Most clients hesitate to ask questions not because the questions are unreasonable, but because something in the dynamic makes them feel unsafe asking.
That feeling is data.
A healthy attorney-client relationship can tolerate scrutiny, documentation, and informed clients. If it can’t, the issue isn’t tone, it’s structure.
Here are questions you should never be afraid to ask, and what competent answers actually look like.
“Who are the insurance carriers for each defendant?” 🧐
You should be able to ask, by name, who insures the parties you’re pursuing.
A competent attorney can identify the carrier, the type of policy (general liability, auto, excess, umbrella), and the applicable policy period.
Vague answers like “we’re still figuring that out” months into a case, or “insurance is complicated,” are not explanations. They are placeholders.
Insurance is not peripheral. It is the case.
“What coverage applies to my specific claim, and what doesn’t?” 🗂️
A strong attorney can explain which policies respond to your injuries and why. They can also tell you what doesn’t apply, without guessing or hedging.
They don’t dramatize. They don’t speculate. And they don’t use insurance uncertainty to manage your behavior. Clarity is competence.
“Do you have the declarations pages for those policies?” 📑
This is not an aggressive question. It is a normal one.
Declarations pages confirm limits, exclusions, policy periods, and named insureds. A competent attorney understands why a client would want to see them and does not treat the request as distrust.
Resistance to sharing basic policy documents is a red flag.
“What steps have been taken so far, and where is that documented?” 📋
You are entitled to know what work has been done on your behalf. A competent attorney can point to emails, filings, correspondence, logs, or summaries that show progress.
If the explanation relies entirely on verbal reassurances, personality, or repetition instead of records, something is missing.
“What is the realistic timeline, and what would change it?” ⏳
Good lawyers can distinguish between delay and strategy.
They can tell you what they are waiting on, why it matters, and what event would move the case forward.
If progress seems contingent on your behavior, that’s not strategy and that’s not professional.
“How are communications documented in my file?” 💻
Written communication protects everyone.
An attorney should document calls, negotiations, and decisions as a matter of routine.
If requests for summaries, confirmations, or emails are treated as burdensome, that’s not about efficiency. It’s about avoiding a record.
“Who on your staff is communicating on my case, and how are they supervised?” 👩💻
You should know who is speaking for you.
Paralegals and staff should operate within defined roles, with attorney oversight.
An attorney knows they take responsibility for what their staff says and fixes mistakes without defensiveness.
“What risks actually exist, and can you show me where those risks come from?” ⚠️
Real risks come with sources: statutes, policy language, deadlines, or precedent. Fear without documentation is not legal advice, it’s pressure.
You are allowed to ask where a risk originates and how likely it truly is.
“Who is your firm’s professional liability (malpractice) insurance carrier?” ⚖️
This question should not cause discomfort.
Every attorney knows who insures their practice and what type of policy they carry.
You are not accusing anyone by asking. You are confirming accountability. A competent attorney answers directly and in a timely manner.
“If I asked for my full file today, would anything surprise me?” 😧
This question goes to transparency.
A strong attorney has nothing to hide and understands that the file belongs to the client.
If the idea of full disclosure feels tense or delayed, that’s a warning sign.
Final Thought
You don’t lose good attorneys by asking informed questions.
You expose weak systems.
Professional lawyers rely on documentation, insurance clarity, and transparency because they know their work holds up under review. They don’t need secrecy, urgency, or fear to manage clients.
Professional attorneys want things in writing because writing stabilizes truth.
Unprofessional or deceptive attorneys avoid it because writing fixes the story in place.
If clarity disappears the moment you ask for specifics, pay attention.
Pro Tip:
If an attorney can explain something convincingly aloud, but resists putting it in writing, the issue isn’t complexity. It’s durability. Good legal explanations survive documentation. Bad ones don’t.