Last Updated Date: April 27, 2026 | Authored by Jason Diamond Arnold | Executive Thought Leadership Series
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.
AI does not replace executive judgment when developing a corporate strategy; it dramatically expands the depth, speed, and quality of analysis that informs strategic decisions. Organizations that embed AI into their strategy process are compressing planning cycles, continuously refreshing competitive intelligence, and generating richer organizational insights at every level.
McKinsey & Company's recent research, How AI is Transforming Strategy Development, calls this "a new inflection point in strategy design”—potentially on par with the creation of late-20th-century core strategic frameworks. This research explains how forward-thinking executive teams are using AI to build 21st century winning strategies and connect them to measurable execution.
Every executive team faces a version of the same problem: the pace of market change has outrun the pace of strategic planning. Annual strategy cycles built on static data and quarterly reviews designed around slow-moving competitive landscapes are increasingly mismatched with reality. According to Gartner, many organizations are expected to shift from piloting to operationalizing AI by 2026 and those that haven't, risk falling measurably behind.
For decades, strategic planning followed a familiar rhythm:
The process was rigorous but limited by the cognitive and analytical bandwidth of a small group of senior leaders. The volume of available data far exceeded their capacity to process it.
AI is fundamentally changing that equation. McKinsey's landmark research identifies five distinct roles AI plays in the strategy process — Researcher, Interpreter, Thought Partner, Simulator, and Communicator — each strengthening and accelerating the analysis that underpins strategic decisions while mitigating challenges posed by human biases and the social dynamics of strategy. According to McKinsey's 2024 Global Survey on AI, 72% of organizations now use AI in at least one business function, up from 55% to just one year prior.
The question for today's executive leaders is not whether AI will transform strategy development. The question is whether they are positioned to lead that transformation within their own organizations.
The generative AI era in business effectively began with the public release of ChatGPT in late 2022. For most executive leaders, that moment prompted curiosity mixed with skepticism.
Chris Wollerman describes the rapid evolution of AI technology:
2022–2023 was the prehistoric age of AI. Then 2024 brought rapid adoption. Last year -(2025) brought us AI agents. And now it has evolved into AI workflows through co-work.
That trajectory from novelty to agents to co-work mirrors what Microsoft has described as the "three waves of Copilot". By 2026, AI co-work environments will have become practical, scalable tools for executive teams. Leaders who have not yet meaningfully integrated AI face a growing risk. As Wollerman puts it, "If leaders aren't embracing AI to improve workflow by now, they're probably going to be out of a job very soon."
This prediction by Inspire’s CEO isn’t a “fear of missing out” scare tactic; it is the new reality. Organizations with AI-enabled strategy processes are compressing the time required to develop, validate, and refresh strategic insight. Those operating without it are competing at a disadvantage that compounds with each planning cycle; not only jeopardizing the job security of executive leaders, but entire organizations.
The challenge with conventional strategic planning is not that the frameworks are wrong — SWOT analysis, competitive benchmarking, scenario planning, and customer voice inputs remain foundational. The challenge lies in executing those frameworks at the speed and depth modern markets require.
A SWOT analysis is a strategic framework for evaluating an organization's Strengths, Weaknesses, Opportunities, and Threats to inform decision-making and direction.
AI enhances SWOT analysis by:
An AI-enhanced SWOT analysis also helps to identify patterns humans may overlook, resulting in a more comprehensive, data-driven, and less biased strategic assessment.
A thorough SWOT analysis requires synthesizing perspectives from individual contributors, functional managers, business unit leaders, and the executive team, potentially hundreds of data points reflecting different vantage points. It requires interpreting competitive intelligence that is constantly shifting, grounding self-assessment in honest customer feedback, and doing so without the distortions of organizational hierarchy and confirmation bias.
Traditional processes handle these challenges imperfectly and slowly. AI meaningfully improves the organization's capacity to address them.
Effective executive teams using AI in strategy development are not replacing their strategic process; they are supporting each of its four foundational advantages.
The most immediate application of AI in strategy development is in the SWOT analysis. A SWOT analysis is the process by which organizational insight flows from employees and teams (where strategy is executed) to the executive suite (where strategy is developed and adjusted).
AI is not just a tool for senior strategists; it elevates the quality of input at every level. Wollerman describes this transformation:
We used AI to get better survey questions and asked employees to use AI in their responses. The responses we got were pretty elaborate and more meaningful because of how AI can prompt individuals to tell the unique stories of the people executing the strategy throughout the organization.
When employees use AI to deepen their own understanding before submitting strategic input, the quality of data reaching executive decision-makers improves substantially. Through Wollerman’s experience at Inspire, helping executive leaders develop and execute strategy, organizations using AI-assisted internal crowdsourcing reports receive more meaningful, detailed responses from employees at all levels.
