In my role as an Online Business Manager (OBM), I often see small business owners in “survival mode.” They’re juggling client work, day-to-day operations, and marketing, which leaves little time to step back and plan strategically for the future.
If that sounds familiar, it might help to know it’s a common issue. About 1 in 4 small business owners (23%) say they’re stuck in survival mode and unable to focus on long-term planning, according to KeyBank’s 2025 Small Business Survey of U.S. small business owners.
Fortunately, strategic planning doesn’t have to be a complicated process. It’s as simple as taking some time to step back and ask questions about goals, roles, and priorities.
These are a few of the questions I like to bring up when I help clients with strategic planning for their small business.
Strategic planning questions OBMs often ask
1. Why does this matter or why now?
Before jumping into a new idea or plan, it’s worth asking why it matters. Why is this important? Why now? And how does it move you closer to your top goal? Strategic planning works best when every idea feeds into your larger goal.
2. What does success actually look like?
“More revenue” or “more clients” are obvious answers, but how can we narrow it down so it’s more defined and easier to measure? How much revenue? How many clients? When your idea of success is measurable it’s much easier to design a strategy leading us there.
3. What role do you want to play?
It’s easy to assume the main role, but is it your best option? We see many business owners taking on far more than they should. Strategic planning is a good time to step back and decide what you want to focus on. What work energizes you? What could you move off your plate? A big part of my work as an OBM is helping clients focus on the areas where they add the most value.
4. Who can take ownership of the areas you want to hand off?
Once we define priorities and the role you want to play, the next step is deciding who should own different parts of the plan. That could be a team member, a contractor or an OBM. Asking yourself, “Who is best suited for this?” builds a stronger team and keeps the business from depending too much on you alone.
5. What’s our backup plan if things don’t go as planned?
Not every plan goes through as expected, which is why we try to be both optimistic and practical when doing strategic planning. By considering the possible obstacles and sketching out backup plans, we stay flexible and prepared.
Start your planning with foundational questions like these. It’s the best way to get out of survival mode and into planning for success in your business.
These questions are examples taken from our work with clients. If you’re curious about how a certified OBM works, click to learn about our Online Business Manager services.
Also, see our recent post for a closer look at what to expect with an OBM: Tips for Success When Getting Started with Your OBM.
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