"Winning" the Mediation vs. Resolving the Dispute: How Mediators Can Prepare Counsel (and Clients) for Real Resolution

There is a certain kind of opening I still see at too many mediations. Counsel strides into the room with the unmistakable glint of Trial Day in their eyes, a binder thick enough to serve as a doorstop, and a speech ready to prove—beyond any doubt—why the other side should surrender. It is polished, it is passionate, and it is pointed squarely at the wrong audience. 

That mindset aims to "win" the mediation. More often than not, such an attitude is also a function of what the client expects of counsel. But our job, as mediators, is to help them resolve the dispute.

This article offers a practical, spirited playbook for mediators to prepare counsel — and by implication, their clients — so the session tilts toward resolution rather than performance. The ideas are simple to implement, grounded in experience, and, yes, a little allergic to grandstanding.

Start Early: A Focused Pre-Mediation Call That Reframes the Mission

A short, structured pre-mediation call (20–30 minutes) is the single most powerful lever you have. Use it to:

  • Define success: Ask each side, "What outcome today would let you call the client and say, ‘this was a productive use of time'?" Push for a concrete answer — not "win," not "send a message," but a real-world endpoint (a number, a term, a non-monetary concession, a process).
  • Name the bias: Gently flag the "win the mediation" impulse: "This isn't court; persuasion here is about possibility, not victory." Make it clear that a closing argument won't move the needle; credible, solution-oriented information will.
  • Surface constraints: Authority, board approvals, insurer layers, lienholders, government approvals — identify them now, not at 4:45 p.m.
  • Target the information gaps: What single document, data slice, or expert assumption is stalling movement? Ask counsel to bring it, summarize it, or agree on a way to exchange it the day before.
  • Set tone and logistics: Explain your cadence (joint time or not, private caucus rhythm, how/when you will reality-test), confirm attendance of true decision-makers, and establish your expectation that everyone comes ready to bargain seriously from the first move.

A mediator-led framing call like this resets counsel's mental model from "advocacy contest" to "problem-solving sprint."

Replace the "Brief" with a Mediation Statement (and Say What That Means)

Language matters. Invite (insist on) mediation statements, not briefs. "Briefs" signal advocacy and winning; "statements" signal factual clarity, risk, and pathways to resolution. Ask for 5–10 pages that do the following:

  • Tell the business story in plain English: who the parties are, how they got here, what matters commercially and personally.
  • Lay out the pivotal uncertainties (legal and factual) that genuinely create risk for each side — not just the other side. A useful statement acknowledges both strengths and weaknesses on all sides; it is hard to move if you only see one hillside.
  • Propose plausible resolution frameworks: numbers and terms (payment timing, confidentiality, cooperation provisions, references, business continuity, transition services, inventory return, non-disparagement, licensing tweaks). Encourage counsel to sketch three versions: "stretch," "likely," and "floor."
  • Avoid law-review detours: Dense Rule 56 excerpts and string cites rarely advance settlement; they can obscure the forest you need everyone to see. Resolution is about workable deals, not motion practice.

If a submission reads like a summary judgment motion, send it back (nicely) and ask for one that helps you settle the case, not win it. 

Prepare Counsel to Prepare the Client (Because Unprepared Clients Derail Good Mediations)

A surprising amount of mediation "friction" has nothing to do with law; it is expectations, emotions, and identity. Ask counsel — explicitly — to do three things before the session:

  1. Normalize discomfort: Explain that mediation involves risk-talk, doubt, and compromise. If the client expects a coronation, the first reality test will feel like betrayal. Help counsel rehearse that conversation.
  2. Define acceptable outcomes: "If we can settle today, what will you be able to live with tomorrow?" Translate that into actual numbers and terms. Clients who cannot articulate a pocket of acceptability are not ready to deal.
  3. Rehearse the "day in court" impulse: Many clients want to be heard. That is human. Help counsel channel that productively — a concise narrative in joint session (or a private caucus "listen first" slot), not a 40-minute grievance monologue. Clients who arrive with four bankers' boxes and a mission to relitigate the complaint are not poised for resolution — and that is avoidable with good prep.

Remind counsel: preparing the person is as important as preparing the case. A lawyer who only polishes arguments but ignores the client's emotional posture has not actually prepared for resolution. 

Co-Design the Opening: Short, Respectful, and Future-Facing

As mediator, set the opening session norms:

  • One purpose: share what each side needs the other to understand to make a deal possible. No jury summations, no blame theater.
  • Three minutes each: enough to be human, too short to inflame. If counsel insists on a longer opening, build a rule: after five minutes of talking about the other side, spend two minutes describing your own risks and what you would need to see to move.
  • Option B: If opening statements would be counterproductive, propose a "meet the people, not the positions" opening — introductions, process, then break to caucus.

