Someone invited you to a presentation, sent you a link, or called with an opportunity. Now they want a decision. Before you say yes—or no—you need answers to the right questions.

This list came out of being on both sides of the recruiting table. Some questions are logistical. Some expose financial structures you probably haven't been told about yet. A few will feel uncomfortable to ask. Ask them anyway. An agency that punishes due diligence is telling you exactly what working there will be like.

Before You Read the List

Disclosure: I recruit for United Trust Life, so I have a financial incentive if you join our agency. I'm writing this anyway because a person who joins with clear eyes and accurate expectations stays longer, serves clients better, and builds something real. A person who joins on hype leaves in three months and resents everyone involved.

Run every answer from our recruiters through this same list. If we dodge, that's information too.

The 12 Questions

01

Can I see the compensation plan in writing before I sign anything?

This is the most important question on the list, so it goes first. Verbal promises about pay structures, commission tiers, bonuses, and advancement are unenforceable and fade the moment a disagreement starts.

Good answer"Absolutely—here it is. Let me walk you through it." Followed by an actual document you can read, keep, and verify.
Red flagAnything that defers the written document until after you sign a contract, complete training, or hit some milestone. "We'll go over that in onboarding" is not an answer.
02

What is the chargeback policy, and how long does it run?

A chargeback happens when a client cancels or lapses a policy. The insurer takes back commission already paid to you, and your agency may debit your account. The duration and terms vary significantly across companies and products.

Good answerA specific timeframe (for example, "12 months on term, 18 months on whole life for most carriers") plus a clear explanation of how it works in practice—whether it comes out of future commission, is invoiced separately, or settles against your active book.
Red flagVague language like "it rarely happens" or "don't worry about that for now." Chargebacks happen in every insurance career. How they are handled shapes your cash flow significantly.
03

Do you or others in this organization earn overrides or bonuses based on my production?

In most independent marketing organizations and agency systems, upline agents earn an override percentage on production from agents below them. That is legal, common, and not inherently a problem. What matters is whether it is disclosed.

Good answer"Yes, I do earn overrides on your production—here is how that works, and here is your street-level commission rate." Transparency about overrides tells you the actual compensation structure and lets you evaluate whether it is fair.
Red flagDenial, evasion, or "that's not how it works here" when it demonstrably does. If you are at a recruiting event with 200 people and the presenter earns nothing from bringing you in, ask yourself what is actually in it for them.
04

Who owns the clients and policies I write?

Client ownership is rarely discussed at recruitment events and almost always matters when you eventually leave. In some agency structures, your book of business belongs to the agency or upline. If you leave, you leave without it.

Good answerA clear statement about whether you own your clients, what happens to your commissions if you leave in good standing, and whether there is a non-solicitation agreement that restricts you from working with those clients at a different agency.
Red flag"Don't think about leaving—focus on getting started" is a deflection, not an answer. Any agent who has built a book of business cares about this question. An agency that won't answer it is one where the answer disadvantages you.
05

What are the actual upfront costs to me—licensing, training, technology, E&O insurance?

Getting licensed costs real money. Your state exam fee, fingerprinting, license application, pre-licensing course (if not covered), background check, and errors-and-omissions insurance are all line items you will pay before writing your first policy.

Good answerAn itemized list of what you pay out of pocket, to whom, and in what order. Some agencies cover pre-licensing course costs—if so, ask exactly what they cover and what you still owe the state. At United Trust Life, for example, you buy the course from the vendor yourself, and the state exam fee, fingerprinting and application go to your state—none of it comes to us.
Red flagAny agency fee, membership fee, or training program cost you pay to the agency itself before writing business. You will always pay the state; you should not be paying the agency to hire you.
06

Am I an employee or an independent contractor? What does that mean for my taxes and benefits?

The overwhelming majority of insurance agents work as independent contractors, not employees. That means no employer-side FICA, no withholding, no W-2, no employer-provided health insurance, and no unemployment insurance if things don't work out. You receive a 1099 and are responsible for estimated quarterly taxes.

Good answerA direct "independent contractor" answer, an explanation of what that means in practice—including the self-employment tax rate and the need for quarterly estimated payments—and ideally a suggestion that you consult a tax professional before you start.
Red flagConfusion about the classification, or glossing over the tax reality. The self-employment tax is roughly 15.3% on top of your income tax, and agents who are not prepared for it often hit a painful bill in April.
07

How are leads sourced, and what do they cost me?

Lead programs vary enormously. Some agencies provide leads at no cost. Some sell leads to agents at a per-lead price. Some require you to generate your own through referrals, social media, or cold calling. Some do all three depending on performance level.

Good answerSpecifics: how leads are generated (mailers, digital ads, referrals), how they are distributed, what you pay per lead if applicable, and what happens to leads you don't close within a set window. Ask to see a sample lead card.
Red flag"We provide leads" with no explanation of cost, quality, exclusivity, or how many you actually receive. Leads that cost $25–$50 each are common; an agent writing three sales a week from $40 leads is spending $300–$500 on leads alone.
08

What does a realistic first-year look like for someone at this agency—including those who don't make it?

Almost every recruiter can show you success stories. Ask about the full distribution of outcomes—including the people who left in the first six months, what they earned, and why they left.

Good answerAn honest acknowledgment that not everyone succeeds, a realistic account of first-year income ranges without cherry-picked top performers, and a straightforward discussion of the time and financial commitment required to make it through the ramp-up period. Be skeptical of any income figure not accompanied by a sample size and timeframe.
Red flagStories about the top producer in the office, screenshots of commission checks, or any income figure presented without context about how many agents were studied over what period. "You could earn six figures" is not the same as "the median first-year agent here earned X, based on Y agents in year Z."
09

Is there a minimum production requirement, and what happens if I miss it?

