Software Sales On Fire

By Dean PatinoBusiness Management

Software Sales On Fire episodes

October 17Bonus Interview: 40 Years Placing Software Sales Reps — What Rich Diekmann Wishes Every Rep Knew
About this bonus episode
A special bonus conversation with Rich Diekmann, an executive recruiter who has spent 40 years placing enterprise software and SaaS salespeople — most of that career across Chicago and Wisconsin, and more recently the West Coast. Dean has called Rich "the mayor of Chicago" for years because of how many software salespeople he has placed, Dean included.
This is the inside view of how software sales hiring actually works: what recruiters do and don't do, how your resume and LinkedIn profile are really read, what hiring managers are asking for right now, and the interview habits that separate candidates who get the next step from candidates who never hear back.
What you'll learn
Why a recruiter finds people for companies, not jobs for people — and what that means for how you approach one
How companies brief a search, and why "close to our space" decides more than years of experience
How Rich vets a candidate's quota history before a company ever sees the resume
How to advertise accomplishments on LinkedIn and on your resume so a hiring manager can see you sell
What it really takes to move from SMB or mid-market into enterprise — and why enterprise isn't automatically a promotion
The biggest interview mistakes, starting with not closing for the next step
What companies praise after an interview goes well: preparation, energy, real questions, and the close
Zoom interviews are now 99.9% of the process — how to show up, and the $35,000 dress t-shirt story
Lightning round: the one question Rich wishes every rep asked, the trait hiring managers want most, what instantly impresses him on a resume, and the subtle red flag that gets reps passed over
Free downloads
Free, no signup. Every resource from this episode is on the episode page:
https://www.softwaresalesmastery.com/episodes/2026-10-17-bonus-rich-diekmann-40-years-placing-software-sales-reps
The Interview Close and Follow-Up Guide — the close Rich coaches, the questions to bring, and what to send afterward
The Sales Resume and LinkedIn Checklist — numbers first, sales language only, and a profile that agrees with your resume
AI Prompts: Rewrite Your Own Accomplishments — four prompts to quantify your history, remove support language, align LinkedIn, and rehearse the close
Scroll to the Free downloads section on that page and the files open directly.
Connect with Rich Diekmann
Rich is easiest to reach on LinkedIn, and he accepts nearly every invitation. His last name is spelled D-I-E-K-M-A-N-N. One note from Rich: he works active searches for software and SaaS sales roles, so he can help most when you already have experience in the space. He does not post jobs.
Timestamps
0:00 — Cold Open
0:28 — Welcome and Guest Introduction
1:31 — Meet Rich Diekmann — 40 Years Placing Software Sales Reps
3:20 — The One Thing Reps Get Wrong About Recruiters
6:20 — What Companies Actually Ask a Recruiter For
8:40 — How Rich Vets a Candidate's Quota History
9:35 — How to Stand Out: Advertise Your Accomplishments
12:40 — Why Working With a Recruiter Changes the Odds
14:40 — Moving From SMB or Mid-Market Into Enterprise
16:40 — How Many Years You Need to Prove Yourself
17:40 — The Biggest Interview Mistakes
20:50 — What Companies Praise After a Great Interview
23:10 — Zoom Interviews: 99.9% and How to Show Up on Camera
25:20 — The $35,000 Dress T-Shirt
27:00 — Lightning Round: The Question Every Rep Should Ask
28:20 — The Number One Trait Hiring Managers Want Right Now
29:50 — What Instantly Impresses Rich on a Resume
31:00 — The Red Flag: Sales Language vs. Support Language
32:40 — Resume or LinkedIn — Which Weighs More?
34:00 — Why Rich Never Posts Jobs
36:40 — How to Reach Rich (and the Spelling Story)
39:40 — Four Things to Write Down
Four things to write down
A recruiter finds people for companies. Make where you fit obvious.
Your numbers are your product — percentages, net new deals, ranking, year by year, matched on LinkedIn.
Write in sales language: closed, sold, hunted, net new. "Managed" and "supported" describe an account manager.
Close for the next step, not the job — and never end an interview without asking whether they see you as a fit.
