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Strategy 
Deep Dives

Lead with Clarity. Grow with Confidence.

Caldwell's Deep Dive is your blueprint for alignment, strategy, and actionable results.

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Why a Deep Dive?

Whether you're a nonprofit, small business, or impact-driven enterprise, operating in today's complex environment requires more than vision. You need a strategic process that engages your team, sharpens your focus, and leads to measurable action.

 

The Caldwell Deep Dive delivers:

  • A structured retreat-style planning session

  • Alignment between leadership, staff, and stakeholders

  • Clear 1–3 year goals with 90-day action plans

  • A detailed implementation toolkit

 

How it Works

Our process is designed to meet you where you are—and take you where you want to go.

 

Option 1: Focused Strategy Session ($2,500)

  • 2-hour virtual retreat with key staff and board

  • SWOT + Needs/Assets Analysis

  • Define 1–3 year goals + next 90-day actions

  • Strategic Report & Toolkit for implementation

 

Option 2: Full-Day Deep Dive Retreat ($4,000)

  • Full-day virtual retreat with leadership team

  • Visioning + Mission & Values refinement

  • Strategic training for board/staff

  • SWOT, 10–20 year dream visioning, 1–3 year goal setting

  • Strategic Report & Implementation Toolkit

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What You Get

  • Strategic Planning Report

  • 90-Day Action Templates

  • Tools to create Objectives, Metrics & Accountability Structures

  • Buy-in from staff and board

  • A sustainable path to execution

 

Who It's Ideal For

  • Nonprofit and for-profit leaders needing a clearer path forward

  • Organizations preparing for growth, change, or strategic initiatives

  • Teams experiencing misalignment or lacking execution clarity

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Ready to Get Aligned? Book your free 15-minute discovery call with Scott Caldwell and learn how a Deep Dive can help your nonprofit grow with clarity and purpose.
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If you have questions, text or call
806-367-4176

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