Wollerman also describes a hybrid synthesis method:
I wrote my own SWOT summary, then asked AI to do something similar and compared the two. I merged those into a more meaningful analysis.
This process maintains the priority of executive judgment while using AI as a reliable, objective second opinion. This hybrid approach to utilizing AI for strategy development exemplifies human-AI collaboration that produces insights neither method could achieve alone.
Competitive analysis has traditionally been one of the most resource-intensive elements of strategy development. A landscape study completed in Q1 is often materially outdated by Q3. Most organizations lack the capacity to refresh more than once a year.
AI dramatically changes that equation. As Wollerman believes, “Competitive analysis is one area where AI is very powerful. And it keeps getting better!"
When it comes to the rapid changes AI is challenging his executive team to keep up with, the Inspire CEO reflects on how his team has responded by changing the rhythm of competitive analysis itself:
We've decided to do a thorough competitive analysis every quarter because competitive advantages are evolving so quickly, and we will likely schedule a weekly competitive sanity check-in using AI features.
McKinsey's research confirms that AI tools can scan public data across millions of companies, monitor competitor announcements, track patent filings, and synthesize trend signals into structured insights at a pace and scale no human team can match. For executive leaders, this means competitive intelligence can shift from a periodic exercise to a continuous strategic input, grounding decisions in substantially more current intelligence than annual review processes ever allowed.
No AI capability can substitute for genuine customer insight. Wollerman emphasizes, "If your customers' voice is not woven into your strategy, you're not really developing a strategy that serves your customers or stakeholders."
AI can interpret existing customer data, synthesize reviews, and identify emerging patterns in customer behavior — but it cannot generate the proprietary, relationship-grounded insight that comes from direct engagement (1). Research from Forrester consistently shows that companies that systematically integrate customer voice into strategic planning significantly outperform those that rely solely on internal assumptions (6).
Proprietary customer information will become even more critical as external data becomes increasingly affordable through AI. As Wollerman puts it, "Customer voice is not just a soft input to your strategy; it is a strong competitive advantage."
As AI provides more data to leaders tasked with developing the company’s strategy, the need for strong data analytics skills grows. McKinsey research highlights this advantage:
The proliferation of data and insights elevates the importance of separating signals from noise. The strategic decisions that matter most — where to compete, where to invest, what bold commitments to make, what “noise” to ignore — will always be human decisions. (1)
What AI changes is the quality of information leaders have when making those calls. Research from Boston Consulting Group suggests that executive teams using AI-augmented scenario planning can explore significantly more strategic options in the same time frame and report higher confidence in their final choices. (7)
When AI handles the heavy lifting of research and analysis, executive teams can spend more time on the work they do best: aligning workflow across the business, weighing risk and opportunity, and rallying the organization behind a clear direction.
Developing a winning strategy is not about a “mountain-top experience” created during an executive retreat. Developing a strategy that the organization can execute requires preparation, endurance, and the right tools at each stage of the ascent to achieve it.
The Four Advantages of Using AI to Develop Strategy outline the capabilities AI now provides to executive teams. But capabilities alone are not a system. Leaders need a structured approach to put those advantages to work.
That is why Inspire Software is introducing the SCALE Your Strategy framework — a five-step model designed to help executive teams scale the strategy mountain by integrating AI across every phase of strategy development and execution process.
S — Surface organizational intelligence through an AI-enhanced crowdsourcing SWOT analysis. Elevate the quality of strategic input from every level of the organization before the executive team begins developing a strategy.
C — Compete through continuous AI-powered competitive intelligence. Replace annual competitive reviews with a quarterly rhythm that keeps strategic decisions grounded in current reality, while also staying at the forefront of waves and trends.
A — Anchor the strategy in an authentic customer voice. Ensure proprietary customer insight, not just AI-processed public data, is woven into every strategic choice.
L — Leverage human-AI hybrid synthesis for decision-making. Use AI to expand what leaders think they know and how quickly they can test their assumptions, while preserving the executive judgment that only humans can provide.
E — Execute by connecting the strategy to a continuous performance management process. Bridge the gap between strategic direction and organizational action by connecting goals, using OKRs, and creating insights through continuous performance conversations, feedback, and recognition in the flow of performance.
*Note: SCALE as used here is distinct from models that use the term "scale" in other business contexts, such as BCG's work on organizational agility at scale. Inspire's SCALE framework is specifically designed for AI-enhanced strategy development and execution, helping leadership teams navigate the full ascent from insight to measurable results.
