Five Questions to Guide Your 2026 Strategic Planning

I’ve been writing a version of this post since 2021, when I was standing in line at Disneyland for the kiddo’s 6th birthday and learned what the COVID delta variant was. The last few years might have left you thinking, why even plan when it’s all chaos? 

Because whether or not you’re ready to move, the timeline continues. My kiddo is 10 now. And whether or not I love the economic environment of the next two or three years, we’ve got milestones to reach and goals to achieve.

When US policy seems to be set by a drunk elephant on a rampage, the urge to wait and see is strong. Standards have been uncertain, supply chains ever-changing. If you’ve been trying to grow or sustain a business, you’ve undoubtedly done your share of primal screaming.

It’s been hard to feel hopeful or like we can count on things. But despite the shaky climate, your centering principles probably haven’t changed. Your risk tolerance and frameworks are likely similar. Planning is a process of looking at the current situation and making a plan based on who you are relative to what you know.

Planning and setting goals are hopeful acts. They bring intention and direction to each day. And when opportunities arise or circumstances change, they help us act quickly and decisively.

See my tips for holding onto (or cultivating) that abundance mindset

5 Questions to Guide Your Business Planning Process

As a business strategy consultant, every plan starts with open questions. Sometimes we get so busy with things like margins and taxes and hiring that we forget to ground ourselves in why we’re doing this and where we want to go. 

I use these five questions to inform the strategic planning process. You don’t need any data or financial reports, or even any deep thinking time. Your answer is right for you, right now.  

  1. Why do I do this work? (Or, what purpose do I want to fulfill?)
  2. What’s my vision for where I want this business to go and how fast do I want to get there? 
  3. How much do I want to pay myself to make this feel worthwhile? (Own it. Write down a number.)
  4. What revenue goal do I want to hit in 12-18 months? (No judgment. Choose the number of zeros.)
  5. What are some things in the business I don’t like doing, or ways that I’m thinking, that are holding me back? Am I working in my zone of excellence or my zone of genius?

 

We can design and run a company in infinite ways. These foundational questions, what I call centering principles, are your real strategic work. We use these to filter the tactics, revenue sources, team, and partners that are right for you.

The right plan for you is the one that aligns with what you want to bring into the world. ​

If you’re wondering whether working with a business strategy consultant is right for you, read this.

Focused Strategic Planning for Your Small Business

As a founder, you imprint your attitudes and approaches onto your company. Honor that and be intentional about it. Once a year, check in on how you have evolved, and how your thinking has changed. 

We can make plans all day that solve for how. Margins, products, services, and people – it’s a puzzle I love to solve. But first, take the time to get grounded and honest in what YOU want, what you believe, and where you want to go. 

Do this core work and you’ll see more clarity and focused action from forecasting or strategic planning, now or in the future. When you get the next alert that you have five minutes to avoid being trampled by a drunken elephant, you’ll be prepared. 

If you’d like to talk through any of these questions, grab 20 minutes with me this week. And don’t forget to subscribe to my newsletter for my most up-to-date tips on growing and running a small business.

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Not sure where to start? Click here to book a free strategy session with Jill.

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