48 Playbooks That Turn Weaknesses into Value

Each playbook is an interactive, guided workflow. Not a PDF. Not a checklist. A step-by-step process that produces real deliverables and moves your Exit Score.

Get My Free Exit Score

Every playbook targets a specific reason buyers walk away.

👤

Personal

4 playbooks · Prepare yourself for the transition
Financial Independence Calculator
Calculate your personal financial independence number. See the gap between projected exit proceeds and what you need for your desired lifestyle.
~45 min6 steps
Post-Exit Identity Planning
Explore what comes after the exit. Define your next chapter, assess readiness for the identity shift, and build a personal transition plan.
~30 min5 steps
Family Alignment Workshop
Align family members on exit timing, expectations, and post-exit roles. Guided conversation framework that prevents surprises.
~60 min4 steps
Deal Fatigue Prevention Plan
Prepare for the emotional marathon of a deal process. Set boundaries, build support systems, and create decision frameworks for high-stress moments.
~25 min5 steps

Financial

15 playbooks · Clean up, optimize, and demonstrate financial strength
Tax Strategy & Structure Review
Review your entity structure, identify tax optimization opportunities, and prepare for the tax implications of an exit transaction.
~60 min8 steps
Financial Statement Cleanup
Audit your financial statements for buyer readiness. Identify personal expenses, inconsistencies, and presentation issues that raise red flags.
~90 min7 steps
EBITDA Normalization
Identify and document add-backs that increase your normalized EBITDA. Owner compensation, one-time expenses, and discretionary spending.
~45 min6 steps
Revenue Quality Analysis
Assess recurring vs. one-time revenue, contract strength, retention rates, and revenue predictability. Buyers pay premiums for quality revenue.
~45 min6 steps
Working Capital Optimization
Analyze your working capital cycle. Identify opportunities to improve cash conversion and reduce the working capital adjustment in a deal.
~40 min5 steps
Financial Projections Builder
Build defensible 3-year financial projections. Bottom-up methodology that buyers and their advisors can validate.
~75 min8 steps
Margin Improvement Roadmap
Identify and prioritize margin improvement opportunities. Every point of margin expands your valuation multiple.
~50 min7 steps
Pricing Power Assessment
Evaluate your pricing strategy and competitive position. Demonstrate pricing power that buyers value in acquisition targets.
~35 min5 steps
Cost Structure Analysis
Map fixed vs. variable costs, identify operational leverage, and highlight cost synergies a buyer could realize.
~40 min5 steps
âš™

Operational

13 playbooks · Build a business that runs without you
Owner Dependency Reduction
Map every function you perform and build a delegation plan. The single biggest factor in transferability scoring.
~60 min8 steps
Management Team Strength Assessment
Evaluate your leadership team against buyer expectations. Identify gaps and build a development plan for key leaders.
~45 min6 steps
Key Employee Retention Plan
Design retention mechanisms for critical employees. Stay bonuses, non-competes, equity plans, and transition agreements.
~50 min7 steps
SOP Documentation Program
Create a standard operating procedure library for critical business processes. Makes the business operable by anyone, not just you.
~90 min8 steps
Technology & Systems Audit
Inventory your technology stack, assess technical debt, and identify systems that need upgrading before a transition.
~45 min6 steps
Vendor & Supply Chain Resilience
Assess supplier concentration, contract terms, and backup options. Single-source dependencies are red flags in due diligence.
~35 min5 steps
Quality Management Review
Document quality standards, track metrics, and demonstrate consistent delivery. Quality systems signal operational maturity.
~40 min5 steps
Scalability Assessment
Evaluate whether your business can grow 2-3x without proportional cost increases. Buyers pay premiums for scalable operations.
~35 min5 steps

