A silent dissenter won't respond to "What are your concerns?". Instead, "soft-float" several potential objections, like giving them a multiple-choice question (e.g., "Is it our integrations, our pricing, or something else?"). This lowers the barrier for them to engage and allows them to latch onto a specific point, revealing their true apprehension.

Use one-on-one breakout meetings to gather intel you can't get in a group setting. Ask directly about competitors, pricing, and evaluation status. The private, trusted environment makes stakeholders more likely to share candid details, effectively turning them into your internal informant on the deal.

Stop trying to convince executives to adopt your priorities. Instead, identify their existing strategic initiatives—often with internal code names—and frame your solution as an accelerator for what they're already sold on doing. This dramatically reduces friction and speeds up deals.

Don't pitch big ideas by going straight to the CEO for a mandate; this alienates the teams who must execute. Instead, introduce ideas casually to find a small group of collaborative "yes, and" thinkers. Build momentum with this core coalition before presenting the developed concept more broadly.

Instead of a typical first sales call that quizzes a prospect, Stripe implemented collaborative whiteboarding sessions. By jointly mapping the prospect's technical architecture, the sales team gathered deep insights while the customer received a valuable asset (their own architecture diagram), establishing a value-add relationship from the start.

Multi-threading isn't just a seller's tactic; it empowers the buyer. An internal champion feels more confident and strengthened when they can approach their CFO with the backing of two or three peers who also see the value. This shared internal momentum makes it easier for them to secure budget and push the deal forward.

Don't measure deal progress by the number of meetings held. Instead, define specific exit criteria for each sales stage. A deal only moves forward when the prospect meets these criteria, which can happen with or without a live meeting. This reframes velocity around outcomes, not activities.

To get the most out of a short mastermind, implement a clear structure instead of "winging it." A schedule combining social connection (dinners) with focused work sessions (roundtables, "hot seats") ensures that the group's limited time is used for maximum impact and return on investment.

Instead of approaching leaders first, engage end-users to gather 'ammunition' about their daily pains. They may not have buying power, but their firsthand accounts create a powerful internal case (groundswell) that you can then present to management, making the approach much warmer and more relevant.