About the show
*Software Sales On Fire* — ignite your pipeline, smoke your quota. Hosted by Dean Patino, with 36+ years in enterprise software sales. Get the book, *10 Secrets of Software Sales Mastery*, loaded with proven ways to generate more pipeline and win deals over the competition, at softwaresalesmastery.com.
42 min
October 16You Didn't Help Write the RFP. Should You Even Respond?
The RFP arrives and you had nothing to do with writing it. Before committing three weeks of your team's time — or walking away on principle — this episode gives you the five assessments that decide it: fit, access, evaluation rules, incumbent advantage, and response cost, and the three honest outcomes: the full response, a different play, or the professional no. Including the full role play of the rep whose two-year chase is begging him to respond.
In This Episode
Today's Pipeline Problem — what "we didn't help write it" actually tells you, the two camps that are both guessing, and the five-part investigation
The Play — What to Say and Do — read the RFP as intelligence, run the five assessments in writing, choose between the full response, a different play, and the professional no; plus the illustrated role play where Daniel's two-year chase argues for three weeks of response work
Put AI to Work — three prompts to build the intelligence brief, score your fit honestly, and draft the portal questions
The Rep Mailbag — the manager who responds to everything, the incumbent facing a rebid of his own contract, and the public-sector RFP with strict contact rules
The Inside Edge — the strongest sellers read an RFP as an intelligence document first, and treat the professional no-bid as a deposit
Your Move Today — run the five assessments on your inbox RFP inside forty-eight hours and make one of three calls
Key Takeaways
"We didn't help write it" is real information — but it tells you less than either camp believes. Wired and unwinnable are both guesses until you investigate.
Run the five assessments in writing: fit (gaps named honestly), access (legitimate channels), evaluation rules (how it's scored, who signs), incumbent advantage (you beat switching costs, not just a proposal), and response cost (in names and hours).
The deadline is for the response, not the decision — decide inside forty-eight hours, and don't let the calendar make the call.
A different play counts: clarifying questions, a scoped response, or a conversation request are often worth more than a padded full response.
The professional no — respectful, reasoned, door left open — earns more credibility than most bids, and it's remembered when the next need comes up.
Do This Today
Take the RFP in your inbox and score the five assessments in writing, including the cost in names and hours.
Make one of three calls: full response, different play, or professional no — inside forty-eight hours.
If it's the no, write the short note: respect for their process, an honest reason, a door left open.
Free Downloads
Everything below is free — no signup. Get it on this episode page: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-16-you-didnt-help-write-the-rfp-should-you-even-respond#downloads
RFP Response Decision Scorecard — The five assessments — fit, access, evaluation rules, incumbent advantage, response cost — scored in writing, with the three outcomes and the 48-hour rule. · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-16-you-didnt-help-write-the-rfp-should-you-even-respond#downloads
Clarifying Questions That Reveal the Real Deal — The questions to send through the RFP question portal — the ones whose answers most change whether a response is worth the cost. · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-16-you-didnt-help-write-the-rfp-should-you-even-respond#downloads
AI Prompts: The RFP Go/No-Go Decision — The three prompts from this episode — the intelligence brief, the honest fit score, and the portal questions. · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-16-you-didnt-help-write-the-rfp-should-you-even-respond#downloads
22 min
October 15“We Can Just Do This on Zoom.” Give Them a Reason to Meet in Person.
The buyer says “we can just do this on Zoom.” This episode shows you the response that earns a room without arguing for travel: decide whether the deal deserves one, propose a working session with the right participants and a concrete output, and give an honest reason physical presence changes the result — including the full role play of the buyer who's been burned by vendor visits before.
In This Episode
Today's Pipeline Problem — what “Zoom-only” usually means, why in-person isn't automatically better, and the one kind of meeting a screen under-serves
The Play — What to Say and Do — decide whether the deal deserves a room, design the working session, make the ask easy to accept; plus the illustrated role play where Victor pushes back and the answer treats his history as information
Put AI to Work — three prompts to design the session, write the no-marketing invitation, and build the facilitation prep brief
The Rep Mailbag — is in-person selling dead, which trips earn themselves, and the champion who keeps rescheduling the onsite
The Inside Edge — the meetings that change deals get scheduled as work, not as meetings
Your Move Today — find your quietest screen-only deal and send the working-session proposal
Key Takeaways
“Just do this on Zoom” is usually a calendar protection and a history of bad vendor visits — not rejection. Investigate before diagnosing.
