Plan Like a Pro: Lessons in Strategy and Leadership for Small Businesses

Every Battle is Won Before It Is Fought

Plan Like a Pro

Strategy and Leadership for Small Business: Lessons from The Art of War

This morning, as I was reading The Art of War, I came across this passage: “Li Ching of the Tang proposed ten plans to be used against Hsiao Hsieh, and the entire responsibility of commanding the armies was entrusted to him.”

My first thought was, “Ten plans? That seems like overkill.” But the more I thought about it, the more I realized how applicable this is to small business. Maybe we don’t have ten plans about one specific thing, like managing our inventory of flour, sugar, or butter, but we absolutely have more than ten plans when it comes to running the business as a whole.

Li Ching’s story is a powerful reminder of two key lessons: the value of strategic planning and the importance of trusting leadership to carry those plans out. Let’s explore how these lessons can help you strengthen your small business.

Strategic Planning: More Than Just a To-Do List

Strategic planning isn’t about writing down tasks and calling it a day. It’s about creating a roadmap that moves your business forward while preparing for the ripple effects of your decisions.

Think Strategically
Start with a clear goal and break it down into actionable steps. Identify the resources you’ll need and assign responsibility for each part.

Example: If your bakery’s goal is to increase holiday sales, your strategy might include launching a pre-order system for pies, setting up a display for festive treats, and running a social media campaign to promote your offerings. Each step moves you closer to the goal while addressing specific needs.

Anticipate the Ripple Effects
Every decision has layers of consequences—what are often called first, second, and third-order effects. Thinking through these layers can help you prepare for challenges and uncover opportunities.

  • First Order Effect: The immediate, direct impact of your decision.
  • Second Order Effect: The indirect consequences caused by the first effect.
  • Third Order Effect: The further-reaching, long-term impact of the second effect.

Example: Suppose you decide to introduce a new holiday breakfast box at your bakery.

  • First Order Effect: You attract more customers and see an initial boost in sales.
  • Second Order Effect: You may need to train your team to assemble the breakfast boxes efficiently or , or your kitchen space could become strained with the added workload.
  • Third Order Effect: Over time, your bakery becomes known for its holiday breakfast offerings, which might shift customer expectations and influence your long-term brand identity.

By thinking through these layers, you can plan for challenges and opportunities beyond the immediate results.

Plan for the Unexpected
Contingency planning isn’t about expecting everything to go wrong—it’s about having a backup plan just in case.

Example: If your supplier can’t deliver a key ingredient on time, having a backup vendor ensures you can keep production running smoothly without delays.

Trusting Leadership: Empowering Others While Staying Accountable

The best plans mean nothing without strong execution, and execution requires strong leadership. Whether you’re leading directly or delegating to your team, clear authority and accountability are essential.

Empower Without Micromanaging
Micromanagement slows progress and frustrates your team, but letting go completely can lead to chaos. Strike a balance by empowering your team to make decisions within specific boundaries

Example: Your bakery staff might have the authority to approve custom cake orders under $100, while anything more complex or expensive requires your approval. This setup allows them to act quickly on smaller decisions while keeping you involved in bigger ones.

Delegate With Responsibility
Delegation isn’t about offloading tasks and forgetting about them—it’s about assigning ownership while providing support.

Example: Your bakery manager might handle staff scheduling and inventory, but you stay involved by reviewing their plans weekly. This gives them the freedom to manage day-to-day operations while ensuring alignment with your goals.

Building Multiple Plans for Success

Li Ching didn’t rely on a single plan, and neither should you. Having multiple strategies gives you the flexibility to adapt when circumstances change.

Why Options Matter
Different strategies allow you to pivot and respond effectively to the unexpected.

Example: For your bakery’s holiday marketing, you could:

  • Send out an email campaign promoting holiday specials.
  • Run a social media contest encouraging customers to share photos of their favorite treats.
  • Partner with a local coffee shop to cross-promote festive offerings.

Prioritize Where It Counts
Not all strategies will have the same impact. Focus on those that align most closely with your goals and resources.

Example: If you’re short on time, you might prioritize setting up a pre-order system for holiday pies. This could streamline operations and ensure your team stays focused on fulfilling orders, making it a better choice than designing elaborate new packaging, which may not directly impact sales.

Reflect and Refine for the Future

Once your plans are executed, take the time to reflect on what worked, what didn’t, and why. Reflection isn’t just about fixing mistakes—it’s about building on successes.

Learn From Experience
Evaluate the outcomes of your decisions and look for ways to improve.

Example: If your pre-order system worked well but strained your kitchen staff, you might schedule extra prep shifts next year to handle peak demand.

Use Data to Plan Ahead
Analyze trends and feedback to refine your approach for future opportunities.

Example: If customers loved your holiday breakfast boxes, consider expanding them into other holidays or creating year-round grab-and-go options.

Your Next Steps: Start Planning for Success

Running a small business means making decisions every day, and thoughtful planning can make all the difference. Here’s how to get started this week:

  1. Develop a Strategic Plan
    Focus on one key area—like marketing or operations—and create a plan that aligns with your long-term goals. Include a backup strategy to handle unexpected challenges.
  2. Empower Your Team
    Delegate one task this week. Set clear expectations but give your team the freedom to act within defined boundaries.
  3. Anticipate Ripple Effects
    Before making your next big decision, map out its first, second, and third-order effects. Think through how each layer might affect your business and prepare accordingly.
  4. Get Support When You Need It
    If you’re unsure how to develop a plan or delegate effectively, reach out to a mentor, colleague, or business coach with relevant experience.

Every decision you make shapes the direction of your business. By planning thoughtfully, empowering your team, and thinking through the ripple effects of your choices, you can set your business up for long-term success. It’s not about being perfect—it’s about being prepared. Start with one step today and build from there.