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July 2, 2025

‘Tis The Season For Planning… Or Is It? Building Year-Round Strategic Agility

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Seasonal planning cycles are a thing of the past. As strategic planning begins earlier each year, organizations that treat planning as a core capability, not a calendar event, are gaining a competitive edge.
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July 2, 2025

Russ Lange

Partner

A fervent believer in the promise of human powered growth, Russ leads CMG in partnering with companies to help them become aligned, agile, customer-driven enterprises that unleash the potential of their organizations with sustainable improvements in focus, teams, culture, and process our clients.

About The Author

Mark Chinn

Partner

Mark leads CMG in partnering with Telecom companies to help them increase customers and accelerate revenue. His 25+ years of experience in growth, strategy and execution includes B2C and B2B multi-channel acquisition programs, customer experiences that surprise and delight, pricing that optimizes customer value, and innovative product development.

Blog by Gary Lancina

Walking through a store this past weekend, I spotted something that stopped me in my tracks: full aisles of Halloween decorations gleaming under the summer sun (or, actually LED lighting). Seeing this "Summerween" phenomenon in multiple retailers, got me pondering how businesses approach the timing and preparation of plans and budgets.

Retailers have learned that getting ahead of seasonal demand creates competitive advantage. The same principle applies to strategic planning, yet most organizations still treat it like a once-a-year Halloween, scrambling when October (or nowadays July) suddenly arrives.

The New Reality of Business Planning

Remember when strategic planning was a September affair? Those days are gone. Today's planning cycles increasingly begin just after the Fourth of July, with market research compressed into the first half of the fiscal year and strategic plan refreshes hitting leadership agendas  in the heat of summer.

This acceleration isn't arbitrary.  It's driven by fundamental market realities. Leaders can't afford surprises, investors demand clarity on future expectations, and competitive windows open and close faster than ever. The result? The second half of most fiscal years requires a complex dance of execution, projection calibration, and future planning that extends through year-end board approvals.

Across industries, the refrain is remarkably consistent: "It snuck up on us again," or "We're being asked to commit to next year while this quarter remains uncertain," or simply, "Really? Already?" The anxiety is real, the timeline pressure intense, and the stakes feel higher than ever.

From Seasonal Scramble to Strategic Rhythm

The organizations that thrive in this environment have discovered a fundamental truth: planning isn't a seasonal activity, it's a core organizational capability. Instead of treating strategy, annual plans, and budgets as discrete events, they've woven them into the ongoing rhythm of running the business.

Think of these elements as layers of detail rather than separate exercises:

  • Strategy establishes your long-term trajectory, setting enduring objectives that guide major decisions and resource allocation
  • Annual plans translate strategy into actionable waypoints: defining concrete steps for the next phase of your journey
  • Budgets provide the fuel allocation to reach those waypoints, sometimes accelerating progress when opportunities arise, other times preserving resources while maintaining momentum

The Power of Integrated Business Planning

The most sophisticated organizations recognize that these planning elements create feedback loops. When unexpected conditions present opportunities or challenges, budget adjustments follow. Significant progress or setbacks may require new waypoints or even strategic recalibration.

Organizations that embrace this interconnected approach—call it agile planning, integrated business planning, or whatever resonates with your culture—create several competitive advantages:

  • Elimination of Planning Surprises - When planning becomes part of the organizational DNA, July strategy sessions feel natural rather than jarring. Teams expect and prepare for these conversations because they're already engaged in ongoing strategic dialogue.
  • Enhanced Market Responsiveness - Continuous planning cycles enable faster response to market changes. Instead of waiting for annual planning windows, organizations adjust course as conditions evolve.
  • Improved Stakeholder Alignment - Regular planning conversations keep all levels of the organization aligned on priorities, progress, and potential pivots. This consistent engagement reduces the communication burden during formal planning periods.
  • Stronger Financial Performance - Organizations with mature planning processes demonstrate better resource allocation, more accurate forecasting, and improved ability to capitalize on emerging opportunities.

Building Your Planning Capability

Transforming planning from a seasonal scramble to a strategic advantage requires intentional capability building. The most successful implementations share several characteristics:

  • Cultural Integration: Planning conversations become part of regular business reviews, team meetings, and leadership discussions rather than special events.
  • Cross-Functional Engagement: Breaking down silos between strategy, product management, sales, marketing, operations, and finance creates more comprehensive and realistic plans.
  • Scenario Planning: Regular consideration of multiple futures builds organizational agility and reduces the shock of unexpected changes.
  • Continuous Market Intelligence: Ongoing research and customer feedback inform planning discussions throughout the year rather than just during formal planning windows.

Coming Next Week: A Conversation About Planning

Stay tuned for a video conversation next week where I will be moderating a candid discussion between CMG’s Kim Scribner and Virginia Brady on three timely planning themes:

  1. The inflection point halfway through the year
  2. Preparing for planning
  3. Why it’s hard (and how to do it better)

This conversation will dive deeper into the ideas I’ve only just scratched the surface of in this blog and will offer practical insight into making planning a more strategic and less stressful part of your year.

Moving Beyond Seasonal Thinking

Done properly—and there are indeed myriad details involved in doing this well—planning and budgeting lose their seasonality. They become embedded organizational capabilities that drive competitive advantage rather than annual stress tests.

At CMG, we've helped organizations large and small transform their planning approaches, moving from reactive scrambles to proactive strategic advantage. The result? Leadership teams that feel confident about their direction, stakeholders who understand the path forward, and organizations that adapt quickly to changing conditions.

Unlike Halloween decorations in June, some business practices are better when they transcend their traditional seasons. Strategic planning is one of them.

Ready to move beyond seasonal planning scrambles? Let's discuss how your organization can build year-round strategic agility that drives competitive advantage.