Presence earns its cost for working sessions with several participants and a concrete output — not for presentations.
Ask for fewer, more relevant people and name the deliverable; no slides.
An agenda under review is not a booked session — record open dependencies honestly in your forecast.
If the buyer still says Zoom, take it and make it a real working session anyway.
Do This Today
Pick your most screen-only deal and write down what decision the customer is trying to make and what output would be useful to build together.
Draft the working-session proposal — participants by role, deliverable, half-day agenda, honest reason for the room.
Send it as a proposal, and expect a refinement — a buyer who edits your session design is already imagining it happening.
Free Downloads
Everything below is free — no signup. Get it on this episode page: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-15-we-can-just-do-this-on-zoom-give-them-a-reason-to-meet-in-person#downloads
Working-Session Agenda Template — The half-day structure: participants by role, timeboxed agenda, and the concrete output the session produces. · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-15-we-can-just-do-this-on-zoom-give-them-a-reason-to-meet-in-person#downloads
Meeting-Worthiness Checklist — Three questions to decide whether a deal deserves a room — and what to do when it doesn't. · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-15-we-can-just-do-this-on-zoom-give-them-a-reason-to-meet-in-person#downloads
AI Prompts: Earning the In-Person Meeting — The three prompts from this episode — session design, the invitation email, and the facilitation prep brief. · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-15-we-can-just-do-this-on-zoom-give-them-a-reason-to-meet-in-person#downloads
20 min
October 14Your Competitor Is 40% Cheaper. What Do You Say Next?
Your competitor came in forty percent cheaper and the CFO wants to know why they'd pay more. This episode gives you the response: five comparisons to run before any price conversation — scope, implementation, support, usage, and outcomes — and a framework for deciding whether a price response is necessary at all.
In This Episode
Today's Pipeline Problem — why a headline price is not a comparison, and what the cheaper number usually hides
The Play — What to Say and Do — stabilize the moment, run the five comparisons, then decide; plus an illustrated CFO call that ends with "send me the comparison"
Put AI to Work — three prompts to find gaps, model two-year total cost, and draft the CFO-ready one-pager
The Rep Mailbag — when the cheaper price is real, competing with cheap-and-familiar incumbents, and the manager who discounts first
The Inside Edge — the forty-percent moment is a confidence problem, not a price problem — complete the evaluation for the person who signs
Your Move Today — stress-test your most important deal against all five comparisons, in writing
Key Takeaways
Never adjust price before you know what you're comparing.
Forty percent cheaper means cheaper to buy — help the buyer find what it costs to own.
When offers are truly equivalent, trade value for value; never concede under panic.
The cheapest way to miss the outcome is the most expensive option on the table.
Do This Today
Run your top deal through the five comparisons and note where you can't answer.
Build the one-page total-cost comparison before the cheaper number appears.
Arm your champion to defend value in one minute without you in the room.
Free Downloads
Everything below is free — no signup. Get it on this episode page: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-14-your-competitor-is-40-percent-cheaper-what-do-you-say-next#downloads
Five-Comparison Worksheet — Scope, implementation, support, usage, outcomes — the five questions to run before any price response. · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-14-your-competitor-is-40-percent-cheaper-what-do-you-say-next#downloads
Total-Cost Comparison Template — The one-page, CFO-ready side-by-side: total cost to the outcome, every assumption visible and correctable. · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-14-your-competitor-is-40-percent-cheaper-what-do-you-say-next#downloads
AI Prompts: Cheaper-Competitor Response — The three prompts from this episode — gap analysis, two-year cost model, and the CFO-ready one-pager. · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-14-your-competitor-is-40-percent-cheaper-what-do-you-say-next#downloads
18 min
October 13Your Competitor Can Check Every Box, Too. Now What?
Every finalist checked the boxes, and now the decision is drifting toward price and brand. This episode gives you the four moves that shift a competitive evaluation to ground your competitors can't stand on: the buyer's own operating requirements, implementation realities, risks, and measurable outcomes.
