Most commercial cases go to mediation on somebody else's schedule. A court orders the case to mediation because the local rules require it before trial. Discovery closes and counsel schedule the mediation because that is what counsel do at that point. A trial date approaches and the parties finally engage because the deadline forces them to. Each of these is a real reason to mediate at a particular moment. None of them is the same as the reason that would produce the best outcome for the client if counsel had actually thought about the timing.
The strategic question is different from the compliance question. It is not whether the case will be mediated. Most commercial cases will be. It is when in the case's arc the mediation actually produces the best outcome, and whether the moment counsel is now approaching is the right moment or the wrong one. The wrong moment costs the client either the settlement value they would have captured earlier or the leverage they had not yet built when they walked into the room. Both losses are real, both are avoidable, and both are more common than the trade press suggests.
I have spent thirty-seven years litigating commercial cases in Florida and now mediate them. What follows is what I see when parties arrive at mediation, when the timing was right, when it was not, and what counsel and clients can think about before scheduling the session that a court has not yet ordered them to hold.
The three windows.
Commercial cases have three broadly identifiable windows during which mediation can produce a settlement, and each window has a different character. Understanding which window a case is in, and whether that is the right window for that particular dispute, is the beginning of the strategic conversation.
The early window is the period before or shortly after suit is filed, before substantial discovery has occurred. The middle window is after key discovery has been taken but before dispositive motions have been ruled on. The late window is after dispositive motions have been decided and the case is preparing for trial. Each window offers different information, different leverage, and different costs, and the case that settles well in one window may not settle at all in another.
The early window.
The early-window mediation happens when the parties know their own case reasonably well but have not yet incurred the substantial costs that discovery, motion practice, and expert work will eventually produce. The claims are still being tested for the first time in a professional forum. The parties have not yet hardened around their positions in the way that six months of adversarial litigation will harden them. The fee bills are relatively small on both sides. The relationship, if there is one, has not been fully consumed by the dispute.
The early window has real advantages for the right case. Commercial matters where the underlying facts are largely undisputed and the dispute is over their legal or contractual consequences often settle well early. Commercial lease disputes with clear rent-and-default arithmetic. Insurance coverage disputes where the policy language and the loss facts are known and the fight is over interpretation. Partnership or shareholder disputes where the parties both want out of the entity but disagree on the mechanics. Disputes where a continuing business relationship is at stake and prolonged litigation will destroy it. In all of these, the early window offers the parties the opportunity to resolve the matter before the fees, the hardening, and the collateral damage have accumulated.
The early window has real disadvantages too, and counsel who send cases to early mediation without candor about the disadvantages produce bad outcomes. The party that has not yet taken discovery does not fully know what the other side's documents say. The party that has not yet deposed the other side's principals does not know what those principals will testify to. The party that has not yet tested its damages theory against an expert has not confirmed whether the theory holds. Early-window mediations sometimes produce settlements that later evidence would have improved on for one side or the other. When that happens, the settled party regrets the deal, and the regret produces performance disputes and future litigation between the same parties.
The middle window.
The middle-window mediation happens after the material discovery is complete but before the court has ruled on summary judgment or motions in limine. Both sides know what the documents actually say. Both sides have seen the other side's key witnesses under oath. Both sides have received their experts' preliminary opinions and have some sense of what the trial testimony will look like. The fee bills are substantial but the trial costs have not yet been incurred. Positions have hardened somewhat but not fully.
The middle window is where most commercial mediations happen and, in my experience, where most of them work best. The information asymmetries have narrowed to the point where both sides can evaluate their own case realistically. The costs already sunk are large enough that the parties feel the incentive to resolve rather than to escalate, but not so large that the parties feel compelled to see the case through to verdict to recover what they have already spent. The looming shadow of dispositive motions concentrates the mind on both sides, because both sides know the case they think they have may be substantially different from the case that survives the summary judgment order.
This is the window where the pre-mediation call, the substantive submissions, and the caucus work I have written about elsewhere have the most to work with. There is enough information on the table for the mediator to conduct a real evaluation exercise. The parties are open enough to hearing hard questions about their own case that the caucus dialogue has traction. The settlement structures that require the parties to model both sides realistically are within reach. The middle window is where structured commercial mediation earns its reputation.
The late window.
The late-window mediation happens after summary judgment has been decided, after the trial court has ruled on the motions in limine, and often within weeks of the trial date. The claims that will actually go to trial have been narrowed. The evidentiary rulings have shaped what the jury will hear. The parties are looking at the trial as a real event rather than a hypothetical.
The late window has particular advantages for cases that have not been well positioned for earlier resolution. Cases where the summary judgment ruling has materially changed the leverage. Cases where a key evidentiary ruling has stripped one side's theory of its supporting evidence. Cases where the trial court has surfaced a legal question that neither side had expected. In these cases, the late window is the first opportunity the parties have to evaluate the actual case that will be tried rather than the case they thought they had.