The organizations seeing the greatest benefit use AI to expand available information and pressure-test assumptions, not to treat AI output as a finished strategic product. The need for Leadership and people connections isn’t going away.
Organizations that curate rich internal data ecosystems — employee input, customer voice, operational performance data — generate meaningfully differentiated strategic insight. McKinsey's research suggests that organizations with the strongest proprietary data practices consistently extract more actionable insights from AI tools than those relying solely on publicly available data.
The quality of the strategic process is far more important to a strategy's success than the quality of any individual insight. AI accelerates insight generation; it does not substitute the need for rigorous processes, structured scenario analysis, or the discipline to follow through.
Organizations that treat competitive intelligence as a continuous process refreshed quarterly will consistently out-position those running annual competitive reviews. AI makes that cadence feasible for the first time.
Developing a winning strategy is essential, but without an effective execution system, it cannot succeed. Research consistently shows that many strategic initiatives underperform not because the strategy was wrong, but because execution was fragmented, goals were disconnected from priorities, feedback loops were too slow, and accountability was never tracked.
This is the gap that separates strategy as an aspiration from strategy as a competitive advantage. Closing it requires execution infrastructure that connects strategic direction — goals, OKRs, competitive priorities — directly to individual and team performance. Strategy must become visible at every level of the organization. Execution must become measurable.
That means translating strategic priorities into clear, connected objectives and sustaining momentum through the disciplines of an effective feedback loop — Check-Ins, CFRs (Conversations, Feedback, and Recognition), 360s, and performance reviews — rather than relying solely on annual planning cycles. Inspire Software was built to bridge the gap between strategy and execution, connecting AI-enhanced strategy to OKR alignment and continuous performance management (also greatly enhanced by Inspire’s AI tools) so that the organization’s strategy is operationalized, tracked, and refined as the year unfolds.
The integration of AI into strategy development is a permanent shift in what is possible and what is necessary. Organizations that build AI-enhanced strategy capabilities will compound that advantage over time. Those who ignore AI to support their strategy will find it increasingly difficult to close the gap.
A great strategy has always required the courage to commit to bold moves. AI gives today's executive leaders something they have never had before: the analytical depth, the competitive intelligence and organizational clarity to make those moves with greater confidence and execute them with greater precision and speed.
That is not a marginal improvement. It is a structural advantage.
Inspire Software helps organizations align strategy with performance to drive effective execution and employee engagement through meaningful, measurable results. To learn how Inspire can help your executive team build and execute a winning strategy, request a demo or contact sales@inspiresoftware.com.
AI is transforming strategy development by accelerating the analytical work that underpins strategic decisions, such as competitive intelligence, SWOT synthesis, scenario modeling, and trend monitoring. McKinsey identifies five roles AI plays: Researcher, Interpreter, Thought Partner, Simulator, and Communicator. According to McKinsey's 2024 Global Survey, 72% of organizations now use AI in at least one business function.
No. AI augments human judgment; it does not replace it. The bold commitments that determine competitive position and the synthesis of complex signals all require executive judgment. McKinsey's research suggests that as AI makes insight generation easier, the value of executive synthesis increases.
SCALE is a five-step model developed by Inspire Software for integrating AI across strategy development and execution: Surface, Compete, Anchor, Leverage, Execute. It provides a practical structure for operationalizing AI in strategic planning and connecting strategy to measurable performance.
AI-powered tools make quarterly updates strategically advisable. Organizations shifting from annual to quarterly refresh cycles gain substantially more current intelligence to inform decisions. AI can scan millions of companies, monitor announcements, and track patent filings at a pace no human team can match.
Customer voice remains a non-negotiable input AI cannot synthesize from public data alone. Forrester Research found companies integrating customer voice into planning are 1.6x more likely to exceed revenue goals. Proprietary customer insight becomes even more critical as external data becomes accessible through AI.
Research shows 60–70% of strategies underperform due to execution failure, not strategy failure. Inspire Software bridges this gap with AI-assisted OKR building, goal alignment, and continuous performance management — creating a closed loop between strategic direction and organizational performance.
The gap between a well-crafted strategy and meaningful results has never been more visible — or more closeable. Inspire Software is built for exactly this moment, helping organizations align strategy with performance so that every goal, every OKR, and every weekly check-in drives execution that moves the business forward. If you're ready to see how AI-powered strategy and performance tools work together in a single, integrated system, we invite you to experience it firsthand. Visit inspiresoftware.com to schedule a demo and discover how Inspire helps your leadership team turn strategic intent into measurable outcomes.
This article was produced by Inspire Software as part of its Executive Thought Leadership Series. For permissions, syndication, or media inquiries, contact sales@inspiresoftware.com.
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.
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.
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.