In This Episode
Today's Pipeline Problem — why checklist ties default to price and brand, and where deals are actually decided
The Play — What to Say and Do — four moves, plus an illustrated call that turns "it's coming down to price" into an operational evaluation round
Put AI to Work — three prompts to rewrite requirements operationally, plan for failure points, and draft success criteria
The Rep Mailbag — beating a brand name, writing evaluation criteria without rigging them, and standing out in a bake-off
The Inside Edge — the evaluation format tells you who the buyer thinks is winning; be the rep who upgrades how they buy
Your Move Today — three written questions on your most contested deal
Key Takeaways
Feature checklists test the software; operating requirements test the fit.
Honest implementation planning differentiates because realism is rare.
Name risks — including your own — and raise competitor concerns only as questions the buyer should ask.
Anchor the decision to measurable outcomes the decision team signs up to track.
Do This Today
Rewrite the buyer's top five requirements as operating requirements for their environment.
Name your own implementation risk before anyone asks.
Draft ninety-day and one-year success criteria you'd let every finalist be measured against.
Free Downloads
Everything below is free — no signup. Get it on this episode page: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-13-your-competitor-can-check-every-box-too-now-what#downloads
Differentiation Planner — Move a competitive evaluation off the checklist and onto operating requirements, implementation realities, risks, and measurable outcomes. · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-13-your-competitor-can-check-every-box-too-now-what#downloads
Success Criteria Worksheet — Draft the measurable outcomes the decision team signs up to track — in the customer's language. · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-13-your-competitor-can-check-every-box-too-now-what#downloads
AI Prompts: Competitive Evaluation Prep — The three prompts from this episode — operational rewrite, failure points, and success criteria. · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-13-your-competitor-can-check-every-box-too-now-what#downloads
17 min
October 12The Partner Owns the Relationship. How Do You Earn a Seat?
A partner owns your biggest account — the history, the trust, the contract. This episode gives you the five moves for earning a customer-facing seat: respect the partner's position, fill the role only you can fill, and deposit value before you ask for the room.
In This Episode
Today's Pipeline Problem — why going around the partner loses the account and the channel, and waiting loses the quarter
The Play — What to Say and Do — five moves plus an illustrated partner call that turns "no direct access" into a co-presented briefing
Put AI to Work — three prompts for the incentive map, your unique-value roles, and the partner-sent invitation
The Rep Mailbag — the partner who blocks all access, the pricing question that went wrong, and building pipeline inside channel rules
The Inside Edge — the deposit-first habit that makes partners a pipeline engine instead of a wall
Your Move Today — three written questions and one message to your most important partner
Key Takeaways
The gate stays closed until you neutralize what the partner is protecting: margin, credibility, or position.
Your seat is built on value only you can provide — roadmap access, deep technical expertise, executive connection.
Deposit before you ask: a lead, an insight, or help on their deal.
Propose one bounded, co-presented engagement — one useful appearance earns the next.
Do This Today
Pick one partner-owned account and write down what the partner is protecting.
Identify the role only you can fill in that account.
Make one deposit — a lead or an insight — before asking for anything.
Free Downloads
Everything below is free — no signup. Get it on this episode page: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-12-the-partner-owns-the-relationship-how-do-you-earn-a-seat#downloads
Partner Seat Playbook — The five moves for earning a customer-facing role in a partner-owned account — what they protect, the role only you can fill, and the deposit-first sequence. · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-12-the-partner-owns-the-relationship-how-do-you-earn-a-seat#downloads
Co-Presented Briefing Planner — Plan the one bounded customer engagement that earns the next one — roles, agenda, and follow-through. · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-12-the-partner-owns-the-relationship-how-do-you-earn-a-seat#downloads
AI Prompts: Partner-Account Preparation — The three prompts from this episode — incentive map, unique-value roles, and the partner-sent invitation. · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-12-the-partner-owns-the-relationship-how-do-you-earn-a-seat#downloads
17 min
October 11Your QBR Is Coming. Can You Defend Your Number?
Your QBR is on the calendar and leadership has already seen the dashboard. This episode gives you the four-part account — performance, forecast evidence, exposure, and gap-closing actions — that turns the review from an interrogation into a working session.