Legal

9 playbooks · Eliminate legal risks before due diligence
Corporate Housekeeping Audit
Review corporate governance, minutes, filings, and records. Messy corporate housekeeping kills deals and reduces multiples.
~75 min9 steps
Intellectual Property Audit
Inventory and protect your IP: trademarks, patents, trade secrets, proprietary processes. Unprotected IP is a deal risk.
~60 min7 steps
Contract & Agreement Review
Audit customer contracts, vendor agreements, and partnership terms. Identify change-of-control clauses and assignability issues.
~60 min7 steps
Employment Compliance Check
Review employment agreements, contractor classifications, benefits compliance, and potential exposure areas.
~50 min6 steps
Regulatory Compliance Audit
Map industry-specific regulatory requirements and verify compliance. Non-compliance discovered in due diligence is a deal breaker.
~45 min6 steps
Data Privacy & Security Review
Assess data handling practices, privacy policy compliance, and cybersecurity posture. Critical for any business handling customer data.
~40 min6 steps
Involuntary Exit Preparedness
Plan for the unplanned. Key-person insurance, succession protocols, and emergency operating procedures.
~35 min5 steps
Partner & Shareholder Alignment
Review operating agreements, buy-sell provisions, and shareholder rights. Misaligned partners derail deals.
~45 min6 steps

Market & Growth

8 playbooks · Demonstrate market position and growth potential
Customer Concentration Analysis
Map revenue concentration, calculate your HHI index, and build a diversification strategy. Top customer representing >20% of revenue is a red flag.
~45 min7 steps
Value Driver Acceleration
Identify and amplify the 3-5 value drivers that have the most impact on your multiple. Focused execution that moves the needle fastest.
~50 min6 steps
Strategic Growth Plan
Build a credible growth narrative with supporting data. Buyers pay for demonstrated growth momentum and addressable market opportunity.
~60 min7 steps
Brand & Reputation Strengthening
Assess brand strength, online reputation, and market perception. Build a plan to strengthen positioning before going to market.
~40 min5 steps
Market Timing Analysis
Evaluate industry cycle position, M&A market conditions, and optimal timing for your exit. Timing can mean a 2x difference in multiples.
~35 min5 steps

Deal Prep

12 playbooks · Run the deal process like a professional · Deal Room plan
Valuation Benchmarking
Compare your valuation against industry benchmarks, recent comparable transactions, and public company multiples.
~45 min6 steps
Deal Team Assembly
Build your advisory team: investment banker, M&A attorney, tax advisor, wealth manager. Evaluation criteria and interview guides.
~40 min5 steps
Buyer Mapping & Targeting
Identify and categorize potential buyers: strategic acquirers, PE firms, family offices, and individuals. Build your target list.
~50 min7 steps
CIM Preparation
Build your Confidential Information Memorandum. The document that sells your business. Guided section-by-section creation.
~120 min12 steps
Data Room Preparation
Organize and populate your virtual data room. Checklist of every document buyers expect, organized by category.
~90 min10 steps
Deal Structure Options
Understand and evaluate deal structures: asset vs. stock sale, earnouts, seller financing, rollover equity. Know what to expect.
~45 min6 steps
Negotiation Preparation
Develop your negotiation strategy: walk-away price, priority terms, concession hierarchy, and BATNA analysis.
~50 min7 steps
Transition Planning
Plan the post-close transition. Knowledge transfer, customer introductions, team retention, and your earn-out performance plan.
~60 min8 steps
Due Diligence Preparation
Prepare for buyer due diligence before it starts. Anticipate questions, prepare answers, and organize evidence.
~75 min9 steps
LOI & Term Sheet Review
Evaluate and negotiate Letters of Intent. Guided framework for assessing terms, identifying red flags, and comparing multiple offers.
~40 min6 steps

Take the Assessment. Get Your Personalized Recommendations.

The assessment identifies your specific gaps, then recommends the playbooks with the highest dollar impact on your valuation.

Get My Free Exit Score
Free · 4 minutes · Personalized playbook recommendations included
Exit Playbooks | Exit OSx | Exit OSx