Questions to ask an attorney before you decide to sue

Deciding to sue is a fork in the road. Money, time and relationship damage lie ahead, and there's no guarantee you'll recover what you're owed. Before you commit, you need to know whether your attorney believes the case is worth fighting, whether they can handle it well, and what you're really signing up for. The conversation that gets you there isn't small talk—it's a series of specific, tough questions that separate lawyers who'll level with you from those who'll tell you what you want to hear.

Does your attorney think you can actually win?

This is the one that matters most. Ask directly: "What are the realistic prospects of success in this case?" Then listen hard to how they answer. A lawyer who says "Oh, we'll definitely win" or "It's straightforward" is either naive or selling you false hope. A competent one will lay out the legal test, identify which facts you need to prove, and tell you which of those facts are solid and which are uncertain. They should name the risks—the argument the other side will make, the evidence that might not hold up, the judge's discretion in your claim.

If they hedge or deflect—"Well, it depends on what comes out in discovery" or "These things are unpredictable"—push back. Ask them to give you a percentage range, or to say whether they'd take the case if their own money were on the line. A good answer sounds like: "Your contract claim is clear, but they'll argue the damage wasn't as high as you say. That weakens our position. I'd rate our chances at 65–70%, assuming the engineer's report backs you up."

What's your attorney's track record with cases like this one?

Litigation isn't generic. A lawyer who's spent five years on divorce matters may be competent but out of their depth on a property boundary dispute. Ask: "How many cases like mine have you run?" and "What was the outcome?" Don't accept vagueness. You want to know if they've actually stood in court on similar facts, whether they won or lost, and what they learned.

Press for specifics:

• How long did the last comparable case take from start to finish?
• Did it settle, go to trial, or end on an interdict?
• What was the biggest surprise or pitfall they encountered?
• Would they handle it the same way again, or differently?

If they've never run a case remotely like yours, that's not necessarily disqualifying—but they need to admit it and explain how they'll get up to speed. If they pretend they know and they don't, you'll pay in wasted time and poor strategy.

What's the realistic timeline and what will it cost?

You're not asking for a quote—that comes later, in writing. You're asking them to paint the picture: How long will discovery take? When do you expect a trial date? What's the path to settlement? A clear answer might sound like: "These cases usually take 18–24 months. Discovery takes six months, then we wait for a trial date, which in this court runs another 12 months out. We could settle earlier if they soften their stance."

Then ask how they charge. Do they bill hourly? Will they require a retainer? Will there be additional costs for expert witnesses or court fees? What happens if the case stalls or settles halfway through? A lawyer who won't discuss money upfront is hiding something.

Finally, ask: "If you were my friend, would you tell me to sue?" Their answer—honest hesitation, clear enthusiasm, or a qualified "only if you can afford to wait"—tells you whether they see you as a client or a billable file.

These conversations are uncomfortable because they force your attorney to plant doubt in your mind. That's the point. The lawyers worth paying are the ones who'll talk you out of a bad case or into accepting a reasonable settlement, not the ones who'll encourage you down an expensive road just because they can bill it. When you're ready to move forward with a lawyer who's earned your confidence, you'll find vetted litigators on Strove who can walk you through exactly what to expect.