Why the Perfect Time for Strategic Planning is Right Now

Tim Weisheyer
Feb 28
3 min read

Updated: Mar 21

Ever found yourself wondering when to kickstart that strategic plan?

You're not alone. Many leaders grapple with this question, often falling into the trap of waiting for the "perfect moment." But here's a secret: the best time to plan is always now. Let's dive into why immediate action trumps perfect timing and how you can set your organization on the path to success, using insights from experienced leaders like Tim Weisheyer.

Strategic Planning: It's Like Planning Your Dream Vacation

Tim Weisheyer, CEO of Strategic Advantage Consulting, offers a refreshingly simple analogy: strategic planning is much like planning a vacation. This approach helps demystify the process and makes it more accessible to everyone in your organization.

Pre-Planning and Goal Setting: Choosing Your Destination

Just as every great vacation starts with picking a destination, strategic planning begins with defining clear goals. Ask yourself:

Where do we want to go as an organization?
What does success look like in the short and long term?
What are our core values and mission?

Budget Allocation: Planning Your Travel Budget

Once you’ve chosen a destination, you determine your travel budget. Similarly, organizations must allocate resources effectively to support strategic initiatives. This involves:

Reviewing financial capacity and funding sources
Identifying areas to reallocate funds
Ensuring investments align with priorities

Start Planning Your Business Strategy

Facilitation: Guiding the Creation of Your Strategic Plan

Just as a well-organized itinerary sets the stage for a successful vacation, a well-facilitated strategic planning process ensures your organization remains focused and aligned. This includes:

Facilitating productive discussions with stakeholders and leadership teams
Conducting an environmental scan to identify key industry trends and insights
Collaboratively prioritizing initiatives that support long-term organizational goals

Implementation: Booking Your Flights and Accommodations

After planning your vacation, the next step is making bookings. In strategic planning, this equates to executing key initiatives, which involves:

Assigning responsibilities to teams
Setting timelines and benchmarks
Establishing accountability measures

Seizing the Moment: Why Now is Always the Right Time

Picture this: It's a crisp Monday morning in February 2025. Your team is buzzing with post-holiday energy, and the year stretches ahead like a blank canvas. Sounds like the ideal time to plan, right? While certain periods might seem more conducive to strategic thinking, the truth is that waiting for the perfect moment can actually hinder your progress.

As management guru Peter Drucker once said, "The best way to predict the future is to create it." By starting your strategic planning process today, you're not just predicting your organization's future – you're actively shaping it.

The Strategic Sweet Spots

While any time is a good time to plan, certain periods offer unique advantages for strategic thinking:

Early Bird Gets the Worm (January - February):

The start of the year brings a fresh perspective and renewed energy. With fewer competing events on the calendar, your team can focus deeply on planning and goal-setting, setting the tone for the months ahead.

Back-to-School Mindset (Late July - Early September):

As summer winds down, the "back-to-school" mentality naturally shifts focus towards planning and goal-setting. Leverage this time to dive into strategic thinking and prepare for the final stretch of the year.

Ongoing Process:

Remember, strategic planning isn't a one-and-done deal. Successful organizations view it as an ongoing process, not just an annual event. Keep the momentum going year-round.

Keeping the Momentum: Your Implementation Timeline

Once your plan is set, keep the momentum with this schedule:

Monthly: 30-60 minute strategy check-ins
Quarterly: 2-hour department reviews and 4-hour organizational reviews

Flexibility & Adaptation

Tim Weisheyer’s leadership experience, including his role with the Greater Orlando Aviation Authority, highlights the importance of adaptability. Whether planning a vacation or a strategy, adjusting to changing circumstances is key.

Engaging the Team

Like planning a family vacation, strategic planning requires collaboration. Weisheyer’s success in building teams of like-minded leaders underscores the value of involving key stakeholders.

Maximizing Value

Just as you seek to get the most out of your vacation budget, optimize your strategic investments by:

Leveraging technology and innovation
Focusing on high-impact initiatives
Continuously measuring and adjusting

The Bottom Line: Just Start

As John C. Maxwell said, “The secret of your success is determined by your daily agenda.” By starting now, you’re setting a powerful course for your organization’s future. The benefits of clear strategy and alignment far outweigh waiting for the “perfect” time.

By applying Weisheyer's vacation planning analogy and combining it with a structured approach to strategic planning, organizations can approach this crucial process with clarity, purpose, and even a sense of excitement. After all, planning for your organization's future should be as engaging and rewarding as planning for that dream vacation!