Because literary agents have connections to the top editors of the world, writers can believe that getting an agent is the key domino to fall on their path to a successful writing career—so they may sign with the first agent who says yes. But that’s not necessarily the wisest move. The relationship needs to be a good fit to work well and last decades. Many writers and agents describe the partnership as a marriage, and you must make sure that you’re compatible in terms of goals and careers as well as each other’s strengths and weaknesses.

If it’s not a good match, you’ll have to break up—and that’s never an easy move. Parting with an agent stalls your career, and it also puts something of a mark on your record. When you leave that agent and seek different representation down the road, those other agents may wonder what exactly went wrong that caused you to leave Agent #1, fearing that perhaps you were a less-than-ideal client to work with.

So, whether you have one literary agent offer or several, you can be more certain of a good fit if you find out a lot about an agent’s skills, goals, and style by asking them specific questions when you speak on the phone. But if you’ve done your homework—researching each rep, looking at their sales, and reading online interviews—you already know plenty of info before you ever speak to them personally. So all questions below may not apply to you.

15 Questions to Ask a Literary Agent Before You Sign

1. How Did You Become an Agent?

Learn about their background. You want an agent who has a history in the publishing business. Almost all agents start their careers as interns, agency associates, or editors. This gives them a necessary knowledge base for their job, as well as valuable industry contacts. Good agents do not become agents overnight.

2. What Books Have You Sold Recently?

By learning what they’ve sold, you learn what kind of titles they have the ability to sell in the future, as well as the breadth of their selling skill and depth of their contact list. Please note that if the agent is new and they have no sales, that is not a dealbreaker. New agents can bring valuable elements to the table, such as time and passion and hands-on editorial help.

3. Tell Me About Your Agency. How Many Agents Are There, and How Do You Work Together?

This will help illuminate whether your agent is part of a larger, powerful team that shares resources and contacts. This is one reason signing with a newer agent is not a bad thing—because she utilizes her co-workers for help and leads.

4. What Did You Like About My Book? What Attracted You to This Project/Story?

You’re looking for passion and enthusiasm from an agent. Indeed, it is the passion and enthusiasm that will keep your agent up late working for you to see your book come to life.

5. What Editors Do You See Us Submitting This Book To, and Have You Sold to Them Before?

If you fear the agent lacks proper contacts to move your work, ask this straight out. The question tests not only her plan for where to send the manuscript, but also her connections and clout. Do not expect her to reply with a comprehensive list. After all, this discussion is just the beginning of the beginning. You’re just looking for her to have some targets in mind.

6. If Those Target Editors Turn It Down, Will You Continue Submitting, or Would It Be Best for Me to Work on a New Project?

Some agents only aim to sell books in “larger” deals to sizable publishing houses and well-known editors. This might not be what you have in mind, so learn her strategy now. It’s an unfortunate situation when an agent fields a dozen rejections for a book and declares it “dead,” even though you protest that many more markets exist. Sometimes all you want is for the book to find a loving home and get released in the world, but your agent wants “a fantastic deal or nothing.” Resentment can build quickly if you’re not on the same page.

7. What Changes Do You Think the Manuscript Needs Before We Submit?

If the agent has grand thoughts on revising the work pre-submission, you need to know that before you sign with them. You don’t want to sign a contract and have them surprise you by suggesting you “cut 30 percent of the book.”

8. Are You an Editorial Agent?

Having an agent that offers editorial suggestions and gets their hands dirty in the editing process can be very important to some authors.

9. May I Contact Some of Your Current Clients?

Most agents will be happy to pass along a few names and e-mails. But if your agent happens to represent a famous New York Times bestselling author, don’t be surprised if you don’t get that phone number. Some agents are more reluctant to pass along names and info. They like to make each of their clients feel extremely special and important. If multiple writers considering the agent start calling that client, it reminds the client his is simply one of many authors in the agent’s stable.

