Choosing a lawyer is one of the few business decisions where the “wrong fit” can cost more than money. It can affect your ability to operate, protect your assets, preserve your reputation, and meet strict court or regulatory deadlines. In Jamaica, that decision can also intersect with cross-border contracting, banking and compliance expectations, data privacy obligations, and sector-specific issues like shipping and IP enforcement.

If you are shortlisting a law firm for the first time (or re-evaluating your current counsel), the most effective approach is to ask a small set of high-signal questions early. The goal is not to interrogate your lawyer, it is to quickly confirm competence, clarity, and trust.

Before the questions: clarify what “success” looks like for your matter

Law firm selection becomes much easier when you define the outcome you actually want. A good firm will help you refine this, but it saves time to arrive with a starting point.

Consider:

• Your objective: win a claim, stop a breach, protect an IP right, close a transaction, reduce regulatory exposure, resolve a dispute quietly, or all of the above.

• Your constraints: timing, budget predictability, confidentiality sensitivity, business continuity, and internal stakeholder expectations.

• Your risk tolerance: some matters call for an aggressive litigation posture, others call for controlled settlement strategy.

Once you have that clarity, the questions below help you spot the firms that can deliver.

Law firm selection: 10 questions to ask first

Question 1: Are you qualified and experienced in the jurisdiction and forum that matters to me?

Ask where the firm is admitted to practise, and whether your matter is likely to be handled in a specific court, tribunal, regulator process, or arbitration setting.

What to listen for:

• A clear explanation of where the dispute or transaction “lives” legally (for example, Jamaica only, Jamaica plus another country, or a contract with foreign governing law).

• Familiarity with procedural realities, not just legal theory (timelines, interim remedies, disclosure expectations, enforcement considerations).

Red flag: vague confidence without specifics about forum, process, or jurisdiction.

Question 2: Who will do the work day-to-day, and who supervises?

You are not hiring a brand name, you are hiring a team. Ask who your primary contact will be, who drafts, who appears, and who signs off.

What to listen for:

• A defined matter lead and a defined day-to-day handler.

• A plan for continuity if someone is unavailable.

• An explanation of how work is delegated to control cost without sacrificing quality.

Red flag: you only meet a senior lawyer in the pitch, but no one can explain who actually runs the file.

Question 3: What similar matters have you handled, and what does “similar” mean?

This is where experience becomes measurable. “Similar” should not mean “we once did something in the same industry.” It should mean similar facts, similar risk profile, similar forum, or similar legal issues.

What to listen for:

• A short set of relevant examples (anonymised where appropriate).

• Lessons learned: what they would do again, and what they would do differently.

• For disputes: their approach to evidence, interim relief, settlement leverage, and enforcement.

Red flag: experience is described only in broad practice-area labels, with no concrete detail.

Question 4: What is your initial strategy, and what are the realistic timeframes?

A strong law firm does not promise results, but it should be able to explain a logical path from today to resolution.

What to listen for:

• A phased strategy (early assessment, preservation of evidence, first filings or pre-action steps, settlement windows, escalation points).

• A realistic range of timelines, with what influences those timelines.

• Clear next steps for the first 14 to 30 days.

Red flag: guarantees on outcomes, or timelines that ignore procedural steps and common delays.

Question 5: How will fees work, and how do you keep costs predictable?

You are entitled to understand how you will be billed and what drives cost. Even when exact totals are impossible to forecast, transparency is.

What to listen for:

• A clear billing model (hourly, staged, capped elements where appropriate, or blended arrangements).

• Practical cost controls (budget ranges by phase, pre-approval thresholds, staffing discipline).

• Upfront discussion of disbursements (court fees, experts, registries, etc.).

Red flag: resistance to giving even a phased estimate, or unclear descriptions like “we’ll see how it goes.”

Question 6: How will you communicate, and what does good reporting look like?

Legal matters often fail at the communication layer, not the legal layer. Ask how often you will receive updates and what those updates include.

What to listen for:

• A cadence (weekly, fortnightly, or event-based updates depending on the matter).

• Clear writing and plain-language explanations of risk.

• A commitment to confirm instructions in writing and keep decision points explicit.

Red flag: you feel rushed, your questions are not answered directly, or communication expectations are left undefined.

Question 7: What are the top risks you see right now (legal, commercial, and reputational)?

A valuable law firm surfaces uncomfortable truths early. This includes legal risk, but also operational and reputational risk.

What to listen for:

• Early identification of “failure points” (missing documents, limitation issues, weak clauses, vulnerable IP, enforcement challenges).

• A plan to mitigate those risks (preservation steps, negotiation posture, compliance remediation, alternative claims/defences).

