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Getting the Most from Your AI Advisor

The Living Company March 11, 2026 10 min read Beginner 2 views

Getting the Most from Your AI Advisor

Your AI Advisor is a strategic thinking partner powered by Claude. It does not give you answers — it helps you think more clearly by asking the right questions and challenging your assumptions. Here is how to get the most from it.


How the AI Advisor Works

The AI Advisor is specifically designed for strategic planning conversations. It:

  • Asks Socratic questions — Guides you to discover insights rather than handing them to you
  • Uses your organization data — References your customers, competitors, financials, and team by name
  • Captures insights automatically — As strategic insights emerge in conversation, they are extracted and saved
  • Remembers context — Uses both recent conversation and semantically relevant past discussions
  • Adapts to your phase — Adjusts its guidance based on which planning phase you are in

Tips for Better Conversations

1. Be Specific and Use Data

Instead of vague statements, provide concrete information:

Less EffectiveMore Effective
"Our sales are declining.""Our B2B sales dropped 12% last quarter, mainly in the Northeast region."
"Competitors are getting stronger.""Acme Corp just launched a product with 30% lower pricing and they won two of our top-10 accounts."
"We need to innovate.""Our product line has not had a major release in 18 months. Customer feedback shows our UX is rated 3.2/5 vs. competitors at 4.1/5."

2. Share Your Thinking, Not Just Facts

The AI is most helpful when you share your reasoning:

"I think we should focus on the healthcare vertical because our three largest customers are hospitals, and we seem to win those deals more easily. But I'm not sure if that's a big enough market."

This gives the AI material to work with and challenge.

3. Be Open to Challenge

The AI is designed to push back respectfully. When it asks a challenging question, do not dismiss it — engage with it. The best strategic insights often come from examining assumptions you took for granted.

4. Use the "Ask Claude" Prompts

Each phase has guided questions in the right panel. Click on any question to send it to the AI. These are carefully designed to guide you through the most important aspects of each phase.

5. Reference Your Organization Data

In the LEARN phase, expand the data reference panels on the right side to see your customers, competitors, products, and financials. Mention specific names and numbers — the AI will incorporate them into its analysis.

What the AI Captures Automatically

As you converse, the AI automatically extracts and saves:

  • Insights — Key findings tagged by category (environment, industry, customers, competitors, own realities)
  • Priorities — Strategic priorities as they are discussed and refined
  • Gap Statements — Current state and future state definitions
  • Competitive Focus — Your market, customer, and offering choices
  • Winning Proposition — Your value proposition statement
  • Leadership Message — The What/Why/How/How Much framework

You can see captured items in the workbook panels. If something was captured incorrectly, you can edit it directly.

Handling Long Planning Sessions

You do not need to complete everything in one session. The platform saves your progress automatically. When you return:

  • The AI has access to your full conversation history
  • It uses semantic search to find the most relevant past discussions for your current question
  • All captured data (insights, priorities, etc.) is preserved
  • You can pick up exactly where you left off

Running Example Scenarios

If you want to see how a full planning conversation looks, click Run Example in the planning interface. Five industry examples are available:

  1. TechParts Manufacturing — Automotive parts facing overseas price competition
  2. GreenValley Regional Health System — Healthcare under reimbursement pressure
  3. Chapters Books & Media — Retail bookstore facing digital disruption
  4. Summit Community Credit Union — Financial services vs. fintech
  5. Westlake University — Higher education with enrollment decline

Each example walks you through the LEARN and FOCUS phases with realistic prompts and responses.

Exporting Your Work

Click the Export button in the planning toolbar to download your plan as:

  • JSON — Raw data for integration or archiving
  • PDF — Formatted document for sharing with stakeholders
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