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The Five Questions Every One Page Plan Must Answer. How to Use AI to Get There

  • Writer: Dan Cholewa
    Dan Cholewa
  • Oct 14
  • 3 min read
A clipboard checklist and glowing lightbulb beside bold text “The Five Questions Every One Page Plan Must Answer,” representing clarity and strategy in business planning with AI.

Most entrepreneurs waste weeks writing business plans that end up sitting in a drawer. Pages of goals, paragraphs of vision statements, endless bullet points that never get used. The truth is that most business owners do not need a 40-page binder. They need one page that forces clarity, cuts out the fluff, and answers the only questions that matter.

 

If your plan cannot fit on one page, you will not use it. And if you do not use it, you are leading blind.

 

Here are the five questions every one page plan must answer. I will also show you how to use AI prompts to break them down so the plan does not just sit there but actually drives your business forward.


Question 1. Where are you now

 

Every plan starts with brutal honesty about your current reality. What are your numbers, your strengths, and your weaknesses. Without this baseline you cannot measure progress.

 

In real estate this could mean knowing your cost per lead, your cost per closing, and your conversion rate by source. It also means recognizing where you are strong, like a high referral rate, and where you are weak, like poor follow-up systems.

 

AI Prompt Example:

“Here is my last twelve months of transactions, lead sources, and expenses. Summarize my current business performance. Identify three strengths and three weaknesses that I should be aware of before building my plan.”

 

AI takes raw data and tells you the truth without sugarcoating it.


Question 2. Where are you going

 

A one page plan needs a clear destination. This is not a vague vision statement about growth or success. It is a specific target. For example, growing from 24 transactions to 36. Increasing net margin from 25 percent to 35 percent. Expanding into a new neighborhood farm and owning ten percent market share within three years.

 

AI Prompt Example:

“Based on my current production, suggest three realistic growth goals for the next 12 months. Make them specific and measurable so I can track them.”

 

Now instead of dreaming, you have direction.


Question 3. How will you get there

 

This is the execution piece. What strategies and actions will actually move the needle. Most entrepreneurs get stuck here because they confuse activity with strategy. Posting more on social media is not a plan. Building a referral system that drives 30 percent more past client closings is a plan.

 

AI Prompt Example:

“Here are my current lead sources and conversion rates. Recommend three strategies I can use to increase my production by 30 percent next year. Show me how each strategy connects directly to my goals.”

 

This moves you from a wish list to a roadmap.


Question 4. Who is responsible

 

A plan without ownership is useless. Every major initiative must be assigned to someone who is accountable. In a solo real estate business that might be you, but even then you can break it down by role. For example, you handle lead generation, your admin handles transaction coordination, and a virtual assistant handles database nurturing.

 

AI Prompt Example:

“Here are the strategies I want to implement. Assign roles and responsibilities between me, my assistant, and my virtual assistant. Clarify exactly who owns what and where I need to stay involved.”

 

This stops the cycle of writing things down and never following through.


Question 5. How will you measure success

 

If you do not define measurement, you will drift back into guessing. The final step of a one page plan is choosing the metrics you will review every single month. These are the scoreboard numbers that prove whether your plan is working.

 

For a real estate business this usually includes cost per lead, conversion rate, cost per closing, net margin, and number of closings by source.

 

AI Prompt Example:

“Here are my five business goals for the next twelve months. Recommend the top three metrics I should track monthly that will tell me whether I am on pace or off pace.”

 

Now you are not just planning. You are building a feedback loop.


Final Word

 

The one page plan is not about looking polished. It is about forcing clarity. If you can answer these five questions and then use AI to help you refine the answers, you will end up with a plan that is simple, sharp, and usable.

 

Where are you now. Where are you going. How will you get there. Who is responsible. How will you measure success. That is it.

 

Stop overcomplicating the process. Stop wasting time writing novels you will never read again. Build a one page plan, use AI to sharpen it, and then run your business with clarity instead of hope.

 

Your future depends on it.

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