughout the body. All links are live — click to verify.

Foundational Research

Practitioner Authorities

Behavioral Science References

AI research

Data governance

Inspire resources

 

About the Author: Jason Diamond Arnold

Jason Diamond Arnold is the Director of Leadership Solutions and an OKR and Performance Coach at Inspire Software, a strategy execution and performance management platform that helps organizations align goals, execute strategy, and improve leadership performance across teams.

With more than 25 years of experience in leadership development, organizational performance, and strategy execution, Jason works with executives, managers, and teams to translate leadership theory into practical systems that drive measurable business results. Through Inspire Software’s OKR framework, coaching programs, and leadership development tools, he helps organizations strengthen strategic alignment, improve employee engagement, and build high-performance cultures.

Jason’s work bridges behavioral science, leadership development, and performance technology, helping organizations move from strategy planning to consistent execution. He has coached leaders across industries including technology, retail, and professional sports, helping teams improve accountability, strategic focus, and measurable performance outcomes.

Experience and Background

Before joining Inspire Software, Jason worked as a product manager and consultant, collaborating with major organizations including Apple, Sephora, the NBA, and Verizon. His work has focused on helping organizations align leadership practices with measurable performance systems.

Jason is currently pursuing a PhD in Leadership at the University of San Diego and is a candidate for certification through the International Coaching Federation (ICF). He also serves as a Lecturer at the University of San Diego School of Leadership, where he teaches and researches modern leadership frameworks and organizational development.

With more than 1,000 hours of coaching and consulting experience, Jason specializes in helping organizations implement leadership systems that support strategic alignment, goal management, and sustainable performance improvement.

Areas of Expertise

  • Jason specializes in leadership development and strategy execution, including:
  • OKR Implementation and Coaching: Helping organizations implement Objectives and Key Results (OKRs) to align teams around measurable strategic goals.
  • Leadership Development and Organizational Coaching: Supporting leaders in building effective leadership practices that drive accountability, engagement, and performance.
  • Strategic Alignment and Performance Management: Helping organizations connect leadership behaviors, team goals, and measurable performance outcomes.
  • Managerial Leadership and Self-Leadership: Equipping managers and employees with the tools to align individual performance with company strategy.
  • Performance Excellence and Behavioral Leadership Science: Using research-based leadership frameworks to help organizations improve team performance and operational efficiency.

Coaching Impact

  • Jason has helped organizations improve leadership performance and operational outcomes across industries.
  • Examples of his work include:
  • Global Retail Organization: Led leadership alignment and strategic restructuring initiatives that improved operational efficiency by 30 percent.
  • Professional Sports Organization: Coached leadership teams to align career development with strategic goals, improving team collaboration and performance by 25 percent.
  • Technology and Software Teams: Implemented coaching and leadership alignment programs that increased engagement and improved goal achievement metrics by 40 percent.

Leadership and Thought Leadership at Inspire Software

As Director of Leadership Solutions at Inspire Software, Jason helps shape how leadership development integrates with strategy execution technology.

He has contributed more than 100 thought leadership articles, research projects, eBooks, and podcasts focused on leadership, OKRs, and performance management. His work helps organizations combine leadership development with modern strategy execution tools to create cultures of accountability, alignment, and sustained performance.

At Inspire Software, Jason’s work focuses on aligning leadership theory, behavioral science, and technology to help organizations build high-performing teams and execute strategy more effectively.