Many agencies have production minimums tied to maintaining your contract, lead access, or commission level. If you miss them, you may lose leads, lose your contract, or face a commission cut—regardless of whether those minimums were clearly explained at the start.

Good answerA clear statement of any production requirements, what the consequences of missing them are, and whether there is a grace period or performance improvement process before consequences kick in.
Red flagUncertainty, or "we just want people who are serious" with no concrete definition of what "serious" means in measurable terms.
10

What training do you provide, and is it free?

Training is one area where agencies genuinely differ. Some provide extensive live mentorship. Some offer video libraries. Some expect you to figure it out on your own once licensed. A few charge separately for advanced training programs after you join.

Good answerA specific description of what the training program includes—format, length, whether it involves a mentor or field trainer, and whether any of it costs money. Ask specifically: "Is there any training I pay for after joining?"
Red flagTraining programs that require a fee to access, or vague descriptions of "ongoing support" with no structure. Also watch for training that is exclusively sales-script based with no product or compliance component—you need to understand what you are selling.
11

What carriers do you contract with, and do I have access to all of them from day one?

Carrier access determines what products you can offer clients. Some agencies gate carrier appointments behind production thresholds, contract tiers, or tenure. Starting with access to only one or two carriers limits your ability to serve clients and compete in the market.

Good answerA list of appointed carriers and a transparent explanation of how and when you gain access. If access is tiered, what does each tier require?
Red flag"We work with many carriers" without specifics, or confirmation that full carrier access requires hitting production targets you can't meet until you already have carrier access. The chicken-and-egg trap is real in some agency structures.
12

Can I talk to two or three current agents at this agency—not ones you've chosen for me?

A recruiter's hand-picked references are people the recruiter knows will say good things. That is not a reference—it is a testimonial. Real due diligence means talking to agents you find independently.

Good answerNo problem at all—here is how you can reach people in our agent network. Or: look us up on LinkedIn and reach out to agents there directly. We have nothing to hide.
Red flagResistance to independent contact, requests that you go through a coordinator, or suggestions that talking to random agents is "not how it works." An agency with satisfied agents wants you to hear from them.

Patterns That Should Give You Pause

Stop and Reconsider If You See These

  • Pressure to decide at the first meeting. A good opportunity will still be a good opportunity in 48 hours. Any recruiter who manufactures urgency around your career decision is prioritizing their timeline over your judgment.
  • The pitch is primarily about income potential with no discussion of effort or risk. Commission sales income is highly variable. Any presentation that leads with top earner numbers without covering median earner numbers, chargeback risk, or time to first paycheck is not giving you the full picture.
  • You're encouraged to recruit before you've made a sale. "Get your friends involved" before you've established whether the opportunity works for you is a structural incentive to spread the risk, not evidence that the role works.
  • The company being sold is primarily the opportunity, not the products. If you spend two hours learning about the business model and fifteen minutes learning about what clients actually buy and why, ask what the focus actually is.
  • They push back when you ask for time to research independently. Independent research is due diligence. Any agency that discourages it is hoping you'll commit before you find something that gives you pause.

Questions That Work in Your Favor

Beyond spotting problems, good questions also help you find the right fit faster. Ask these to calibrate whether the agency's culture and structure match how you work:

These are not trick questions—they help you picture the actual job, not the recruiting pitch. A recruiter who welcomes them is signaling that the agency expects agents to think and plan, not just execute scripts.

Bottom Line

There are agencies where recruiting matters more than agent success, and there are agencies where those two things align. The questions above help you tell the difference. An agency built on high turnover needs you excited before you've asked hard questions. An agency built on retention wants you to ask them.

If you are considering United Trust Life, run us through this entire list. Our recruiters are trained to answer every question on it directly. If they can't, we want to know too.

See what we're currently looking for →

Author disclosure: Justin Crow is a licensed agent at United Trust Life. He earns overrides on production from agents he recruits. This article was written to help candidates ask better questions of any agency—including this one. United Trust Life is an independent agency contracting with multiple carriers. Insurance sales is commission-based; income results vary and depend on individual effort, market conditions, carrier terms, and other factors.

Frequently Asked Questions

What is the most important question to ask an insurance recruiter?

Ask for written documentation of the compensation plan before you sign anything. Verbal promises about pay structures, bonuses, or advancement are unenforceable. If a recruiter won't hand you a written comp sheet, that alone is reason to walk away.

What are red flags from an insurance recruiter?

Key red flags include: pressure to decide at the first meeting, vague or verbal-only compensation promises, refusal to explain the chargeback policy, no clear answer on who owns the clients you bring in, and any suggestion that you need to buy the product yourself to sell it. Legitimate agencies welcome your questions and give written answers.

Do insurance recruiters get paid to recruit me?

In most independent and IMO-model agencies, yes—the person recruiting you often earns an override or production bonus on business you write. That is not automatically bad; it is simply a financial incentive that is worth knowing about. Ask the recruiter directly: "Do you earn overrides or bonuses based on my production?" A recruiter who answers that question honestly is a better sign than one who dodges it.

Should I have to pay anything upfront to join an insurance agency?

A legitimate agency does not charge you to join. You will have real out-of-pocket costs—your state exam fee, fingerprinting, licensing application—but those go to your state, not to the agency. If a recruiter asks for a membership fee, training fee, or any payment to them or their company before you are licensed and writing business, that is a serious red flag.