Jeremy Diamond: The CEO’s Playbook for Challenging Corporate Giants

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Published August 15, 2025 12:58 AM PDT

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Asymmetrical negotiation is a strategic confrontation where one party possesses substantially greater resources, influence, and structural power than its opponent. This imbalance is a hallmark of disputes between individuals and corporate institutions, particularly within the insurance sector, where initial settlement offers often fail to reflect the true value of a claim. In this exclusive interview, CEO Today sits down with Jeremy Diamond, managing lawyer and founding partner of Diamond & Diamond Lawyers, to deconstruct the strategic framework used to counteract this power disparity. The principles discussed offer a functional playbook for any C-level executive facing a formidable adversary, framing legal disputes through the lens of high-stakes business strategy.

An Interview with Jeremy Diamond, CEO of Diamond Law

CEO Today: Mr. Diamond, corporate opponents often begin negotiations with a lowball offer. From a strategic standpoint, how do you advise leaders to interpret and respond to this initial move, which many find disheartening?

Jeremy Diamond: The initial offer from a corporate giant is not a starting point for negotiation; it is a calculated psychological anchor. Its purpose is to devalue the case immediately, condition the opposing party to think in smaller terms, and frame the entire dialogue around an artificially low ceiling. The most critical first maneuver is to categorically reject this anchor, not by arguing its merits, but by dismissing it as irrelevant to the factual basis of the claim. The correct counter is to table an entirely new, evidence-based valuation that fundamentally reframes the discussion. This action forces the more powerful entity to abandon its preferred script and engage on substantive grounds, effectively moving the conflict from their territory to a neutral, fact-based arena where data, not capital, determines the outcome.

CEO Today: Once that initial anchor is dismissed, the focus shifts to substance. What role does evidence play in shifting the balance of power, and how does a firm build a case that a corporate opponent cannot logically or legally dismiss?

Jeremy Diamond: In these asymmetrical confrontations, power is derived not from capital but from irrefutable evidence. The strategy involves commissioning and assembling a comprehensive portfolio of expert analyses that transforms a subjective grievance into a quantifiable and defensible business case. This is where a top-tier personal injury lawyer demonstrates immense value, acting as a strategic partner who builds a fortress of data that an opponent cannot breach. The key components of this evidence portfolio are non-negotiable for establishing maximum leverage. They must include:

  • Forensic economic reports that meticulously quantify long-term financial damages, including lost future earnings and operational disruption.
  • Third-party expert testimony from respected leaders in relevant fields to validate the core arguments and lend unimpeachable credibility to the case.
  • Comprehensive risk assessments that detail the opponent's full potential exposure, including legal costs, reputational damage, and the setting of a negative precedent.
  • In-depth documentation of procedural non-compliance by the opposing party, which can be used to challenge their good faith during the process.

By compiling this data, the negotiation is no longer an argument but a review of established facts. This makes a low offer appear unfair and objectively unreasonable, forcing an escalation within the opponent's internal risk management structure.

CEO Today: Large organizations are known to use procedural delays to exhaust a smaller party's resources, a common frustration in the insurance industry. How can this be effectively neutralized or even turned into an advantage?

Jeremy Diamond: Delays are widely perceived as a weakness for the smaller party, and corporate opponents rely on this perception. They use time to apply financial and emotional pressure, hoping to force a premature and unfavorable settlement. The correct strategic response is to invert this dynamic. We anticipate delays and utilize that time to fortify our case aggressively. Each delay tactic initiated by the opponent becomes a valuable window of opportunity for our team to file additional motions, conduct further discovery, and commission deeper expert analysis. Every month, our case strengthens, and their potential litigation exposure grows. The delay ceases to be their weapon and instead becomes a self-inflicted liability that methodically increases their ultimate cost to settle or litigate.

CEO Today: What is the ultimate point of leverage in these negotiations? How do you compel a large, resource-rich corporation to arrive at a favorable settlement when they could theoretically prolong a fight indefinitely?

Jeremy Diamond: The ultimate leverage is the opponent's internal risk calculus, a language every C-level executive understands. A law firm's reputation for being willing, fully prepared, and historically successful in court is its single most valuable asset. When that reputation is established, the negotiation is no longer about the specifics of a single claim; it becomes a critical business decision for the corporation. They are forced to weigh the cost of a fair settlement against the immense financial and reputational costs of a public trial, the distraction to their executive team, and the danger of setting a precedent that invites future challenges. We ensure the threat of litigation is not a bluff but a credible and documented business risk. At that point, settling on fair terms is no longer a concession—it becomes the most prudent and logical business decision for them to make.


Disclaimer: This article is for general information only and should not be construed as financial, legal, or investment advice. CEO Today Magazine is not a registered investment, legal, tax advisor, or a broker/dealer.

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