Deals often stall because customers don't know the next steps. Effective salespeople prevent this by proactively presenting a prescriptive, opinionated roadmap for evaluation, onboarding, and purchase. This creates momentum and surfaces blockers like legal or security reviews early.

A champion for a $500k deal often lacks the influence for a $5M deal. As a deal expands, sellers must proactively re-evaluate their champion. It's often necessary to find a new, more senior sponsor who has the authority to shepherd the larger transaction through the organization.

Don't improvise multi-threading. Beforehand, map out the common organizational archetypes you sell to and the ideal sequence of stakeholders to engage—the "golden path." This allows you to confidently prescribe the next steps in the buying process for each specific deal structure.

How a champion describes their upcoming board presentation reveals their authority and the deal's likelihood of closing. 'Telling' indicates high confidence, while 'presenting' suggests a need for external validation and more risk. This insight allows you to tailor your coaching strategy for them.

Instead of only tracking major sales stages, monitor a deal's health by securing a series of small agreements. Consistent 'micro-commitments'—like scheduling the next meeting, agreeing to review technical specs, or making an introduction—are more reliable indicators that a complex deal is actively progressing and not just sitting idle in the pipeline.

Two clear red flags indicate a deal is at risk: relying on a single contact and having a close date not tied to a specific buyer deadline. To de-risk a deal, sales reps must engage multiple stakeholders (multi-threading) and anchor the timeline to the buyer's critical business needs.

Most buyers lack a formal evaluation process, creating deal risk. Proactively offer to build a decision scorecard with them. This positions you as a helpful advisor while allowing you to influence the evaluation criteria and weighting to favor your solution's key differentiators, thereby steering the deal in your favor.

To avoid stalled deals, continuously test the prospect's engagement. If a stakeholder consistently fails to meet small commitments—like providing requested information on time—it is a strong indicator that the deal is not a priority for them and is at high risk of stalling.

Instead of a linear process, treat M&A as a spiral. Constantly revisit and adjust deal structure, diligence findings, and integration plans. A discovery in one area (e.g., diligence) should trigger a reassessment of the others (e.g., deal structure), ensuring a cohesive and de-risked outcome.