Breakthrough the Echo Chamber
Think beyond the slide. Creative but business-appropriate ways to explain, sell, and convince, always anchored in who you are talking to, where they are, and what they need right now.
Live, interactive session with Jammers during PMM Jam 2026 Beta
How to connect with any audience, cut through business noise, and make content that actually gets remembered
PMM leader, seasoned author, and AI enthusiast and critic. In his third act and still making five mistakes a day on purpose
Gary opened with a rule: if he does not make five meaningful mistakes a day, he has not worked hard enough. That set the tone for a session built around live debate, challenge, and the kind of creative thinking that corporate environments tend to train out of people.
The central premise was simple. Most business content, according to brain science researcher Carmen Simon, stimulates the human brain no better than staring at a beige wall. Gary's session was about what to do instead. Not by adding flash or gimmicks, but by starting with three questions that most PMMs skip.
Product marketing is teaching
Before the framework, Gary posed a challenge to the room: name one atomic task a PMM does that is not, at its core, a form of teaching. Sell, inform, warn, validate, synthesize, engage. The group pushed back, added verbs, debated the edges. The conversation landed somewhere interesting: what we do is teach, but we teach with a business end in mind. The goal is always to move someone from where they are to where they need to be next.
Three questions for any communication challenge
Gary's framework strips any communication task down to three questions. They sound simple. They are not always applied.
The session spent a lot of time on the third question, because it is where most requests go wrong. A CEO asking for a white paper is not actually asking for a white paper. They are asking for something that will solve a problem they have not yet named precisely. Gary's analogy: if the boat is sinking, you do not hand someone a manual. You hand them a life raft. Understanding what someone actually needs right now, not what they asked for, is the real job.
"Most business content stimulates the human brain no better than staring at a beige wall. Our job is to be the thing that is not a beige wall."
Gary Dietz, PMM Jam 2026 Expert SessionWhere Gary's session fits.
Gary's three questions did not exist in isolation during PMM Jam. They showed up in conversation with ideas the other sessions had already introduced, and the room made those connections in real time.
Zach Messler's work on message clarity is about building the foundational answer to these questions before a single word of copy gets written. Gary acknowledged this directly: in an ideal world, Zach's work on the why and the essence comes first. His three-question framework is what you reach for when you need to communicate before all of that foundational work is done, or when someone throws a deliverable request at you and you need to redirect it fast.
Eve's gamification session covered player types, motivation, and how different people engage with content differently. That is the audience dimension of Gary's first question taken further. Knowing someone is a Socializer or an Achiever changes everything about what they need to know and how you should say it.
Together, these sessions form a progression: understand the essence of what you are selling, understand who you are selling it to and what motivates them, then apply the right communication framework for the right moment. Gary's session is the connective layer that ties the work back to the practical reality of being asked to produce something on a deadline by someone who has not done any of the upstream thinking.
Gary Dietz is a PMM leader and seasoned author in his third act, still making five mistakes a day on purpose. He works with people interactively to find creative but business-appropriate ways to explain, sell, and convince, always anchored in three questions: who are you talking to, where are they in the cycle, and what do they need to know right now. He loves improv, teaching, and being proven wrong.
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