10. What Can I Do to Help You Sell This Book and Secure the Best Deal Possible?

This is a great open-ended question for two different reasons. First, it immediately shows you’re a helpful, proactive writer who wants to be involved. If the agent had any doubts about you, those doubts may dissipate for the time being. Secondly, this question gives the agent an opportunity to honestly convey suggestions and thoughts concerning how you can truly make a difference moving forward. Perhaps she’ll say, “Start a website so editors know you’re a professional.” Or perhaps she’ll say, “I can probably sell the book as is, but if you can find a way to trim five thousand words, I’ll have an even better chance.” Listen to what your agent suggests and take her concerns seriously.

11. Take Me Through the Process of When You Submit to Editors. How Involved and Updated Will I Be?

This question allows your agent to be upfront concerning how many phone calls and spreadsheets you will get during the process. When you know what to expect, you will not feel like you’re being left out of conversations—or bogged down with information.

12. If, for Whatever Unforeseen Reason, You Were to Step Down as an Agent in the Future, Would I Be Passed to a Co-Agent?

The first thing an agent will say when asked this question is probably, “I have no intention of leaving, so this is not a concern.” But don’t give up; press her for an answer. You deserve to know if, in the event of any circumstances leading to the agent temporarily or permanently leaving her work (such as, God forbid, a major illness), you will have the safety net of being passed to a co-agent. If the agent works alone and has no co-agents, you can ask if she will refer you to agent-friends in the industry.

13. If You Switch Agencies, Would I Transfer With You?

If your agent is part of a larger agency, do not skip this question—because this area gets real tricky real fast. Agents switch agencies all the time. But the agent may have signed an employment contract that says, if she leaves, the clients stay with XYZ Literary. If you make a deep connection with an individual agent, it’s not an ideal situation to know you legally cannot stay with that agent should she find employment elsewhere.

14. Will You Represent Every Book I Write?

Just because an agent signs you does not mean she will be willing to send out everything you write. She has signed you based on the strength of the book you submitted, and the ideal scenario that everything you continue to write will also connect with her in some way—but that isn’t always the case.

An agent should be forthcoming with you if she doesn’t feel that your most recent material is marketable or appropriate for their editors, as it is her reputation at stake. From an agent’s point of view, it is very, very difficult to gain an editor’s trust—and an agent doesn’t want to lose such an important relationship simply because a client pushes them to submit something she doesn’t want to submit.

Ask an agent about how future books will be handled. Some agents, if they don’t connect with the book, will offer editorial notes on how to make it better. Other agents will simply “pass” on the work and invite you to send your next book when it’s complete. Obviously these two approaches are extremely different, so make sure you know what you’re getting into before you get into it. If you believe in a book that the agent does not, you have to know if the agent is okay with you sending it to publishers on your own.

15. How Much Do You Think I’ll Be Paid for the Book?

Most writers will not ask this question during this initial conversation, and I consider that a good thing. I only include the question because some authors—most often nonfiction author-personalities and up-and-coming media figures—may want to know this upfront to see if the book will be worth their time.

That aside, it’s next to impossible for agents to speculate how much money a first book, especially a novel, will garner in an advance from the publisher. (Money estimates are easier to pinpoint when dealing with a sequel or second book, because the track record and payment for the first book can help paint a clearer picture.)

Here’s the danger and complication involved in asking this question: When my agent and I began to pitch our first nonfiction book together, I asked this question at some point, and the answer told to me was a medium amount. But then several key publishers passed on the work, and our target estimate suddenly dropped 40 percent. More publishers said no, and the estimate continued to drop like a rock again. We finally got one offer on the book, which we would eventually turn down. The amount? $1,000 and bad royalties. Needless to say, my agent’soriginal target estimate was that figure many, many times over. I learned a valuable lesson from that experience even though the book never got published: Have loose or no financial expectations going in, because you never know what the offer will be.

Asking an agent questions is a delicate process. Definitely do not skip any hard questions if you have pressing concerns or if the agent has a small track record. The agent is used to such inquiries and will respect you for politely asking them. At the same time, agents do not like to be pushed too hard too fast—as if a writer is forcing them to “prove their worth.” In other words, ask questions, but do not “grill” the agent or come off too pointed. Again, you should have already done plenty of homework and known this agent was a good fit for you.

Wordplayers, tell me your opinion! What would be your top question for a potential literary agent representing your work? Tell me in the comments!