Use this as a working guide, not a passive read. Skim the sections, copy the frameworks, then connect the advice to a real role, interview, call, or account you are working on this week.
Start with a free resourceDownload this guide's free practice worksheetNo signup required.
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The Enterprise Playbook
$19 USD · One-time purchase · Downloadable PDF
Preview this playbookBefore proposing expansion at renewal, understand whether the customer is receiving value from the current purchase. Ask about use, outcomes, unresolved problems, and who owns the renewal decision. More seats or a larger package should respond to a real need, not merely the seller's growth target.
GitLab's retain-and-expand guidance includes ongoing account discovery. The questions below are original and should be coordinated with your customer-success and account teams.
Begin with the current agreement
Review the actual renewal timing and process in approved records. Coordinate with the account owner before contacting the customer. Do not invent a deadline or assume that a contract automatically renews on terms you have not checked.
| Area | Question |
|---|---|
| Current value | Which workflow is working better, and how do you assess it? |
| Adoption | Where is the purchased capability not yet being used as intended? |
| Friction | Which unresolved issue matters most before renewal? |
| Ownership | Who will review the renewal and its scope? |
| Change | Has a new team or use case created a different requirement? |
Separate retention work from expansion work
Original fictional example: a customer uses routing successfully in one team but has not completed onboarding in another. A larger package may not solve the onboarding gap. First clarify what prevents adoption and who will address it. A separate new workflow may justify evaluation later, but it should not obscure the unresolved commitment.
Keep the current renewal decision and any proposed expansion scope visible as different questions. They may share stakeholders without being the same approval.
Use evidence rather than enthusiasm
A positive relationship is useful, but it does not establish budget or renewal approval. Ask what evidence the buyer needs for the review and who can provide it. If value is not measured, describe the observed workflow and uncertainty instead of inventing a savings figure.
Document changed stakeholders and responsibilities. The person who sponsored the original purchase may no longer own the process, and their replacement may need different context.
Agree a proportionate next step
The next step might be an adoption review, a support escalation, a renewal-scope discussion, or a bounded evaluation of a new need. Choose the action that addresses the customer's actual situation.
For practice, review two fictional accounts: one with strong adoption and a new team request, another with unresolved onboarding. Write different agendas for them. If both agendas lead immediately to an upsell presentation, revisit the evidence and the purpose of the renewal conversation.
Use the free worksheet
Download the saas renewal discovery questions before an expansion pitch worksheet. It opens in a spreadsheet and requires no signup. Use fictional details for practice and your approved systems for real customer or employer information.
Choose your next step
Renewal and Expansion Conversation Practice for Account Teams explains the free exercise, the relevant paid resource, and who it fits. Read the product preview before deciding whether you need the broader self-study manual.
Continue with Economic Buyer Meeting Agenda: Prepare a Decision Conversation.
Put this guide to work
The Enterprise Playbook
Plan complex accounts, align stakeholders, and guide evaluation through rollout.
$19 USD · One-time purchase · Downloadable PDF
Preview this playbookRead the sample and see what is included before you buy.
Need the broader set? Compare The Deal Execution Bundle for $39. Includes this book.
