Writing Workshop of Chicago: Pitching and Listening

During the spring of our discontent, which has turned into the summer of our discontent, the bad news for writers is many conferences have been canceled. But the good news is that many conferences have moved online. I attended the 2020 Writing Workshop of Chicago in June. While I missed engaging in-person with writers and agents, the event was a success. For me, it was efficient and enlightening, largely due to the expertise of the event facilitator, who is a combination of writing guru, tech-genius, and email wizard. Brian Klems, I lift a glass of bubbly in honor of your wonderful work during this three-day event. Writing Workshop of Chicago - Pitching and Listening

The sessions were both craft- and marketing-oriented. Workshops included tips about plotting a novel, sidekicks and supporting players, and romance-writing basics. Agents in attendance were top-notch and attentive during pitch sessions. I had a few technical issues, but they quickly were resolved. I was thrilled with the convenience of being in contact with so many agents. Pitch sessions were $29 and only ten minutes long. (The cost of the entire event was $149, not including the cost of each pitch session.) I’m glad I attended the New York Pitch Conference to improve my pitching skills. There was little time for error! (Read more about my visit to the New York Pitch Conference HERE.)

Pitching to many different agents offered a perspective about the type of feedback a writer should expect. Basically, it depends. Each agent had a unique style and his or her own way of conducting the pitch session. I didn’t take any of the feedback as a failure, even if they weren’t interested in my work. (Though fortunately many were interested.) As I pitched throughout the day, I understood that it was a learning experience as much as a pitching experience. Depending upon the agent, responses included feedback about my pitch rather than my novel; a stopwatch and a request to communicate succinctly; and probing questions about plot.


Agents will provide feedback about your pitch: A few agents treated the pitch like a workshop. They offered advice about my pitch rather than the book I discussed. I was advised about the length of my pitch, the inclusion of character names (don’t include too many!), and improvements to my log line. I took careful notes and my pitch improved during the day.


Agents will time you: With a couple of agents, small talk was discouraged, the clock was started—and it was go-time. If this happens to you, don’t be nervous. Launch into the best pitch you have, make eye contact to show the clock isn’t intimidating to you, and do your best. Ten minutes is not a lot of time. Don’t talk too fast but be succinct. Have that pitch polished because you’re being evaluated to see if truly know your work. Condensing a book into three paragraphs is not easy. Tip: Read your pitch out loud. Practice it. Time yourself before attending one of these events. You’ll be glad you did.

Plot holes

Agents will question your plot: Agents will drill down to holes they perceive in the narrative. He or she may point out an event that seems too large to overcome, that it’s unrealistic to expect it to happen. Others will ask about major plot points such as the inciting incident or point-of-no-return. I was pitching mysteries and there are aspects to a main street mystery that need to appear in the story for it to work. Amateur sleuths need assistance in all kinds of ways. For example, they’re not licensed private investigators, so who will be providing that kind of expertise? I took the questions as a test to my knowledge of the genre. Fair game, as far as I’m concerned. As a mystery writer, I should know how to incorporate those necessary elements into the story.

Listen carefully

If you’re pitching to agents, listen carefully to the questions being asked: Several agents asked about the potential for a series. One agent asked about the writing groups I belonged to. Another asked about my marketing skills. All great questions that I was prepared to answer. Few writers can just write and expect someone else to do the marketing behind a novel. In this age, we also must have a knowledge of website creation, social media, and group memberships. (Side note: Jane Friedman offers more information about agents and pitching in this article.)

While I prefer to attend events in-person, this workshop exceeded all my expectations. It transformed from a one-day event in Chicago to a three-day online meeting where I could attend all the sessions at my leisure rather than have to rush from one meeting to the next due to multiple pitch-sessions jammed into the day. I have an email with links to all the workshops I missed, and I’ll watch them several times to learn more about writing and pitching. Further, the interaction with many agents was an invaluable lesson in pitching. As the day evolved, I gained great insight about how different agents communicate and provide feedback. I’ll take that knowledge and move forward in my writing journey.

Happy summer, writers.

Stay safe.

Tracey Kathryn


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