For managers with large pipelines to review, asking three core questions can quickly get to the heart of a deal's health: Why do they need to buy? Why won't they buy? And why do they need to buy now?

Before hunting for acquisitions, the internal business owner (deal sponsor) must write a thesis answering "what problem are we solving?" This prevents reactive M&A driven by inbound opportunities and ensures strategic alignment from the start, separating the "why" from the "who."

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.

Effective due diligence isn't a checklist, but the collection of many small data points—revenue, team retention, customer love, CVC interest. A strong investment is a "beam" where all points align positively. Any misalignment creates doubt and likely signals a "no," adhering to the "if it's not a hell yes, it's a no" rule.

Salespeople often keep dead deals in their pipeline out of hope. To get realistic, ask a simple question for each opportunity: "If I had to bet my own money on this closing by year-end, would I?" If the answer is no, immediately remove it from the active pipeline and replace it.

The paradox of long-term planning is that focusing on sustainability and succession—building a company that doesn't need an exit—makes it far more valuable and appealing to potential buyers. Robust, self-sufficient companies built to last are inherently better investments.

Before an LOI, share your high-level vision, then have the target's founders pitch back their own 6- and 12-month post-acquisition roadmap. This pre-commitment exercise reveals true alignment and integration potential far more effectively than traditional diligence, creating a joint vision early on.

When acquiring a business, don't rely on a single outcome like achieving a growth target. Instead, seek assets that offer multiple ways to win. Even if the primary goal is missed, the acquired data, technology, or talent could create significant value for other business units, providing built-in insurance for the deal.

A profitable business can be a bad investment if it creates unsustainable operational stress. This non-financial "return on headache" is a key metric for evaluating small business acquisitions, especially for hands-on owner-operators who must live with the daily consequences.