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.

Executives don't care about tactical benefits like 'five fewer clicks'. A crucial skill for modern sellers is to extrapolate that tactical user-level gain into a strategic business outcome. You must translate efficiency into revenue, connecting the dots from a daily task to the company's bottom line.

Generic use cases fail to persuade leadership. To get genuine AI investment, build a custom tool that solves a specific, tangible pain point for an executive. An example is an 'AI board member' trained on past feedback to critique board decks before a meeting, making the value undeniable.

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.

Enterprise leaders aren't motivated by solving small, specific problems. Founders succeed by "vision casting"—selling a future state or opportunity that gives the buyer a competitive edge ("alpha"). This excites them enough to champion a deal internally.

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.

When pitching a long-term strategic fix, regional leaders prioritized immediate revenue goals. The product team gained traction not by dismissing these concerns, but by acknowledging their validity. This respect builds the trust necessary to balance short-term needs with long-term investment.

Structure your final presentation by calling out specific problems you learned from individual contributors by name. Then, immediately pivot to show how solving their problem directly contributes to the high-level business objective owned by the executive decision-maker. This makes every stakeholder feel heard and demonstrates their strategic value.

When progress on a complex initiative stalls with middle management, don't hesitate to escalate to senior leadership. A brief, well-prepared C-level discussion can cut through uncertainty, validate importance, and accelerate alignment across teams or with external partners.