In This Episode
Today's Pipeline Problem — why leadership attends your QBR to judge your read on the future, not admire the past
The Play — What to Say and Do — the four parts of a defensible QBR, plus an illustrated review where the rep answers every question with evidence, exposure, or an action
Put AI to Work — three prompts that build your QBR account from your own deal data in under an hour
The Rep Mailbag — presenting a 60% quarter, naming risks without sounding negative, and how long a QBR should really be
The Inside Edge — why the pre-read and the working-session mindset now beat the forty-slide deck
Your Move Today — write the four headings on a blank page and find the section your business needs this week
Key Takeaways
Account for performance in three sentences: result, what drove it, what you learned.
Forecast evidence is what the customer has done — stages are your opinion.
Name your own exposure first; the rep who names the risk gets the room's help.
Every gap-closing action needs a target, a date, and a weekly leading indicator.
Do This Today
Write the four headings — Performance, Forecast Evidence, Exposure, Gap Actions — and fill them in within twenty minutes.
The section that's hardest to write is where your business needs attention this week.
Send a concise pre-read before your next review so the meeting is spent on decisions, not reporting.
Free Downloads
Everything below is free — no signup. Get it on this episode page: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-11-your-qbr-is-coming-can-you-defend-your-number#downloads
QBR One-Pager Template — The four-section account — performance, forecast evidence, exposure, gap actions — on a single page. · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-11-your-qbr-is-coming-can-you-defend-your-number#downloads
Gap-Closing Action Plan — Turn a quarter gap into specific actions with dates, owners, and weekly leading indicators. · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-11-your-qbr-is-coming-can-you-defend-your-number#downloads
AI Prompts: QBR Preparation — The three prompts from this episode to build your QBR account in under an hour. · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-11-your-qbr-is-coming-can-you-defend-your-number#downloads
16 min
October 10Your Manager Wants It in Commit. You Don't Believe It Belongs There.
Your manager needs a number they can defend, and your gut says the deal isn't there. This episode gives you the exact conversation — evidence, missing milestones, and a recovery plan — that protects the deal and your credibility at the same time.
In This Episode
Today's Pipeline Problem — why the commit conversation is really a credibility conversation
The Play — What to Say and Do — the five moves: evidence inventory, naming missing milestones, leading with your own category, recovery actions with dates, and handling the pressure moment, plus an illustrated forecast review with a manager pushing for commit
Put AI to Work — two prompts that build your evidence sheet from your own deal notes in ten minutes
The Rep Mailbag — the verbal-yes commit, rebuilding trust after a slipped deal, and a VP who wants everything in commit
The Inside Edge — how engagement-data inspection is changing the rep's job in the forecast meeting
Your Move Today — find the deal your gut is arguing with and circle the one milestone with no date and no owner
Key Takeaways
Separate what the customer has confirmed from what you are assuming — say both out loud.
A commit without dated, customer-owned milestones is a hope with a label on it.
Offer your own category call first: "best case, and here's what moves it to commit."
Bring recovery actions with dates, never objections.
Credibility is compound interest on every forecast conversation you'll ever have.
Do This Today
Pick the deal you're least sure about and write the two columns: confirmed vs. assumed.
Circle the most consequential milestone with no date and no owner — that circle is your week.
Walk into your next forecast review with the evidence sheet before anyone asks for it.
Free Downloads
Everything below is free — no signup. Get it on this episode page: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-10-your-manager-wants-it-in-commit-you-dont-believe-it-belongs-there#downloads
Forecast Evidence Checklist — The two-column evidence inventory to run before any forecast meeting. · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-10-your-manager-wants-it-in-commit-you-dont-believe-it-belongs-there#downloads
Commit Conversation Prep Sheet — Structure the honest forecast conversation with your manager, including the exact talk tracks. · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-10-your-manager-wants-it-in-commit-you-dont-believe-it-belongs-there#downloads
AI Prompts: Forecast Evidence Review — The two prompts from this episode to build your evidence sheet in ten minutes. · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-10-your-manager-wants-it-in-commit-you-dont-believe-it-belongs-there#downloads
18 min
October 09🔥 Nobody Asked for Your Proposal. Give Them a Reason to Read It.