This keeps the front end from sabotaging the back end.

Actively Debias the Room

Mediators see the same cognitive traps repeatedly. Name them and design around them:

  • Reactive devaluation: if it comes from "them," it feels worse. Use neutral language and consider "mediator's number" techniques late in the day to short-circuit this bias.
  • Anchoring: the first ridiculous number can warp the day. Coach counsel to open credibly — not with a threat dressed as an offer.
  • Confirmation bias: lawyers are professional story-builders. Require each side to list the two best facts for the other side. That exercise alone cools a lot of heat.
  • Sunk-cost fallacy: "We've spent too much to stop now." Remind them: sunk costs are past; your job is to optimize from here.

When counsel feels you are working to protect them from predictable human errors, they let you reality-test more deeply.

Equip Counsel with a Practical Valuation Toolkit

You don't need a Ph.D. in finance to help people think clearly about value. Push for simple, comparable, and credible:

  • Outcome-weighted expected value: three outcomes × probabilities × net values (after fees/costs/appeal risk). It is back-of-the-envelope math, but it forces specificity.
  • Time-value reality: a "better" litigated outcome in two years may be worth less today than a "worse" settlement paid next month. Ask them to discount.
  • Variance awareness: high variance favors settlement when parties are risk-averse (which most real clients are once contemporaneous costs and distraction are priced in).
  • Shadow prices for non-monetary terms: what is a neutral reference, a license, a transition service, or a standstill worth in dollars to your side? Put a number on it. If they can price it, they can trade it.

Invite each side to arrive with a one-page Deal Math sheet. A Deal Math sheet is essentially a working spreadsheet or chart that breaks down the numbers behind a proposed settlement so everyone can see exactly what is being agreed to and how it will be implemented. It provides for all financial components being accounted for so that everyone understands "net" outcomes. It clarifies thinking, accelerates movement, and gives counsel a client-approved map to follow when adrenaline spikes.

When to Push, When to Park

Not every case is ripe the first time. Your job is not to force closure; it is to create the best conditions for resolution. If a party arrives unprepared — the wrong people, no numbers, "we'll just listen today" — pivot:

  • Turn the day into a preparation sprint: exchange key documents, schedule a targeted deposition, set a second session date, and agree on an agenda and decision-maker attendance.
  • Capture partials: stipulate facts, settle sub-issues, agree on standstill terms. Movement begets movement.
  • Leave with assignments: each side gets a concrete task (valuation memo, board authority, updated reserves, lien verification). Set calendar holds for reporting back.

Even a "non-settling" day can meaningfully advance the ball if you design it that way.

The Mediator's Prep Checklist (Share This with Counsel)

Two weeks out

  • Pre-mediation calls completed; success definitions recorded
  • Information gaps identified and a plan to fill them
  • Attendance/authority confirmed across parties and insurers

One week out

  • Mediation statements exchanged/submitted (strengths and weaknesses for both sides; plausible resolution frameworks)
  • One-page Deal Math prepared and client-approved
  • Logistics finalized (rooms, remote attendees, draft term sheet template)

Day before

  • Counsel confirm client's acceptable outcome range and emotional readiness
  • Draft closing language/press lines prepared (if needed)
  • Document shells ready for rapid capture

Day of

  • Civility rules set; opening structure affirmed
  • Early, credible anchors; reasons paired with moves
  • Live drafting once the zone narrows

After

  • Paper it quickly; schedule a short post-mediation check-in to shepherd signatures

A Word on "Winning the Mediation"

It bears repeating: trying to win the mediation usually loses the mediation. The impulse to argue one's way to surrender — to "prove" the other side out of its position — is strong and deeply human for litigators. But mediation is not adjudication. Filing a submission that reads like a brief, or delivering an opening like a closing, is a tell that the mindset is misaligned. A mediation statement that candidly addresses both sides' strengths and weaknesses, and that outlines how a resolution could actually work, is the opposite: it is a signal you've come to make a deal. 

As mediators, we can reset that mindset before the door closes. We can model the language of resolution, keep the process future-facing, and equip counsel to prepare their clients for the real work of compromise. If we do that consistently — with a little humor, a lot of clarity, and a strict weight limit on banker's boxes — we dramatically improve the odds that everyone leaves having achieved what they came for: resolution.

About the Author

Christopher M. Ernst is a full-time arbitrator and mediator, having retired from the active practice of law in 2025 after 34 years of fighting for his clients.  His ADR practice, Nationwide ADR (www.nationwideadr.com), focuses on resolving complex disputes in the areas of business, tort, consumer, employment, and securities law.  While based in Cleveland, Ohio, he oversees cases across the country.  He is also the author of Baldwin’s Ohio Practice: Tort Law 2d, published by West/Thomson Reuters.  

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December 02, 2025

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