Red flag: the firm only tells you what you want to hear.

Question 8: How do you handle confidentiality, data privacy, and sensitive documents?

This matters for every client, and especially for regulated businesses, cross-border matters, and disputes involving personal data.

What to listen for:

• Document-handling practices (access controls, secure sharing, retention and deletion approach).

• Awareness of data privacy requirements that may apply to your business (for example, local obligations in Jamaica plus overseas standards if you operate internationally).

If data privacy is central to your matter, it is reasonable to ask whether the firm has dedicated capability in data privacy, compliance, and risk.

Red flag: casual handling of sensitive material, or no clear protocol for secure sharing.

Question 9: Do you have the right depth for my matter (specialists, support, and escalation capacity)?

Some matters need more than one lens, for example litigation plus regulatory, or IP plus commercial, or shipping plus arbitration.

What to listen for:

• Whether the firm can cover the relevant areas without forcing you to coordinate multiple firms.

• How they bring in specialist support (internally or via trusted external partners) without losing accountability.

This question is particularly important for complex work like commercial litigation, banking litigation, competition law and policy, intellectual property, and admiralty and shipping.

Red flag: the firm overextends beyond its real capability, or cannot articulate how it will staff a heavy matter.

Question 10: If we can resolve this without court, what options do you recommend and why?

Litigation is sometimes necessary, but not always optimal. Ask how the firm approaches settlement strategy, mediation, and arbitration.

What to listen for:

• A view on which dispute resolution forum matches your priorities (speed, confidentiality, enforceability, relationship preservation).

• Negotiation strategy backed by preparation (evidence, leverage analysis, quantified risk).

A firm with experience in arbitration and mediation and appellate work can be especially valuable when disputes evolve quickly.

Red flag: “we litigate everything” or “we settle everything” without a fact-driven explanation.

A simple comparison table to keep your shortlist objective

Use the questions above as a scorecard so you are not relying on gut feel alone.

Jamaica-specific considerations (especially for cross-border clients)

Even when the underlying issue is universal, contracts, enforcement, regulatory expectations, and practical timelines vary by jurisdiction. For Jamaica-linked matters, consider asking:

• Enforcement reality: If you obtain a judgment or award, what is the practical path to enforcement against assets?

• Regulatory exposure: If the issue touches financial services, data handling, or competition concerns, how will the firm coordinate a compliance-focused approach?

• Industry fit: For sectors like shipping, logistics, and trade, does the firm have credible admiralty and shipping knowledge, including how disputes actually arise (cargo issues, charterparty disputes, maritime liens, insurance and claims coordination)?

These are not “extra” questions, they often determine whether the legal strategy works in practice.

What good law firm selection feels like

When you leave the initial call or meeting, you should have:

• A clearer understanding of your options than you had before.

• A short list of next steps, with who does what and by when.

• A candid view of risk, cost drivers, and likely timelines.

• Confidence that the firm can execute, not just advise.

If you do not have those, keep looking.

Frequently Asked Questions

How many law firms should I speak to before choosing one? Two to three serious conversations is usually enough for most matters. More than that can delay action, especially when deadlines are in play.

Is the cheapest law firm ever the best option? Low fees can be sensible for straightforward work, but for high-risk disputes or regulated issues, value is usually about strategy, responsiveness, and avoiding costly missteps.

What should I bring to a first consultation? A short timeline of events, key documents (contracts, emails, notices), names of decision-makers, and your objective. If it is a dispute, bring any deadlines and information about assets or counterparties.

Should I choose a specialist boutique or a full-service firm? Choose based on the problem, not the label. Complex matters often benefit from a firm that can coordinate multiple practice areas (for example litigation plus compliance, or IP plus commercial strategy).

How do I know if a law firm is being realistic about my case? Look for balanced advice: strengths and weaknesses, risks that could change outcomes, and a plan that includes contingencies rather than certainty.

Can a law firm help me avoid litigation altogether? Often, yes. Strong firms treat negotiation, mediation, and arbitration as strategic tools, not afterthoughts, and they can help you resolve disputes earlier where appropriate.

Need help evaluating your options in Jamaica?

If you are selecting counsel for a dispute, regulatory issue, or high-stakes commercial matter, you want a team that can combine clear advice with strong advocacy.

Henlin Gibson Henlin is a leading international law firm in Jamaica, offering client-focused support across areas including commercial and civil litigation, banking litigation, data privacy, compliance and risk, intellectual property, competition law and policy, admiralty and shipping, appellate work, and arbitration and mediation.

Learn more or get in touch at Henlin Gibson Henlin.