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:
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A structured retreat-style planning session
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Alignment between leadership, staff, and stakeholders
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Clear 1–3 year goals with 90-day action plans
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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)
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2-hour virtual retreat with key staff and board
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SWOT + Needs/Assets Analysis
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Define 1–3 year goals + next 90-day actions
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Strategic Report & Toolkit for implementation
Option 2: Full-Day Deep Dive Retreat ($4,000)
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Full-day virtual retreat with leadership team
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Visioning + Mission & Values refinement
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Strategic training for board/staff
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SWOT, 10–20 year dream visioning, 1–3 year goal setting
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Strategic Report & Implementation Toolkit
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What You Get
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Strategic Planning Report
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90-Day Action Templates
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Tools to create Objectives, Metrics & Accountability Structures
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Buy-in from staff and board
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A sustainable path to execution
Who It's Ideal For
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Nonprofit and for-profit leaders needing a clearer path forward
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Organizations preparing for growth, change, or strategic initiatives
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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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