Deal Sparring Partner: The 8-Step Checklist

A Deal Sparring Partner stress-tests your deals before you are in the room. They ask the questions your prospect will ask. They find the holes before the deal does. This is the system Simon Severino uses with 2,400+ B2B founders in software, consulting, and financial services.

The Deal Sparring Partner Prompt

Paste this into Claude or ChatGPT. It interviews you about the one deal you want most right now, then hands you your opener, your ask, your walk-away, and the question you are not asking yet.

The 8-Step Checklist

Work through these in order. Every step must be complete before moving to the next.

Step 1 ... Rapport and Trust

Have you mirrored, paced, and led? You cannot move to Step 2 until trust is established. The prospect's body language and tone will tell you when you are there.

Step 2 ... Frustration

What is the frustration? What has the prospect already tried? What has not worked? Surface the real pain, not the presenting symptom.

Step 3 ... Importance and Context

How important is this problem in the context of everything else going on? Connect the problem to what matters most to them right now. If it does not rank in their top 3, it will not move.

Step 4 ... Cost of Inaction

What happens if they do nothing? Let the prospect say the consequence out loud. Do not say it for them. Silence is a tool.

Step 5 ... Deliverables

What do they want to achieve? Deliverables for the next 10 days. The prospect defines success in their own words. This becomes the basis of the SOW.

Step 6 ... Investment

Time investment first. People investment second. Monetary investment third. Never lead with price.

Step 7 ... Starting Date

To which starting date are you committing? A specific date, not "soon" or "next week." Commitment is the close.

Step 8 ... Statement of Work

SOW sent via PandaDoc or DocuSign before the next meeting. Ready to sign. This is not a draft.

The 8 Steps, at a Glance

Rapport at the base. The signed Statement of Work at the peak.

Where This Comes From

None of this is theory invented on the spot. It is in Time Freedom, the book Simon wrote with Jay Abraham this year.

“Jay and Simon compress decades of hard-won breakthroughs into clear, actionable business strategies. Each chapter pays for itself in time saved and revenues added.”

— Verne Harnish, Founder, Entrepreneurs’ Organization (EO) & Scaling Up

Time Freedom · Jay Abraham & Simon Severino · on Amazon

One More Free Gift: Sales Coach

Sales Coach is a free Claude Code plugin: pre-call coaching in 5 minutes, built on this same 8-step system. Tell it who you are meeting and it preps your call.

www.strategysprints.com/tools — free download, email required.

Want to install this system in your sales team? Simon Severino has helped 2,400+ B2B founders double revenue in 90 days using the 8 Steps of the Repeatable Sale. Book a 30-minute conversation: calendly.com/simonseverino/coffee-with-simon

www.strategysprints.com