The Unfiltered Conversations Product Leaders Are Having Right Now
From Columbus to Chicago to San Francisco, leaders shared their challenges during our Summer 2025 Product Invitationals.
So… what's keeping product leaders up at night?
This summer, we hosted ZoCo’s Product Invitational across three cities—Columbus, Chicago, and San Francisco. At each stop, product leaders posed their big “How do I…?” questions, and the group dug in to listen, reflect, and problem solve together.
Were we swapping war stories? Arguing about AI? Sharing therapy-level confessions? Below is a peek at the cross-city themes that emerged and kept leaders talking.
When the math doesn’t math
Leaders wrestled with the messy middle of product work: the gap between sky-high expectations and real-world constraints.
- How do I secure the resources I need when everyone wants Apple-level quality without Apple-level investment?
- How do I build trust with users when adoption feels like pushing a boulder uphill?
- How do I actually talk to users when sales teams or budget blockers are in the way?
- How do I increase my team’s influence when decisions are already made before we’re in the room?
Leaders shared visibility and trust-based tactics like over-communicating tradeoffs, weaving onboarding into the natural user journey, and marketing their team’s insights internally like storytellers, not just researchers. Sometimes, the job isn’t just to deliver. It’s to make the invisible visible.
The CEO Paradox and the Tooling Whirlwind
Visionary CEOs. Shiny new tools. Both can be inspiring and destabilizing, if not exhausting.
Energy and new opportunities can inspire teams to do their best work. But that same energy—when it seeps into day-to-day execution—can derail focus, undo progress, and create whiplash. Leaders described it as walking a tightrope: you want to believe in the potential without letting it bulldoze the structure your teams need to actually deliver. The conversations circled around:
- Convincing leadership when their brilliant idea might not be the right product direction
- Redirecting founder energy toward business-aligned priorities
- Getting the benefits of new tools (yes, AI included) without losing the magic of human collaboration
- Helping teams feel safe, capable, and clear on when tools add value—and when they don’t
The big lesson: success is about channeling energy, setting boundaries, and anchoring decisions in business outcomes.
Oh, and if you think “just adding a new tool” solves problems—Chicago leaders would like a word.
Personal Value and the Burnout Reality
Our final theme was more personal. Leaders admitted they’re tired, sometimes questioning their own value in the process. Leaders asked:
- How do I define my own value proposition in today’s job market?
- How do I survive burnout cycles and find purpose again?
- How do I keep morale up when headcount shrinks and roles aren’t backfilled?
- How do I make an impact when I’m new to a company or role?
The conversation turned practical and refreshingly human. Leaders swapped strategies for framing their personal “pitch,” normalizing career cycles with the Hudson Model of Change, and carving out rituals for feedback and celebration—even in tough times.
You’re not just leading products, you’re leading people, including yourself. Protecting energy and defining your own story is as critical as shipping features.
The common thread
Across cities, one thing kept bubbling up: Product leadership is less about having the right answer, and more about creating clarity—whether that’s for your users, your team, your execs, or yourself.
Sometimes that clarity comes from scrappy experiments. Sometimes it’s from storytelling. And sometimes, it’s just admitting the hard stuff out loud so the team can move forward together.
ZoCo's roundtables bring together product leaders for small, roundtable discussions to process challenges, share insights, and build community. If you're interested injoining us in 2026, request an invite here.
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