20 Questions Before Signing The Deal

A practical checklist with essential questions across role design, equity structure, integration & exit planning to ensure you don't sign away decision rights or lock yourself into a role you never wanted.

Most founders enter M&A negotiations focused on valuation and equity splits—only to discover post-close that they've lost control over pricing decisions, gotten stuck with uncontrollable earn-out KPIs, or trapped themselves in operational responsibilities they hoped to leave behind.
This checklist walks you through the 20 critical questions that separate successful acquisitions from miserable earn-out periods.

Distilled from 30+ M&A advisory engagements with tech services founders navigating strategic acquisitions, PE buyouts, and holding company integrations.

8-page PDF covering role clarity, KPI negotiation, equity mechanics, integration planning, and exit protections. Access yours now.

What You Get

● 20 Critical Pre-Deal Questions - Structured across 5 categories, each with clear rationale for why founders who skip these questions regret it post-close.

● "Why It Matters" Context for Every Question - Real scenarios showing what goes wrong when these questions aren't answered. 

● Readiness Self-Assessment - Score yourself on how many questions you can confidently answer right now, if you're below 80%, this checklist shows exactly where your blind spots are before you enter final negotiations.

● Next Steps Framework - Clear guidance on how to use this checklist with your advisors and the holding, whether you take it to your M&A lawyer or use it to pressure-test the deal structure with experts.

Who Is This For

This checklist is for tech services founders and CEOs in active M&A discussions who need to validate their deal structure before signing, including:

● Founders reviewing term sheets or LOIs, who need to identify gaps and negotiate protections before deal terms are locked

● Leaders 6-12 months from expected closing, who are in earn-out conversations and need to define post-acquisition roles and decision rights

● Leaders considering strategic acquisitions or PE buyouts, who are committed to staying post-deal but unclear on what that commitment actually entails

Use this checklist when you're preparing for term sheet discussions, reviewing your employment agreement and earn-out structure, or trying to get written clarity on integration plans and future role expectations before closing.

How To Use This Playbook

1. Answer what you can (self-assessment)Go through the 20 questions and mark which ones you can confidently answer today. If you're scoring below 80%, don't panic, this is your wake-up call to get clarity before you're locked into deal terms.

2. Take it to your advisors
Share this checklist with your M&A lawyer, financial advisor, and the buyer's integration lead. Push for written answers, not verbal assurances. Questions that get "we'll sort it out later" responses are exactly the ones that derail founder transitions.

3. Negotiate protections before you sign
Use the gaps you've uncovered to strengthen your employment agreement, earn-out structure, and governance terms. If critical questions remain unanswered or the holding is evasive, that's a signal to pause and get external advice before proceeding.