Nobody asked for your proposal — and that's exactly the problem with the way most of us write one. This episode shows how to build a short, one-page unsolicited business proposal buyers actually read: a relevant observation, a clearly labeled hypothesis, potential value, and an invitation to validate it.
In This Episode
Today's Pipeline Problem — why the scaled-down sales proposal reads as marketing and gets deleted
The Play — the four building blocks, with a full illustrated follow-up conversation
Put AI to Work — draft the one-pager and catch every guess stated as a fact
The Rep Mailbag — the requested proposal, pricing in an unsolicited note, and the activity-metric manager
The Inside Edge — the short note as the credential that earns the long proposal
Your Move Today — write the four-part note for one account in twenty minutes
Key Takeaways
A proposal is a response to a request; without a request it needs a different job — testing an idea.
Label hypotheses as hypotheses. A confident diagnosis makes buyers defend; a labeled guess makes them correct you.
Describe potential value as illustrative capacity and time — never manufacture a savings figure.
The invitation is the smallest test of the hypothesis, on the buyer's terms — not a meeting ask.
No genuine, defensible observation? Choose a different account.
Do This Today
Pick one target account and write the four-part one-pager — observation, labeled hypothesis, illustrative value, invitation.
Run the AI confidence-inflation check before you send.
If you can't write a real observation, move to a different account.
Free Downloads
Everything below is free — no signup. Get it on this episode page: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-09-nobody-asked-for-your-proposal-give-them-a-reason-to-read-it#downloads
Unsolicited Proposal One-Pager Template — the four-part structure with adaptable wording · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-09-nobody-asked-for-your-proposal-give-them-a-reason-to-read-it#downloads
Observation-to-Hypothesis Worksheet — the 20-minute pre-outreach exercise · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-09-nobody-asked-for-your-proposal-give-them-a-reason-to-read-it#downloads
AI Prompts: Drafting the Unsolicited Proposal — copy-ready prompts · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-09-nobody-asked-for-your-proposal-give-them-a-reason-to-read-it#downloads
17 min
October 08"We're All Set." How to Open a Conversation With a Satisfied Account
"We're all set" ends most prospecting conversations — but it doesn't have to. This episode shows how to open an honest conversation with a satisfied account, uncovering problems the customer genuinely hasn't solved without attacking the incumbent or manufacturing dissatisfaction.
In This Episode
Today's Pipeline Problem — why attacking the incumbent and manufacturing pain both backfire
The Play — outcome questions, change questions, and stakeholder questions, with a full illustrated conversation
Put AI to Work — separate facts from assumptions and draft questions buyers thank you for
The Rep Mailbag — CEO-chosen vendors, fresh three-year renewals, and the surprise "yes" meeting
The Inside Edge — standards questions: what top sellers ask instead of "what's broken"
Your Move Today — three questions to write for one "all set" account
Key Takeaways
Criticizing the incumbent asks the buyer to argue with their own past decision — don't.
Ask what still takes more effort than it should; let the customer decide whether it matters.
Requirements drift after every purchase decision — ask what changed, don't claim anything broke.
Standards questions ("what would right look like next year?") let the customer discover the gap themselves.
Do This Today
Pick one "all set" account and write one outcome question, one change question, and one standards question.
Run the AI facts-vs-assumptions prompt on your notes before the conversation.
Accept "we're genuinely well served" as a good answer and keep the relationship warm.
Free Downloads
Everything below is free — no signup. Get it on this episode page: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-08-were-all-set-opening-a-conversation-with-a-satisfied-account#downloads
Satisfied Account Conversation Guide — the full question bank · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-08-were-all-set-opening-a-conversation-with-a-satisfied-account#downloads
Satisfied Account Preparation Worksheet — the 15-minute pre-call exercise · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-08-were-all-set-opening-a-conversation-with-a-satisfied-account#downloads
AI Prompts: Satisfied Account Research — copy-ready prompts · Download: https://www.softwaresalesmastery.com/podcast/episodes/2026-10-08-were-all-set-opening-a-conversation-with-a-satisfied-account#downloads
15 min

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