How to Strategically Plan for 2025 as a Business Owner | Entrepreneur

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Scaling a business in 2025 will require a strategic approach, blending preparation, execution and follow-through. As leaders prepare for annual strategic planning, success hinges on both clarity of vision and disciplined execution.

Drawing on three decades of experience in helping companies scale, applying the 10 Rockefeller Habits has consistently yielded improved growth, revenue and profitability for businesses that follow these principles.

To ensure your strategic planning session for 2025 is impactful, here are the essential components, key lessons from Scaling Up, and common mistakes to avoid.

What is strategic planning, and why does it matter?

Strategic planning is often thought of as a single activity, but it should be viewed as two distinct processes:

Strategic Thinking involves your senior leadership team and focuses on long-term strategic issues. The key is regular meetings—weekly, not just quarterly or annually—so leaders can focus on big-picture challenges without getting bogged down in day-to-day operations.
Execution Planning: Once the strategy is set, a larger team engages in execution planning. This process involves setting annual and quarterly priorities, establishing KPIs and aligning resources to meet goals.

Together, these two components form the Think, Plan, Act, Learn cycle, which drives clarity and organizational focus.

Creating a communication rhythm to support strategic planning

Communication rhythms are crucial to ensuring that information flows accurately and efficiently. Establishing a daily, weekly, monthly, quarterly and annual rhythm is one of the most powerful ways to engage your entire organization in executing the plan.

Here’s how these rhythms can support your strategic planning:

Daily Huddle: A brief 5-15 minute meeting involving all employees to track progress and address immediate challenges.
Weekly Meeting: A 60-90 minute session to review progress on quarterly priorities and tackle one or two strategic issues.
Monthly Management Meeting: A half-day or full-day session with executives to learn and resolve significant problems.
Quarterly and Annual Planning Meetings: These offsite meetings, involving executives and middle managers, should focus on four decisions: People, Strategy, Execution and Cash.

By maintaining these rhythms, you ensure alignment and clarity across the organization, enabling faster decision-making and smoother strategy execution.

How to effectively run your strategic planning meetings

Consistency is key to the productivity of strategic planning sessions. Annual sessions typically last two to three days, while quarterly sessions take one to two days. Here is an agenda breakdown:

First Third of the Meeting:
- Review the SWOT analysis and update the first three columns of your One-Page Strategic Plan (OPSP), focusing on the Big, Hairy, Audacious Goal (BHAG) and Core Values.
Second Third:
- Examine your company’s financials to assess cash flow. Define specific priorities for the upcoming year.
Final Third:
- Focus on process improvement strategies. Select one process to redesign and improve for the quarter. Review the Rockefeller Habits Checklist and select one or two habits to refine.

Mistakes to avoid during strategic planning

While the structure of your planning session is crucial, avoiding common pitfalls is key to its success. One mistake is neglecting employee and customer feedback. Planning in a vacuum limits effectiveness, so it’s essential to survey employees and customers beforehand to gather insights on what to start, stop, and continue doing. Incorporating their input creates a more grounded and actionable plan, keeping your team highly engaged as they implement their own ideas.

Another pitfall is jumping into an operational review too early. Diving into past performance details at the start can cause the meeting to get bogged down in minutiae, distracting from the broader strategic vision. Additionally, a lack of consistent communication can undermine even the best plans. Establish a clear communication rhythm with daily huddles, weekly meetings and monthly reviews to ensure alignment and smooth execution.

Strategic planning in action: A case study

Take the example of Jack Harrington, the former CEO of Virtual Technology Corporation, who scaled his company dramatically after being acquired by Raytheon. Harrington implemented the Rockefeller Habits, including daily huddles and quarterly planning sessions, which improved alignment, strategic thinking and collaboration. As a result, his company transitioned smoothly into a $750 million division within Raytheon, with enhanced clarity and execution across the team.

Running a strategic planning session is not just about the meeting itself — it’s about the discipline, rhythm and focus you instill throughout the year. As we look ahead to 2025, it’s crucial to understand that scaling a business requires more than ambition. It demands structured processes, robust systems and continuous iteration to ensure alignment and execution.

The Think, Plan, Act, Learn cycle is at the core of successful strategic planning. It balances long-term vision and short-term execution. This cycle fosters an environment where strategic decisions are not only discussed but also consistently reviewed and refined, ensuring the organization remains adaptable and aligned.

Establishing communication rhythms, such as daily huddles and weekly, monthly and quarterly meetings, is pivotal in reinforcing this alignment. These practices foster real-time problem-solving and ensure everyone — from the executive team to frontline employees — stays focused on the company’s most important goals. These daily interactions maintain clarity, accountability and momentum throughout the year.

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