The Strategist's Craft: Honing Your Inquisitive Mind and Foresight Through Intentional Practice
- Jonathan H. Westover, PhD
- 11 hours ago
- 5 min read
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Abstract: This article explores practical approaches for leaders to demonstrate strategic thinking capabilities in their daily work, a critical skill for navigating today's complex business environment. Strategic thinking—defined as synthesizing information to envision future states and formulate long-term plans—is characterized by systems thinking, change anticipation, and cross-functional perspective. The article outlines five key practices: engaging in strategic conversations that connect disparate issues; championing strategic initiatives that visibly translate strategy into action; conducting regular environmental scanning to identify emerging trends and opportunities; cultivating strategic capabilities in team members through mentorship and learning opportunities; and applying structured frameworks to analyze complex challenges. Through these deliberate practices, leaders can build credibility, earn stakeholder trust, and effectively guide organizations toward their long-term vision despite volatility and uncertainty.
Strategic thinking is a critically important skill for leaders at all levels of an organization. In today's fast-paced, constantly changing business environment, the ability to think strategically sets leaders apart and enables them to effectively navigate complexity and guide their teams towards achieving long-term goals and vision. As a strategic leader, you have a responsibility to consistently demonstrate your strategic thinking abilities so that stakeholders can trust your leadership and decision making.
Today we will explore practical ways for you to showcase your strategic skills through your everyday work.
Defining Strategic Thinking
Before diving into specific actions, it is important to define strategic thinking. At its core, strategic thinking is the process of synthesizing information to envision the future and formulate plans and actions to achieve long-term objectives (Bonn, 2005; Mintzberg, 1994). Some key characteristics of strategic thinking include:
Taking a broad, systemic view rather than focusing on isolated details
Anticipating change and its impacts
Balancing creativity with pragmatism
Aligning actions with core values and overarching goals
Thinking interconnectively across departments and functions
Questioning assumptions to gain new perspectives
Strategic thinkers focus on implementing a coherent strategy rather than reacting to short-term pressures. They connect the dots between external opportunities/threats and internal strengths/weaknesses. Let's now explore ways to demonstrate these strategic thinking abilities.
Focus on Strategic Conversations
One of the most direct ways to showcase your strategic mindset is through strategic conversations. Research shows strategic leaders spend 30-50% of their time engaged in strategic discussions (Gerry et al., 2008). Schedule regular meetings specifically focused on strategic matters with your boss, peers, and direct reports. Come prepared with thoughtful questions to stimulate strategic thinking in others rather than just reporting out updates. Ask questions that surface connections between issues rather than isolating topics (e.g. "How might shifts in the political climate impact our supplier relationships and product roadmap?"). Push discussions beyond operational details to the bigger implications and alternative scenarios.
For example, the CEO of a global hotel chain regularly conducts "strategic coffee meetings" where she meets one-on-one with different levels of leaders to discuss the industry's direction. She asks questions like "What new consumer trends do you see emerging that could disrupt our business model?" and "What untapped opportunities do you think we're missing internationally?" These kinds of probing conversations help uncover strategic insights across the organization.
Champion Strategic Initiatives
Beyond words, demonstrate your strategic mindset through visible actions and initiatives. Identify strategic projects or programs aligned with your organizational strategy and goals. Effectively championing these initiatives requires breaking large strategies into actionable components, allocating resources strategically, gaining alignment across silos, and tracking progress carefully. For all stakeholders to recognize your strategic orientation, you need to roll up your sleeves and spearhead strategically significant work.
For example, the CIO of a major pharmaceutical company led an enterprise-wide digital transformation initiative that streamlined processes, enhanced data analytics capabilities, and laid the groundwork for new virtual care offerings - all strategic priorities for remaining competitive amid changing industry dynamics. His hands-on project leadership signaled to the C-suite and board his strategic framing of IT's role beyond day-to-day operations.
Conduct Environmental Scanning
As a strategic thinker, you need to continually assess trends, threats and opportunities in your industry, technology landscape, political/regulatory space and broader environment. Schedule recurring time on your calendar for environmental scanning activities like reading industry reports, attending conferences, speaking with thought leaders, talking to customers, and monitoring innovations in adjacent industries. Then, look for ways to apply insights from your scanning to your organization's strategic direction.
For example, a hospital CEO takes a day each quarter for environmental scanning activities after which she shares her observations and discoveries in a board meeting. Discussions around population health trends, care delivery innovation pilots, and healthcare payment reforms directly influence their strategic plan updates. Her scanning ensures strategy remains closely tethered to emerging realities.
Cultivate Strategic Mindset in Others
One sign of great strategic leadership is developing strategic thinking abilities in those around you. Investing in the strategic growth of others burnishes your reputation as a long-term oriented leader. Provide strategic learning and development opportunities such as strategic off-sites, executive coaching or leadership books/podcasts to listen to together. When mentoring direct reports, have strategic career discussions focused on big picture aspirations rather than just task-oriented goals. Praise strategic insights from others and encourage constructive debate around strategic questions.
For example, the incoming CEO of a utilities company facilitated strategy "office hours" where anyone could drop in to discuss strategic issues on their mind. This fostered a culture where strategic thinking was considered everyone's job, not just senior leadership's. It also helped surface new strategic perspectives from across divisions.
Apply Strategic Frameworks
Lastly, demonstrate your strategic acumen through structured analyses using strategic frameworks like Porter's Five Forces, PESTEL/PESTLE, SWOT, scenario planning or innovation frameworks. Lead strategic planning efforts employing such models, or include frameworks in presentations and reports. Applying frameworks shows your ability to systematically break down complexity and derive implications. It also leaves an imprint of your strategic mindset on key organizational artifacts like strategic plans and board reports.
For instance, a university provost led an environmental scanning process applying a PESTEL analysis to systematically understand political, economic, social, technological, environmental and legal trends impacting higher education. This robust yet elegant analytical approach engendered confidence that strategy appropriately accounted for the institution's context.
Conclusion
In today's VUCA (volatile, uncertain, complex and ambiguous) world, effective leadership requires the ability to think strategically. Consistently demonstrating strategic thinking through your work helps connect stakeholders with your long-term orientation and solution-based mindset. This practitioner-focused essay has aimed to equip leaders with concrete actions and examples for communicating their strategic acumen on a daily basis through strategic conversations, initiative leadership, environmental scanning, developing strategic skills in others, and leveraging strategic frameworks. By cultivating opportunities to shine a light on your strategic thinking, you can positively influence strategy formulation and build credibility as a strategic leader.
References
Bonn, I. (2005). Improving strategic thinking: A multilevel approach. Leadership & Organization Development Journal, 26(5), 336–354.
Gerry, J., Kershaw, C., Van Bergen, P., & Newton, B. (2008). Measuring strategic performance: The balanced scorecard and beyond. Measuring Business Excellence, 12(1), 3–14.
Mintzberg, H. (1994). The rise and fall of strategic planning: Reconceiving roles for planning, plans, planners. Free Press.
Jonathan H. Westover, PhD is Chief Academic & Learning Officer (HCI Academy); Chair/Professor, Organizational Leadership (UVU); OD Consultant (Human Capital Innovations). Read Jonathan Westover's executive profile here.
Suggested Citation: Westover, J. H. (2026). Unpacking the Dynamics of Illegitimate Tasks: How Variability and Previous Experiences Ignite Job Crafting and Meaningful Work. Human Capital Leadership Review, 22(2). doi.org/10.70175/hclreview.2020.22.2.4
