Litigation is rarely a “bolt from the blue” for established companies. Disputes tend to leave a trail, missed payments, strained emails, performance issues, regulatory flags, or an employee grievance that escalates. The companies that handle litigation best in Jamaica are usually the ones that treat it as an operational risk, not a last-minute emergency.

This checklist is designed for directors, founders, general managers, compliance leads, and in-house teams that want a practical way to stress-test their readiness for court proceedings, arbitration, or mediation in Jamaica.

What this checklist is (and what it is not)

This is not a substitute for legal advice on a specific case. It is a structured way to:

• identify litigation exposure early

• preserve evidence properly

• avoid procedural missteps

• reduce costs and business disruption

• improve your negotiating position for settlement

It is especially useful before you send a demand letter, respond to one, terminate a major contract, or notify a regulator.

1) Confirm governance, authority, and decision rights

Many disputes become more expensive because the business cannot answer basic questions quickly: Who can instruct counsel? Who can approve settlement? Who can sign affidavits? Who speaks to the other side?

Checklist actions

• Identify the internal decision-maker(s) for litigation strategy (board, CEO, managing director, committee).

• Confirm who has authority to:

  • retain lawyers

  • issue a formal response to allegations

  • make without prejudice settlement offers

  • approve mediation or arbitration

  • approve disclosure of documents

• Gather your core corporate documents in one secure location (company filings, board resolutions relevant to the dispute, major shareholder agreements).

Why it matters: When timelines are short, unclear authority leads to delay, inconsistent positions, and avoidable admissions.

2) Map the dispute in one page (before you “lawyer up” internally)

A concise dispute map helps management make better decisions and helps external counsel get to the point faster.

Checklist actions

• Create a one-page summary covering:

  • parties involved (including related entities and key individuals)

  • the contract(s) or legal relationship

  • key dates and milestones

  • what went wrong (your position and their likely position)

  • what you want (payment, injunction, declaration, specific performance, apology, etc.)

  • what you can live with (settlement range and non-monetary terms)

• Identify business impact beyond money, for example operational interruption, reputation risk, regulatory exposure, key customer churn.

3) Put a document preservation plan in place immediately

In commercial disputes, the “facts” are often proven by documents, not memory. Jamaican proceedings can require disclosure, and courts can draw adverse inferences where relevant documents are lost or destroyed.

Checklist actions

• Issue a litigation hold as soon as litigation is reasonably contemplated.

• Suspend auto-deletion for relevant systems (email, messaging tools, CRM, shared drives).

• Preserve mobile device data for key custodians (executives, account managers, HR).

• Preserve backups carefully, but do not rely on backups as your only source.

• Keep a log of what you preserved, when, and by whom.

Practical scope: what you should preserve

4) Identify the likely forum and procedure early

Your strategy changes depending on where the matter will be decided.

Checklist actions

• Check whether your contract requires:

  • Jamaican court proceedings

  • arbitration (and seat of arbitration)

  • mediation as a precondition

  • exclusive jurisdiction clauses

• Confirm whether urgent interim relief might be needed (for example to prevent dissipation of assets, protect confidential information, or restrain misuse of intellectual property).

• Consider whether the dispute could escalate to an appeal and what that means for cost, time, and risk tolerance.

Why it matters: Forum selection affects timelines, disclosure obligations, confidentiality, enforceability, and the practical leverage each side has.

5) Stress-test your contracts before the dispute hardens

When a dispute breaks out, businesses often discover their contract management is weaker than they assumed, missing signed copies, unclear scope, or informal variations.

Checklist actions

• Locate the executed contract (not just a draft).

• Identify the clauses that usually decide the dispute:

  • scope of work and acceptance criteria

  • payment terms and interest

  • limitation of liability and exclusions

  • termination for convenience and for cause

  • notice clauses (and how notice must be given)

  • dispute resolution clause

  • confidentiality and data handling

• Check if your operational reality drifted from the contract (informal changes, extra work, new deliverables). Gather proof of agreed variations.

Tip: In fast-moving industries, vendor disputes can turn on implementation timelines, service levels, and compliance responsibilities. If you operate a regulated online gaming or payments-adjacent business, document exactly which party owns KYC/AML checks, fraud monitoring, and payment flows. Even your platform choice can shape the dispute profile, for example where you rely on a third-party provider such as Spinlab’s modular iGaming platform with integrated payments and compliance tooling.

6) Quantify exposure with a damages and remedies worksheet

You should not wait for a lawsuit to compute the “real number.” Litigation decisions, including settlement strategy, should be anchored in defensible calculations.

Checklist actions

• Prepare a damages view with assumptions clearly stated:

  • principal sums

  • contractual interest (if any)

  • consequential losses (be conservative and evidence-based)

  • mitigation efforts (what you did to reduce losses)

• Identify potential counterclaims and set-off.

• Identify non-monetary remedies that matter:

  • injunctive relief

  • declarations

  • delivery up (for IP or confidential information)

  • specific performance (where relevant)

Governance note: Ensure finance and operations sign off on the numbers, not only legal.

7) Check limitation periods and timing risks

Timing can determine whether you can bring a claim at all, and it can also impact available remedies.

Checklist actions

• Record key dates: breach date(s), termination date, last payment date, last acknowledgment of debt, discovery date (if applicable).

• Ask counsel to confirm the applicable limitation period for each cause of action.

• Do not assume you can “negotiate first and sue later” without deadline risk.

Practical reminder: In many common law systems, simple contract claims are often subject to multi-year limitation periods, but the rules vary by claim type and facts. Treat this as a time-sensitive verification item, not a guess.