The late window also has real disadvantages. The fees on both sides are enormous by this point, and the sunk-cost dynamic pushes parties toward completing the trial rather than settling shortly before it. Counsel who have prepared intensively for trial are, quite naturally, in a trial posture rather than a negotiation posture, and switching modes at the last minute is difficult. Trial dates in Florida civil courts, particularly with the 2025 procedural amendments that disfavor continuances, are less flexible than they used to be, which means the mediation has to work quickly or the trial happens on schedule. And the leverage of the party against whom summary judgment has just been granted is often materially lower than it was in the middle window, which means the settlement number reflects a case that has already been substantially decided.
Late-window mediations settle at rates roughly comparable to middle-window mediations in my experience, but the settlements are often less favorable for the party that lost the significant procedural ruling. The party that would have gotten a better deal in the middle window sometimes takes a worse deal in the late window because the alternative to the deal has become worse. That is a strategic loss that counsel could have avoided with earlier timing.
When mediation is not the answer.
Not every case belongs in mediation, and not every dispute that lawyers reflexively route to mediation would actually benefit from it. This is the observation that mediators are professionally disinclined to make, but it should be made honestly. There are commercial disputes where mediation is unlikely to produce settlement, and where the mediation day is a cost the client bears with limited return.
Cases where one party genuinely needs adjudication of a legal question rather than a compromise on a dispute belong in front of a judge. Cases involving fraud or dishonesty where the injured party is not willing to trade the vindication of trial for the pragmatism of settlement should proceed to trial. Cases where one side is judgment-proof and the other side needs the judgment for reasons other than immediate collection sometimes should not settle. Cases where a party is using mediation strategically to delay or to obtain discovery without producing its own are not really mediating in good faith and will not settle at any reasonable number. And cases where one side has publicly committed to a position it cannot walk back without severe reputational consequences are difficult to settle regardless of what the merits suggest, at least until the reputational cost has been separately addressed.
Counsel who evaluate honestly whether the case is a candidate for mediation before scheduling the session are doing better work for their clients than counsel who route every case through the mediation checkbox because that is the local practice. Sometimes the honest answer is that mediation is not the right mechanism for this dispute, or that it is not the right mechanism at this moment. Recognizing that is worth as much to the client as scheduling the mediation at the right moment for the right case.
The court-ordered mediation problem.
Florida state courts routinely order commercial cases to mediation, sometimes multiple times during the pendency of the case. The order arrives on the docket and the parties comply. That is the compliance question. It is not the strategic question, and it is worth being honest about the gap between the two.
Court-ordered mediation happens on the court's schedule, not the parties' schedule, and the court's schedule is set to reduce the docket rather than to optimize any particular case's timing. A court-ordered mediation early in the case may fall in the early window when the case would have been better mediated later. A court-ordered mediation shortly before trial may fall in the late window when the case would have been better mediated earlier. Counsel who treat the court order as if it defined the correct mediation timing rather than as a compliance obligation to be satisfied are conflating two different things.
The strategic response to a court order for mediation depends on where the case actually is in its arc. Sometimes the right answer is to conduct the ordered mediation seriously and try to settle at the ordered moment. Sometimes the right answer is to conduct the ordered mediation with the recognition that this is a compliance event rather than a strategic one and to prepare for a second mediation at a moment that will actually work. Sometimes the right answer is to move the ordered mediation, if the court will permit it, to a moment that fits the case rather than the docket. All three answers are legitimate. The mistake is to treat the court order as if it removed the strategic decision from counsel's hands.
What counsel should think about before scheduling.
The scheduling decision, when counsel controls it rather than the court, is worth more thought than it commonly receives. A short list of questions counsel might work through before picking a date. How well does each side know its own case at this moment, and how much would it help to know more? What discovery is still outstanding, and what leverage would the completed discovery produce that is not yet available? What dispositive motions are pending, and how would the rulings on those motions change the leverage on both sides? How much has each side spent in fees to date, and how does the sunk-cost dynamic shape each side's willingness to settle? What is the relationship between the parties beyond the litigation, and is prolonged litigation going to make settlement harder or easier? Is there a business event on the horizon, a fiscal year close, a financing transaction, a regulatory filing, that would make one side or the other more receptive to settlement at a particular moment?
The answers to these questions rarely point to the same moment, and the strategic timing decision is the counsel's judgment about which factors matter most in the particular case. That judgment is what a client is paying counsel for, and it is one of the things a good mediator and a good lawyer can usefully discuss in the pre-mediation call I have written about elsewhere.
Closing observations.
Timing in commercial mediation is not a neutral variable. The same case mediated at three different moments will produce three different outcomes, and the difference between them is often larger than the difference the mediator's skill produces at any single moment. Counsel and clients who recognize this and choose the timing deliberately are making a decision worth substantial money to the client, in either direction. The default of scheduling the mediation whenever the court's order or the discovery cutoff or the trial calendar happens to place it is the wrong default. It is not always the wrong answer, but it is the wrong process for arriving at the answer.
The mediation practice at Rosenthal Resolutions is available to discuss the timing question with counsel considering an engagement, in advance of any date being set, and at no additional charge. The conversation about when to mediate is one that the mediator can usefully participate in without conflict of interest, because the mediator has no financial stake in whether the case ultimately mediates or not. Counsel who use that conversation as part of the strategic decision are making a better decision than counsel who do not.