The generic phrase "any questions?" often invites irrelevant, time-wasting queries. Instead, ask more insightful questions like, "What's going through your mind as you're watching this?" or "On a scale of 1-10, how does this align?" These prompts reveal a prospect's genuine thoughts and feelings.
On an early call, casually ask what the executive sponsor thinks about an initiative, using only their first name (e.g., "What does Sarah think?"). The prospect's response validates both if you've identified the right sponsor and the strength of their relationship with that executive.
Enterprise sellers should prioritize building a relationship with the executive assistant (EA). The EA controls the executive's calendar, agenda, and priorities, making them a powerful gatekeeper and strategic partner for gaining access, not just an obstacle to overcome.
Instead of a standard sales pitch, propose a strategic meeting between your executive and theirs (e.g., your CDAIO meets their CIO). CC your executive's EA to add credibility. This reframes the request from a low-value sales call to a high-value networking opportunity for their boss.
If a CIO delegates your meeting request to their SVP, keep your executive involved. However, if they delegate you far down to a director, match that person with a peer from your organization. This preserves your executive's capital for a crucial moment later in the sales cycle.
If you can't identify an executive's specific assistant, email a senior EA and deliberately guess the wrong names (e.g., "Is it Jane or Mike?"). This leverages reverse psychology, as people have a natural tendency to correct misinformation, often resulting in a helpful reply that identifies the right person.
Create your best guess of a prospect's org chart in a visual tool like Miro, then screen-share it with your champion. Ask them to correct it live. This collaborative exercise helps uncover the 'power base'—the invisible political structure and key influencers who hold sway regardless of their official title.
Treat EAs like key stakeholders, not just gatekeepers. Maintain a spreadsheet with their personal details and engage beyond meeting requests. Send personalized holiday emails and bring small gifts, like homemade brownies, to on-site meetings to build genuine, long-term goodwill that pays dividends.
When a blocker emerges, first ask your champion if they are 'savable.' If so, uncover their motivations and use a non-sales resource to build a relationship. If 'unsavable,' assess their influence. If high, you must crowd them out by winning over other key influencers who have the executive's ear.