8) Review employment and HR dispute readiness (if people are part of the story)

Even when a dispute begins as “purely commercial,” an internal personnel issue may sit underneath it, a termination, alleged misconduct, whistleblowing, harassment, or commission/bonus disputes.

Checklist actions

• Secure personnel records relevant to the dispute (contracts, handbooks, warnings, performance reviews).

• Confirm that disciplinary steps were documented and consistent.

• Identify potential witnesses and ensure they do not “coordinate stories.” Preserve their original notes and communications.

• Prepare a communications plan for staff, especially where the dispute affects morale or operational continuity.

9) Evaluate regulatory, data privacy, and compliance spillover

Litigation often triggers regulatory attention, and regulatory issues often trigger litigation.

Checklist actions

• Identify whether the dispute touches regulated activity (financial services, shipping, telecoms, gaming, health, energy, etc.).

• Check whether there are mandatory reporting or notification obligations.

• For data-driven disputes, confirm:

  • what personal data is involved

  • where it is stored and transferred

  • who has access

  • what legal basis you rely on for processing and disclosure

• Make sure your litigation disclosure approach does not create a secondary data privacy breach.

Why it matters: Mishandled disclosure can expand the dispute into enforcement risk, reputational damage, and parallel proceedings.

10) Prepare witnesses and a clean internal narrative (without coaching)

Companies lose credibility when their witnesses contradict each other or when key people “remember” facts only after litigation begins.

Checklist actions

• Identify likely witnesses early (commercial lead, finance lead, project manager, compliance officer).

• Collect a chronology supported by documents, not recollection.

• Ensure witnesses understand:

  • they must tell the truth

  • they should not destroy documents

  • they should not engage the opposing party directly once counsel is involved

Operational tip: Centralise communications. A dispute is not the time for multiple executives to send reactive emails.

11) Choose dispute resolution strategy: negotiate, mediate, arbitrate, litigate

The “best” process is usually the one that protects your commercial position at acceptable cost, risk, and time.

Checklist actions

• Assess whether early settlement is realistic based on:

  • strength of documents

  • urgency of relief

  • relationship value

  • the other side’s solvency and incentives

• Consider mediation where:

  • there is a relationship to salvage

  • facts are not sharply disputed but expectations diverge

  • confidentiality matters

• Consider arbitration where:

  • you need privacy

  • you want a specialist decision-maker

  • enforceability across borders is important

• Consider litigation where:

  • you need urgent court orders

  • you need public precedent or declaratory relief

  • the other side will not engage unless compelled

12) Budget and resource the case like a project

Litigation costs tend to spike when businesses treat the case as “legal’s problem” rather than a cross-functional project.

Checklist actions

• Assign an internal case owner.

• Establish a reporting cadence for leadership (for example fortnightly).

• Define approval thresholds for key steps: filing, interim applications, expert engagement, settlement.

• Plan for e-discovery costs and staff time (especially for document collection and witness preparation).

13) Prepare for interim applications and urgent scenarios

In commercial disputes, speed can matter as much as being right. If assets can move, data can be copied, or a vessel can sail, you may need urgent relief.

Checklist actions

• Identify whether you may need urgent applications to:

  • preserve assets

  • preserve evidence

  • restrain misuse of confidential information

  • protect IP

• Gather the documents needed to support urgency (banking records, logs, correspondence).

• Identify who can sign affidavits at short notice.

14) Don’t ignore specialised risk areas (banking, competition, shipping, IP)

Certain disputes require specialised handling because the legal rules, evidence, and commercial consequences are distinct.

Checklist actions

• If the dispute involves lending, guarantees, or security enforcement, map the banking documentation precisely and confirm notice requirements.

• If the dispute involves market conduct, exclusivity, or dominant position issues, consider whether competition law arguments could arise.

• If the dispute is maritime or shipping-adjacent, identify:

  • bills of lading and charterparty documents

  • forum and governing law

  • time-sensitive operational constraints

• If the dispute involves brands, software, or creative assets, preserve proof of creation, ownership, licences, and usage history.

This is where engaging a firm with the relevant practice depth matters. Henlin Gibson Henlin is an international law firm in Jamaica with experience across commercial litigation and related areas such as arbitration and appellate advocacy, which can be important when cases evolve beyond first-instance proceedings.

15) Protect reputation: plan communications and confidentiality

Even when you are confident in your case, uncontrolled messaging can harm settlement prospects and customer trust.

Checklist actions

• Appoint one internal spokesperson.

• Coordinate legal and PR positions, especially where media interest is possible.

• Reinforce confidentiality obligations internally.

• Avoid public statements that could be used as admissions.

16) After the dispute: capture lessons and tighten controls

Win or lose, every dispute should reduce future disputes.

Checklist actions

• Run a short post-matter review:

  • what triggered the dispute

  • what evidence was missing

  • which contract terms failed you

  • where decision-making slowed down

• Update templates: dispute clauses, notice provisions, acceptance criteria, data handling schedules.

• Improve recordkeeping and retention, especially for “informal” business communications.

A final practical note on speed and discipline

Most companies do not lose disputes because they lacked a clever legal argument. They lose leverage because they moved too slowly, failed to preserve documents, underestimated timing risks, or let internal communications become inconsistent.

If your business is facing a brewing dispute, consider using this checklist as a rapid internal audit and then seeking tailored advice on forum, remedies, and next steps. You will typically save time and cost by getting early clarity on documents, decision rights, and the most realistic resolution path.