Strategy is not merely a plan that can be executed—it is a perspective, an approach to complexity that anticipates change before it arrives. Effective leaders do not simply react to circumstances; they cultivate a strategic mindset that enables them to maintain a competitive advantage, identify opportunities, and navigate uncertainty with confidence.
While our team offers strategic planning services, we also believe that leaders should always be strategizing—embedding strategic thinking into their daily leadership rather than treating it as an occasional exercise. Here are some of the ways you can do that in your organization.
A strategic mindset is not about rigid long-term plans. Instead, it is about maintaining agility, foresight, and continuous learning. The Harvard Business Review describes strategic thinking as the ability to "create connections between ideas, plans, and people that others fail to see."
Many leaders become consumed by day-to-day operational demands, inadvertently neglecting their responsibilities for the organization’s “tomorrow” to handle the issues of “today.” Urgent tasks often take priority over long-term positioning. However, leaders who fail to look ahead risk stagnation, missed opportunities, and increased vulnerability to industry disruptions.
So, what tools can leaders use to consistently focus on the future of their organizations?
It’s impossible to think big picture when constantly switching between tasks or drowning in meetings. Many managers remain overly involved in day-to-day execution, leaving no mental space for strategic thinking. In fact, 96% of leaders surveyed by the Strategic Thinking Institute cited lack of time as their biggest roadblock to strategic thought. This is why Bill Gates famously took “Think Weeks,” during which he retreated from the business to focus on what was ahead for the business. When leaders can stop executing temporarily, they can begin to devote more time to the strategic side of their roles.
Practical Steps:
Honestly assess how you spend your time.
Delegate tasks to empower your team and create learning opportunities for them.
Audit your schedule and eliminate or outsource unnecessary meetings.
Set firm calendar boundaries, blocking off dedicated strategic thinking time.
The “urgent” often overshadows the “important.” If you are constantly reacting to crises, you’ll never get ahead strategically. Instead, focus only on projects that directly advance the organization’s core objectives—saving time, increasing revenue, or fueling growth.
Practical Steps:
Define the most important strategic objectives of your role.
Keep these priorities front and center, saying no to distractions and competing demands.
Push back on nonessential tasks that do not align with your long-term vision.
Strategic leaders stay ahead by deeply understanding their industry’s trends, potential disruptors, and evolving customer expectations. Those who actively seek knowledge position themselves to innovate before external pressures force reactionary change. Learning about your industry, adjacent industries, and other important trends will keep you thinking ahead.
Practical Steps:
Set aside dedicated time weekly for industry research.
Join professional associations or advisory groups to stay informed.
Engage with thought leaders through podcasts, webinars, and academic journals.
Monitor competitors and industry benchmarks.
Strategic leaders challenge assumptions and examine problems from multiple angles before making decisions. Powerful frameworks like the Six Thinking Hats, mental models, the 5 Whys or the 7 So-Whats can help shift perspectives. When leaders can posture themselves to ask before answering, they engage their team and invite them into strategic problem solving.
Some of the best solutions will come from the most unexpected places. Organizations that foster curiosity and adaptability are better positioned to seize opportunities. Leaders should encourage teams to question assumptions, challenge the status quo, and propose innovative solutions.
Practical Steps:
Create forums for open dialogue where team members can share insights and trends.
Encourage scenario planning exercises to explore potential industry shifts.
Reward innovative thinking, even when it challenges conventional wisdom.
Promote cross-functional collaboration to leverage diverse perspectives.
Strategic thinking does not happen in isolation. Leaders should actively seek diverse input from their teams and colleagues. At times, external perspectives can also help break through
seemingly insurmountable barriers(we see this happen frequently in our Leadership Core Groups). Wherever the source, leaders should always engage other voices in the conversation.
Practical Steps:
When team members bring up challenges, coach them with questions like:
What possibilities have you considered?
If you were in my position, how would you approach this?
Based on your experience, what next steps do you propose?
Encourage a culture where employees know their insights are valued.
Join a peer group to regularly discuss challenges and opportunities.
Many leaders hold back from making bold moves due to fear of failure. However, calculated risk-taking is necessary for strategic success. Start with small-scale pilots and expand based on results and feedback.
Practical Steps:
Identify low-risk initiatives to test strategic ideas.
Use pilot programs to gradually introduce change.
Balance risk-taking with safeguards to prevent unnecessary disruptions.
Maintaining a strategic mindset is not a one-time effort but a continuous discipline. Leaders who commit to ongoing learning, adaptability, and proactive engagement position themselves and their organizations for long-term success.
One of the most valuable ways to think more strategically is to invite objective voices into the conversation. If you’re ready to refine your strategic approach, we offer specialized consulting services to help leaders and their organizations anticipate change and align their vision for the future. Contact us to explore more!
1Brenda Steinberg and Michael D. Watkins, “10 Ways to Prove You’re a Strategic Thinker,” Harvard Business Review: October 31, 2023.
2Rick Horwath, “The Three Roadblocks to Strategy,” Strategic Thinking Institute: October 10, 2013.
One of the most consistent fears leaders express to our team is not “what’s next,” but “who’s next?” It’s a fear that isn’t specific to one type of organization—it affects small-to-medium business owners, nonprofit CEOs, and university presidents. As leaders anticipate the future of their organizations, they are often uncertain who will take the reins when they inevitably step aside in full or in part.
An organization is only as strong as its people. One of the biggest threats to long-term success is talent leak. Losing high-potential employees isn’t just expensive—t drains institutional knowledge, disrupts culture, weakens leadership pipelines and can really set your organization’s goals back a step or two. To build a resilient, high-performing organization, leaders must take an intentional, strategic approach to retention.
Leadership is often framed as an individual pursuit, but the best leaders know the value of collaboration. Small groups harness the collective wisdom of diverse experiences, creating a space for innovative solutions and enhanced decision-making. These groups become incubators for strategic insights as leaders share best practices, test ideas, and refine approaches based on real-world experiences. Additionally, having completely objective voices around you opens you up to learning in a new way.