The first conversation with a target CEO shouldn't focus on the deal. Instead, focus on their personal story to uncover their core motivation—money, legacy, or team success. This "why" provides the key to framing the acquisition in a way that resonates with them and dictates the entire negotiation strategy.

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.

The desire to appear intelligent causes founders to avoid simple questions and instead anticipate needs. This leads to incorrect assumptions. Asking basic, even "stupid," questions like "Why did you take this call?" is the key to understanding the customer's real needs and ultimately closing the deal.

To vet potential investors or acquirers, founders should ask them to articulate their vision for the startup's next five years. Hearing their story told through the buyer's eyes reveals the depth of their strategic thinking and helps assess whether their vision aligns with the founder's, ensuring a better post-transaction fit.

Companies don't sign six-figure contracts to solve one person's frustrations. To justify a large purchase, you must anchor the sale to tangible business outcomes. Frame discovery questions around the company's goals, not just an individual champion's personal pain points.

When M&A negotiations stall, the root cause is often sentimental, not financial. Uncovering a seller's personal attachment (e.g., hunting rights, a favorite truck, community sponsorships) allows for creative, non-monetary solutions that have high emotional value for the seller but low cost for the buyer, getting the deal across the finish line.

In enterprise deals, discovery shouldn't stop at company objectives. Ask your champion about a key stakeholder's personal career goals. Are they newly promoted and need to prove themselves? Are they aiming for their next promotion? Aligning your solution to their personal ambitions creates a much stronger motivation to buy.

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.

To avoid sounding pushy when asking critical questions about a deal's viability, frame them as necessary steps to ensure the customer's success post-implementation. This shifts the intent from closing a deal to building a successful partnership, encouraging open answers.