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.

After addressing a prospect's concern, don't assume you've solved it. Explicitly ask if your explanation was sufficient by asking, "Was that enough to satisfy your concern?" This simple check ensures the issue is truly resolved and prevents it from resurfacing later to kill your deal. Most reps answer and move on, which is a critical mistake.

When a prospect asks for a free pilot, treat it as a sign that you failed to build enough confidence in the outcome. Instead of agreeing, diagnose their uncertainty by asking what they still need help predicting. This shifts the conversation back to value and avoids deploying your best resources on your least committed customers.

To truly understand a prospect's decision-making process, ask for more than you expect to get, such as requesting to be part of their internal evaluation meeting. Even a "no" often prompts them to reveal more about their process, criteria, and stakeholders than a standard discovery question would.

After a group discovery call, don't just set one follow-up. Schedule brief, individual breakout sessions with every stakeholder. This creates multiple parallel threads, uncovers honest feedback people won't share in a group, and builds momentum across the entire buying committee, dramatically increasing deal velocity.

True connection requires humility. Instead of trying to imagine another's viewpoint ("perspective taking"), a more effective approach is to actively seek it out through questions and tentative statements ("perspective getting"). This avoids misreads and shows genuine interest.

When you identify a deal blocker, don't confront them alone. First, approach your champion and ask for their perspective on the dissenter's hesitation and advice on the best way to engage them. This provides crucial internal political context and helps you formulate a more effective strategy before you ever speak to the blocker.

To elicit candid answers from fund managers, the most effective technique is not the question itself but the silence that follows. Resisting the psychological urge to fill the space forces the manager to sit with the question, often leading to less rehearsed and more truthful responses.